Vacation Rentals By Owner In Madison, CT

Fully furnished home with one floor living and its own private beach in a quiet neighborhood. 3 bedrooms: master with king; second with double; brand third with twin beds. Two full bathrooms. Master bathroom is a brand new rennovation. Bright living room with cozy bay window seat and adjoining dining room. Eat in kitchen with skylight, full appliances, and separate laundry/pantry. Spacious glass enclosed sunroom patio with dining area and ceiling fan. Large yard with deck and gas grill. Ready to move in. All cookware, linens, cable tv, and wifi provided. Kayaks, bikes and board games are available. 2 min walk to home's private beach and 5 min drive to scenic downtown Madison. Monthly rental is preferred. Available January-June. Shorter term stays (weekly, long weekends, wedding visits, graduations) are available upon request by contacting Leslie, 404-401-0469. 20 min drive to New Haven. Approximately 2 hours from New York City and Boston.

Great 3BD/2BA Sunny Ranch with Private Beach and Large Yard

Madison, Connecticut, United States

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Exceptional(3)

$495.01

Bring the whole family to this great place with lots of room for fun. This newly-renovated home is just a short walk to Kelsey Place's private beach. There is a huge master suite with private balcony & full bath in its private wing over the 3-car garage. 3 additional bedrooms include 1 on the 1st floor with a full bath and queen bed; 2 upstairs bedrooms share a full bath (1 room with 2 twin beds, the 2nd with 1 queen). The entire house is newly-renovated with new furniture & appliances.

7 Min Walk from Water: Cheerful 4 Bedroom Home

Madison, Connecticut, United States

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$165.14

Unwind in Madison at this peaceful cottage. Guests find a cozy queen bed in the bedroom and an extra outdoor shower to wash off the sand. The cottage offers two additional living spaces, featuring a sofa bed and a set of bunk beds in the loft perfect for relaxing. Enjoy a pleasant atmosphere with heating and air conditioning to keep you comfortable. Whether you’re curling up with a book or spending time on the beach this marvelous spot provides a welcoming retreat. We're happy to assist with any questions while you stay at our cottage.

Nice 1-bedroom cottage with AC in charming Madison

Madison, Connecticut, United States

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$542.14

This 3-bedroom house is perfect for your escape to Madison. Steps from the beach - beach chairs and towels included. Beautiful views of the marsh with osprey, herons, and egrets. brCan walk or bike to quaint shops and cafes in town with a famous bookstore or bike or walk along the shoreline.

3-bedroom house on the Madison, CT shore with outstanding views of marsh.

Madison, Connecticut, United States

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$476.43

Take your vacation at this newly renovated adorable cottage in a great family community, and a 4 min walk to private beach! The cottage has a brand new kitchen and bath. 3 bedrooms and an additional breezeway space perfect for reading or an additional private sleeping space. The cozy living room has a large TV, with Amazon firestick to watch your favorite streaming services. The dining area has a table ready for meals and games. The home has a large outdoor patio, with table for outdoor dining and an outdoor shower. Spend the day at the private association beach. Close to downtown Madison, the state boat launch and restaurants. brPlease note **This close knit, family community has a strict, no large gathering rule **

Newly renovated cottage in a private beach community.

Madison, Connecticut, United States

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Exceptional(12)

$1019.48

Situated on one of the premier sandy beaches on the Connecticut coastline, this house is a true gem. The owners only list it on occasion so it gets less wear and tear than other listings.brbrLocated on almost .75 lush acres, this 4-bedroom home sleeps 8 (plus a crib) and is a private oasis for just lounging around on the beach, playing in the yard with kids, or exploring Connecticut's coastal towns.brbrWalk outside and relax on one of your decks overlooking the ocean. Take a dip in the water - this exclusive beach is only accessible to the few homeowners who have houses on it. Explore nearby towns such as Guilford and Old Saybrook or spend the day in New Haven visiting the many downtown museums and shops.brbrFeatures:br- Direct beach access (only available to neighborhood homeowners and their guests)br- Two outdoor decks on the first floor and a balcony off master bedroombr- Outdoor furniture including dining table, lounge chairs and plush seating (in season)br- Covered porch overlooking the oceanbr- Gas grillbr- Central A/Cbr- Outdoor shower (in season)br- Wifibr- Full kitchen with coffee maker, blender, pots, pans, etc.br- Washer & dryerbr- DVD player with a selection of DVD'sbr- Fireplacebr- Swing set on community beach next doorbr- A selection of board games and outdoor gamesbr- Beach chairs and beach toys (in season)br- Linens including beach towelsbrbr__ BEDROOM / SLEEPING CONFIGURATION __brbrMaster Bedroom (Water Views):brKing BedbrAttached Full BathbrOutdoor BalconybrbrGuest Bedroom (Water Views):brQueen BedbrBaby Crib (not counted in total sleeping count)brbrKids Bedroom:br2 Twin BedsbrA third, trundle bed is also located in this room (but not counted in total sleeping count)brbrFirst Floor Bedroom:brQueen BedbrAttached bathroom/showerbrGreat for in-laws and older folks because of first floor locationbrbrHouse Rules:br- This property does not allow petsbr- Minimum 3 or 4 night stay (depending on season)br- Check in after 3 pm, check out by 11 ambr- This house is professionally cleaned between each guestbrbrNote: There is also a guest house on top of the garage that is sometimes occupied. When in use, the person in the guest house does not have access to the rest of the property.

