House vacation rentals in Madison

Find and book unique houses on Airbnb

Top-rated house rentals in Madison

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Top guest favorite

A charming single-story house features a classic shingle exterior with a brick chimney. A spacious front deck is bordered by white railings and overlooks a manicured lawn surrounded by trees. Soft sunlight filters through the leaves, enhancing the serene setting.

Home in East Hampton

4.95 out of 5 average rating, 230 reviews

Private beach, fully updated cottage, on 2 acres.

Each the special magic that only the Hamptons offer—historic charm, a rural atmosphere, white sandy beaches and a relaxed lifestyle—while staying in this light-filled three-story cottage. Tucked away on a beautiful 2.2-acre wooded lot, this bayside oasis offers a tranquil retreat, with deer sightings, private beach access, stunning view and picture-perfect sunsets. A short drive to the beaches and town, quick trips to nearby shops, market stands, restaurants, museums and Jackson Pollack house.

Guest favorite

The entrance of the home is framed by white, picket fencing and vibrant floral landscaping. A covered porch with classic columns supports a welcoming entrance. The door features decorative glass elements, providing an inviting touch to the exterior.

Home in North Fork

4.98 out of 5 average rating, 100 reviews

Designer's Dream - Charming Boathouse

An architect's and interior decorator's dream home! This home is a historic boathouse built in the late 1890's, and recently & lovingly fully renovated and restored. In the middle of Greenport Village - walking distance to train station, Jitney stop, and Shelter Island Ferry as well as the best North Fork restaurants, vineyards, bars, and beaches. Two bedroom home with ground floor fireplace, outdoor shower (not enclosed), and beautifully landscaped outside patio w/grilling & dining areas.

Guest favorite

A waterfront home with a unique tower design is reflected in the calm waters of Bantam Lake. The house features multiple outdoor decks, large windows, and is surrounded by trees, providing a serene setting. A private dock extends into the lake, inviting exploration.

Home in Morris

4.87 out of 5 average rating, 149 reviews

Bantam Lake Waterfront Retreat with Private Beach

Waterfront home on Bantam Lake, 3BR/2BA. Relax on the deck, enjoy the sunrise, swim at your private beach. Kayaks available for use (4); bring your boat or jet ski. Minutes away from hiking, snow skiing, vineyards, biking, and so much more. The area offers great restaurants and family friendly activities that are minutes away. BBQ on the gas grill, enjoy the fire pit on the beach. House is great for couples, individuals & families. Please check first if you plan to bring a boat. 7 maximum.

Guest favorite

A charming stone exterior is visible, featuring a private entrance with a sliding glass door. The path is made of stone, surrounded by a well-maintained lawn. In the background, sitting areas and greenery are discernible, enhancing a serene outdoor experience.

Home in Clinton

4.93 out of 5 average rating, 135 reviews

Amazing 2BR Riverfront Gem

Unwind at this happy getaway on the river. Comfy cozy with amazing views. Come experience the charm of New England in any season! The well-equipped, intimate kitchen overlooking the river is a pleasure for any cook. You will love our fairy-lit lawn, wishing well, and warm charming décor. Only minutes to groceries, coffee shops, beaches and amazing CT scenery. Other favorites include Chamard Vineyard, Shopping Outlets, Essex Steam Train, fantastic Restaurants with music, and lots more!

Top guest favorite

The exterior of a two-story house is featured, showcasing a light tan façade with white trim. A covered front porch is adorned with multiple seating areas, surrounded by well-kept landscaping and tall trees. The clear blue sky adds a serene backdrop, enhancing the home's welcoming appearance.

Home in Stonington

4.97 out of 5 average rating, 187 reviews

Relax or roam from our private spacious home

Bright and sunny newly renovated second and third floor of house built in late 1800s. Three blocks from Mystic Seaport, a short walk to downtown Mystic. Off street parking on the side of the house. House has plenty of space with two bedrooms plus a bonus room with a queen size futon. I Homey and comfortable to make you feel you can put your feet up and relax. User friendly. First floor is used as an office only on weekdays. Only 1/2 mile from Mystic Amtrak station, an easy walk.

Top guest favorite

A covered porch area features woven seating with bright green cushions and a chaise lounge. The wooden railing complements the light green siding of the house. Potted plants add color, while light filters through the oversized windows, providing a warm and welcoming atmosphere.

