Top Airbnb Options for Your Stay in Greenport, NY

ZEY HOTEL offers accommodations in Greenport, 26 miles from Splish Splash. The bed and breakfast also offers free Wifi, free private parking, and facilities for disabled guests. The bed and breakfast offers a flat-screen TV and a private bathroom with bathrobes, slippers, and shower. The units have air conditioning, and some units at the bed and breakfast have a terrace. The rooms are equipped with heating facilities. The area is popular for cycling and fishing, and free use of bicycles is available at ZEY HOTEL. An indoor play area is also available at the accommodation, while guests can also relax in the garden. Long Island MacArthur Airport is 48 miles from the property.

- "Unbeatable location right in the heart of Greenport! Mia was an excellent host and very attentive." - "Beautiful space to stay.and enjoy Greenport" - "Excellent stay will definitely be back" - "ZEY Stay" - "Perfect" - "Awesome!" - "Recommended 100%" - "Loved the place! The staff is super hospitable. Mia is fantastic" - "A charming and affordable gem in Greenport" - "Great comfy community living spaces to place board games or just relax. Nice bright Sunny room to have free coffee juic"

On private beach with seasonal outdoor pool, near East End Seaport Maritime Museum
At Sound View Greenport, hit the private sand beach, dine onsite at The Halyard, or enjoy a drink at one of the hotel's 2 bars/lounges.
Housekeeping is available on request.
Sound View Greenport offers 65 accommodations with minibars and coffee/tea makers. These individually decorated and furnished accommodations have separate sitting areas. Pillowtop beds feature Frette Italian sheets, down comforters, and premium bedding. LCD televisions are featured in guestrooms. Bathrooms include showers, designer toiletries, complimentary toiletries, and hair dryers.

This Greenport hotel provides complimentary wireless Internet access. Business-friendly amenities include desks and desk chairs. Housekeeping is provided on request.

The recreational activities listed below are available either on site or nearby; fees may apply.

- "Great time as always." - "Excellent place" - "Right on the water " - "We loved our stay at Soundview! Hearing and seeing the waves crash as you lay in bed was amazing even in the winter. The perfect weekend getaway. There are some extra fees when you book through Expedia for parking and taxes/fees which was a little annoying because we did not notice that when booking but that is also our fault because it does state it on expedia. "

American Beech Hotel has free bikes, garden, a restaurant and bar in Greenport. This 4-star hotel offers free WiFi. The property is allergy-free throughout and is located 26 miles from Splish Splash. At the hotel the rooms have air conditioning, a seating area, a flat-screen TV with cable channels, a safety deposit box and a private bathroom with a shower, free toiletries and a hairdryer. All rooms will provide guests with a closet and a coffee machine. Guests at American Beech Hotel will be able to enjoy activities in and around Greenport, like cycling. Long Island MacArthur Airport is 48 miles from the property.

- "Super fun overnighter" - "Relaxing mini getaway with husband in beautiful Greenport" - "Love it !" - "Nice getaway, funky boutique vibe, excellent restaurant - needs some TLC. Showing signs of wear" - "American Beech has it all for a great getaway." - "Cute but not pristine."

On a private sand beach, near Railroad Museum of Long Island
Catch some rays on Silver Sands Motel & Beach Bungalows's private sand beach or spend the day relaxing at the full-service spa. Then enjoy a meal at one of the hotel's 3 restaurants.
Silver Sands Motel & Beach Bungalows offers 33 air-conditioned accommodations with minibars and laptop-compatible safes. These individually decorated accommodations have separate sitting areas. Pillowtop beds feature down comforters and premium bedding. A pillow menu is available. 43-inch Smart televisions come with digital channels and Netflix.

Bathrooms include bathrobes, slippers, and hair dryers. This Greenport hotel provides complimentary wired and wireless Internet access. Additionally, rooms include complimentary bottled water and irons/ironing boards. Housekeeping is offered daily and hypo-allergenic bedding can be requested.

The recreational activities listed below are available either on site or nearby; fees may apply.

- "We had a lovely stay. " - "The recently renovated motel was designed with meticulous attention to detail. We were blown away by the immaculate and spotless space which had all the modern updates and conveniences. The food served on site in the 50s-inspired diner called Nookies was also delicious. I wish we had a longer stay at Silver Sands and we will definitely be back again! " - "Everything was wonderful-staff, cleanliness, great weather and good food at Nookies 😃"

Featuring a terrace, bar and views of city, The Menhaden Hotel is located in Greenport, 26 miles from Splish Splash. Featuring free bikes, the 4-star hotel has air-conditioned rooms with free WiFi, each with a private bathroom. The property has a 24-hour front desk, a concierge service and luggage storage for guests. At the hotel, rooms are equipped with a closet. The rooms in The Menhaden Hotel are equipped with a flat-screen TV and free toiletries. Long Island MacArthur Airport is 47 miles from the property.

- "Warm, cozy, and well worth it!" - "Incredible place, though pricey, the staff and management go the extra mile." - "Wonderful!" - "Great location, great service, and great people. 10/10 would come again." - "We were very warmly welcomed and attended to." - "Great stay , clean the best Staff" - "Overnight escape" - "Great winter weekend" - "A nice clean establishment, with lovely staff. It was just a room. Not an expetience."

Bayside hotel with free breakfast and a 24-hour fitness center
A 24-hour fitness center, self parking, and a seasonal outdoor pool are available at this smoke-free hotel. Free continental breakfast and free WiFi in public areas are also provided. Additionally, concierge services, tour/ticket assistance, and a TV in a common area are onsite.
The Harbor Front Inn offers 35 air-conditioned accommodations with MP3 docking stations and laptop-compatible safes. Each accommodation is individually furnished and decorated. Pillowtop beds feature Frette Italian sheets, down comforters, and premium bedding. 50-inch flat-screen televisions come with cable channels. Bathrooms include shower/tub combinations, bathrobes, slippers, and designer toiletries.

This Greenport hotel provides complimentary wireless Internet access, with a speed of 50+ Mbps. Business-friendly amenities include desks and desk chairs, as well as phones; local and long-distance calls are complimentary (restrictions may apply). Additionally, rooms include hair dryers and irons/ironing boards. Housekeeping is provided daily.

- "Great hotel!" - "Don't push it." - "Just a great olace" - "Great stay, get a harbor facing room with a balcony and enjoy a beautiful sunrise! " - "The view! Alpina Restaurant was amazing! " - "Hotel was cozy, great location on the main street of all entertainment. View was amazing. Will definitely stay again!" - "We just got back from a lovely 2 night stay. It was wonderful and we look forward to returning. " - "I loved the cozy neighborhood environment and the weather was bad but still a great place to be"

Located in Greenport, 25 miles from Splish Splash, Silver Sands Motel & Beach Bungalows has accommodations with free bikes, free private parking, a garden and a private beach area. With free WiFi, this 4-star hotel has a restaurant and a bar. Some rooms at the property feature a patio with a sea view. At the hotel, the rooms are equipped with a closet. Complete with a private bathroom equipped with a shower and free toiletries, all rooms at Silver Sands Motel & Beach Bungalows have a flat-screen TV and air conditioning, and certain rooms also offer a terrace. Guest rooms will provide guests with a fridge. Guests at the accommodation will be able to enjoy activities in and around Greenport, like hiking and cycling. Long Island MacArthur Airport is 47 miles from the property.

- "We loved it and will come back!" - "Absolutely splendid stay" - "Very impressive with new breakfast nook." - "Would come back" - "My stay was lovely." - "We had a great time and enjoyed the room, restaurants, bikes and beach." - "Relaxing weekend stay by the beach" - "Wonderful!" - "I nice relaxing getaway. You need to go off season because prices are too high in season!" - "Everything was really beautifully and tastefully furnished and decorated and the location perfect"

Adults-only hotel with a coffee shop and a bar
Along with a bar/lounge, this hotel has a coffee shop/cafe and coffee/tea in a common area. Free WiFi in public areas and free self parking are also provided. Other amenities include a meeting room, free use of bicycles, and concierge services.
Zey Hotel offers 10 accommodations with minibars and complimentary bottled water. Beds feature premium bedding. Cable television is provided. Bathrooms include bathrobes, complimentary toiletries, and hair dryers. Housekeeping is offered daily and irons/ironing boards can be requested.
Recreational amenities at the hotel include complimentary bicycles.