Rare! Private Beachfront House in Madison CT - Sleeps 8 - Last Min Availability

Madison, Connecticut, United States

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Exceptional(8)

$449.35

Fully Renovated | Barbecues w/ Gas Grill | 2 Mi to Hammonasset Beach State ParkbrbrEnjoy a memorable retreat at this 3-bedroom, 3-bath vacation rental in Madison, CT! With quick access to Hammonasset Beach State Park, this 100-year-old home offers the perfect base for a comfortable coastal escape. When you're not relaxing on nearby shores, visit local hotspots like Bishop's Orchards or shop and dine downtown. After blissful days, gather around the fire pit for s’mores and captivating stories!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 queen bedbr- Bedroom 2: 1 full bedbr- Bedroom 3: 1 full bedbrbrOUTDOOR LIVINGbr- Private yardbr- Furnished deckbr- Fire pit (wood provided)br- Gas grillbrbrINDOOR LIVINGbr- Fireplacebr- Flat-screen TVsbr- Booksbr- Dining tablebr- En-suite bathroomsbrbrKITCHENbr- Refrigerator, stove/oven, dishwasher, microwavebr- Keurig coffee makerbrbrGENERALbr- Free WiFibr- Central A/C & heatingbr- Electric heating & window A/C unitsbr- Linens & towelsbrbrFAQbr- 2 exterior security cameras (facing out)brbrACCESSIBILITYbr- 2-story home, exterior stairs to enterbr- 1 full bathroom on 1st floorbr- All bedrooms on 2nd floorbrbrPARKINGbr- Driveway (3 vehicles)brbr-- THE LOCATION --brbr- Quiet area, 1 mile to Madison Green Historic Districtbr- 4 miles to Clinton Premium Outletsbr- 7 miles to Jacobs Beach + Bishop’s Orchards Farm Market & Winerybr- 8 miles to Chatfield Hollow State Parkbr- 11 miles to The Woodwinds - event venuebr- 18 miles to Tweed New Haven Airportbrbr-- REST EASY WITH US --brbrEvolve 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.brbr-- POLICIES --brbr- No smoking br- No pets allowed br- No events, parties, or large gatherings br- Additional fees and taxes may apply br- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This 2-story home requires exterior stairs to enter. While it offers 1 full bathroom on the 1st floor, interior stairs are required to access all bedroomsbr- Your safety matters. This property features 2 exterior security cameras. Camera 1 is located on the garage facing the driveway. Camera 2 is located at the rear of the home facing the backyard. These cameras do not look into any interior spaces. The cameras record video and sound when activated by motion

2 Mi to Dtwn: 2-Acre Retreat w/ Large Yard!

Madison, Connecticut, United States

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Exceptional(19)

$837.86

Beautifully designed and Remodeled Beach home and 1/2 acre native garden paradise with incredible views of Long Island Sound and steps away from a sandy private association beach. This is a perfect place to unwind, connect with nature and enjoy time with family or friends.

Beautiful Beach Home and Garden Paradise

Madison, Connecticut, United States

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$1536.07

Centrally located, walking distance to downtown Madison, town green, & beautiful town beaches. With a private pool, large yard & gardens, this property is an ideal family retreat. This spacious & comfortable summer home enjoys a cool beach climate, comfortably sleeps 12, and is ideal for a large family or two families. The large private yard includes an outdoor grill area, hammock, fire pit & multiple relaxing garden spots. Have fun together with the ping pong/ pool table, play badminton or croquet in the yard (sets included with rental), gather together to watch movies or sports on the large screen TV (subscription separate). The open floor plan seamlessly connects the living and dining areas, both indoor and outdoor. The fully equipped kitchen offers plenty of counter space for preparing meals, the outdoor grill is convenient to the house & eating areas. Madison is a picturesque town with a rich history and plenty of local charm. Guests can easily explore the area's many attractions, including the famous RJ Julia Booksellers, Ashley's Ice Cream, restaurants, boutiques, and the local movie theater. The town green hosts summer concerts, weekly farmers markets, antique fairs, and other events, offering plenty of opportunities for entertainment and relaxation.

