Best Vacation Rentals in Southold

Located in Southold, 23 miles from Splish Splash, The Shoals Suites & Slips provides accommodations with a garden, free private parking, a terrace and a bar. This 4-star hotel has air-conditioned rooms with a private bathroom. Free WiFi and a concierge service are featured. All guest rooms will provide guests with a fridge. The hotel also provides a business center and guests can use the on-site ATM machine at The Shoals Suites & Slips. Long Island Railroad is 14 miles from the accommodation. Long Island MacArthur Airport is 45 miles away.

Fireplace/Heating • Bar • Air Conditioner • Other • Internet • View • Security/Safety • Guest Services • Sports/Activities • Business Services • Balcony/Terrace • Parking

Bayside hotel with a coffee shop and a bar
This smoke-free hotel features a bar/lounge, a coffee shop/cafe, and a business center. Additionally, free use of bicycles, concierge services, and a computer station are onsite.
Housekeeping is available on request.
The Shoals Suites and Slips offers 20 air-conditioned accommodations with espresso makers and bathrobes. Rooms open to furnished balconies or patios. These individually decorated and furnished accommodations have separate sitting areas. Beds feature down comforters and premium bedding. A pillow menu is available. 43-inch flat-screen televisions come with Netflix.

Bathrooms include showers with rainfall showerheads, and hair dryers. This Southold hotel provides complimentary wireless Internet access, with a speed of 50+ Mbps. 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.

- "Great stay!" - "Nice, comfy, and stylish " - "The room was beautiful and what a view! We will definitely be back!" - "It was a cute and lovely place and I really impressed by the smiles and attitudes of the staff " - "The count staff was very friendly and clean and all the facilities were comfortable and nice." - "Check in was quick and the young lady at the front desk was super friendly. I had sent a message prior to my visit with a small request and the reason why. When we got to our room, not only did they honor my request, but there was a very sweet surprise waiting for us! So thoughtful and definitely above and beyond. The room itself was so beautifully decorated and well thought out. It had a naturally comfortable feel while being a step above the norm. There is an area at check-in that has provisions like snacks and adult beverages while also offering clothing, jewelry and gifts. I absolutely loved the sitting area off the lobby. Such a well designed and beautifully decorated space. It's the type of area you would just love to spend time in. The views of the port, and the water were just fantastic. If this hotel was this impressive off season, I would absolutely choose this property for a vacation during the summer. The Shoals is little hidden gem, trust me. "

Classic Southold Country Charmer offers accommodations in Southold, 21 miles from Splish Splash. The vacation home has access to a restaurant. The vacation home also offers facilities for disabled guests. Offering a patio, this vacation home also features a satellite flat-screen TV, a well-equipped kitchen with a dishwasher, an oven, and a microwave, as well as 1 bathroom with a walk-in shower and a hair dryer. The property has an outdoor dining area. Long Island MacArthur Airport is 43 miles from the property.

Wheelchair Accessible • Security/Safety • Balcony/Terrace • Barbecue/Outdoor Cooking • Laundry • Restaurant • View • Sports/Activities • Accessibility • Fireplace/Heating • Child Friendly

Beach bed & breakfast with a nearby private beach and free breakfast
Start your day with a complimentary full breakfast, then head to Shorecrest Bed and Breakfast's private beach where you can enjoy kayaking.
Shorecrest Bed and Breakfast offers 5 air-conditioned accommodations with complimentary toiletries. Each accommodation is individually furnished. Beds feature premium bedding. Flat-screen televisions come with satellite channels. This Southold bed & breakfast provides complimentary wireless Internet access. Housekeeping is provided daily.
The recreational activities listed below are available either on site or nearby; fees may apply.

- "Excellent amenities, great service, and wonderful location! " - "BEautiful place, with friendly and accomodating inn keeper, with extremely clean and comfortable accomodations." - "When you think of a beautiful bed & breakfast...this is it ,inside & out. A lot attention to detail. Breakfast was presented beautifully and was delicious. Across the street was a private small beach, perfect for peaceful time." - "We had a beautiful experience. The owner was just amazing, breakfast was delicious."