- "Lovely boutique hotel" - "hotel garden was amazing. My idea would be to buy land next door or remove half the parking spots (renting out the supermarket lot for cars if necessary) and make a pool.." - "Great location and friendly staff " - "Such a cool vibe. Hip decor and plenty of space to relax and chill. Nice continental breakfast. Love the wine fridge in the room and provided wine glasses. Great outdoor space. Excellent location. Close to restaurants and shops. Local winery near by was nice too. "

Located in Greenport, 24 miles from Splish Splash, Hotel Moraine provides accommodations with free bikes, free private parking, a seasonal outdoor swimming pool and a fitness center. Among the various facilities are a private beach area, a shared lounge, as well as a bar. Certain rooms at the property include a terrace with a sea view. Free WiFi is available to all guests, while certain rooms include a patio. Guests at the hotel will be able to enjoy activities in and around Greenport, like hiking. Long Island MacArthur Airport is 46 miles away.

- "Awesome" - "We will be back!" - "Home run for us!!" - "Spectacular" - "Such a beautiful hotel and ambiance. The staff was friendly and very attentive. Will definitely come back!" - "A perfect way to spend the week before Labor Day" - "Came here for a getaway with my girlfriend. The hotel was perfect and am planning on coming back." - "Relaxing getaway" - "Serene property, dog friendly and great staff!" - "Disappointed that they do not pay attention to smaller details that make a difference"

Beach aparthotel in Greenport with free parking
Guests at this beach aparthotel will appreciate convenient onsite amenities such as barbecue grills and a picnic area.
Each apartment provides a kitchenette with a refrigerator, a stovetop, a microwave, and a dishwasher. Guests can appreciate conveniences like 2 bathrooms and a sitting area, and other amenities include free WiFi and a furnished balcony. Change of towels is available on request.
Cliffside Resort Condominiums offers 68 accommodations with coffee/tea makers and hair dryers. Rooms open to furnished balconies. Accommodations offer separate sitting areas. Accommodations at this 3-star aparthotel have kitchenettes with refrigerators, stovetops, microwaves, and cookware/dishes/utensils. Bathrooms include bathtubs or showers.

This Greenport aparthotel provides complimentary wireless Internet access. Flat-screen televisions are featured in guestrooms.

- "Wonderful stay and super clean! Can’t wait to come back. " - "quiet" - "Spacious and they allowed an early check in. " - "Excellent location with access to private beach" - "Clean, beautiful place on the shore of the ocean, very comfortable apartment for a family, the bedrooms are located far from each other, each bedroom has its own separate toilet and bathroom, there is a shower and a bath, the apartment is very clean, cozy. The staff is very nice and helpful. There are many good restaurants and cafes in Greenport, tasty and not expensive. I give this rezoot 5 stars"

Providing a garden, The Stirling House Waterfront Inn Greenport features accommodations in Greenport. This 4-star bed and breakfast offers luggage storage space and a concierge service. The bed and breakfast provides sea views, a sun terrace, and free Wifi is available throughout the property. The bed and breakfast will provide guests with air-conditioned units with an oven, a coffee machine, a shower, bathrobes, a flat-screen TV with cable channels, and a DVD player. Every room has a private bathroom with a hair dryer and free toiletries. Additional in-room amenities include wine or champagne, fruit, and chocolates or cookies. There is a snack bar, bar, and lounge. Sightseeing tours are available nearby. A bicycle rental service is available at the bed and breakfast. Splish Splash is 26 miles from The Stirling House Waterfront Inn Greenport. Long Island MacArthur Airport is 48 miles away.

- "The Best B&B" - "Very nice place and host. Would recommend." - "Clay and Frank were very nice and accommodating." - "Wonderful weekend getaway spot!!" - "We have a wonderful stay and would love to go back and spend more time. Highly recommend" - "Overall my visit was very pleasant."

Inn with free breakfast, near Kontokosta Winery
Along with a restaurant, this smoke-free inn has a bar/lounge and a snack bar/deli. Free on-the-go breakfast and free WiFi in public areas are also provided. Additionally, free use of bicycles, express check-in, and express check-out are onsite.
American Beech Hotel offers 11 air-conditioned accommodations with iPod docking stations and minibars. Each accommodation is individually furnished and decorated. Beds feature Frette Italian sheets and premium bedding. Guests can make use of the in-room refrigerators and espresso makers.

Bathrooms include bathrobes, designer toiletries, complimentary toiletries, and hair dryers. Flat-screen televisions come with cable channels. Additionally, rooms include safes and irons/ironing boards. Housekeeping is provided daily.

The recreational activities listed below are available either on site or nearby; fees may apply.

- "Great stay!" - "Great stay and service. " - "A beautiful and very relaxing place to stay. Really appreciated the little touches like a breakfast basket delivered to your doorstep in the morning! Very friendly and helpful staff too. Perfect place for a Long Island getaway! " - "We live locally but wanted to try it out in the off season for a quick staycation. Our stay was a sweet treat! Inviting decor and we enjoyed our breakfast in bed. We made mimosas with the fresh OJ! "

Modern on 9th offers accommodations in Greenport, 25 miles from Splish Splash. The vacation home has access to a restaurant. Opening onto a patio, the vacation home consists of 3 bedrooms. The air-conditioned vacation home also provides a TV, a fully equipped kitchen with a dishwasher, a seating area, washing machine, and 3 bathrooms with a walk-in shower. The property has an outdoor dining area. Long Island MacArthur Airport is 47 miles away.

Balcony/Terrace • Child Friendly • Guest Services • Air Conditioner • Laundry • Restaurant • Pet Friendly • Security/Safety • Fireplace/Heating

Hotel in Greenport with free breakfast and a rooftop terrace
Along with a restaurant, this smoke-free hotel has a bar/lounge and a snack bar/deli. Free self-serve breakfast and free WiFi in public areas are also provided. Other amenities include a rooftop terrace, a coffee shop/cafe, and a refrigerator in a common area.
The Menhaden offers 16 accommodations with complimentary bottled water and bathrobes. Each accommodation is individually furnished and decorated. Memory foam beds feature down comforters and premium bedding. 40-inch Smart televisions come with cable channels and Netflix.

Bathrooms include bathtubs or showers with rainfall showerheads, designer toiletries, complimentary toiletries, and hair dryers. This Greenport hotel provides complimentary wireless Internet access. Hypo-allergenic bedding and irons/ironing boards can be requested. Housekeeping is provided daily.

The recreational activities listed below are available either on site or nearby; fees may apply.

- "excellent experience " - "Excellent stay and service." - "Wonderful stay. Kitchen was awesome, chocolate chip cookies were amazing!" - "Fantastic!" - "Perfect hotel with friendly staff, immaculate condition and very desirable neighborhood close to water views/restaurants." - "Can’t imagine a nicer place to stay in Greenport. Incredibly well run and appointed place. " - "Quick overnight getaway. I only wish we had stayed longer. The staff was fantastic and our room was very comfortable."

Cozy Greenport Cottage offers accommodations in Greenport, 26 miles from Splish Splash. Guests can benefit from a patio and an outdoor fireplace. The vacation home has an outdoor pool and a sauna. The spacious vacation home is composed of 3 bedrooms, 2 living rooms with dining area, a fully equipped kitchen, and 3 bathrooms. Towels and bed linen are provided in the vacation home. The property has an outdoor dining area. The vacation home has a picnic area where you can spend the day outdoors. Long Island MacArthur Airport is 47 miles away.

Child Friendly • Guest Services • Balcony/Terrace • Wellness Facilities • Barbecue/Outdoor Cooking • Fireplace/Heating • Security/Safety • Pool • Sports/Activities • Laundry

Bayside bed & breakfast with a nearby private beach and free breakfast
This smoke-free bed & breakfast features a bar/lounge, a snack bar/deli, and concierge services. Free full breakfast, free WiFi in public areas, and free self parking are also provided. Additionally, express check-in, express check-out, and free newspapers are onsite.
Stirling House Bed & Breakfast offers 3 accommodations with fireplaces and iPod docking stations. Beds feature premium bedding. Flat-screen televisions come with premium cable channels and DVD players.

Bathrooms include bathrobes, designer toiletries, complimentary toiletries, and hair dryers. Guests can surf the web using the complimentary wireless Internet access. Additionally, rooms include minibars and complimentary newspapers. Housekeeping is provided daily.

- "Very comfortable king size bed. Excellent gourmet breakfast, discreet host. Older house, but all the comforts. Absolutely every need provided for. " - "This was a great place to stay with old word charm. If you are looking for a quiet getaway with a beautiful view of the ocean this is it. The breakfast that we had were much better that what you could get in town. My wife and I can't wait to go back." - "We booked this property to celebrate our 17th anniversary for an 1 night night getaway. Upon check in we were greeted with the most delicious homemade cupcakes with our name on it and warmly welcomed by Clay, the property host. We parked right in front, and walked to various bars and restaurants so it was so convenient and vibrant and didn’t have to worry about driving. On the way back we saw the most amazing moonset on the water (the property is basically on the water separated by a street), there’s a dock you can walk out to. Clay cooked us the best farm to table breakfast, it was so delicious, he really takes the time and effort to make everything perfect. We will definitely stay here again!"

