Charming Bed and Breakfasts in Old Saybrook, CT

The Homestead offers accommodations in Madison, 18 miles from Yale University and 20 miles from The Yale Bowl. 13 miles from Thimble Islands and 18 miles from City Hall, the property features free bikes and a garden. There's a sun terrace and guests can make use of free Wifi, free private parking, and an electric vehicle charging station. At the bed and breakfast, units include a wardrobe, a flat-screen TV, a private bathroom, bed linen, and towels. All units are equipped with air conditioning, and some units at the bed and breakfast have a patio. The rooms are equipped with heating facilities. A selection of options including warm dishes, local specialities, and fresh pastries are available for the buffet breakfast. There is a snack bar and lounge. Guests can also warm up near the outdoor fireplace after a day of cycling. Wesleyan University is 22 miles from the bed and breakfast, while Goodspeed Opera House is 25 miles from the property. Tweed-New Haven Airport is 16 miles away.

- "Exceptional, one of the nicest and most creatively thought out places we have every visited." - "The most tranquil, serene, experience! Can't wait to bring my family back!" - "An Unexpected Treat!" - "This is truly a pet-friendly haven, your home away from home!" - "Heaven on earth!" - "Cozy and welcoming Inn near the Seashore" - "Everything you could possibly need" - "We didn’t want to leave!" - "Amazing! Highly recommend."

Bed & breakfast with free breakfast, near Connecticut River
Along with express check-out, this smoke-free bed & breakfast has a garden and free breakfast. Free WiFi in public areas and free self parking are also provided.
James Pharmacy Bed & Breakfast offers 3 air-conditioned accommodations with fireplaces and complimentary bottled water. Each accommodation is individually furnished and decorated. 32-inch flat-screen televisions come with cable channels.

Bathrooms include showers with rainfall showerheads, designer toiletries, and hair dryers. Guests can surf the web using the complimentary wireless Internet access.

- "Near nice shops and restaurants " - "This inn provides the traveler with everything they would need and want. Cleanliness, great bedding, great mattress, security, and charming decor." - "Cute bnb on top of Cocotte. Nicely decorated and comfortable. I only saw 1 trash can - wished there were another since I stayed 3 nights and almost filled up the trash can in the bathroom on the last night. It was a little easy to hear the church bell across the street. Also, I stayed over the July 4th weekend, and some local youths were chatting loudly from late night to past midnight in front of the BnB, which was annoying."

Scranton Seahorse Inn in Madison provides accommodations with a garden and a terrace. Both free Wifi and parking on-site are accessible at the bed and breakfast free of charge. The accommodation offers airport transfers, while a car rental service is also available. Some accommodations include a patio and a cable flat-screen TV with DVD player, CD player as well as air conditioning and heating. At the bed and breakfast, units come with a private bathroom. As an added convenience, Scranton Seahorse Inn offers packed lunches for guests to bring on excursions and other trips off-property. The area is popular for cycling and hiking, and bike rental is available at this 4-star bed and breakfast. The bed and breakfast has a picnic area where you can spend the day outdoors. Hammonasset Beach is 1.6 miles from the accommodation, while Thimble Islands is 15 miles from the property. Tweed-New Haven Airport is 18 miles away.

- "A great stay in Madison!" - "We will definately return" - "Our night at the Inn was exceptional, with excellent accommodations and a fabulous breakfast in the morning." - "Very nice B&B in a great location with an excellent host." - "Seahorse is Comfortable and peaceful sanctuary"

Georgian bed & breakfast in Westbrook with free breakfast
This smoke-free bed & breakfast features a refrigerator in a common area, free use of bicycles, and a garden. Free continental breakfast, free WiFi in public areas, and free self parking are also provided. Other amenities include a picnic area and a TV in a common area.
Housekeeping is available on request.
The Captain Stannard offers 11 air-conditioned accommodations with iPod docking stations and MP3 docking stations. Each accommodation is individually furnished and decorated. Beds feature premium bedding. Guests can surf the web using the complimentary wireless Internet access. Bathrooms include showers, bathrobes, complimentary toiletries, and hair dryers. Housekeeping is provided on request.
Recreational amenities at the bed & breakfast include complimentary bicycles.

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

- "Everything was perfect!" - "Quaint, within walking distance to the beach! Lots of great restaurants nearby. We went to a great antique mall and winery close by and the neighboring small towns also have plenty to do (and we went in the off season the weekend before Thanksgiving!). Carolyn was attentive and friendly at the B&B. It was safe, quiet, cozy and charming. The breakfast had a nice selection and was fresh. " - "Amazing place! Immaculate cleaned ! Excellent areas around. Caroline was very acomódate and friendly We enjoyed breakfast and all services provided. Definitely will come back"

Westbrook Inn Bed and Breakfast features air-conditioned accommodations in Westbrook. Housed in a building dating back to 19th century, this bed and breakfast is 16 miles from Goodspeed Opera House and 23 miles from Thimble Islands. On clear days, guests can head outside to enjoy the bed and breakfast's outdoor fireplace, or simply kick back and relax. The bed and breakfast offers a TV and a private bathroom with bathrobes, slippers, and shower. Free Wifi is accessible to all guests, while certain rooms are equipped with a terrace. The rooms are equipped with heating facilities. À la carte and American breakfast options with warm dishes, pancakes, and fruit are available. The area is popular for hiking, and free use of bicycles is available at Westbrook Inn Bed and Breakfast. After a day of cycling, fishing, or canoeing, guests can relax in the garden or the shared lounge area. Wesleyan University is 26 miles from the accommodation, while City Hall is 27 miles from the property. Tweed-New Haven Airport is 25 miles away.