Home in Milford

5 out of 5 average rating, 101 reviews

Steps2Beach, Fish Pond w/Tropical Backyard Oasis!

🌴Steps from Walnut Beach & Silver Sands State Park, this guest-favorite escape offers a tropical backyard oasis with a cascading fish pond, multiple lounges, & a seasonal palm tree. Explore the scenic coastline, build sandcastles, or enjoy a day of kite flying. Inside, relax in luxury with a gourmet kitchen, elegant furnishings, & modern amenities. Just 90 minutes from NYC & 15 from New Haven, it’s the perfect retreat for beach days, nature adventures, & coastal charm!

Guest favorite

An inviting entryway features a decorative bench with the word 'HOME' displayed. A wooden staircase leads to the upper level, and a stained glass window adds color to the otherwise neutral space. Bright light enters through the front door, illuminating the hardwood floor.

Home in Stonington

4.98 out of 5 average rating, 169 reviews

Historic charm & modern luxury in downtown Mystic

We are long-time AirBNB guests who have tried to create the home we are always looking to book -- family friendly with modern amenities. Open floor plan on the main level, new heat and air con throughout the house, three bedrooms and family bathroom on the second floor. Art supplies, toys and children's books all ready for you as well as a pack n play and booster seat. Backyard oasis with pergola, walking distance to drawbridge. Pets considered on a case by case basis.

Guest favorite

The front exterior of the home is framed by lush greenery and a flower-lined pathway made of stone. Two trees add natural shade, while a charming yellow door welcomes guests. A fenced yard and gravel accents enhance the inviting entrance.

Home in North Fork

4.94 out of 5 average rating, 108 reviews

Maritime Village Getaway with Backyard

Well located Greenport 3 bedroom, 2 bath home. Historic renovated private home with modern furnishings and updated appliances and finishings. Patio and yard with outdoor shower, fire pit, and yard. Central AC and heat. Properly licensed as a rental with Greenport Village and Suffolk County. I now add the airbnb fees and local and state taxes onto the listing. If you have questions about this please reach out. Not sure how transparent the fee structure is for guests.

Guest favorite

A bright living area is illuminated by natural light through large windows. A decorative black wall with a welcome message adds character. A comfortable seating arrangement and dining space is featured. Art pieces are displayed, enhancing the creative ambiance of the space.

Home in Montauk

4.99 out of 5 average rating, 101 reviews

6 minute walk to Ditch Plains Beach

IMPORTANT: From Memorial Day 2024 - Labor Day 2024: weekly (1 week/2 week/3 week rentals must start and end on Saturdays. Monthly rentals can start on the first of the month regardless of the day of the week. Great beach house close to Ditch Plains beach with 3 bedrooms and 2 bathrooms. 2 queen beds and 2 bunk beds, deck, barbecue, outside shower, huge yard, recreation room. Spend your days at the beach and grill at night. Wifi, tv, and outdoor fire pit.

Guest favorite

A dining room table with eight chairs is set beneath ambient lighting. The room opens to a cozy living area featuring a comfortable sofa and blue curtains. A doorway leads to a well-lit kitchen, enhancing the home's spacious layout.

Home in New London

4.94 out of 5 average rating, 134 reviews

House in NL near CGA, Sub Base, Mohegan Casino

House is located in New London CT. Off I95 near Coast Guard Academy 3 mins, Connecticut College 4 mins, Mitchell 11 mins, Navy Base 9 mins,Yale L&M Hospital 10 mins, Branford House Avery Point 15 mins, Ocean Beach 16 mins, Millstone 19 mins, Mohegan 16 mins, Foxwoods 24 mins, Electric Boat 9 mins. Enjoy private house with full kitchen, and dining room for family get together. 20% Discount weekly stay. 35% on monthly stay

Superhost

A rocky shoreline is framed by a silhouetted tree against a colorful sunset. Clouds display shades of pink and orange as the sun sets over the water, creating a serene atmosphere. The beach area offers a peaceful view of nature.

Home in Shelter Island

4.9 out of 5 average rating, 115 reviews

There's a Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Cleaning fees for winter stays are 0$.