Offering a seasonal outdoor swimming pool and a fitness center, The Harbor Front Inn is centrally located near the shops and restaurants in Greenport. Free WiFi access is available. Beach access is 1.2 mi away. A flat-screen cable TV and refrigerator are included in each guest room. The private bathrooms are equipped with a hairdryer and a bathrobe. A balcony is available for certain room types. A front desk is available at the Harbor Front Inn. North Ferry Terminal is just 3 minutes’ walk from the property. Kontokosta Winery is 3 minutes’ drive.

- "Great location. Lovely staff. A nice breakfast bar." - "Awesome!" - "Great girls getaway!" - "Wonderful" - "Great stay and staff Fantasic, especially Lauren and Dan" - "It is a great place to stay and unwind for a few days." - "Very clean hotel with a great location." - "Suited our needs-comfortable" - "Great overnighter" - "This was my second time staying at this hotel. It’s clean comfortable friendly and well situated in town."

Beachfront, with seasonal outdoor pool
This smoke-free bed & breakfast features a bar/lounge, a seasonal outdoor pool, and a meeting room. Free WiFi in public areas and free self parking are also provided. Additionally, a library, a garden, and a picnic area are onsite.
Harbor Knoll Bed & Breakfast offers 3 accommodations with private pools and complimentary newspapers. Rooms open to balconies or patios. Each accommodation is individually furnished and decorated. Select Comfort beds feature Egyptian cotton sheets and premium bedding. Guests can surf the web using the complimentary wireless Internet access. Bathrooms include showers with hydromassage showerheads, bathrobes, slippers, and hair dryers. Additionally, rooms include complimentary bottled water and irons/ironing boards. Housekeeping is provided daily.
Recreational amenities at the bed & breakfast include a seasonal outdoor pool.

The recreational activities listed below are available either on site or nearby; fees may apply.

- "Charming bed and breakfast in a great location right on the water…perfect for a romantic getaway!" - "We stayed here for our mini moon and couldn't have asked for a better weekend! We loved hanging out at the inn and getting to know Leueen and the other guests. The inn is walking distance to the main streets and the train. Will definitely visit again!" - "Beautiful bed and breakfast with gorgeous views. Close to shops and restaurants but far enough to be private and quiet. Will definitely be coming back"

With beautiful views of the sunsets over Long Island Sound, this Greenport resort features spacious grounds and a private beach. Free Wi-Fi is available in all areas. A private balcony provides a relaxing viewing point from each apartment of Cliffside Resort Condominiums – Greenport. A flat-screen TV, wine refrigerator and kitchenette are included. Guests of Cliffside Resort can enjoy the seasonal outdoor pool or relax in chairs nestled on the bluffs. A club house and barbeque grills are also provided. Downtown Greenport is less than 2.5 miles from the resort. The Hortons Point Lighthouse is 7 minutes away.

- "Best trip" - "Amazing experience!" - "Went out east for a party. This was a very comfortable overnight stay that had everything we needed at a reasonable off" - "We like The Cliffside Resort so much, we are already looking to book our next stay." - "Clean, great value!" - "Great base to explore the North Fork!" - "We would, definitely, return. The resort was close to everything." - "Very good for family vacation"

Hotel with free parking, 4-minute walk to Greenport Carousel
This smoke-free hotel features a fitness center, a hot tub, and a seasonal outdoor pool. Free WiFi in public areas and free self parking are also provided. Additionally, a business center, conference space, and free use of bicycles are onsite.
Housekeeping is available on request.
Greenporter Hotel offers 34 air-conditioned accommodations, which are accessible via exterior corridors and feature safes and complimentary bottled water. Each accommodation is individually furnished and decorated. Pillowtop beds feature Egyptian cotton sheets, down comforters, and premium bedding. 42-inch flat-screen televisions come with cable channels.

Bathrooms include shower/tub combinations, designer toiletries, and hair dryers. Guests can surf the web using the complimentary wireless Internet access. Additionally, rooms include irons/ironing boards and blackout drapes/curtains. Hypo-allergenic bedding, change of towels, and change of bedsheets can be requested. Housekeeping is provided on request.

The recreational activities listed below are available either on site or nearby; fees may apply.

- "My stay was amazing very friendly and very clean." - "Staff were very welcoming and friendly. Room was spacious and clean. Bath products were awesome." - "Staff was amazing! So helpful and accommodating! Great location, clean room! Will definitely be staying there again! " - "Would stay again! Perfectly located, very cute hotel with easy free onsite parking. " - "Was a great overnight getaway! We will be back! " - "The Greenporter was a perfect location for our weekend stay. Walking distance to cute shops, restaurants and the harbor, and a short drive from many fun activities like wineries and wandering the waterfronts. Would definitely stay here again. "

Set on the North Fork in Greenport, 98 mi from New York City, Sound View Greenport features a seasonal outdoor pool and views of the Long Island Sound. Guests can enjoy a drink at the bar. Some units include a seating area where you can relax. The rooms have a private bathroom fitted with a shower. For your comfort, you will find free toiletries and a hair dryer. There is a shared lounge at the property. There is a private beach area and bike hire is available. You can play tennis at the property. Montauk is 24 mi from Sound View Greenport, while East Hampton is 14 mi away.

- "Absolutely the best. We will be back" - "Excellent" - "We are definitely coming back" - "A nice place to stay" - "Seaview" - "The perfect getaway! Close to the village shops as well as any of the many wineries to choose from." - "The views of the sound were fabulous/ sunsets especially!" - "Beautiful views, great food, thoughtful space." - "It’s all about the ocean" - "Restful" - "Updated motel with fantastic view and great vibes"

On private beach with seasonal outdoor pool, near Greenport Carousel
At Hotel Moraine, hit the private sand beach where you can enjoy yoga, then dine onsite at the restaurant.
Change of towels is available on request.
Hotel Moraine offers 20 accommodations, which are accessible via exterior corridors and feature minibars and safes. 40-inch LED televisions come with digital channels.

Bathrooms include showers with rainfall showerheads, bathrobes, complimentary toiletries, and hair dryers. Business-friendly amenities include desks and desk chairs. Additionally, rooms include coffee/tea makers and blackout drapes/curtains. Hypo-allergenic bedding and change of towels can be requested. A nightly turndown service is provided and housekeeping is offered daily.

Children under 16 years old are not allowed in the swimming pool without adult supervision.

The recreational activities listed below are available either on site or nearby; fees may apply.

- "Beautiful hotel, great location. Wish someone was at the front desk all night though." - "The views from the hotel were amazing, making it a special place to relax. The price for a single night was a bit high. the amenities like the cottage, firepits, and a fireplace in our room were the highlights after the view. I particularly enjoyed the Lavazza coffee machine in the room. However, one downside was the limited dining options at the hotel itself. We ended up going to the nearest town, Greenport village. Overall, this hotel is great if you're looking for a clean and cozy stay with great views, and don't mind a short trip for more food options."

Harbor Knoll Bed and Breakfast in Greenport provides accommodations with a seasonal outdoor swimming pool, a garden, and a bar. This beachfront property offers access to free Wifi and free private parking. Guests can make use of the sun terrace or the outdoor fireplace, or enjoy views of the sea and garden. Featuring a patio, the units offer air conditioning and have a flat-screen TV and a private bathroom with walk-in shower and bathrobes. Every room includes a coffee machine, while selected rooms are equipped with a fully equipped kitchen with an oven, a microwave, and a toaster. At the bed and breakfast, every unit includes bed linen and towels. A private beach area is available on-site and cycling can be enjoyed close to the bed and breakfast. Splish Splash is 26 miles from Harbor Knoll Bed and Breakfast. Long Island MacArthur Airport is 48 miles away.

- "Will be back to stay longer next time!" - "An ideal location to experience all that the North Fork has to offer" - "Very nicely luween who is the owner very nice room and pool can be improved and not a place for chil" - "Lovely stay in a beautiful home very close to the town centre"

Your family will be close to everything Greenport has to offer when you stay at this centrally-located 2 bedroom apartment. Close to scenic beaches, local vineyards and brewery. Walking distance to Long Island Railroad, Hampton Jitney, Shelter Island Ferry and downtown boutiques. Enjoy fine dinning at our neighborhood restaurants. There are many opportunities for boating, fishing and water sports.

- "We loved our stay in Greenport. The location is perfect to explore the town and the area. Very comfortable apartment and the owners were friendly and helpful. We would definitely stay again. " - "Lovely newly renovated modern apartment right in the heart of Greenport. Walk to everything - restaurants, docks, stores, groceries, …. We parked our car and didn’t use it again for the four days of our stay. Host was responsive but had we no issues. Will definitely return."