- "A great stopover for us, with the extra benefit of beach gear and a wonderful host" - "Charming and tranquil. Friendly staff and would definitely return."

Bed & breakfast in Madison with a full-service spa and free breakfast
This smoke-free bed & breakfast features a full-service spa, a meeting room, and concierge services. Free full breakfast, free WiFi in public areas, and free self parking are also provided. Additionally, dry cleaning, laundry facilities, and a library are onsite.
The Scranton Seahorse Inn offers 7 air-conditioned accommodations with DVD players and bathrobes. Beds feature premium bedding. Flat-screen televisions come with cable channels. This Madison 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.

- "Beautiful! " - "Perfection 💕 I had such a great time. Michael was a great host. Traveling solo I felt very safe. If you are looking for a quiet and safe place to lay your head down, definitely do not pass this place up. Breakfast was luxurious. I will most definitely book this place again. I had a great time. " - " Wry clean and quiet. Very comfortable." - "Nice quaint quiet property. " - "Great place great owners" - "Amazing experience!"

Higganum House B&B features a garden and accommodations with a kitchenette in Higganum, 7.3 miles from Goodspeed Opera House. There's a private entrance at the bed and breakfast for the convenience of those who stay. The bed and breakfast offers rooms with air conditioning, free private parking, and free Wifi. There's a private bathroom with bath in some units, along with slippers, a hair dryer, and free toiletries. At the bed and breakfast, the units are fitted with bed linen and towels. Guests can make the most of the warm weather with the property's barbecue facilities. Guests at the bed and breakfast will be able to enjoy activities in and around Higganum, like hiking. Guests can also warm up near the outdoor fireplace after a day of cycling. Wesleyan University is 7.7 miles from Higganum House B&B, while Central Connecitcut State University is 22 miles away. Tweed-New Haven Airport is 32 miles from the property.

Security/Safety • Fireplace/Heating • Barbecue/Outdoor Cooking • Guest Services • Sports/Activities • Parking • Internet • Air Conditioner • View • Balcony/Terrace • Entertainment • Tv

Riverfront bed & breakfast in Westbrook with free breakfast
This smoke-free bed & breakfast features a snack bar/deli, coffee/tea in a common area, and a refrigerator in a common area. Free full breakfast, free WiFi in public areas, and free self parking are also provided. Other amenities include conference space, free use of bicycles, and an arcade/game room.
Housekeeping is available on request.
Westbrook Inn B&B offers 9 air-conditioned accommodations with bathrobes and slippers. Each accommodation is individually furnished and decorated. Beds feature premium bedding. 32-inch flat-screen televisions come with cable channels.

Bathrooms include shower/tub combinations, designer toiletries, complimentary toiletries, and hair dryers. Guests can surf the web using the complimentary wireless Internet access. Hypo-allergenic bedding, change of towels, and change of bedsheets can be requested. Housekeeping is provided daily.

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

- "Very sweet hosts who served us great breakfast!! Felt so comfortable " - "It was wonderful " - "Spotless. Contactless self check in. Meri is friendly, informative and loves what she is doing, making her guests feel welcome and at home. Breakfast was fantastic. We would love to go back!" - "Mary was a great host. Walked in and immediately felt like we were old friends. She upgraded us to a king bed at no extra cost. We had the best night sleep of our two week trip. Deb’s breakfast was fantastic and she was very welcoming too. We highly recommend this B&B 👍"

The Captain Stannard is a recently renovated bed and breakfast in Westbrook where guests can make the most of its free bikes and garden. The air-conditioned accommodations are 16 miles from Goodspeed Opera House. The bed and breakfast also offers free Wifi, free private parking, and facilities for disabled guests. At the bed and breakfast, all units are equipped with a wardrobe. There's a private bathroom with shower in every unit, along with bathrobes, a hair dryer, and free toiletries. At the bed and breakfast, units come with bed linen and towels. A buffet, continental, or American breakfast is available at the property. There is a snack bar and lounge. Guests at the bed and breakfast can enjoy hiking nearby, or make the most of the sun terrace. Thimble Islands is 23 miles from The Captain Stannard, while Wesleyan University is 26 miles from the property. Tweed-New Haven Airport is 25 miles away.

- "Gracious. The hosts attentive and warm and welcoming." - "We'd come back!"

Beach bed & breakfast with a nearby private beach and free breakfast
Along with a snack bar/deli, this smoke-free bed & breakfast has free use of bicycles and express check-out. Free continental breakfast, free WiFi in public areas, and free self parking are also provided. Additionally, wedding services, a garden, and a lobby fireplace are onsite.
Housekeeping is available on request.
The Homestead offers 10 air-conditioned accommodations with complimentary bottled water and hair dryers. Each accommodation is individually furnished and decorated. Memory foam beds feature Egyptian cotton sheets, down comforters, and premium bedding. 36-inch Smart televisions come with premium cable channels and Netflix.

Bathrooms include showers. This Madison bed & breakfast provides complimentary wireless Internet access. Hypo-allergenic bedding, irons/ironing boards, and change of towels can be requested. Housekeeping is provided on request.