Bright Oasis in Beautiful North Fork Wine Country offers accommodations in Southold, 21 miles from Splish Splash. There's an outdoor fireplace and guests can use free Wifi and free private parking. Providing access to a patio with garden views, the spacious air-conditioned vacation home consists of 4 bedrooms. Offering a terrace with river views, this vacation home also features a flat-screen TV, a well-equipped kitchen with a dishwasher, an oven, and a microwave, as well as 2 bathrooms with a walk-in shower and a hair dryer. The property has an outdoor dining area. Guests at the vacation home will be able to enjoy activities in and around Southold, like canoeing. A baby safety gate is also available at Bright Oasis in Beautiful North Fork Wine Country, while guests can also relax in the garden. Long Island MacArthur Airport is 43 miles from the property.

Other • Parking • Pet Friendly • Air Conditioner • Internet • Oceanfront • Sports/Activities • Child Friendly • Balcony/Terrace • View • Fireplace/Heating • Security/Safety

A coastal cottage on the water surrounded by vineyards and farm stands on the North Fork. Unwind in the backyard with a private view of the Goldsmith's Inlet where you can watch the sunrise, bird watch, and admire our local swans. A quick 5-minute walk to the Long Island Sound where you can sunbathe, swim, kayak, and watch the beautiful sunset. Conveniently located near Greenport, Orient, and Southold. A 20 minute drive from the Orient Point Ferry Terminal.

*IMPORTANT*

Seasonal items like the grill are only available from May 1st to October 31st.

- "Our stay at Mae’s house was everything we could have ever wanted. Her home and property are gorgeous! Mae was very responsive and so pleasant to deal with. Everything was perfect and as described! What you see is what you get and so much more! We had a wonderful time and will definitely be back and are already counting the days!" - "Spent a week in this lovely cottage that was the perfect size for the three of us. The cottage is quaint and private and is surrounded by the inlet and land preserve so while neighbors are nearby, they are not on top of you. Backyard was relaxing and took advantage of the hammock nestled in between trees. Kayaks were a plus and many launches on the inlet gets you up close to the many birds living around the inlet (not often you are within a few feet of Osprey hunting!). Beach was a short walk away and took advantage on hot days. The house is the prefect location as it is close to many hikes, towns, shops, and vineyards to explore. Never more than a 20 minute drive to exploring the whole region. Mae was such a responsive and lovely host and appreciated her help when needed. Only wish was that the primary bed was a Queen or King size to accommodate two larger people comfortably. Regardless, I hope to be able to come back and rent again! Thanks for a great stay!"

Minnehaha Marvel offers accommodations in Southold, 21 miles from Splish Splash. The vacation home has access to a restaurant. Outdoor seating is also available at the vacation home. The air-conditioned vacation home consists of 1 bedroom, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 2 bathrooms with a walk-in shower and a hair dryer. Towels and bed linen are offered in the vacation home. There's also a seating area and a fireplace. Long Island MacArthur Airport is 43 miles from the property.

Fireplace/Heating • Pet Friendly • Ocean View • Guest Services • Balcony/Terrace • Restaurant • Sports/Activities • Security/Safety • Barbecue/Outdoor Cooking • Private Beach • Laundry • Air Conditioner

Welcome to the NOFO—where you'll be greeted by beautiful beaches, dozens of wineries and some of the best cuisine New York has to offer!

And welcome to our home: a fully-renovated, brand new everything stylish retreat located in Southold—just minutes from Goose Creek Beach, North Fork Roasting Company, Southold Fish Market and Corey Creek Winery.

Every inch of the house and its furnishings are brand new. It features tons of natural light via vaulted ceilings and multiple skylights throughout the living, family and kitchen areas. With an open concept, this property offers the perfect space for families looking to entertain, dine, grill and enjoy the peacefulness of this cul-de-sac property.

The house has been curated with love and we hope you enjoy it as much as we do!