17 miles from Long Island Railroad in Greenport, Bright Apartment - half Mi to Greenport Harbor! provides accommodations with access to a spa center. Guests staying at this apartment have access to a patio. Free Wifi is available throughout the property and Splish Splash is 26 miles away. The air-conditioned apartment is composed of 1 separate bedroom, a fully equipped kitchen with a dishwasher and an oven, and 1 bathroom. Towels and bed linen are provided in the apartment. For added privacy, the accommodation features a private entrance. Long Island MacArthur Airport is 48 miles away.

- "It was perfect" - "100% satisfied" - "Beautiful appartment close walk to everything" - "Lovely apartment, clean and updated, close to town, very easy to park and walk." - "Cozy and comfortable apartment" - "Excellent location.Easy to walk to town. Parking was on street and lots of it! HIGHLY recommend this great place! Great" - "Wonderful place to stay!" - "Beautiful, convenient apartment!" - "Loved Greenport & the surrounding area more fun than staying in a hotel"

1896 Restored Victorian located within steps to a lovely Bay Beach. Village restaurants, shops, NYC Hampton Jitney Express Bus and Shelter Island Ferry are all within a short stroll. Fresh produce farms, vineyards, hills and fields surround this very special place to rejuvenate your spirit and have fun. Fishing off the pier, sun bathing, swimming and people watching are all available within a two minute walk. Orient State Park is within a few miles and also offers nature lovers breath taking views of birds and marshes as well as the Long Island Sound. Also in Orient is a Sea Jet Ferry available to those who may want to enjoy the Mohegan Sun Casino in Connecticut across the Long Island Sound or travel north.

Private and spacious accomodations for four adults include two bedrooms each with a separate living space and a fully equipped kitchen and bath decorated in a casual antique pine style. Our charming second floor apartment is peaceful, perfect for two couples or a family.

2021 HVAC upgrade includes UV /HEPA airflow filtration. Exterior security cameras offer added measure of safety during your stay.

Typical Day : Easy to rise in the morning and have a cup of coffee in the garden ..take a stroll down to the beach and people watch.. come back..get ready for the day..

Leave the 'House'.. walk left toward the village and turn right on Clark Street ..now take a three block walk to the village along fourth street and the bay..enjoy the many restored village homes and the simple life..
So... are you ready to explore the village? The antique Carousel on Front Street..antique shops..maybe a cup of stronger coffee at Aldo's...
Stroll up and down Main Street..and Front Street and find your favorite shops/spots...Book, Toy, Cooking, Clothing......Art Galleries..Restaurants...Antiques...something for everyone.

- "We spent a wonderful 5 days in this beautiful home. John and Maritza are the most gracious hosts, offering recommendations and good cheer. The house is 1/2 block from the beach, or 1 block to the lagoon, which we also enjoyed. It is approximately a 15 minute walk or quick drive into town. The home is ideally situated. The kitchen was well-stocked with utensils, cookware and dishware; each bedroom has a sitting room/living room so there is plenty of privacy. Would love to return to this lovely home!"

Charming Greenport Gem 1, 1 Mile to Ferry! offers accommodations in Greenport, 17 miles from Long Island Railroad. Free Wifi is available throughout the property and Splish Splash is 26 miles away. The air-conditioned apartment consists of 2 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 1 bathroom with a shower and a hair dryer. Towels and bed linen are available in the apartment. For added privacy, the accommodation features a private entrance. Long Island MacArthur Airport is 48 miles from the property.

Sports/Activities • Guest Services • Child Friendly • Internet • Accessibility • Other • Fireplace/Heating • Security/Safety • Parking

Combine peace and quiet with bustling downtown action when you book this charming Greenport vacation rental! The 1-bedroom, 1-bath apartment sits on a peaceful side street right off of Main Rd allowing you easy access to unique shops, restaurants, and the Shelter Island ferry. With inviting decor, large windows, a Smart TV, and a fully equipped kitchen, this home is perfect for solo travelers and couples looking to explore all that Greenport has to offer. Plan your vacay your way - book now!

-- THE PROPERTY --

Greenport STR Permit 22-082 | Walkable Location | Free WiFi | 3 Blocks to Front St.

Ride the famous Antique Carousel, take a wine tour, or simply enjoy some R&R - the choice is yours when you book this delightful Greenport getaway!

Bedroom: King Bed

OUTDOOR LIVING: Front porch, lounge & rocking chairs
INDOOR LIVING: Smart TV w/ streaming capabilities, dining table
KITCHEN: Fully equipped, drip coffee maker, toaster, ice maker, microwave, stainless steel appliances, spices, dishware & flatware
GENERAL: Internet connection, A/C, central heat, complimentary toiletries, towels/linens, hair dryer
FAQ: Stairs required for entry, steep staircase, not childproofed
PARKING: Driveway (1 vehicle), safe street parking in front of house
ADDT'L ACCOMMODATIONS: An additional property is available on-site with separate nightly rates. If you would like to reserve both rentals, please inquire for more information prior to booking

-- THE LOCATION --

WINERIES: Long Island North Fork Wine Tours (0.5 miles), Kontokosta Winery (1.4 miles), The Old Field Vineyards (3.9 miles), One Woman Wines & Vineyards (4.5 miles), Sparkling Pointe (6.4 miles)
THINGS TO DO: Stirling Historical Society of Greenport (0.3 miles), Antique Carousel (0.4 miles), North Ferry to Shelter Island (0.8 miles), East End Seaport Museum and Marine Foundation (0.8 miles)
FOOD & BEVS (~0.5 miles): Greenport Harbor Brewing Company, Stirling Sake, SpecialTea House, 1943 Pizza Bar, Crazy Beans, Claudio's and Fortino Tavern, The Frisky Oyster
AIRPORT: LaGuardia Airport (91.7 miles)

-- REST EASY WITH US --

Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.

-- POLICIES --

- No smoking
- No pets allowed
- No events, parties, or large gatherings
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
- NOTE: This property may not be suitable for young children due to the steep staircase and lack of childproofing
- NOTE: The property requires stairs and may be difficult for guests with limited mobility
- NOTE: There is another bookable vacation rental on-site; other travelers may be present during your stay

- "Great place. Have stayed there before. Wonderful location and owner. Highly recommend!!!" - "Very good location, minutes away from all businesses but a quiet street. Clean, airy and roomy apartment. Great communication with the host" - "Great stay in Greenport. The hosts, accommodations are location are wonderful. Look forward to another visit." - "The hosts, accommodations and location were all wonderful. The house was clean, well decorated, comfortable and had all the amenities you would need. We really enjoyed our stay and would definitely recommend this place to anyone considering staying in Greenpoint."

Featuring a spa and wellness center, Quaint DT Greenport Apt - 2 Mi to Shelter Island! features accommodations in Greenport. Guests staying at this apartment have access to a patio. Free Wifi is available throughout the property and Splish Splash is 26 miles away. The air-conditioned apartment is composed of 1 separate bedroom, a fully equipped kitchen with an oven and a toaster, and 1 bathroom. Towels and bed linen are offered in the apartment. For added privacy, the accommodation features a private entrance. Long Island MacArthur Airport is 48 miles from the property.

Fireplace/Heating • View • Parking • Internet • Spa • Accessibility • Other • Security/Safety

The Property
Charming and newly updated second floor apartment, less than a 5 minute walk to downtown. Enjoy our incredible restaurants, shopping and more. Large living room with bay window, ample seating and flat screen TV, nicely equipped kitchen, large dining area for 6, and newly remolded bathroom.
Private entrance and laundry room included. Relax on the front porch, grill in private side yard reserved for our guests, enjoy the outdoor shower after your day at the beach.
This second floor apartment in our historic home has been updated while
maintaining the original wide pine floors and historic details. Windows are plentiful providing a bright and cheerful feel.

Location
The sparkling village of Greenport is a 5 minute walk away.
Restaurants and Shopping are steps away....
Greenport offers dining experiences from casual to upscale. You can enjoy fresh seafood, wood-fired pizza, delicious Latin American, new American, pub-style, sushi, mediterranean and more within walking distance. There are also tasting rooms for beer, wine and tea, as well as coffee shops and restaurants specializing in breakfast and lunch. Stop in at the galleries, boutiques and antique stores as you stroll to and from your dining destination
And be sure to make time for....

Other attractions within walking distance.
Enjoy Greenport's seaport by taking in the picturesque sites along the docks or in the historic neighborhoods. Be sure to visit the Seaport Museum, the Railroad Museum, vintage Greenport Movie Theater, the antique carousel, the fire fighter boat, and our beautiful century old public library.
If you'd like to explore beyond the village, you are also within walking distance to the ferry to Shelter Island (a beautiful10 minute cruise), the Long Island Railroad which allows you to take make a day trip to New York City or the Hampton Jitney also enables jaunts to the city or airports.