Top guest favorite

An open-concept living space is highlighted by a wooden dining table set with neutral décor. A comfortable seating area features a dark couch and large windows allowing natural light. Ceiling fans provide airflow in this bright and airy environment.

Home in North Fork

4.98 out of 5 average rating, 179 reviews

Greenport Village walking distance to all

Large spacious home in the heart of wine country. Roomy den for relaxing after the wineries. Screened in patio for al fresco dining and enjoying the spacious yard. Hot tub operational year round! Strong, fast wifi with multiple extenders. Message me with any questions or for special offers on 4/5 day stays or midweek 2/3 night specials.

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What guests are saying

Charming Downtown Mystic Historic House

4.98 out of 5 average rating, 183 reviews1 week ago

The house is historic and charming. Very walkable to downtown mystic and other activities as described. Wendy and James were amazing hosts and very responsive and helpful. They responded on short notice late in the evening to help me set up an extra bed so that I could be on the main floor with my mother who is handicapped. Would definitely stay here again!

Home in mystic

What guests are saying

Shell House

5 out of 5 average rating, 3 reviews8 months ago

The home was exactly as described! It was lovely. A serene and peaceful vibe throughout and in the yard. both roomy and spacious. We were even surprised to get a water view from the top deck! All and all the house was very well appointed with everything we needed from chef quality pots and pans and dishes as well as a new out side gas grille! Beautiful artwork through out! Julie was great to work with and gave us excellent ideas for what to do and where to go in the area. We will surely go back! A great place for couples or a family with children.

Home in Stonington

What guests are saying

Stylish Beach Getaway: pool & walking location

5 out of 5 average rating, 9 reviews6 months ago

Maher’s house was an amazing peaceful experience. I enjoyed my time there and he had great recommendations to restaurants and activities! He was very responsive with all questions we had. I will totally stay here in the future if I can get the chance again!! Thank you Maher!!

Home in North Fork

What guests are saying

Greenport Village-sunny 3 bedroom/3 full baths

4.94 out of 5 average rating, 62 reviews5 months ago

Cassie’s place was adorable! Cozy and clean and just as described. We were a group of 4 women on LI for a girls weekend and the house was perfect for us. Plenty of space and bedrooms/baths. We walked into the town of Greenport a few times and loved the shops and restaurants. Cassie was always quick to respond to any questions or concerns. Would definitely stay here again!

Home in North Fork

What guests are saying

Captains Quarters | July avail!

5 out of 5 average rating, 16 reviews1 month ago

This house served our family very well for a multi-month stay. The house and property are just like the photos and all the amenities were great to have. Would recommend staying here if you are looking for a quiet place near the water in East Hampton. Petra was always very responsive with anything we needed and was an excellent host.

Home in East Hampton

What guests are saying

Light-filled Beach House Steps from the Sand

4.92 out of 5 average rating, 26 reviews20 months ago

Mougeh's place is a lovely home with ample space, toys, books, games for entire family, within walking distance to the beach, and four mile drive to all shopping needs. The reason for the three star rating given in the "clean house" question was because when we arrived we noticed dog hair in the living area. We contacted the host and immediately the next day the cleaning service arrived and cleaned it. We were refunded the cleaning fee. Mougeh is very caring and responsive to her guests's needs.

Home in Woodmont

What guests are saying

Large Island Lake House, near casinos

4.94 out of 5 average rating, 33 reviews4 months ago

We loved the lakehouse! The setting and house were more beautiful than the photos. Panoramic lake views abound from inside and outside the house. The kitchen has new appliances and the house was toasty on a few very cold days. Also, there is a nice fire pit, outdoor lounge area, and a new dock that is amazing at night to walk out onto and gaze up at the stars. The sunrises and sunsets are visible from the property and provide a bonus. It’s very peaceful and everyone in my group slept well. I hope to be back in the warmer weather to swim, kayak, and unwind.

Home in Preston

What guests are saying

Newly built twin beach house within steps to beach

5 out of 5 average rating, 8 reviews8 months ago

We stayed here for a wedding at The Burr Mansion, which was extremely close to the house! The house was clean and updated. A few spots to walk to including a local bar. Just a walk to the beach. Bedrooms are all spacious and were very clean. Would definitely stay again.

Home in Fairfield