
House vacation rentals in Madison
Find and book unique houses on Airbnb
Quick stats about house rentals in Madison

Total vacation rentals
Explore 60 vacation rentals in Madison

Nightly prices starting at
Madison vacation rentals start at G$14,619 GYD per night before taxes and fees

Verified guest reviews
Over 2,140 verified reviews to help you choose

Family-friendly vacation rentals
50 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
60 of Madison vacation rentals include wi-fi 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!
Top-rated house rentals in Madison
Guests agree: these houses are highly rated for location, cleanliness, and more.

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.

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON
INSTANT BOOK: June 2026 - Jan 2027 = All Open Availability SUMMER 2026: June + July + Aug $2995 TOTAL COST 4 DAY PACKAGE: Sat 6/27 - Wed 7/1 Steps away from CT Shoreline in back of beach house! Amazing Views - Waterfront Outdoor Deck w/ Seating (2nd week May - until Nov 6th) *certain holidays/summer excluded in booking minimums *discounts applied to nightly rate only *we can not combine multiple discounts, yet highest % will apply *if available, also apply 10% non-refundable booking option

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.

3BR Waterfront Oasis on Joshua Cove, Private Beach
Kick back & relax in this modern, stylish waterfront home with a private beach. Newly renovated, this house offers beautiful, unobstructed views of the Long Island Sound and a backyard equipped with an outdoor patio & dining area, hammock, firepit, adirondack chairs, chaise lounges, and cushioned outdoor furniture (in season). You can enjoy swimming at the home's private beach in summer, leaf-peeping in fall, and bird watching in spring. The house is located 5 minutes from downtown Guilford.

“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.

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.

The Farmhouse
Enjoy staying at our charming Farmhouse in the heart of our working dairy farm. Our farm sits on some of the most beautiful hills in Cornwall with the famous Gateway to Cornwall view where you can see our dairy cows grazing in the grandeur of nature. Come say hello to the cows in the barn during milking or watch the herd cross the road evoking sites you might expect to see in small European farming villages. You'll likely see us on our tractors bringing hay and water to our cows!

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

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!

Coastal getaway with water views in every room
This sophisticated getaway by the sea overlooks the Long Island Sound. The bedrooms offer views of the beautiful and diverse East River. The second floor provides a second living room and another expansive look at the Long Island Sound. Recently completed, this property is the ultimate way to unwind in style!
Popular amenities for Madison house rentals
House rentals with a pool

Private Oasis W/Stunning Vinyard and Pool Views

3 BR/Pool. Walk to Beach & Town!

Breathtaking home with unforgettable views & pool!

Serene with large pool ~ 1 block to water + dining

Sag Harbor, Designer w large Pool (3 bed/2.5 bath)

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

Secluded Farmhouse - Studio Apartment Style Unit

Explore the Water & Woods at a Relaxing Retreat
Weekly house rentals

Adorable Beach House on LI Sound

The Davis House

Boulder Lake House Retreat

Guilford Field House

Soundscape Beachfront House!

Coastal Farmhouse walking distance to town

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

Mulberry Seaside Cottage
Private house rentals

Scenic Mulberry Point Connecticut Beach House

Beachside Bliss w/ Game Room, Gym & Golf Green

Bliss by the Sea - Cozy Beachside Escape

Whispering Meadow House

5* Branford Cottage with access to Owenego Club.

Fortune Retreat

Zaku’s Lake House

Charming 3 bedroom Beach Front Cottage
When is the best time to visit Madison?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$64,115 GYD | G$71,007 GYD | G$72,051 GYD | G$78,316 GYD | G$83,328 GYD | G$99,201 GYD | G$91,473 GYD | G$92,935 GYD | G$83,537 GYD | G$79,778 GYD | G$69,962 GYD | G$83,955 GYD |
| 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 |
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- Rentals with a patio Madison
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- Yale University
- Mohegan Sun
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- Fairfield Beach
- Charlestown Beach
- Ocean Beach Park
- Southampton Beach
- Mystic Aquarium
- Mystic Seaport Museum
- Sunken Meadow State Park
- Hammonasset Beach State Park
- University of Connecticut
- Powder Ridge Mountain Park & Resort
- Sleeping Giant State Park
- Compo Beach
- Ski Sundown
- Yale University Art Gallery
- Long Island Aquarium
- Wölffer Estate Vineyard
- Sherwood Island State Park
- Meschutt Beach
- Wesleyan University
- Mount Southington Ski Area