Other Local Amenities
Beaches, wineries, fishing, golf, charter boats, and hikes are all an easy walk, bike or car ride away.
Closest winery: 1.3 miles. There are 40 vineyards on the North Fork.
Closest golf course: 1.5 miles.
Closest State Park: Orient State Park (10 miles)
Beautiful maintained hiking trails: The North Fork offers many trails between Orient and Riverhead.
Charters: Both fishing and sailing charters are available within the village.
We are happy to provide information on these and other happenings in the area.

- "I highly recommend Eileen’s place! The location is fantastic, the apartment is very spacious and comfortable, and Eileen is a responsive and helpful host. A perfect stay" - "This spacious second floor rental was a perfect location for walking to downtown and a central starting point for exploring the North Fork. Having been our first visit to the North Fork, we felt lucky that we picked Greenport and the accommodations we chose. I was the liveliest of the area villages (making it a good home base) and we had the best, most attentive hosts we could hope for. The space was fresh and clean; the hosts provided special touches (wine, snacks, a folder that included information on all things to do in the area, kind notices, etc.), offered to supply whatever else we might need and to quickly take care of any incidents that may occur. We would definitely request to re-book the same address on future visits."

North Fork Cottages & RV Resort in Greenport provides accommodations with a seasonal outdoor swimming pool and a garden. With free private parking, the property is 25 miles from Splish Splash and 16 miles from Long Island Railroad. Outdoor seating is also available at the campground. Some units are air conditioned and include a seating and/or dining area and a flat-screen TV. At the campground, the units include a private bathroom. Westerly State Airport is 45 miles from the property.

Parking • Child Friendly • Pool • View • Air Conditioner • Security/Safety • Other

Waterfront Water's Edge luxury suite, Suite C-204 accommodates up to 6 guests (see below) with two bedrooms and two bathrooms located on the North Fork of Long Island at The Cliffside Resort Condominiums in Greenport, New York.

The property is owned and operated by Tocaro Realty LLC. since 2007.

THE SPACE
As the owners of Suite C-204, my wife and I take pride in welcoming you to our personal getaway retreat, which is truly la crème de la crème within the preferred Water's Edge category offering you one of the best all season panoramic waterfront views in the entire complex.

The resort is well maintained and feels like it is brand new. Each of the 68 condominium suites are individually owned, decorated and maintained. Similar units my not be similar at all.

Our Water’s Edge suite is in the waterfront Captain's Roost Building on the second floor. The unobstructed views of the Long Island Sound and Connecticut from the master bedroom and its balcony as well as from the living room and its separate private covered deck are breathtaking. The stairs to the beach are located just yards away from the suite’s rear stairway. At approximately twenty feet above sea level, the bluff is just the right height to offer both fabulous panoramic views and access to the beach below.

The master bedroom has two sliding glass doors, one leading to a balcony and one leading to the private covered deck. Only a limited number of units have a master bedroom with two screened sliding glass doors that let the light and sea breeze pour in and a balcony that faces the water. If you love romantic sunsets, the balcony off of the master bedroom offers one of the best all season waterfront views to the west in the entire resort.

Suite C-204 is in the Captain's Roost Building and offers a panoramic view that feels surprisingly secluded. The feeling of romance and privacy is enhanced by the separation of the Captain's Roost from the reception building, pool area and the other waterfront building.

The master bedroom has a queen sized bed. The second bedroom has two extra length twin beds. The couch has a pull out full sized bed.

Although the unit can theoretically sleep 6 people, think carefully if you are considering six adults for more than a long weekend. The indoor and outdoor dining tables accommodate 4 people each. Make your own decision as to whether the space is adequate for six based on how you intend to use it and the personalities in your party. For some groups that is part of the fun, for others, not so much.

GUEST ACCESS
Full access to condominium property, private beach, pool (through Labor Day), and coin operated washers and dryers in the basement ($1.00 per machine cycle, bring quarters).

THE NEIGHBORHOOD
See the North Fork Promotional Council's or other websites for things to do on the North Fork.

Water, waves, wineries, shopping, auto racing, fishing, boating, swimming, restaurants, antiques, golfing, etc. is all here on Long Island’s North Fork for your enjoyment.

Some people prefer the rural North Fork of Long Island during the spring and fall seasons. Don't miss the strawberry festival in the spring and pick your own pumpkins and apples in the fall before attempting to navigate a corn maze.

GETTING AROUND
Suffolk County Transit - local bus
Hampton Jitney - long distance bus, more frequent service than the LIRR
Long Island Rail Road - train
taxi service
bike rentals
ride share services such as Uber or Lyft are scarce, if available at all

LOCATION
Some websites beyond my control describe the property being "in the city center". The property is approximately 2 miles from downtown Greenport Village. While the terrain is relatively level making for a leisurely bike ride, it is a fairly long walk, so I strongly advise you to look at the map and make your own assessment of the property's location.

OTHER THINGS TO NOTE
The resort condominium has quite times beginning at 9:00 pm to 8 am. Call the resort's managing agent using the after hours emergency option if loud guests are an issue.

- "Property has access to a pool and beach. Short drive to downtown and easy drive to other vineyards. Very enjoyable stay" - "The Cliffside Resort Condo was a perfect home base for our son’s wedding weekend. It was close proximity to the Peconic Bay Yacht Club and could not have been more beautiful. The views of sunset from the bedroom balcony, living room and covered porch were amazing. The family enjoyed the lounge chairs at the private beach as well as the resort pool. The kitchenette was well stocked. This was our perfect home away from home, and we hope to return again!"

Beachfront Greenport Villa offers accommodations in Greenport, 23 miles from Splish Splash and 14 miles from Long Island Railroad. The vacation home features both Wifi and private parking free of charge. The air-conditioned vacation home is composed of 3 separate bedrooms, a living room, a fully equipped kitchen, and 3 bathrooms. A flat-screen TV is featured. The accommodation is non-smoking. Long Island MacArthur Airport is 45 miles away.

Security/Safety • Barbecue/Outdoor Cooking • Air Conditioner • Parking • Child Friendly • Internet

Charming 2-bedroom cottage located on a family-owned waterfront estate that was converted from a circa 1920s chicken coop. This retreat has inspiring views of Shelter Island and is only steps away from the peaceful waters of the Peconic bay. Described by as 'one of the last saltwater farms,' the estate is not only picturesque, but is also an exemplary model of a traditional working farm. Gentle breezes off the bay keep the house naturally cool, so air conditioning is rarely, if ever, needed. Lots of room indoors and out makes the cottage both kid- and pet-friendly. The deck and sprawling lawn make for a great place to entertain friends and family, or the perfect spot to lie back, relax, and relish the view. Stroll along the estate's expansive private beach or have a picnic overlooking the water. The beautiful tree-filled grounds complete the pristine view of the bay and Shelter Island, making the estate an artist’s paradise for all seasons. The cottage is quiet and secluded, yet within easy walking distance to Greenport Village, offering the best of both worlds.

With a strong nautical history, Greenport is a water-lover’s paradise and the perfect destination for sailing, boating, fishing, swimming, kayaking, and canoeing. Mitchell Park Marina is just a short walk from the estate and provides transient slips by the day or week. Please call in advance for reservations to secure your spot.

While downtown in the village of Greenport, explore the local boutiques and stores. Take advantage of the history-rich Railroad, Stirling–Ireland House, and East End Seaport museums. Ride the antique carousel, or take a tour of the harbor on The Glory, an electric launch. Sample the local bounty from land and sea in a variety of restaurants offering casual fare to award-winning dining. Tour the over 42 vineyards located here on the North Fork. Discover the art galleries featuring local and international artists who represent the contemporary to the classic. So much tucked into one square mile and all conveniently within walking distance!

Greenport's proximity to Manhattan, Connecticut, and the South Shore means you don’t have to go far to get away. Enjoy a casual drive from the city, or let the LIRR or Hampton Jitney carry you here stress free. Either way there is something for everyone, so come and experience what makes Greenport charming and unique. For more information about Greenport and all it has to offer,

The estate also offers additional accommodations that when combined can be perfect for family gatherings. Please visit listing #173361--“The Gate House” or 234929 the main house

Keywords: Cottage

- "this property is stunning and special, with a saltwater creek and marsh meeting the bay, at a private natural beach. the cottage is comfortable, functional and more utilitarian, but this is appropriate to such a natural setting. it also has a beautiful main bedroom exploiting its amazing spot adjacent to the marsh, with ocean views in distance. the host is an excellent guy, attentive, with just the right balance of involvement.... letting us have maximum privacy on our own. my family just loved it here, especially with our puppy along, who had her first swim experience. we all enjoyed seeing such variety of water fowl, deer, wild turkey, rabbits..... just a perfect, quiet and peaceful beach spot."

FALL 2025 AVAILABILITY!

Looking to escape the city for a couple of weeks or even a month? The house is well set up for working remotely and we are pet friendly!

We value inclusion and respect and happily welcome guests of all backgrounds.