Amenities include, but are not limited to:
- 4 bedrooms (1 king, 2 queens, 2 twins)
- 2 full bathrooms
- propane gas grill
- firepit
- Adirondack chairs
- outdoor shower
- outdoor dining room
- outdoor lounge area
- smart TVs (70' and 55') with Netflix, Hulu, Amazon, etc.
- Google Home
- washer & dryer
- Wifi included
- concierge garbage pick-up
- queen blow-up mattress

- Dogs allowed for an additional fee ($150/dog)
- No smoking permitted
- located in quiet cul-de-sac
- Town beach parking permits available for stays of 30 days or longer

Ocean View • Tv • Child Friendly • Laundry • Kitchen • Security/Safety • View • Air Conditioner • Wellness Facilities • Other • Spa • Barbecue/Outdoor Cooking

Private Waterfront Home: Dock, Kayaks offers accommodations in Southold, 22 miles from Splish Splash. Both free Wifi and parking on-site are accessible at the vacation home free of charge. Private Waterfront Home: Dock, Kayaks features 3 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a hair dryer. Towels and bed linen are available in the vacation home. The accommodation has a fireplace. Long Island MacArthur Airport is 43 miles from the property.

Air Conditioner • Security/Safety • Child Friendly • Fireplace/Heating • Parking • View • Internet • Pet Friendly

Calendar NOT always up to date check for availability

Beach Parking good at all Southold Town Beaches Pass INCLUDED free with rental

Come listen to the bands while tasting the local wines (See local vineyards and events). Walk to Southold Village or Beautiful Bay Beaches or just relax on your own patio while overlooking green lawns and mature trees.

On the sought after 'Bayside' of the North Fork In the heart of the North Fork Wine Country and beautiful beaches we have a 1840's home with a furnished attached cottage available for weekend's, week or month rental. Apartment has small eat in kitchen, bath, living room and 2 bedrooms. One bedroom has a queen size bed the other a full size bed. Separate entrance with own lawn / patio area with lawn chairs. Comfortably furnished with Sat TV (Including HBO). Both bedrooms have center AC units. Beautiful property with century old lilacs and gorgeous perennial gardens.

- "The cottage was very comfortable and cozy. Mark and Mona are great hosts." - "The property was just perfect for us and my dog. The location is very central." - "This property was perfect for our family of 5. Our daughters (6 & 4) shared the full bed, and our baby slept in the queen room with us, in a Pack & Play. The outdoor area was very nice! The only thing we missed having was a dryer…it was humid/muggy, so after a day at the beach, our towels and bathing suits wouldn’t air dry just by being outside. Other than that, the unit had mostly everything we needed!"

Relax on the large wrap-around front porch of this Long Island, New York bed and breakfast. Free Wi-Fi and daily breakfast are offered. Cedar Beach is 1 mile away. Each uniquely styled room at A Walk in the Woods Bed and Breakfast features private bathroom. Decorated with antique accents, these rooms include a seating area. This estate is located directly on the 14 mile Bayview bicycle loop. Pindar Vineyards is 5 miles away.

- "Can’t wait to go back!" - "We will definitely be going back!" - "Excellent place to stay"

Charming cozy cottage located in the heart of the Northfork, East End of Long Island. Come explore the beautiful vineyards, farms & beaches, all within minutes from the home. Cottage is steps from the Town of Southold which offers excellent restaurants, cafes & adorable boutiques. Property sits on an acre & a half overlooking a sliver of the Peconic Bay. Located off a dirt road for the ultimate in privacy. Backyard is completely fenced in for the safety of your pup. All pups welcome! This home is impeccably maintained with high end furnishings, fully stocked chefs kitchen & luxurious linens. Bedrooms have blackout shutters for sleeping in late. Backyard has a Weber grill, hammock & outdoor furniture. And the evening star gazing is incredible. The enclosed front porch overlooks a sliver of the Bay, offering super comfy furniture for those lazy days, sipping coffee, reading your book. Cottage has a funky, cozy vibe, super relaxing. Start making your memories at this gem of a property! Welcome :)

- "We loved the property. The host was very responsive, the home was lovely, quiet, well appointed, well stocked with start up items including some goodies. I only wish I could see some water from the house although water was a short walk away. We will return." - "My family has been coming to the north fork for years. This is the first property I’ve stayed at that had a fully fenced in yard for my dog. Not only is the house perfect and fully stocked with everything (and more) that you could possibly need and want, but the yard is HUGE and beautiful. My dog was in heaven. The home is also just a short walk to downtown Southold. I highly recommend Erin’s home and I hope to return in the future. She was such a gracious host and even left us snacks and beverages. We could not have asked for a better stay."