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

- "Fabulous, uniquely decorated B&B with accommodating hosts. Luxurious beds and bedsheets, corner to corner squeaky clean. Will definitely return." - "This is a very charming B&B. Staff and owners were great. Very friendly and accommodating. Rooms were clean and well appointed; very clean; nice firm beds and selection of pillows. Will definitely stay again." - "Great people and accommodations " - "Great area , Great people,"

- "We had a wonderful stay at Riverwind. From the moment we arrived, we were welcomed with friendly service. The room was pristine as was the bathroom! I can actually say that the floors shined. The bed was also the most comfortable I have ever slept in. The breakfast was above and beyond what I expected. We will certainly be back again." - "The property is beautiful! Very charming with great attention to detail. " - "First floor wood stove is marvelous, and second floor gas fireplace is equally enticing."

Bed & breakfast with free breakfast, 4-minute walk to Higganum Reservoir State Park
Along with a garden, this bed & breakfast has barbecue grills and a picnic area. Free continental breakfast, free WiFi in public areas, and free self parking are also provided.
Housekeeping is available on request.
Higganum House B&B offers 4 air-conditioned accommodations with complimentary bottled water and slippers. Each accommodation is individually furnished and decorated. Guests can surf the web using the complimentary wireless Internet access (speed: 100+ Mbps (good for 1–2 people or up to 6 devices)). Additionally, rooms include complimentary toiletries and fans. Housekeeping is offered on request and irons/ironing boards can be requested.

Business Services • Fireplace/Heating • Air Conditioner • Smoking • Guest Services • Balcony/Terrace • Barbecue/Outdoor Cooking • Laundry • Breakfast • Internet • Bedding/Linens • Entertainment

The Mansion is a 3,200 square foot structure. You are renting 1 bedroom with a full en-suite bathroom on the first floor, a large living room with a private main entrance and porch. Enjoy a vacation stay in this rustic country mansion built 1841, listed on the State Register of Historic Places. For a group larger than 2 guests there are more bedrooms available for an additional charge on the second floor.
Experience the New England countryside in this charming estate situated on 4 acres of lawns, gardens, wooded areas, picnic area with open fire pit and open fields. We are located in the Connecticut River Valley in the village of Higganum.

Early English settlements in the Higganum area are documented since 1660. At that time the sachem or sovereign of the territory around Higganum was Towwehashque of the Wongunk tribe. In 1697 she was succeeded by her daughter Pampenum.

The surrounding areas are used for many recreational activities like biking, boating, swimming, fishing, and hiking.
Stay overnight on your way along the New England Coastline; we are only a 20 minute drive away from the shoreline on route 9, exit 9. We are about 100 miles northeast from Midtown Manhattan.
Commuter trains travel from Grand Central Terminal to New Haven and Shoreline East trains connect to Old Saybrook.

Explore this eccentric old mansion and the many hidden treasures along the Connecticut river.
Higganum Reservoir - The lake is within a 5-10 minute walk from the Higganum House B&B.
The original dam was constructed in 1868 by the 2 brothers George M. and Thomas J. Clark of the Higganum Manufacturing Company called the Clark Company. Their firm, later known as Clark Cutaway Harrow, was one of Higganum's most successful industries. They produced an extensive line of farm equipment including 400 types of plows, disk harrows, cider presses, hay spreaders and carriage jacks. The factory, located at the site of a now empty lumberyard, was powered by water from the reservoir and Candlewood Hill and Bible Rock Brooks. The factory burned in the early 20th century but the dam and reservoir remained until its 2003 reconstruction as Higganum Reservoir State Park. The new dam is 30 feet high and has a walkway which allows you to gaze at the water rushing over an old stone spillway down into a beautiful clear brook.
Watershed Area: 6.6 Square Miles, Lake Area: 32 Acres
Higganum Reservoir State Park covers 147 acres. Meandering trails through the woods surrounding the lake are ideal for hikes and mountain biking. It is a walk-in park with car-top boating, fishing and swimming.
Higganum Village - Once a commercial hub for shipbuilding, primarily for whaling in the 1600's and
1700's then a place of manufacturing during the 1800's; Higganum is now a qaint
little community nestled at the river banks and home of the Higganum House B&B.
East Haddam Village - home of the Goodspeed Opera House, final destination of the River Steam Boat
Chester Village - a beautifully restored little village with art and design galleries and restaurants all
along main street
Deep River - situated on the Connecticut River banks; many restaurants, small shops, and a
piano-key factory
Essex Village - home of the Griswold Inn, one of the oldest operated inns in the country open for
business since 1776; many boutiques, reaturants, art galleries and the
Connecticut River Museum; situated right where the Connecticut River meets the
Long Island Sound; board the historic Essex Steam Train
Old Saybrook - visit the marina or one of the public beaches right at the Long Island Sound; once
the home town of Kate Hepburn the town named their new cultural center after
the late actress; visit the many shops and restaurants
Westbrook - a quaint shoreline community with several public beaches right at Long Island
Sound between New Haven and New London
Middletown - home of the Wesleyan University; enjoy their cultural program open to the public
( ) or, visit the local movie theater

A 45 min. drive away you find two large casinos offering gambling, dining, spas and entertainment:
Mohegan Sun Casino and Foxwoods Resort Casino

- "Owner was easy to contact and communicate with. Very friendly and was there to greet us and show us the house upon our arrival. Lots of old family pictures on the walls that were great fun to look at. Spacious rooms with comfortable beds." - "Great place for a getaway! Charming, clean as a white, excellent host. He had fresh baked cookies waiting for us when we got back from the baby shower we came up to attend. Comfy beds, quilts, and cozy atmosphere. Great place to stay for a getaway!"

