
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.

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

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.

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.

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.

Mulberry Seaside Cottage
Enjoy direct water views any time of year in this cozy cottage. Relax on the generous porch swing, eat dinner overlooking the water, watch the sunset on the secret waterfront terrace, and stay active kayaking, biking, and swimming. The large backyard is great for yard games. In the cooler months, cozy up to the outdoor gas fire or inside with a book while watching a stunning winter sunset over the water. Minutes to the charming Guilford green, restaurants, Yale University and train station.

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!

“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!

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.

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.

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

Treasured 1924 Colonial "Sweet Caroline"
"Sweet Caroline" is a charming 4 bedroom shoreline colonial that has been recently renovated to provide an up-to-date feel while maintaining it's 1920's charm. We fell in love with this home last summer while visiting friends and family and decided to make it our home away from home. We have enjoyed her so much that we decided to share her with others seeking similar cozy, New England shoreline, accommodations.

Guilford Field House
Enjoy a wonderful guest house with all the amenities on a historic property in Guilford, Connecticut. The main house built in 1779 extends its character to the guest house which has views of an open field. On property there is a working restored horse barn. We are minutes to the spectacular downtown area of Guilford and easy access to Durham, Madison, and other surrounding towns and highways!
Popular amenities for house rentals in Madison
House rentals with a pool

Casino Wine Down House w/Pool, Game Room, Big Deck

Private Oasis W/Stunning Vinyard and Pool Views

Breathtaking home with unforgettable views & pool!

Private & Pristine with Pool and Kid’s Playard

Beach Barn w/ Heated Pool & Sauna - Dog Friendly

Chic + Serene w/ pool~1 block to waterfront dining

Hot Tub~Pool~GameRoom~FirePit~BBQ~King Bed~Casinos

Secluded Farmhouse - Studio Apartment Style Unit
Weekly house rentals

Scenic Mulberry Point Connecticut Beach House

Whispering Meadow House

“11:11” 🙏 Updated Stylish Retreat 🌊 2 Mi To Beach

Fortune Retreat

The Farmhouse Stay

Field of Dreams Hot Tub - Fire Pit Retreat

South Beach Oasis

Entire home - Cheerful 4 bedroom on the shoreline.
Private house rentals

Adorable Cottage with porch, walk to water & town

Private Entire Home • Close to New Haven & Shore

5 Star Branford Cozy Cottage Steps from the Beach

Coastal Getaway - walk to town and waterfront

Cedar Grove

Coast and Country Private Estate

Zaku’s Lake House

Summer is filling up-Beach, Shopping and Golf
When is the best time to visit Madison?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $393 SGD | $435 SGD | $442 SGD | $480 SGD | $511 SGD | $608 SGD | $561 SGD | $570 SGD | $512 SGD | $489 SGD | $429 SGD | $515 SGD |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 16°C | 21°C | 24°C | 24°C | 20°C | 14°C | 8°C | 3°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 $90 SGD 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!
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Waterfront rentals Madison
- Beach house rentals Madison
- Cottage rentals Madison
- Rentals with a fireplace Madison
- Pet-friendly rentals Madison
- Rentals with a patio Madison
- Rentals with beach access Madison
- Flat rentals Madison
- Rentals with a firepit Madison
- Rentals with outdoor seating Madison
- Rentals with a washing machine and dryer Madison
- Beachfront rentals Madison
- Family-friendly rentals Madison
- House rentals Connecticut
- House rentals United States
- Yale University
- Cooper's Beach, Southampton
- Fairfield Beach
- Charlestown Beach
- Ocean Beach Park
- Mohegan Sun
- Sunken Meadow State Park
- Mystic Seaport Museum
- Foxwoods Resort Casino
- Hammonasset Beach State Park
- Sleeping Giant State Park
- Powder Ridge Mountain Park & Resort
- Yale University Art Gallery
- Long Island Aquarium
- Amagansett Beach
- Sherwood Island State Park
- Orient Beach State Park
- Compo Beach
- Ski Sundown
- Ocean Beach
- Mount Southington Ski Area
- University of Connecticut
- Wölffer Estate Vineyard
- Meschutt Beach