A cozy getaway in the heart of the Village of Greenport. 2 Bedrooms and 3 baths, sleeps 6 adults. On a quiet street with very little through traffic.

Living Room with flatscreen TV and cozy seating (includes full sofa bed). Spacious dining room perfect for enjoying leisurely meals. Well stocked kitchen with large island for cooking or hanging out.

Bedroom 1 (also has a small room attached): Queen bed
Bedroom 2: Queen bed
(There is also a full sofa bed sleeping 2 in the living room.)

Bathroom 1: Tub & Shower
Bathroom 2: Shower
Bathroom 3: Tub

Wi-Fi available. Apple TV. DVD player.

Large backyard with a swingset for the kids. BBQ grill for your use. The home has a lovely side porch perfect for morning coffee or evening cocktails.

Two week minimum stay.

- "Great house for a small family. We had a great time. There was an issue with the hot water heater one morning, but Jen was easy to get ahold of and the problem was fixed in no time!" - "Great location in great destination. Perfect host. Very well equipped kitchen. Only negative is a lack of a guest bath on second floor." - "Just got home from a two night stay at this property. I almost don’t want to give it 5 stars, because I want it to be my secret. The house is absolutely adorable, but unlike a real estate listing, that doesn’t mean small. Located on a quiet residential street just two short walkable blocks from town, the house is equipped with everything you could possibly need for a stay of any length. The house is beautifully decorated, clean, comfortable, with a deep, private yard, and a porch swing you will not want to get out of. After one night, you will wish it were YOUR house. Couldn’t recommend it any more enthusiastically. I will be back."

Designed and built in 2003, this cozy house has water views of Peconic Bay, enormous glass skylights, fully equipped kitchen, two bedroom, two bath, washer, dryer, Wifi, flat screen tv, private rose garden, outdoor studio/bedroom, private parking, a kayak, bicycles, public swimming dock at end of block, and is one block from the charming seaside village of Greenport, NY. We are located 95 miles east of New York City on Long Island's North Fork with 5 minute walking access to NY city bus and train. Great small restaurants & a terrific micro brewery are 1/2 block away.

- "House was compact, modern house filled with art & light. Lots of windows & sliding doors with screens leading to front & back patios. Small private backyard with table, chairs & umbrella. Open concept living, dining, kitchen, bedrm & bathrm on ground floor. High ceilings in living & dining areas. House clean & well stocked. Property on lovely street about 11/2 blocks to town & shops. Great vac rental." - "I put a lot of stock in guest reviews, and they were on point for this listing! The house is even better than it appears in the photos. It is incredibly bright and cheerful, and it is so charming to stay in a place with such a sense of personality and history. You can tell that it is a much beloved home. It is full of wonderful art; my personal favorite was the huge, medieval city (?) sketch (watercolor?) in the darling studio. The location truly can’t be beat: on a gorgeous, tree-lined, friendly, PEACEFUL street, with a beautiful view at the bay dock - and yet just steps away from multiple good restaurants, and just around the corner from the main drag, with many more restaurants and shops. The host was very easy to communicate with, as was access to the house. One thing I really loved that isn’t mentioned or obvious from the pictures is that the backyard has really good visual privacy. I always feel weird when I’m sitting on a patio and can be seen by neighbors. Not here! FYI to future guests: the second bedroom (with the full-size bed and the futon) - along with the second bathroom with shower stall - is up the stairs in a beautiful, airy, bright loft with no door or walls fully separating it from downstairs. As such, most of the space has decent visual privacy, but not sound privacy, with the downstairs open common area (kitchen, dining, living, foyer, hallway to downstairs primary bedroom). Didn’t bother us but mentioning for those who may need to know."

Newly renovated and charming home in the NorthFork, a short walk to the village of Greenport, vineyards, and the breathtaking 67 Steps beach, among other local attractions. Spend an afternoon or evening entertaining your friends at the home's outdoor oasis complete with a year-round hot tub.

The home features two bedrooms with queen beds. There is also an air mattress / rollaway twin bed if needed.

This is a perfect stay for a small family, two couples or a small group of friends.

Backyard party deck complete with year-round hot tub, enclosed outdoor shower (seasonal), built-in grill, outdoor bar, giant table plus lounge area.

The interior features a beautiful dining/sun room plus state-of-the-art kitchen with stainless steel appliances, washer & dryer, A/C, music sound-system, TV and more.

This home has all the North Fork has to offer for a summer, autumnal or winter getaway.

Inquire within for monthly rental rates.

- "We loved our stay here. Such a nice house and it was so close to Greenport’d downtown, beaches, and the Shelter Island Ferry. The back yard was such a great place for the kids too!" - "We loved our stay in Greenport for a long weekend! The back yard is undersold in the photos. It’s a gorgeous oasis and great place to relax, the hot tub was amazing. Adam was very responsive and made sure we got in okay and didn’t have any issues. We are already planning our next trip back!"

LI Sound Waterfront Cottage with 2 Bedrooms and 1 Bathroom. Completely Renovated and Modern Living Space with Open Layout. Home comes complete with Quality Appliances, including Wine Fridge. Approx 1 Acre of Manicured lawn, Private Heated Pool, Vineyard and Beach. Plenty of room in front and back for play or relaxation. 18x40 Gunite Pool, 104' of Private Beach and expansive views of the lovely LI Sound with Picture Perfect Sunsets. Plenty of parking and garage. Home Vineyard. Perfectly located between both Southold and Greenport Villages and close to dozens of vineyards. This is a one of a kind home. Please feel free to ask as many questions as needed to make sure your stay is what you desire. Thanks, Ted

- "Amazingly beautiful property. The photos don’t do it justice and the sunsets cannot be beat." - "Beautiful views of the LI Sound. Nice new pool. Special to have grapevines on the property. Short drives to both Southold and Greenport. Excellent getaway for family of four. Owner was super-responsive and friendly. Everything was easy." - "Let’s briefly go over the property and the host. The house has stunning unobstructed north-facing views of the Long Island Sound, facing Connecticut. It’s a modest 2BR but plenty of space and big icthen and living area facing the water. Ted us super responsive as a host, but also generous. It’s their home and it feels like that, and Ted treats you like a guest. Would highly recommend."

Travel to the North Fork of Long Island for a much-needed getaway and experience both modern luxury and historic desire at this 2-bedroom, 1-bathroom vacation rental! Situated in the heart of Greenport, this apartment provides an updated interior, historic feel, a fully equipped kitchen, and a walkable location near town attractions. Take the ferry to Shelter Island and enjoy a day on Shell Beach. Explore Orient Beach State Park and grab a glass of wine at a vineyard on the way back.

-- THE PROPERTY --

2nd-Floor Apartment in Historic Home | Walk to Downtown Boutiques & Restaurants | Near Beaches

Bedroom 1: Queen Bed | Bedroom 2: Full Bed | Living Room: Queen Sleeper Sofa | Additional Sleeping: Pack ‘n Play

APARTMENT FEATURES: 3 flat-screen TVs w/ cable, dining table, laptop-friendly workspace, garden
KITCHEN: Stainless steel appliances, dishwasher, cooking basics & spices, Keurig coffee maker, blender, toaster, tea kettle knife set, dishware & flatware
GENERAL: Free WiFi, central A/C, linens & towels, central heating, complimentary toiletries, trash bags & paper towels, hair dryer, hangers, self check-in
FAQ: Ring Doorbell device (facing front door entry), quiet hours (11:00 PM-8:00 AM), no porch access, addt'l rental on-site (separate unit & entrance)
ACCESSIBILITY: Stairs required for access, entire 2nd-floor unit
PARKING: Street parking (first-come, first-served), no driveway parking
ADDT’L ACCOMMODATIONS: An additional 1-bedroom property for 4 guests is available on-site with a separate nightly rate. If you would like to reserve both rentals, please inquire for more information prior to booking

-- THE LOCATION --

THINGS TO SEE + DO: Antique Carousel (0.4 miles), East End Seaport Museum & Marine Foundation (0.7 miles), The Fire Fighter (0.7 miles), Ferry to Shelter Island (0.7 miles), Railroad Museum of Long Island (0.7 miles), Horton Point Lighthouse Nautical Museum (5.5 miles)
OUTDOOR RECREATION: 67 Steps Beach (1.1 miles), Norman E. Klipp Marine Park (1.8 miles), Crescent Beach (2.7 miles, accessible by ferry), Truman’s Beach (4.0 miles), Mashomack Preserve (6.4 miles, accessible by ferry), Shell Beach (6.4 miles, accessible by ferry), Orient Beach State Park (10.4 miles)
WINERIES + BREWERIES: Greenport Harbor Brewing Company (0.3 miles), One Woman Winery Greenport (0.4 miles), Kontokosta Winery (1.2 miles), The Old Field Vineyards (4.0 miles)
AIRPORTS: Long Island Islip MacArthur Airport (44.0 miles), Laguardia Airport (90.9 miles), John F. Kennedy International Airport (91.9 miles)

-- REST EASY WITH US --

Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.