The Gardener's Cottage, less then a mile from the Long Island Sound, is a great alternative to the common hotel. Situated a stones throw from Hammonasset State Park and Beach, Clinton Outlets, and the Shore Line East train station. Near by you will find places to kayak, Chamard Wineries, Marinas and many quaint New England towns. The Cottage is fitted with it's own router coupled with an eating nook that can double as a work space. Pets are allowed. Self check-in

Other things to note
self check-in lock box

Washer • Shower gel • Conditioner • Shampoo • Hair dryer • Hot water • Bathtub • Dryer • Hangers • Essentials

Peaceful & centrally located studio cottage on Connecticut shoreline. Close to beaches, restaurants, winery, outlet shopping, and I-95. Approximately 20 minutes outside of New Haven. Ideal for exploring the shoreline & river valley. Bright, clean, efficient, well- equipped cozy studio cottage with queen bed, sitting area, kitchen & full bathroom . Outdoor space with fire pit & grill. Onsite parking. Ideal for two people whether traveling through the area or for a little rest & relaxation

The space
We reside in a single family home with our family. Cottage is located in the back of our house in a fenced in backyard.

Guest access
Single free standing studio cottage with small private outdoor sitting area with outdoor seating and fire pit. Access through gate in our driveway .

Other things to note
Studio Cottage is located on our property in our backyard . We are easy going and friendly and spend A LOT of time outside . We have two dogs. You need to walk through our yard to access the cottage. We will certainly respect your privacy.

Bed linens • Conditioner • Hot water • Shower gel • Cleaning products • Hair dryer • Essentials • Shampoo • Hangers • Body soap

1 bedroom with adjoining bathroom in 12 room rustic country mansion, State registered historical site, Connecticut River Valley - situated on 4 acres of lawns gardens and open fields .

The space
The Italianate /Greek revival style house was built in 1841. It has a stucco faced exterior the interior hallways and rustic bedrooms are finished with local native white oak floorboards fitted in 1909. One enters the mansion through the main entrance door and hallway, both for guests only. At the end of the hallway on the first floor you will find your quaint bedroom with 3 windows - all with garden views. This bedroom has 2 single beds that can be comfortably connected with a special doubling system to a king size bed. Across the hallway is a large double parlor living room for guest use only. Sometimes we do rent out the upstairs 3 bedrooms to groups of 4 people and more who will also have access to the double parlor living room on the first floor.
We serve a light breakfast in the morning.
We have 1 indoor cat. He stays in our quarters.
The House has been in the family since 1908 and we continue the tradition of hospitality and jovial country living. Enjoy the New England countryside in this charming estate situated on 4 acres of lawns gardens and open fields. We are located in the Connecticut River Valley in the village of Higganum. Early English settlements in the Higganum area are documented since 1660. At that time the sachem or sovereign of the territory around Higganum was Towwehashque of the Wongunk tribe. In 1697 she was succeeded by her daughter Pampenum.
The surrounding areas are used for many recreational activities like biking, boating, fishing, swimming and hiking.
We are located in the center of Higganum, where you find 2 restaurants, a pizza place, pharmacy, hardware, and a grocery store.
We are a 20 minutes drive from the Connecticut shoreline and a 2 hour drive to either New York or Boston.

Guest access
The downstairs double parlor living room which has a TV, a Baby Grand piano and stereo music system is for guest use only; continental breakfast is served in this living room.
All our guests enjoy the surrounding 4 acres of gardens and meadow. Please find a map of the entire property with buildings and paths under pictures.

During your stay
My wife and I are living in the other part of the house and are available for any questions.

Other things to note
Enjoy a vacation stay and discover the charm of New England:
Higganum Village - Once a commercial hub for shipbuilding, primarily for whaling in the 1600's and 1700's then a place of manufacturing during the 1800's; Higganum is now a qaint little community nestled at the river banks and home of the Spirit of 76 House
Starting in Higganum Center, follow the scenic route #154 south towards Old Saybrook and the shoreline. The modern street is build upon the historic route dating back to the 1600’s; it follows the Connecticut River all the way to the Long Island Sound. Along this road you will pass through the picturesque historic villages of Haddam, Chester and Deep River, Essex and Old Saybrook.
East Haddam Village - home of the the Goodspeed Opera House and final destination of the River Steam Boat - (URL HIDDEN)
Chester Village - a beautifully restored little village with art and design galleries and restaurants all along main street; at the Chester street crossing on route 154 you can also turn away from Chester and towards the river. You will get to the Chester-Hadlyme Ferry, in service since 1769. It will take you to the other side of the Connecticut River and further on to the Gillette Castle State Park
Deep River - situated on the Connecticut River banks; many reaturants, small shops, and a piano-key factory
Essex Village - home of the Griswold Inn, one of the oldest still operating inns in the country, open for business since 1776 - (URL HIDDEN) ; many boutiques, restaurants, art galleries and the Connecticut River Museum; situated right where the Connecticut River meets the Long Island Sound; board the historic Essex Steam Train - (URL HIDDEN)
Old Saybrook - visit the marina or one of the public beaches right at the Long Island Sound; once the home town of Kate Hepburn the town named their new cultural center after the late actress - (URL HIDDEN) - visit the many shops and restaurants
Westbrook - a quaint shoreline community with several public beaches right at Long Island Sound between New Haven and New London
Middletown - home of the Wesleyan University; enjoy their cultural program open to the public - (URL HIDDEN) visit the local movie theater
A 45 min. drive away you find two large casinos offering gambling, dining, spas and entertainment: Mohegan Sun Casino and Foxwoods Resort Casino

Hair dryer • Shampoo • Bidet • Bathtub • Hot water • Conditioner • Meyers body soap • Hangers • Essentials • Bed linens

An intimate B&B in downtown Clinton, CT that offers two rooms in the original 1760's part of the house: one queen and one with twin beds(can be made into a King bed), with a shared bathroom. A cozy fireplace in the winter and a breezy deck in the summer. Pricing includes tax. Winter fare

The space
There is a second bathroom on the first floor that offers a standing shower.