Madison Beach House, Private Pool, Walk to Beach & Town

Madison, Connecticut, United States

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$389.79

Beach Cottage rental brbrRare opportunity to rent the enchanted cottage . Situated on a peninsula with the East River on one side and Long Island sound on the other!brbrPrivate beach yet access to many one block away. Madison - a picture perfect New England shoreline town.brbrAvailable July only or academicbrbrOptions:br1) rent at 2 weeks ($5000) or by the month at $9000br2) academic rent $3300/month plus utilities,brbrDogs negotiable. Deposit required.

Available July 1, 2025 2 week or monthly.

Madison, Connecticut, United States

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Exceptional(14)

$447.02

** 4th of July 2026 will be a two week stay from 6/27/26-7/11/26 ** Built in 1937, Summersalt combines quintessential New England beach house charm with modern updates and fun, unique touches throughout. The kitchen is well-stocked with everything you might need to cook at home, including a gas range, Instant Pot, crockpot and air fryer. Warm summer evenings invite cookouts on the grill and meals on the patio. With access to the private Lee Manor beach just a 2-3 minute walk away, you'll be able to soak up the sun from a lounge chair, swim in the gentle waves of the Long Island Sound and search for seashells along a private and pristine section of shoreline in Madison.

Summersalt Madison: New England shoreline charm 2-3 minutes from private beach

Madison, Connecticut, United States

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Exceptional(2)

$997.89

Enjoy panoramic views of the Long Island Sound and the East River marsh area while you stay in this recently completed house with 3 bedrooms, 3 full baths, open kitchen and living room floor plan, and deck directly at the water's edge. The kitchen has quartz countertops and big screen televisions which are also provided in each bedroom. A bar setup underneath the house with a heated infinity pool offers an extra space to relax and enjoy the beautiful views. Located in the unique Circle Beach community, from this house you can walk to the historic Grass Island, kayak up the East River or take a sunset cruise. Construction completed in July 2021. Guests will need to climb a staircase to enter the house. Inquire about using our dock for your boat. Please note that there is a second guest house next door that may be occupied during your stay.

Beachfront home with heated pool

Madison, Connecticut, United States

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Exceptional(3)

$289.64

This property has been lovingly renovated and features cathedral ceilings, hardwood floors as well as a large kitchen that cooks will love! The kitchen features a huge island that seats five people. There is one full bath with a walk-in shower. We are located in a quiet neighborhood that is approx. 4 miles from the town village, three town beaches & Hammonasset State Park. You can enjoy the many boutique shops of Madison. The area also offers lots of great dining opportunities. Enjoy Al fresco dining on the private deck. There is also a terrace with a firepit to enjoy those cool late summer and fall evenings. The lower level of the cottage has a studio apartment that we stay in when we are in town. It has it's own private entrance and terrace. The laundry room is located in the lower area and is the only shared space. **MIN 1 WEEK (6 nights) STAY FOR MO OF JULY.

SHABBY CHIC RETREAT

Madison, Connecticut, United States

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Exceptional(6)

$503.13

Walking distance to the a private beach (4 houses back from the beach), classic CT shoreline cottage has air conditioning and all the amenities for the idea family vacation. Built in 1934, the house was updated in the 1970s. Large living room and enclosed sun porch accommodates family gatherings. Bedrooms are upstairs. Master has queen bed. Two additional 2 bedrooms each with two twin beds. Three additional beds available on upstairs enclosed porch (not air conditioned). Small bathroom with shower downstairs. Upstairs bathroom with bathtub. Outdoor shower in enclosed latticework to shower off sand and salt water after your day at the beach. High def flat screen TV and wifi. 10 minute drive to town and grocery store Many excellent stores restaurants in the area as well as shopping and local farms and farmers markets. .

Classic shoreline cottage 5-minute walk to the beach, Madison CT private beach

Madison, Connecticut, United States

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Exceptional(46)

$1185.77

Iconic Middle Beach Road Summer House, with Private Waterfront, low tide beach and shared In ground Swimming Pool! This beautiful cottage sleeps 20 comfortably in 9 bedrooms. Big open living spaces with expansive views from every room. Private Waterfront area has new beach area and private waterfront Pavilion, then steps down to Long Island Sound, with a low tide beach. This lovely cottage is the perfect place for a large family gathering, with a quick walk to Madison Center and Madison Town Green. Located in the middle of Madison’s prime waterfront, with a short walk to both East Wharf Beach and West Wharf Beach.

