Vacation Rentals By Owner In Madison, CT

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 has beach area and private waterfront Pavilion, then stairs down to Long Island Sound, for the 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 - Pool and Private Beach Pavilion - East

Madison, Connecticut, United States

Bed

Bath

Sleeps

Exceptional(5)

$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

Bed

Bath

Sleeps

Exceptional(2)

$837.86

Cozy family beach cottage just steps to the sand! Enjoy your perfect New England family getaway/vacation in our quaint beachside cottage. Make memories by playing provided lawn games in the front yard at the end of a quiet cul-du-sac, or explore any of the unique local places to see. Walk down the path to the beach and spend the day soaking up the sun on the private association beach. Quick 5 minute drive into downtown Madison’s iconic shops and restaurants.

Cozy Family Beach Cottage

Madison, Connecticut, United States

Bed

Bath

Sleeps

Exceptional(19)

$780.36

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

Bed

Bath

Sleeps

Exceptional(5)

$1586.05

Stepping inside the Bunce Cottage at Seaview Beach is travelling back in time to the Connecticut Shoreline of 1927. Lovingly maintained with appropriate modern updates, little has changed for almost a century. Step off the front porch to a private boardwalk across the marsh to your own private beach and Long Island Sound.brbrThe Bunce Cottage is a spacious and historic vacation rental that offers a unique blend of New England Shoreline old-world charm and modern amenities. With just over 3,000 square feet of living space, the Cottage offers 6 bedrooms and 2.5 baths plus an enclosed outdoor shower. The Cottage has beds for up to 12 people. The large screened front porch provides a panoramic view of Seaview Beach and Long Island Sound, while the Great room includes a large screen LCD TV, a magnificent stone fireplace, and a dining area also with views of the Sound.brbrThe Bunce Cottage has sun filled Southern exposure and is located on the only double lot along Seaview Beach. Set up Adirondack chairs in the front yard and enjoy the beautiful view of Long Island Sound, play croquet or other games in the side yard, and have a family gathering in the large backyard.brbrThere is a 2-car detached garage behind the Cottage on Fairview Ave with parking available in the driveway and along the property perimeter on Fairview Ave and Brookside Ave brbrVideos:brWatching from the front porch as Ospreys fish for breakfastbrhttps://youtube.com/shorts/J-_6DuNtlnA feature=sharebrA visit to Madison:brhttps://youtu.be/Y2N7gbaOIDI si=ko17bXGxEaeP2AN-

Beachfront Cottage with panoramic views of Long Island Sound in Madison CT

Madison, Connecticut, United States

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Bath

Sleeps

$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

Bed

Bath

Sleeps

Exceptional(1)

$188.88

Quaint + Walkable | 1 Mi to Beach Park | Washer/DryerbrbrThe classic charm of the Connecticut coast is just a click away! Tucked behind acclaimed French restaurant Bar Bouchée, this downtown Madison vacation rental near Hammonasset Beach State Park is cute, walkable, and perfect for couples exploring the area. Spend your days beachcombing or biking the Shoreline Greenway Trail, then return to your open and airy hideaway. Book this convenient cottage and create lasting memories on the coast!brbr-- THE PROPERTY --brbrPROPERTY HIGHLIGHTSbr- Open living spacebr- Queen bed & queen sleeper sofabr- Smart TVbr- Dining areabr- Balcony w/ sitting areabr- Located behind acclaimed French restaurantbr- Pack 'n Play availablebrbrKITCHENbr- Refrigerator, stove/oven, microwavebr- Cooking basics, dishware & flatwarebr- Drip coffee maker (starter coffee provided)brbrACCESSIBILITYbr- 2-story studio cottage, step-free entrybr- Kitchen & full bathroom on 1st floorbr- Stairs required to access sleeping areabrbrPARKINGbr- Lot (1 reserved space)brbr-- THE LOCATION --brbr- Downtown Madison location walking distance to East Wharf Beach Park & Seaview Beachbr- 1 mile to Shoreline Greenway Trailbr- 2 miles to Hammonasset Beach State Parkbr- 4 miles to Meigs Point Nature Centerbrbr-- 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 smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This 2-story studio cottage features step-free entry; the kitchen and full bathroom are on the 1st floor, however the main sleeping area requires stairs to access brbrSECURITY CAMERA INFORMATIONbr- 1 exterior devicebr- Location: rear of buildingbr- Coverage: parking area

Apartment

Walk to Coast! Convenient Cottage in Dtwn Madison

Madison, Connecticut, United States

Bed

Bath

Sleeps

$498.33

Your Madison adventure begins at this fabulous 4-bedroom house. Inside, guests find three queen beds, two twin beds and a sofa bed, perfect for families or groups. Three full bathrooms with refreshing showers or relaxing tubs, make getting ready a breeze. The house stays comfortable year-round with heating and air conditioning, and a back porch overlooking Long Island Sound. Relax in a soothing atmosphere that feels like a true home away from home. We’ll be available to answer any questions while you stay at our place.

Waterfront home in charming Madison

Madison, Connecticut, United States

Bed

Bath

Sleeps

Exceptional(2)

$1173.49

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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Bath

Sleeps

Exceptional(86)

$872.08

Newly renovated cottage. Direct waterfront home in Madison’s most desirable waterfront area. Four bedrooms, 2 full and one 1/2 bath. Outdoor private shower. Sleeps 7. Walk to the Madison beach hotel and into town (restaurants, shops, grocery store, cvs, starbucks) or along Madison’s beautiful coastline. Bike to hammonaset state park along the green mile trail. Beautiful green lawn from your deck to the Long Island sound. At low tide, there is sand between our seawall and rock outcroppings where you can walk & put a chair & enjoy the sunshine. There also is a sandy beach (regardless of the tide) approximately 6 homes away that you can use. See photos. There is room for 6 cars to park on rock driveway. Enjoy all Madison has to offer from the best view in town. Short walk to Madison Beach Hotel for outdoor/indoor dining , spa and entertainment. Also, a short walk to Madison Beach Club and Madison Country Club which are for members only.brbrAir conditioning units in June, July & August. One ac unit is based for family room and dining room. All three upstairs bedrooms have ceiling fans and will have individual AC units. There is no heat in the cottage. April & October can be chili, but beautiful! There is a wall heater that heats the family room and dining area.

Direct waterfront renovated cottage.

Madison, Connecticut, United States

Bed

Bath

Sleeps

Exceptional(5)

$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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Bath

Sleeps

$165.14