Smoke alarm • First aid kit • Indoor fireplace • Carbon monoxide alarm • Wifi • Fire extinguisher • Heating • Air conditioning • Essentials • TV with standard cable

This first floor deluxe room has a fireplace, private bath, large two person Jacuzzi, rain shower and queen size bed. The back window overlook the vista of the gardens, water fountain and gazebo. A cozy sun porch, and a large porch with wicker rockers to relax with lemonade, or wine as you watch the town go by the front view of the inn. This guest room is pet friendly.

Essentials • Smoke alarm • Shampoo • TV • Air conditioning • Carbon monoxide alarm • Indoor fireplace • Heating • Hangers • Hair dryer

This room is named after the homestead's original owner, Sereno H. Scranton. Tucked away in the rear of the home, this a bright and sunny gem of a room with 4 big windows looking out on to the rear gardens. You also have the beautiful view of our giant Norway Spruce which is the tallest tree in Madison. This room offers a full sized bed and a private bathroom with shower. This guest room is not pet friendly.

This guest room is situated in the back of the inn with a private entrance. A bright and sunny large room with queen sized bed and private bathroom with shower. There are two cozy chairs to relax in after a long day at the beach or shopping. This room comes with a small additional space and is outfitted with a small refrigerator, a microwave and table & chairs ideal for long term stays. This guest room is pet friendly.

Smoke alarm • TV • Hangers • Carbon monoxide alarm • Essentials • Iron • Hair dryer • Shampoo • Air conditioning • Heating

Come enjoy a cozy lake-front hideaway! With one bedroom with a twin bunk bed and a comfortable queen sized pull-out couch in the living room, the 500sqft studio is perfect for a weekday getaway! This studio includes a small kitchen area, and a bathroom off of the bedroom with a compost toilet. Clean off with the outdoor shower after a long day of fishing swimming! Or relax underneath the outdoor patio and watch ducks float across the lake.

The space
Just across the way is Lake-Side Dan’s, which includes a boat-launch, there are two kayaks here to cruise the lake . Grocery and package stores are just a short drive away, and this location means easy access to casinos and highly-rated restaurants! If you need a break from the fun in the sun, enjoy the high-speed internet and Smart TV & air conditioning in the living room!

Other things to note
The cottage is surrounded by 300 acres of farm land and a park of 55 acres across the street .. this is deluxe CAMPING !!

There are a few chickens in the yard and always a duck or two 🦆
And it has a composting toilet
There is no water in the kitchenette, but paper plates & silverware & cups.. I will be glad to wash what ever you need !
Out side shower is awesome 😎
Bring a bathing suit or little fishing boat! I have a few kayaks!
Over 400 acre lake for fun!

Quick stroll to river, restaurants, Goodspeed Airport and a marina is across the bridge. East Haddam is a mecca for hiking, cycling, kayaking, shopping, and farmers markets. The CT River Valley offers big-city sophistication, along with the charm of rural New England.

Shampoo • Cleaning products • Hair dryer • Hot water • Outdoor shower • Conditioner • Essentials • Extra pillows and blankets • Lake view • Bed linens

740 sq. ft. of newly remodeled and decorated modern beach apartment. This 1 bedroom 1 bath with full kitchen sleeps 4, but can accommodate 6 if needed. With 1 full bed in the treehouse like bedroom and 2 sleeper sofas you can bring the whole family to enjoy Madison’s beautiful beaches.

Modern amenities like the 50” led smart tv and fast WiFi internet allow you to sync up your Netflix and binge or get some work done during your stay.

In unit washer and dryer allows you to pack light.

The space
Meticulously remodeled and decorated in 2018. This 1 bedroom 1 bathroom carriage house is just steps from the water. Outfitted with modern amenities like the 50” led smart tv, high speed internet, in unit washer and dryer coupled with the relaxing modern beach decor and tree house like bedroom.

Walk or bike to several of Madison’s beaches, downtown, or Hammonasset State Park.

Guest access
Guest will have full access to the carriage house. Access code will be provided prior to stay.

Other things to note
The Upper Deck Carriage House is a one bedroom one bathroom second floor apartment. It is located above our detached 3 car garage. The carriage house has its own long driveway and is private. Apartment is accessed by an exterior staircase.

Hot water • Bathtub • Cleaning products • Dryer • Essentials • Hair dryer • Bed linens • Washer • Hangers • Body soap

Cozy beach cottage, steps from private beach, comfortably sleeps 4, queen bed and pullout couch, full kitchen, full indoor bathroom, outdoor shower, grill and outdoor private area, private parking, numerous antique shops, great restaurants and bars, close to casinos

Renting weekly/monthly Saturday to Saturday

May 29, 2022 thru September 10,2022

Ceiling fan • Hot water • Bed linens • Essentials • Outdoor shower • Cleaning products • Air conditioning • Smoke alarm • TV • Hair dryer

Charming coastal guesthouse in Madison’s historic district—just a 5-min walk to a private beach, 5-min drive to town, and 20 mins to New Haven. Bright, beachy, and newly renovated with a king bedroom, full kitchen, private deck, and huge backyard. Set on nearly an acre in the heart of New England, it’s perfect for couples, families, and girls’ getaways. Walk to cafes, shops, and the iconic RJ Julia bookstore.