-- POLICIES --

- No smoking
- No pets allowed
- No events, parties or large gatherings
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
- NOTE: This apartment is an entire 2nd-floor unit of the building and requires stairs to access
- NOTE: There is an additional rental unit on-site with a completely separate entrance
- NOTE: Your safety matters. This property features a Ring Doorbell device with an exterior security camera facing the front outdoor entry. The camera does not look into any interior spaces. The camera actively records video when motion is detected by the device (including devices linked to the camera such as the alarm system’s motion detector) or when the video doorbell button is pressed
- NOTE: Please observe quiet hours between 11:00 PM to 8:00 AM
- NOTE: The porch is not available for guest use

- "This home was gorgeous inside and out. Every time we walked through the garden, we were so happy. The unit was extremely clean and nicely appointed. It was a beautiful and quick walk into town; within a block, you’re hitting restaurants and stores. The kitchen had everything we needed and there were extras of everything (paper goods, towels, blankets, etc!). Nice to have smart TVs in each room too. Toni and Frank were kind, responsive, and generous hosts."

Enjoy this beautifully renovated first floor “Captains House” apartment in the heart of Greenport Village. Harbor Views! Walk to town.

This 2 bedroom, 2 full bathroom home is bright with sunshine, has soaring ceilings and hard wood floors, easy to maintain for beachside living.

Gourmet kitchen - top of line appliances

- "This historic house is completely renovated inside. We easy and comfortably fit 2 adults and 4 children. The beds and bedding were fresh and cosy. z the house was clean. A quick walk to all Greenport has to offer." - "Pristine beautiful property. Loved the bedding and decor. Walked into GreenPort. It was lovely." - "Clean, large, modern, great shower pressure. The owner was quick to respond throughout. Thank you!!" - "Cute little apartment. Great location and very helpful and accommodating host. Thank you for having us."

Luxury 2 bedroom, first floor apartment located across the street from Townsend Manor Marina in the heart of Greenport Village . Walk to town and enjoy the amazing restaurants and shopping that Greenport has offer. This custom Victorian Farmhouse has been fully renovated with all modern amenities.

The custom gourmet kitchen has a sub zero refrigerator, Wolf stove, farmhouse sink. Gas grill located outside where you can enjoy evening dinner under the stars.

You will find 2 Flat screen SMART TVs. There is Wifi throughout the house.

The large wrap around deck is the perfect spot to have your coffee or glass of wine with marina views and great people watching.

The first floor apartment is bright with sunshine and hard wood floors. Easy to maintain for beachside living.

The airy master bedroom has a Samsung smart flat screen TV. Enjoy a great nights sleep on the temperdic King Size bed.

The guest bedroom has a queen size bed as well as a gorgeous wood barn door.

There is a full bathroom, laundry in the apartment and an outdoor shower in the private backyard.

The driveway can fit 3 cars and the home has plenty of public parking in front and behind.

This apartment has it all. Under 1 mile from the fifth street public beach. 1/2 mile to the Commuter station - train, bus, ferry is located walking distance to restaurants, shopping and bars. Close to wineries

- "The house was beautiful, spacious and very comfortable! The beds also were super comfortable, which is so important for a few nights away from the kids when sleeping in is one of the luxuries! :) The house was well stocked, clean and in a convenient location! Very close to town and also not far from a lot of the wineries. It made for a very memorable 40th birthday getaway with friends. I would definitely return!" - "I stayed in the house with my family for a long weekend. The house was a quick walk to town and short drive to the beach. The house looked as pictured. The host answered all our questions with quick and helpful replies! The house is newly renovated but still has the charm and noises of an old house."

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney.
Aqua Vista is the second floor apartment with a separate entrance.
My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).
This property has two apartments. The Aqua Vista Apt.2 and The Sandpiper Apt. 1 (see listing on VRBO website that can accommodate 12 people when available at the same time for larger families and wedding parties

- "Great spot for all things North-Fork" - "I was looking for a quiet, enjoyable place near the water and got just what I was looking for. My visit was during the off season early in the week so there wasn’t much to do in town but that was exactly what I was looking for. Really enjoyed it and look forward to returning in the future." - "What a great little spot in a great little town. The location couldn’t be easier and convenient. The train is literally across the street and Main Street a 5 min walk to the water and shops! The Apt is clean, well appointed, and so comfortable. This was a real find!!"

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney.

My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).
The space
The house has been completely renovated and everything is brand-new.
Everything is walking distance to the house and the location is unbeatable.

This property has two apartments. The Blue Bay Dream Apt.1 and Harbor Heights Apt. 2 (see listing on VRBO website that can accommodate 12 people when available at the same time for larger families and wedding parties

We have recently added new amenities to the VRBO rental Apartment 1 that you would occupying. In the backyard, the blue garage has been converted to a cabana, which includes two televisions, lounge area with a wet bar, refrigerator, game area for the kids and a home office work station with a full size convertible bed in the cabana section and a queen size futon in the home office work room. Wifi is available in the cabana and office. As a bonus, there is a 5 person jacuzzi outside with complete privacy. (PLEASE NOTE - that outdoor BBQ and jacuzzi are only available from April to November)

- "As described, Nice little rental very close to GPV. Clean, Well maintained place. Had the good fortune of meeting the owners, very good people. Would stay here again." - "Thanks Christopher! Great location! Only a few minutes walk from Greenport’s Main Street and the Fifth Street beach The house was nicely furnished and clean Felt like a hone away from home" - "Great communication from the owner. Comfortable apartment. Walking distance to town. Apartment is well-appointed with comfortable beds, plenty of towels, soap/shampoo, pretty much all you need for a stay. Street parking was easy."

This 2-bedroom house in Greenport with modern amenities for stylish uncluttered living. Perfect for a small family or couples and conveniently located in a quiet neighborhood near town, park and beach.

- "The house was spotlessly clean and well-maintained, making me feel comfortable right from the start. The location was perfect—local attractions and great restaurants, which made exploring the town very convenient. Walter was incredibly responsive and accommodating, always quick to reply to any questions or requests. Overall, I highly recommend this home for a friendly and hassle-free stay!" - "Our family were completely overjoyed by our week in this beautifully decorated and updated farmhouse. Sitting on the porch, grilling in the backyard, strolling to the beach and walking into Greenport were all this gem offers and much more. Couldn’t be happier with the communicative host. Highly recommended. "

Lovely Victorian home with private entrance, porch, and brick patio. Floor to ceiling windows in light filled large bedroom with en suite bathroom. Cozy den has a beautiful bay window and a queen size pull out sofa bed for additional guests. Sunny sitting room just off of the kitchen for reading or games. Full kitchen, washer dryer, high speed internet, brand new flat screen TV can be found in the unit. The West Elm king size bed, mattress and sofa bed are all new.
No car needed as the train station, fantastic restaurants, bars, shops and Shelter Island ferry are less than half a mile walk from the house.
Enjoy all that Greenport and the North Fork have to offer from this amazing location!

- "Great spot! Great location! Lots of room - especially loved the little porch with swing! Highly recommend!" - "huge flat, very bright and clean. plenty of kitchen and bathroom supplies. easy check in and check out, plenty of parking space on the street in front of the house. very pretty, quiet and safe neighborhoods (i’m travelling solo). lovely town of Greenport within walking distance as well as 2 beaches and a big park. i loved it! thank you Kevin and Laura"

A beautiful waterfront condo just a short walk from historic Greenport village, this newly remodeled unit provides stunning waterfront views, two modern bathrooms, a renovated kitchen, a dedicated boat slip, and community tennis/pickleball courts, an award-winning swimming pool on the Peconic Bay, and is located close to all the wineries, farm stands and beaches the North Fork has to offer. With four comfortable bunk beds in one bedroom and a new queen-sized bed in the master, your whole family will love staying here. Note: Inquire about renting our additional unit located right next door and enjoy extra accommodations for friends and family.

We are not allowing pets; however, if you have a small pet (under 10 lbs.) there will be an additional fee of $35 p/night.

Also, if A/C is used, there will be a fee of $100 for the entire stay.

Additional guests (more than two adults) will be charged an additional fee of $100 p/guest p/night.

- "We had a wonderful time. Carole, the owner, was a delight. She was extremely responsive and helpful. She and her husband even lent us a fishing pole for our 7 year old …his first time fishing! It’s a short walk to town, beaches are close and so ilare many wineries…and the condo is beautifully renovated. We enjoyed watching the boats sail by each day on the deck. We hope to stay there again and highly recommend it to anyone looking for a great place to stay!"

