House holiday 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.

1 of 1 pages1 / 1
Top guest favourite
Home in Milford
5 out of 5 average rating, 140 reviews

Fully renovated/Walk to water & shops/fenced yard!

*Feb and Mar available for longer stays!Inquire!* *Brand New Major Renovation in 2023* • Fully renovated, designer beach house • Steps away from quaint downtown •1 block from water •Walk to beach, restaurants, coffee, ice cream, deli & convenience store, liquor and more... • Luxe, white, 100% cotton sheets & fluffy duvets •FULLY FENCED backyard with outdoor seating, BBQ grill, & fire pit .Easy drive to Sacred Heart, Fairfield, & Yale .STEPS to Tyde wedding venue .Fiber internet for fast speed

Guest favourite
A charming two-story farmhouse is surrounded by well-maintained greenery. The white exterior is complemented by dark shutters and a stone chimney. Steps lead to a welcoming front entrance, while manicured bushes and trees provide a natural border around the property.
Home in Guilford
4.82 out of 5 average rating, 120 reviews

Spacious 5 BR Home near town

Spacious 5 Bedroom 2 story farmhouse in quiet neighborhood of Historic Guilford. Perfect for family gatherings, reunions, special occasions, traveling work crews, or a simple vacation getaway. There is ample room for everyone to relax and unwind. The kitchen is stocked with enough dinnerware and appliances for all Just 1 mile from town, the home offers easy access to I-95, New Haven, Yale Univ. and the scenic Connecticut shoreline. Hiking trails & local PYO Farm Market are a short walk away.

Top guest favourite
A tranquil lake scene is captured at sunrise, featuring a wooden dock extending into the water. Soft pink and orange hues reflect on the lake's surface, complementing the surrounding greenery. Two Adirondack chairs sit near a fire pit, inviting relaxation by the scenic view.
Home in East Haddam
4.93 out of 5 average rating, 323 reviews

Romantic Getaway at The Lake!

Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.

Guest favourite
A charming cottage is set amidst lush greenery and colorful hydrangeas. The front porch is adorned with rocking chairs, inviting relaxation. A red door adds a vibrant contrast to the light exterior, while gravel pathways guide the way through the well-kept yard.
Home in Madison
4.96 out of 5 average rating, 27 reviews

Perfect Cape Beach Cottage in Madison CT!

Come enjoy your perfectly quintessential New England vacation in this beautiful beach cottage in Madison, Conncecticut - modern, luxe, and pull-at-your-heart-strings-endearing, your worries will melt away in this peaceful property. DEEDED BEACH ACCESS TO PRIVATE NEIGHBORHOOD SANDY BEACH - pics of the beach included. Note that bedrooms are located at the top of a (one-story) spiral staircase - if anyone in your party has mobility issues or questions on access, please contact host for inputs.

Guest favourite
An aerial view showcases a coastal neighborhood with homes situated along a sandy beach. Vibrant blue waters and marshlands surround the area, emphasizing its seaside location. The arrow points to the property's location within the community, illustrating proximity to the beach.
Home in Milford
4.97 out of 5 average rating, 263 reviews

Designer Beach Retreat on Exclusive Cedar Beach

Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!

Top guest favourite
An open-concept kitchen and living space features modern appliances and a wood-topped island with seating for three. Light cabinets and blue walls create a bright environment, while a hallway visible in the background leads to the entrance of the cottage.
Home in Branford
4.98 out of 5 average rating, 233 reviews

“The Lighthouse” A Beach Cottage by the Sea!

Relax at this unique and tranquil getaway. Long Island Sound to the left, hiking trails to the right. Come kick your feet up at this quiet dead-end road. Enjoy all the modern amenities in this gem of a cottage community. Restaurants and nightlife are just a quick stroll away. Avoid roadside hotels and take a vacation for a night, week, or longer! Check in anytime and at your convenience!No keys to lose or to return! This property provides secure, keyless entry with an August Smart Lock!

Guest favourite
A historic New England home features a classic white exterior with multiple windows. Surrounding greenery includes mature trees and a well-maintained lawn. The side of the house provides a glimpse of a separate structure, enhancing the spacious outdoor area.
Home
4.97 out of 5 average rating, 211 reviews

Waterside Beach Retreat

Beautiful New England period home steps from the beach on the Long Island Sound. Recently renovated from top to bottom with new kitchen and bathrooms, hardwood floors throughout. Idyllic location on quaint & quiet street. Hide away and relax or discover the many local attractions - water sports, fishing, winery, antique stores, scenic walks, premium outlet shopping are all on your doorstep. Ideally located off the I-95 halfway between NYC & Boston, both of which are a train ride away.