The space
Beautifully Renovated Carriage House | Walk to Beach | Kid-Friendly Coastal Escape

Tucked beside a historic 1830s farmhouse in Madison’s charming Historic District, this bright, newly renovated second-story guesthouse is the perfect coastal retreat for families, couples, or girls’ getaways.

Inside, enjoy a spacious king bedroom, a brand-new king pull-out sleeper, luxe linens, and a spa-style bathroom with a walk-in shower. The fully stocked kitchen features a Nespresso machine, toaster oven, two-burner hot plate, and coastal antique touches.

Outside, your private deck overlooks one of the most beautiful backyards in town—complete with a kid’s playhouse, swings, and a fire pit for roasting s’mores. Private parking for 2 cars and your own entrance make for a seamless, stress-free stay.

Just a 5-minute walk brings you to Surf Club Beach with a large playground and a local beach shack voted best fish & chips. Madison Beach Hotel is just 5 minutes away for waterfront dining, and Hammonasset Beach State Park is a 10-minute drive with trails, boardwalks, and miles of sandy shoreline.

You’re also close to cozy cafés, lobster shacks, RJ Julia Booksellers, and postcard-perfect towns like Guilford, Essex, and Old Saybrook—each packed with New England charm, harbor views, and boutiques.

Perfect for:
✔️ Families and couples
✔️ Romantic getaways
✔️ Girls’ weekends
✔️ Yale visits (20 min)
✔️ Beach and food lovers

Amenities include:
• Private entrance + parking (2 cars)
• Fast WiFi + smart TV
• Air conditioning + heat
• Walk to beach + playground
• Historic coastal neighborhood
• 20 min to New Haven | 90 mi to NYC/Boston

Your boutique beach retreat in the heart of Connecticut shoreline living.

Guest access
Please note: The pool and trampoline are not available for guest use.
However, everything else—from the private yard access to your own beach path, deck, and driveway—is yours to enjoy.

Guests have full private access to this beautifully renovated second-story carriage house, located in the heart of Madison’s Historic District. You’ll have your own private entrance, a dedicated driveway with parking for up to two cars, and a private deck overlooking the stunning backyard.

The expansive backyard is a true highlight of the property. Guests are welcome to enjoy the lush green space, complete with:
• Swings and jungle gym — perfect for kids to play and explore
• A cozy fire pit area for roasting marshmallows or relaxing under the stars
• Ample room for outdoor games, picnics, or lounging with a book

Other things to note
No access to pool or trampoline.

The Rising Tide Cottage is recently updated and located in a quiet neighborhood on the Connecticut shoreline. Downtown Madison is less than a mile away and home to award-winning restaurants, a movie theater, and many shops. We are 5 houses down from our neighborhood Pent Road Beach and supply complimentary beach chairs, towels and umbrella. Enjoy your morning coffee on the private patio watching the tide rise and fall, overlooking a protected wildlife sanctuary at Hammonassett Beach State Park

Guest access
Backyard, Adirondack chairs, hose for washing sand off your feet

Other things to note
TV has Netflix, Amazon Prime, Hulu, and Disney+ APPs available - we ask that you please use the guest profile.

Escape to this sunny cottage just steps from the historic town green. Featuring vaulted ceilings and a light-soaked living area, this two story space offers a quiet backyard with a country feeling. Less than a 15 minute walk to the beach, 10 minutes from the train and a quaint New England downtown area complete with movie theater, restaurants, a world-famous bookstore and library, the location of this property is hard to beat.

Hangers • Free washer – In unit • Hair dryer • Conditioner • Hot water • Cleaning products • Iron • Shampoo • Bed linens • Extra pillows and blankets

Imagine the clinking of glasses, laughter and friendship during prohibition. This was Pierre Houpert's private distillerie with quite a history. Burned down before the feds stepped in, after almost 100 years it waited for new life whilst almost crumbling to the ground. Now new life breaths from every stone. Enjoy the views from any of the 3 porches. Take a walk on the trails across the street or just walk down to the reservoir to see the sunset or just listen to the history tell you the stories.

The space
Recently completely renovated, the late 1800's meets the new. This incredible stonehouse now showcases the stone inside where possible, new windows in all the original window openings, porches created from the flat roofs and designing with thoughts of what might have been to include the comforts of today, all while preserving the stone structure that was in horrible disrepair. It now stands proudly as part of the Windjammer's property which overlooks the Kelseytown Reservoir.

Guest access
Guests have access to all but the workshop and basement which consists of a kitchen, laundry/bath, hall and living room on the first floor. 2 bedrooms and 2 baths on the 2nd floor. There are 2 entrances, but the main entrance is in the front of the building across from the parking spaces.

Other things to note
There are other animals on the property. Perhaps the cats may be frolicking around, the horses should be behind the fence and the dogs should also be in the back yard. We are working on gates to give guests access to walk down to the water, but this may not be available until late winter. Access to back can be through the main house if requested.