The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern and tasteful American Beech Boutique Hotel, Restaurant & Bar. During your stay, you can explore the vibrant village, natural scenery, and return to a memorable and comfortable room at the end of your day. The boutique hotel features eleven suites, including two, double-bedroom apartments.
All of our rooms come with a fully stocked mini-bar and mini-fridge, Smart TV, glass shower door, iron, ironing board, hairdryer and Maison Margiela amenities. Each room has robes, Frette beach towels, and a safe, make your stay as comfortable as possible. We also provide a Nespresso machine with complimentary coffee to enjoy. Our bicycles and WiFi are also included in this great complimentary package! If there is anything else you need, please let us know!

Please note: In order to access this room, you are required to climb one flight of stairs — But don’t worry! We only have a maximum of 2 floors at this hotel. Free public parking are on the streets surrounding our hotel. We highly recommend parking on Bay Avenue, which is perpendicular to Main Street and has direct access to Sterling Square.

Guests can shop, eat, drink, and spend the night—all within arms’ reach! Stirling Square can be quite lively at night; please consider this before booking.

- "We were in Greenport for a wedding and the location couldn’t have been any better. Right in the middle of all the action. Restaurants, nightlife, Main Street, free bike rentals, wine every night from 4-5. Would absolutely stay here again when back in Greenport." - "Perfect Great place" - "Clean, comfortable, and convenient" - "My husband and I brought our rescue dog Beau with us. One of the few places found that allow dogs. We all had a great time. Bar and restaurant on the property. Nicely appointed room. The most comfortable king bed we ever slept in away from home. Loved it and we will return soon."

We welcome you to our cottage away from it all but still close to all activities that make the North Fork a magical place to visit. Within 5 - 15 minutes you can walk to all that the Greenport town has to offer and to 2 beaches. No need to have a car as you can walk from the train or bus from the city. Our fenced in back yard is perfect for dogs and little humans to roam freely and has a basketball hoop, dining table, metal firepit and lounge space.. The cottage is simple, clean and cozy, a real home full of character and charm, with a fully stocked kitchen, screened in front porch, and large flat screen TV with Xbox. Sheets and towels are high end and mattress is new for maximal comfort. Our home is perfect for those seeking peaceful relaxation yet close to terrific restaurants, farms and wineries. Beach chairs and basic beach bikes also available on request so you really can pack minimally. Beach pass obtainable for long term renters.

Please note - local law requires 14 night stay for home rentals. While we offer significant discounts to enable you to stay longer, we will adhere to this law by blocking dates after shorter term stays. Rental permit ID 965.

- "We enjoyed our stay at this peaceful cottage with all the necessities. Lovely morning walks into town and the fenced in backyard was a plus for our dog! The owners were so kind and easy to reach. Definitely recommend!" - "Lover our stay perfect location to town and beaches! Enclosed backyard was nice" - "We stayed for a week with our pets for a memorial service and to visit family & our FD friends. The yard is fenced a big plus! Plenty of room for us and although we don’t have kiddos there’s a bunk room for them as well. Front porch with tons of windows and a nice comfy couch and plenty of our door seating in the yard. Host was very accommodating and prompt wit answers. "

The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern and tasteful American Beech Boutique Hotel, Restaurant & Bar. During your stay, you can explore the vibrant village, natural scenery, and return to a memorable and comfortable room at the end of your day. The boutique hotel features eleven suites, including two, double-bedroom apartments.
All of our rooms come with a fully stocked mini-bar and mini-fridge, Smart TV, glass shower door, iron, ironing board, hairdryer and Maison Margiela amenities. Each room has robes, Frette beach towels, to make your stay as comfortable as possible. We also provide a Nespresso machine with complimentary coffee to enjoy. Our bicycles and WiFi are also included in this great complimentary package! If there is anything else you need, please let us know!

Please note: In order to access this room, you are required to climb one flight of stairs — But don’t worry! We only have a maximum of 2 floors at this hotel. Free public parking are on the streets surrounding our hotel. We highly recommend parking on Bay Avenue, which is perpendicular to Main Street and has direct access to Sterling Square.

Guests can shop, eat, drink, and spend the night—all within arms’ reach! Stirling Square can be quite lively at night; please consider this before booking.

- "Wonderful weekend getaway. American Beech offers a perfect blend of privacy and indulgence. Great communication, cool vibe, and a variety of fun food and drink options." - "Excellent one night stay."

The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern and tasteful American Beech Boutique Hotel, Restaurant & Bar. During your stay, you can explore the vibrant village, natural scenery, and return to a memorable and comfortable room at the end of your day. The boutique hotel features eleven suites, including two, double-bedroom apartments.

Our guests pay a resort fee of $35 per night, including additional taxes at check in.
Looking for a king sized room fit for an actual king? Look no further! American Beech’s Grand Master Deluxe King Suite, Room 14, has all the fittings to make your stay as comfortable as it will be unforgettable. Located on the third floor, the highest of the rooms at our hotel, you will enjoy a quiet stay with a king sized bed, bathroom fit with a shower and separate bathtub, a makeup table, Frette robes, mini bar, and plenty of shelving for storage. This room also doubles as the perfect bridal suite due to these accommodations. All of our rooms come with a fully stocked mini-bar and mini-fridge, Smart TV, glass shower door, iron, ironing board, hairdryer and Maison Margiela amenities. Each room has robes, Frette beach towels, and heated floors to make your stay as comfortable as possible. We also provide a Nespresso machine in the room. If there is anything else you need, please let us know! Please note: In order to access this room, you are required to climb one flight of stairs — But don’t worry! We only have a maximum of 3 floors at this hotel. Free public parking is on the streets surrounding our hotel. We highly recommend parking on Bay Avenue, which is perpendicular to Main Street and has direct access to Sterling Square. Guests can shop, eat, drink, and spend the night—all within arms’ reach! Stirling Square can be quite lively at night; please consider this before booking.

- "Right in the heart of Greenport Villiage "

The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern and tasteful American Beech Boutique Hotel, Restaurant & Bar. During your stay, you can explore the vibrant village, natural scenery, and return to a memorable and comfortable room at the end of your day. The boutique hotel features eleven suites, including two, double-bedroom apartments.

Our guests pay a resort fee of $35 per night, including additional taxes at check in.
Our Luxurious two bedroom apartment styled room, comes with two separate rooms one king size bed in each one, one bathroom and a shared living room. All of our rooms come with a fully stocked mini-bar and mini-fridge, Smart TV, glass shower door, iron, ironing board, hairdryer and Maison Margiela amenities. Each room has robes, Frette beach towels, and heated floors to make your stay as comfortable as possible. We also provide a Nespresso machine with complimentary coffee. If there is anything else you need, please let us know!

Please note:

In order to access this room, you are required to climb one flight of stairs — But don’t worry! We only have a maximum of 2 floors at this hotel. Free public parking are on the streets surrounding our hotel. We highly recommend parking on Bay Avenue, which is perpendicular to Main Street and has direct access to Sterling Square.

Guests can shop, eat, drink, and spend the night—all within arms’ reach! Stirling Square can be quite lively at night; please consider this before booking.

- "This is an amazing hotel with high end finishes and a staff to match. The staff are polite, attentive, helpful in all ways and thoughtful in all their communication. I highly recommend to anyone looking for a boutique experience!"

North Fork living doesn’t get better than this. Enter to stunning waterfront views from every corner of this unique, light-filled, freestanding corner unit, just a short walk from historic Greenport’s shops, restaurants, and waterfront.

Experience spectacular sunrises from the upstairs bedrooms, watch an endless parade of boats on the upstairs or downstairs deck overlooking Peconic Bay. Prepare fresh, farmers market cuisine in the fully remodeled kitchen. And bask in the amenities of our private community, including an award-winning, waterfront pool, two tennis courts, and a designated boat slip.

The home includes a pull-out queen-sized couch, a king-sized guest bed, and a queen-sized bed in the master bedroom, where a vaulted ceiling and a wall of glass deliver an airy, relaxed vibe.

One of just two corner units in all of Stirling Cove, this home offers some of the best views you'll find in the area. It’s your perfect home base for days exploring Shelter Island, Orient, and all the wineries and farm stands the North Fork has to offer.

We are not allowing pets; however, if you have a small pet (under 10 lbs.) there will be an additional fee of $35 p/night.

Also, if A/C is used, there will be a fee of $100 for the entire stay.

Additional guests (more than two adults) will be charged an additional fee of $100 p/guest p/night.

- "I had a wonderful stay at Carole’s property. The home has everything you need and the views of the water, boats and beach are absolutely amazing. Carole was very pleasant, responsive and answered all questions almost immediately. The pool and grounds are impeccably kept. There is also a fireplace which would be lovely in the winter. You can walk right to downtown Greenport for shopping, food and sightseeing. It was an amazing stay and I will be back."