Happiness Comes in Waves is situated in Southold, 1.6 km from Cedar Beach County Park and 37 km from Splish Splash, in an area where cycling can be enjoyed. It has a garden, a terrace, sea views and free WiFi throughout the property. The air-conditioned holiday home consists of 4 bedrooms, a living room, a fully equipped kitchen with a fridge and a coffee machine, and 3 bathrooms with a shower and free toiletries. Towels and bed linen are available in the holiday home. The nearest airport is Long Island MacArthur Airport, 72 km from the holiday home.

Child Friendly • Internet • Kitchen • Balcony/Terrace • Pet Friendly • Air Conditioner • Parking

Peaceful pondfront cottage with two bedrooms , 1 1/2 baths, pull out couch in Living room can sleep two more , and lovely screened in front porch to enjoy the beautiful pond view-watch ospreys fly over, or enjoy the pond by using kayaks, paddle boats or canoe that comes with the rental. 10 minute walk to beautiful sound beach around the corner-minutes to wineries, Southold village, and Greenport.

- "Lovely cottage with access to a beautiful large pond and use of kayak, paddleboard, acanoe. Host very responsive." - "We booked this beautiful cottage last minute for a quick weekend getaway and it was everything we hoped it would be. Eileen was also a pleasure to work with!" - "It was clean, comfortable, and had everything we needed. The gas fireplace was welcoming on a cool November evening. Location was great, 20 minutes to many of the wineries, restaurants and the beach. Canoe and kayaks were great on the small pond. It was delightful."

NF Wine Country Retreat with Dock offers accommodations in Southold, 12 miles from Long Island Railroad. The air-conditioned accommodation is 21 miles from Splish Splash, and guests can benefit from on-site private parking and complimentary Wifi. Guests can use a garden. The vacation home is composed of 1 bedroom, a fully equipped kitchen, and 2 bathrooms. A flat-screen TV is provided. The accommodation is non-smoking. Long Island MacArthur Airport is 43 miles away.

Security/Safety • View • Ocean View • Child Friendly • Parking • Oceanfront • Guest Services • Barbecue/Outdoor Cooking • Internet • Pet Friendly • Air Conditioner

Calendar NOT always up to date check for availability

Beach Parking good at all Southold Town Beaches Pass INCLUDED free with rental

Come listen to the bands while tasting the local wines (See local vineyards and events) ,

Walk to Southold Village or Beautiful Bay Beaches or just relax on your own patio while overlooking green lawns and mature trees.

On the sought after 'Bayside' of town In the heart of the North Fork Wine Country and beautiful beaches. We have a 1840's home with a furnished attached cottage available for weekend's, week or month rental.

Cottage has small eat in kitchen, bath, living room and 2 bedrooms. One bedroom has a queen size bed and the other a full size bed. Separate entrance with own patio area and comfortable patio furniture.

Comfortably furnished with Sat TV (Including HBO). Both bedrooms have center AC units.

Beautiful property with century old lilacs and gorgeous perennial gardens.

Ocean Beaches: The infamous 'Hampton' ocean beaches are within a 45 minute Drive.

Bay and Sound Beaches are within a few minutes from the cottage.

Vineyards: The North Fork of Long Island is famous for it's award-winning wines. Adventure out and taste them at the numerous vineyards on the North Fork.