Hangers • Air conditioning • Hot water • Ceiling fan • Central heating • Smoke alarm • Carbon monoxide alarm • Clothing storage • Bed linens • TV with Roku

Spend your days in this newly renovated Coastal Barn Retreat, (which is immediately adjacent to our house). With a modern design and large windows, enjoy views of Neck River. Kayak down river to the Sound at high tide or bike to nearby local beaches with bikes (2) and kayaks (4) provided by owner. Close to town beaches, Hammonasset, Vineyards, Hiking trails.

Tons of natural light. Living area is under a cathedral ceiling with forced air heat, air conditioning, and wireless wifi.

The space
Coastal Barn Riverside Retreat, on 2 acres adjacent to the owners house. Barn has private entrance, parking, open kitchen/dining/living area with 8 foot high windows overlooking river, two bedrooms and a full bath. Guests can enjoy sitting on wide and secluded bridge over river, and use of kayaks (during a 4 hour high tide window). Parking, main backyard, and 2 bridges are shared access. Property is located in quiet residential neighborhood near town and beaches.

Guest access
Property is located 2 miles from the Madison train station (accessible by Shoreline East and MetroNorth) and 18 miles from the New Haven Union Train Station. Centrally located between the Surf Club Beach (1 mile) and Grass Island Beach (2 miles). Hammonasset State Beach is 4 miles away. Madison Town Center is within 2 miles and sports several restaurants, an amazing bookstore, fabulous gift shops and boutiques. Liquor store, and Deli is just 3/10s of a mile up the road.

Other things to note
Life jackets and paddles provided for kayak use. Guest is responsible for providing their own bicycle helmets.
Minimum age of responsible adult is 25 years and older.

River view • Iron • Hot water • Hair dryer • Assorted body soap • Bed linens • Hangers • Essentials • Extra pillows and blankets • Cleaning products

Enjoy the best of both worlds with this remodeled 2 bedroom and 1 bath antique home located on the coveted North Main Street in Essex Village. You are close enough to walk downtown but away from the hustle and bustle. The park-like back yard with an antique trolley bridge and Falls river running through it will give you the perfect place to unwind after a day of activities. Come see why Essex was named “The Perfect Small Town" in the book 1000 Places to See Before You Die!

The space
This is a cozy but comfortable space with many rooms having original wide plank pine floors.

The dining area has a small table set up for
two guests but can be pulled out and set for four people.

The living room has two love seats, coffee table and TV above the fireplace. Note that the fireplace is nonfunctional at this time. There are also plenty of books and games to enjoy. The windows in the living room have top down/bottom up shades allowing for both privacy and light.

The kitchen is well equipped and we are adding things all the time! It has a brand new electric stove, refrigerator, microwave, Keurig coffee maker, variety of k-cup coffee and tea, non-dairy creamer, French press, pots and pans, cooking utensils, wine glasses…etc. We have it stocked with paper towels, cleaning supplies, napkins, salt, pepper, sugar, and olive oil. If you need something and you can’t find it just ask! Please note that there is no dishwasher.

In the basement of this 1837 colonial we do have a washer and dryer that you can use. If you prefer there are several local laundromats.

The bathroom has just been completely remodeled and has a nice shower with tile walls and a pedestal sink. We do provide towels, hair dryer, soap, shampoo and conditioner.

The master bedroom has a comfortable queen size bed, luxurious bamboo sheets, blanket, comforter, plenty of pillows and
blackout shades. You will also find a good size bureau, closet, ironing
board, iron and two robes to enjoy!

The second bedroom has a daybed and pull out trundle, luxurious sheets, pillows and blankets. You will also find a desk in this room making it a perfect office for a summer away from the city. It also has blackout shades.

The large outdoor stone patio has a comfortable seating and dining area that looks out over the large lawn and small river. Part of the patio is shaded by a beautiful pergola covered in Wisteria. You have a gas grill and a large storage box to keep the patio cushions dry.

Down by the river you will find a wood burning fire pit and picnic table.

We are a pet friendly rental for those with dogs that are well behaved and comfortable traveling.

We have two dogs and live in the unit next door. We do our best to keep them quite while guests are occupying the property but you may be able to hear occasional barking.

Please be aware that we are in a village setting located on North Main Street and the house is set close to the road. You can hear traffic but the speed limit is 25 mph and it does get very quiet at night.

We are here to answer any questions so feel free to reach out.

Guest access
You will have access to the whole guest house, patio and large yard. We are on almost 2 acres and have a small river in our backyard. There is also a fire pit down by the river. Our two resident dogs have access to most of the property but there is an area of the yard along with the guest parking area and the guest house that they cannot access.

If you are bringing your pet you must keep them on a leash at all times and keep them in the designated guest areas for the safety of our dogs and yours.

If you want to explore the property but aren’t comfortable with dogs please let us know and we will try to arrange dog free time.

Garden view • Free washer – In unit • Free dryer – In unit • Ginger Lily Farms Club & Fitness shampoo • Essentials • Hangers • Hot water • Bed linens • Cleaning products • Hair dryer

Stay in an upscale place that’s near everything you want to visit.

Total privacy. Self-check-in keypad entry w staircase access to your keypad entry 2nd floor room. Walk everywhere. Air cond. Fast Wi-Fi. Free parking space. Sparkling ensuite bathroom w oversized shower / designer toiletries. Four-poster bed. Luxury sheets. Gas fireplace. Free chilled Pellegrino sparkling & Saratoga spring water. 32" TV w cable. Secluded garden. Daily breakfast voucher (up to $25) for Mirsina’s (5 min walk).