Guest favourite
A spacious living area features large windows that allow natural light to fill the room. Neutral-coloured furnishings, including a sectional sofa and a sleek wooden TV console, create an inviting space. Decorative elements, such as a geometric wall art piece, enhance the modern aesthetic.
Home in Guilford
4.92 out of 5 average rating, 51 reviews

Beach Sanctuary on the Long Island Sound

Kick back and relax in this stylish, retro, newly renovated coastal oasis with beach access & stunning views of the Long Island Sound. You can enjoy bird watching in the backyard garden in the spring, swimming and fishing at the private association beach in the summer, and leaf-peeping in the fall. The Beach Sanctuary is located in charming, historic Guilford CT, minutes from the town green, train station, local restaurants, and shopping as well as 20 minutes from New Haven and Yale.

Guest favourite
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
4.92 out of 5 average rating, 181 reviews

Amazing 2BR Riverfront Gem

Unwind at this happy getaway on the river. Extremely comfortable house with amazing views in a peaceful neighborhood. The well-equipped kitchen overlooking the river is a pleasure for any cook. You will love to see our fairy-lit lawn, wishing well, chimenea, and charming décor. Only minutes to beaches, groceries, coffee shops, hiking trails and amazing CT scenery at every turn! Other favorites include Chamard Vineyard, Shopping Outlets, fantastic Restaurants, music, and lots more.

Guest favourite
A comfortable living area features a light-colored sofa accompanied by two lamps on side tables. A textured area rug lies beneath a coffee table, while natural light filters through multiple windows, creating a bright and open space. A dining area is visible in the background.
Home in Branford
4.93 out of 5 average rating, 130 reviews

Charming home, easy access to everything Branford

Full home, comfortable and very well equipped. Private fenced in backyard with patio dining area. Off-street (driveway) parking. Short Walk to the Shoreline Greenway trail. Less than a mile to downtown, parks, beaches, restaurants, marina, Stoney Creek Brewery. Near event venues, The Owenego and Pine Orchard club. Close to New Haven. Family(kid) Friendly home with private fenced in backyard with patio dining area. Equipped with Pack N Play, highchair, booster seat, etc

Top guest favourite
Home in Madison
5 out of 5 average rating, 45 reviews

Stylish Modern Home, 4-Bedroom, Madison CT

Beautiful 4-Bedroom Residential Home in Madison, Connecticut - Contemporary Scandinavian Interior Design - Close to Local/State Beaches (~10 Minute Drive) - Close to Local Parks and Hiking Areas (~3 Minute Drive) - Welcoming Open Floorplan - Quality Furnishings and Finishes - Up-to-Date/Modern Features/Clean and Comfortable - Wonderful Garden and Grass Lawn - Private (House Sits on 2-Acre Parcel) - Enclosed Outdoor Shower - Surrounded by Natural Beauty of the Countryside

Top guest favourite
A living area features a comfortable sectional sofa adorned with decorative pillows. Two light blue armchairs are positioned beside a small table with a patterned top, while a television stand and a floor lamp complete the inviting space. Sunlight is visible through a window.
Home in Old Saybrook
4.92 out of 5 average rating, 107 reviews

Best of both worlds!

Great location- 1 mile to the beach, 1/2 mile to shops and restaurants, and less than a 1/4 mile to a park! The house is set back from the road with a good size driveway. The inside is newly renovated and we are working to finish the yard area for the summer! The house has WiFi, large yard, and a great front porch that gets a ton of sun. We’ve made great memories there over the years and are now looking to share it with others!

Popular amenities for house rentals in Madison

When is the best time to visit Madison?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price£228£253£256£279£296£353£325£331£297£284£249£299
Avg. temp0°C1°C4°C10°C16°C21°C24°C24°C20°C14°C8°C3°C

Quick stats about house rentals in Madison

  • Total holiday rentals

    Explore 60 holiday rentals in Madison

  • Nightly prices starting at

    Madison holiday rentals start at £52 per night before taxes and fees

  • Verified guest reviews

    Over 2,140 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    60 of Madison holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Madison rentals

  • 4.9 Average rating

    Madison stays are highly rated by guests – averaging 4.9 out of 5!