Waterfront Estate Home - Beach and Shared Pool - East

Madison, Connecticut, United States

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Exceptional(7)

$1127.82

Stunningly updated waterfront beach house. Water access best for boating, kayaking and paddle boarding! Never leave the house or venture out in town. Located in charming Madison, CT. Close to adorable downtown, local beaches and Hammonassett state park/beach! Home has 3 bedrooms and 1 bath. Window unit air conditioning.

Waterfront home surrounded by stunning water views.

Madison, Connecticut, United States

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Exceptional(6)

$770.5

Enjoy a relaxing experience at this centrally-located home. Steps from the historic Madison Beach Club and within walking distance to the Madison Beach Hotel, both of Madison's beloved Wharf Beaches (1/2 mile) and beautiful downtown (1 mile). Water views from 3rd floor suite and the screened in front porch. A large backyard is the perfect spot for family gatherings. Sleeps 10 comfortably and is recently refreshed with brand-new furniture including all beds and mattresses.

1 Block from Water - Welcoming 4 Bedroom Home

Madison, Connecticut, United States

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$494.5

Stylish 4-Bedroom Home in Madison Connecticutbr- Features Contemporary Scandanavian Interior Designbr- Proximity to Local/State Beaches (Approximately 10 Minutes Drive)br- Nearby Access to Local Parks and Hiking Areasbr- Inviting and Open Floorplanbr- High-Quality Furnishings and Finishesbr- Clean and Comfortable Atmospherebr- Delightful Garden and Expansive Grass Lawnbr- Private Setting (Situated on 2-Acre Parcel)br- Enveloped by the Natural Beauty of the Countrysidebr- Up-to-Date/Modern Features