Self check-in • Indoor fireplace • Free parking on premises • Smoke alarm • TV • Air conditioning • Building staff • Carbon monoxide alarm • Beach access – Beachfront • Wifi

Right in the middle of all Essex Village offers: shopping, dining, boating.
Short drive to beaches, farm-stands, golf, hikes, theatre, colleges...

Very special little waterfront cottage with unrivaled views, private deck & access to town. Park your car once and enjoy all the wonders of Essex Village by foot during your visit.

🌟 Secluded, yet utterly central Village location.
🛶 Access to swimming pool WITH ARRANGEMENT (towels provided)
🚣‍♀️ No proper launch for kayak/SUP- but several close

The space
Guests stay in our little renovated freestanding boathouse. Its new kitchen & bath, low-key nautical decor, personal touches and fully thought through details/amenities make this a very special and upscale accommodation.

Location: Just off the beaten path. Down an elegant cobbled lane, behind a thick hedgerow sits an idyllic retreat with unobstructed waterfront views and great vibes.

First floor: Modern kitchen and comfortable living space. A wall of windows & covered outdoor deck with cushioned teak seating & a cocktail table have our visitors telling us they feel like they’re staying aboard a spacious yacht.

Kitchen is clean. Uncluttered, yet well-equipped. Everything you need is provided.

Upstairs: Second floor has the queen size bedroom and only bathroom. Custom upholstery, art, and antique accent furniture create the perfect place to lounge late in bed on crisp cotton linens, or read your book enjoying the vista outside from the large chair.

The small but updated bathroom with its glass door/tiled shower & pedestal sink is also located upstairs. (Plenty of extra towels, hairdryer and soap/shampoo can be provided.)

The Privateer's Boathouse is a thoroughly comfortable residence for a couple's visit. However, if traveling for just a few nights you can REQUEST our “double height” airbed to accommodate a child or to create a separate sleeping arrangement for another adult. If available, we will bring it to the Boathouse and before you arrive.




* Thank you for considering that using an additional bed is something extra our housekeepers must prepare, and clean up. Thus: we will ask for an additional "linen fee" of $25.
* Reminder, we cannot accommodate pets.

Guest access
Guests have exclusive use the two-story, one-bedroom Boathouse during their stay.

The Boathouse has incredible views, a fabulous & private in-town location, and its own private deck with curtains that billow in the ever-present summer breezes. There is also a lower patio that is exclusively for guests' use. Other outdoor amenities may be shared with host, so please ask.



Yes...
• Let us know about your special circumstances, and we will try to accommodate (as long as consideration of our neighbors' privacy at the forefront).

• We love hosting Brides & Grooms, and can make accommodations for you to setup for them, etc.

• If we are hosting your bridal attendants, or wedding guests, you can make special arrangements for them as well.


Sorry...
(1) Launching paddle boards, kayak, canoe, etc. directly from the property is quite "complicated", so please discuss in advance.
• It is inconvenient, but yes, you can "try it".
• Yes, there are better launch sites very nearby.

(2) We cannot accommodate docking at our property.
• We are close to the marinas.
• If arriving by water, we can help you plan for your stay.

(3) Use of the property, especially the swimming pool, assumes you agree to all risks.
• Persons outside those in your reservation cannot swim.
• AirBnB requires you to name yourself and guests in res.

(4) We love pets but cannot accommodate pets at Privateers Boathouse.

Other things to note
DETAILS:

If you have questions, please ask. We love hosting, and take pride in providing our guests with an outstanding experience.

Here are some answers to FAQ.

The Accommodation:
•. This is a small, private cottage.
• It is a separate dwelling, on a shared property.
•. On-site parking is included (one car, in a designated space out front)
+ Supplemental parking is at the end of the Lane, or, you can ask us where to put a second car. (We usually accommodate it without hesitation.)

Outdoors:
• Views, views, views (waterfront, seasonal boat action, birds, wildlife, etc.)
• Private deck with unobstructed waterfront views.
• Use of waterfront is tidal and therefore limited, just ask, we can explain.
• There is a "lounge area" (not pictured) that provides a private place to sit on the Cove.
• There is a completely private patio under the deck off the house, next to swimming pool that is also exclusively for guests-use. (Ideal for yoga.)
• Swimming pool is set into terraced gardens between the Boathouse and the Host's home. It is semi-private.
• There are poolside loungers, an outdoor dining table and many umbrellas to make a "pool day" comfortable.
• Please discuss swimming in advance. We will provide you with pool towels, and explain the situation (which changes based on season and weather). For example, sometimes the pool has a cover on it.

Indoor Amenities:
• Phenomenal waterfront views.
• Full kitchen & living room furnished in upscale, but comfortable style.
• Queen size bedroom & bathroom are both *upstairs*
• Sheets and towels are provided as part of your rental.
• The house will be clean and setup for you.
• Hairdryer & basic toiletries are provided in the bathroom.
• Kitchen stocked with essential cooking and dining utensils (condiments & seasonings)
• Twin size air bed & bedding (upon request) extra linen fee applies ($25)

Misc:
• Basic wi-fi
• Wi-fi television (adequate, but not huge, see photos)
• Gas grill is in shared outdoor area.
• We appreciate understanding if you'd like to use the outdoor facilities beyond your deck (specifically: pool/pool area, hidden waterfront area, and grill) so we can plan and make things available accordingly.





• NO parties
• No photo/film shoots without advance agreement (fees apply)
• NO PETS

Discounted weekly rates.
Ask about monthly rentals.

Dove body soap • Cleaning products • Harbor view • Shampoo • River view • Bathroom • Hair dryer • Marina view • Scenic views • Conditioner