- "The cottages at the White Blossom House are absolutely lovely. Everything about the cottage, the grounds and location were perfect. Very charming in every respect and really nice decor. Will definitely return and recommend to friends. The hosts were so wonderful and helpful. Bikes, beach passes and beach chairs were readily available super easy to access and use. Made everything that much easier and enjoyable. We had a couple of friends who live in the area we were visiting and they stopped by and we’re equally impressed with how lovely the cottages are. Perfect visit - can’t say enough good things about this lovely place."

Watersedge Retreat is located in Southold, just 1.7 miles from Cedar Beach County Park and 23 miles from Splish Splash. This vacation home is 13 miles from Long Island Railroad. The vacation home features 3 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with free toiletries. 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 44 miles away.

Private Beach • Barbecue/Outdoor Cooking • Balcony/Terrace • Security/Safety • View • Child Friendly • Sports/Activities • Laundry • Ocean View • Guest Services • Oceanfront

Two bedroom PERFECT beach house located on a private beach. If you love the beach, fishing, swimming and sunsets in a quiet place, this is for YOU.
This is NOT a bluff beach. Walk right out the FRONT sliding door and you are ON the beach. Walk out the SIDE sliding door you are on the wrap around deck, with patio set barbecue grill, lounge chairs, and views in every direction. You can walk in either direction ON the beach for miles. Crystal sand, rocks, beach glass and glistening water around you. Public beaches require town parking permits which can quickly increase the cost of your stay at other non-beach front properties, but you don't need a permit since this is a private beach (no crowds, no restrictions).
57035

One Bedroom has a full size bed, the other bedroom has twin bunk beds. Wrap around deck, with furniture on BOTH sides of house for morning and afternoon sun + beach chairs included. This house does have heat for cooler nights in Spring & Fall. Perfect for a long relaxing Summer, weekend get away, or family retreat. Really great fall fishing weekends, winery trips, pumpkin picking. Give us a call, you're going to LOVE IT !

All rates listed are for a family of 4 (2 adult, 2 children). There are additional charges for extra guests and these need to be confirmed and agreed upon at time of reservation. Please note that we are vigilant about the number of people renting the house. Sorry, not pets allowed due to guests with allergies.

Keywords: House

- "We enjoyed every second of the peace & quiet. Access to the beach couldn't be better. The cottage offers comfortable accommodations both inside and outdoors and the host is just wonderful" - "Third year vacationing at this beautiful cottage overlooking the Long Island Sound! We keep coming back! Sunsets are spectacular!" - "This was our fourth stay at this lovely little house on the Long Island Sound. It is quiet and peaceful and the proximity to the beach is ideal. The sunsets are breathtaking. Gaelle communicates well and in a timely manner. Looking forward to returning in 2023."

Offering free bike hire and free WiFi access, Historic White Blosson House is a uniquely furnished inn located in Southold. The property features scenic gardens. Patio access is included with the self-catering apartment. The kitchenette is equipped with an oven and a dishwasher. The bathroom has free toiletries. An array of activities can be enjoyed on site or in the surroundings, including golfing and cycling. Southold Historic White Blossom House offers free parking. Cedar Beach Point is 7 minutes’ drive from the property. Lenz Winery is 2.3 mi away.

- "Good stay overall but with some issues"

Great location close to all the North Fork has to offer. The entire upstairs of an Historic Home built in the 1830's with quaint lower ceilings typical of 1800's with claw ft tub and full kitchen, 2 bedrooms and outside patio area with gas grill and private lawn area. Bike and Beach chair rentals available at no cost.

* Kindly note property calendar not always up to date due to multiple booking sites...please check for availability.

Vehicle Beach Parking Pass Available free with rental

- "My husband and I stayed in Apt 2 for 5 nights. The house is close to Southold beaches and all North Fork wineries and restaurants. It has a private entrance leading you upstairs to a clean 2 bedroom, 1 bath apartment. It's well maintained but very old, so be aware that it has low ceilings and even lower doorframes. My husband is 5'11" and had to duck through doorways. One of the best parts of renting this home was the host provided a parking pass and beach pass so that we could easily enjoy all Southold beaches, which were wonderful! We also enjoyed the observatory down the road; whether permitting, on Saturday nights, they open the roof for incredible views of the night sky through one of their several telescopes."