Contemporary and Stylish, 4-Bedroom, Madison CT

Madison, Connecticut, United States

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$607.2

There are few places like this on the shoreline that sit directly on a quiet, private, sandy beach. brbrLife is good at the beach, especially when it's right outside the door! brbrbrbrRelax, chill out, and watch sunrises on the porch with your morning coffee. brbrCatch sunsets from the lower beach deck with your wine cooler or brew. brbrDrop your line into the surf in front of the cottage and catch tonight’s supper. brbrOr launch kayaks into the river and explore the Ox Marsh wildlife preserve behind the cottage. The public boat launch is just down the street.brbrbrbr— Unplug but still be connected —brbrNeed to keep in touch with work while you vacay This is the place. With a dedicated desk/work area (with both wired and WiFi connections), you can connect remotely to work or school while enjoying an exquisite view of Long Island Sound and the wildlife marsh. The WiFi reaches to the beach deck, so bring your laptop and iced tea down to the beach level. What a way to work! You’ll never want to go back to your office.brbrbrbrAll photos on this website were taken from the cottage or the surrounding wildlife area. It is just like you see it in the photos!brbrbrbr— About our family’s cottage —brbrThis is a quiet nature retreat that's perfect for couples, singles, and families. The recently updated cottage is beautifully restored with new kitchen appliances, a well-outfitted cook's kitchen, and internet/smart TV. The cottage is open, airy, and comfortably furnished. Large windows and ceiling fans carry the ocean breezes throughout the cottage.brbrbrbrWith nearly 360-degree views, you’ll watch spectacular sunrises and sunsets from the porch, living room, and bedrooms. Gaze at the ospreys in the marsh while you're still in bed. Identify the various sandpiper, egret, and gull species from the waterside porch. Watch the sailboats and ships pass Falkner's Lighthouse about 5 miles off shore. Everywhere you look, it's gorgeous. brbrbrbrOur cottage is family owned (70+ years and 6 generations). It's our treasured home that we've put a lot of TLC into, not a commercial real estate venture. We rent only the weeks when family members aren't using it.brbrbrbr— Right on a private sandy beach —brbrOur family's 1938 historic wood cottage is directly on Circle Beach, a quiet cove on Long Island Sound with 20 cottages on a small peninsula of sand. Long Island Sound is right outside the door, and Ox Marsh wildlife management area is behind us.brbrbrbrA spacious wall-to-wall beach deck is under the cottage and provides a private, shaded outdoor living room with ample patio seating and dining area. The surf is just a few steps away. And the WiFi reaches the beach deck, too. brbrbrbrUpstairs, the large screened porch overlooks the beach where you can read a book while watching the kids and sandpipers on the beach below. Perfect place for dining and sitting.brbrbrbr— It's a restful, beachside sanctuary — brbrOur family's cottage is located just 20 miles east of New Haven. It's a classic New England cottage with original rustic knotty-pine walls, but recently updated with all the modern creature comforts you need, too. It’s a charmer that is bright, airy, and nicely appointed.brbrbrbrCircle Beach is a small, residential beach used by owners for R&R. It is not Hammonasset (that's on the other side of town) or Fire Island NY (that's across the Sound!). brbrbrbrAnd it's quiet because this is a residential neighborhood of property owners, not a commercial rental.brbrbrbr*** Having a wedding, family reunion, or large gathering brbrThis is NOT the place. NO EVENTS are allowed.brbrbrbr— Nature retreat — brbrThe cottage is surrounded by nature: Long Island Sound on the south, and Ox Marsh / East River Wildlife Area on the north and west. It's adjacent to 100+ acres of preserved beach and marshland that's perfect for birding and kayaking. Egrets, great blue herons, gulls, sandpipers, ducks, ospreys, and dozens of other shorebirds thrive here and you'll often spot them from the porch while having your morning coffee in your PJs.brbrbrbr— Boaters and kayakers delight —brbrA free state public boat launch is just down the road where you can launch your boat across from Guilford Harbor and head out to the Sound, or launch your kayak for leisurely trips up the East and Neck Rivers that run behind the cottage through the wildlife saltwater preserve where you'll spot countless shorebirds.brbrbrbr— The fishing's great — brbrSurfcast from in front of the cottage and catch tonight's supper...striper, porgie, flounder and more. Or launch your boat and fish farther offshore for larger fish. Or join a fishing charter at a neighboring harbor and go for blues.brbrbrbr— Our family's home for 70+ years — brbrSix generations of our family have enjoyed the cottage and we're sure your family will love it, too. Because it's our family's summer home, we maintain it with lots of TLC and outfit it with comfortable, inviting furnishings. Enjoy our seashell collection from our beach and from beaches around the world. With several artists in the family, you'll find family oil paintings, photographs, and pottery. brbrbrbrAnd don't hesitate to tap into our book library, kids toys and picture puzzles. This is not an ordinary beach cottage rental, that's for sure!brbrbrbrInternet (both WiFi and wired) and cable TV are provided. The smart-TV is internet-connected, so bring your streaming account info.brbrbrbr— It's ready for your family to enjoy — brbrThere are always breezes here at the beach, so come cool off and chill out for a while. Expect temperatures 5-to-10 degrees cooler than inland. Just bring your bed linens, pillows, towels, and flip-flops and you're all set for a relaxing, cooling vacation at the beach.brbrbrbr— NOTES — brbr1. WEEKLY rentals only, Friday @ 4pm - Friday @ 10am (7 nights) — No exceptions except for multi-week rentals. No single-night, partial weeks, or 'weekends-only' reservations. brbr2. June-September only (this is an unheated summer beach cottage). brbr3. Sleeps a maximum of 6 people — No exceptions.brbr4. Bed linens, personal towels, blankets, mattress pads, and pillows are NOT provided. You must bring your own.brbr5. Our historic cottage is NOT appropriate for weddings, wedding receptions, reunions, or other large events. brbr6. No large gatherings. The number of daytime occupants allowed is 10, including the 6 sleeping there. brbr7. There is parking for 5 vehicles maximum. No more are allowed, even on the street. Parking is strictly enforced.brbrbrbr**** Contact the owner for contracts and the cottage's website URL with more details and photos.

Chill and relax. Or remote to work from the beach.

Madison, Connecticut, United States

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Most popular vacation rentals in Madison

$498.61

Madison, CT - Coastal Modern Farmhouse w/Outdoor Kitchen & Large Fenced in Patio

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$683.92

Spacious, quiet suburban getaway in Madison. 15 min from beach & hiking trails!

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Madison, Connecticut, United States

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Chill and relax. Or remote to work from the beach.

Madison, Connecticut, United States

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Bath

Sleeps

$503.13

Classic shoreline cottage 5-minute walk to the beach, Madison CT private beach

Madison, Connecticut, United States

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Sleeps

$476.43

Newly renovated cottage in a private beach community.

Madison, Connecticut, United States

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$394.50

Apartment

Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn

Madison, Connecticut, United States

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Bath

Sleeps

$447.02

Summersalt Madison: New England shoreline charm 2-3 minutes from private beach

Madison, Connecticut, United States

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Sleeps

$745.62