
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$14,645 GYD per night before taxes and fees

Verified guest reviews
Over 2,270 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.

Beachfront Paradise
Beautiful beachfront home available weekly in season third week of June through Labor Day) and nightly (2 night min.) off season. Step out the door and into the sand. Sit on the porch and watch sailboat races from Niantic Bay Yacht Club just steps away. Close to downtown Niantic with restaurants, shops, etc. 18 miles from Mohegan Sun Casino. Attractions within 1/2 hour: Beautiful Mystic, CT, several vineyards, Harkness State Park, Eugene O'Neill Theatre, U.S. Coast Guard Academy, golf courses.
FamilyLocationGrill

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.
LocationFamilyLong stay

Year Round Beach House in Old Saybrook, CT.- Pets
Our Beautiful Home is Located in Saybrook Manor Association and only a short walk to the beach . We have 4 Bedrooms that can accomadate 8 people,pull out couch,2 bathrooms, a Dining Room,Kitchen, and Spacious Living room.Our Yard is fenced in for your privacy & pets.Our home comes with many ammenities such as movies,games,kayaks, Clamming &Crabbing tools,Bikes,Floats & Beach Chairs.We have a beautiful backyard to enjoy games,barbecue or just to relax & unwind.Enjoy our beautiful & quaint beach
ValueLocationKitchen

Steps to Beach! *Cozy Cottage* Pet Friendly
Relax and enjoy the beach life in this newly renovated charmer just steps from The Saybrook Manor Assoc private beach which is only available to Saybrook Manor Assoc members. Enjoy cooking your favorite family meals in our fully stocked kitchen or venture out to some of the best restaurants on The CT Shore with a short 5-15 min drive. Free wifi for work or entertainment , private outdoor patio dining and serenity await you. You will feel at home in our little slice of heaven on The Shore.
FamilyLocationNearby

Modern farmhouse w/ pool, beach, horses and winery
A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.
ValueFamilyGrill

The Lighthouse: Beach Cottage Getaway 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!
LocationFamilyCheckout

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.
FamilyValueAir conditioning

Steps to Beach • Hot Tub • Game Room • Water Views
Beautiful coastal beach house directly across from a private beach and tennis club with complimentary guest access. Backing up to a serene marsh with stunning views, this home offers a peaceful, upscale setting perfect for families and groups. Relax in the hot tub with outdoor TV, fire pit, and kayaks. Inside features 4 bedrooms, a workspace, and a new game room with a 100” TV, pool table, shuffleboard, and darts. Minutes from Branford’s town center, dining, and waterfront attractions.
FamilyLocationCleanliness

Purple Button Factory Sleeps 8, Walk to Town Green
Close to CT shoreline. 4 bdrm, 2 bath, 2,200 sq ft home on dead-end street, across from Meadow River, tidal marsh. Great bird-watching! Mid-week specials. Walk to Guilford Town Green, restaurants, shopping. Fully-equipped kitchen. Wood-burning fireplace. Clean, airy, peaceful space. Eclectic art & beach-comber decor. Large back yard with fire pit. Deck for functions, family gatherings, relaxing. Historic property was once a button factory! Original chestnut, wide-board floors.
ValueFamilyGrill

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.
FamilyLocationView

Hot Tub & Firepit•Sunsets & Beach Walk | Fireplace
Explore our Old Saybrook retreat on Great Hammock Rd, a cozy spot near the beach. Perfect for romance or family fun, it boasts stunning views and amenities. Relax in the hot tub, use bikes for local exploration, and enjoy evenings by the fire pit. Indoors, a fireplace adds warmth. Book now for a delightful getaway with views, memories, and the charm of Old Saybrook! Please note Our property is strictly an animal-free zone due to severe allergies persisting in the family.
FamilyValueComfort

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON
INSTANT BOOK: Sept '26 - End Sept '27 SUMMER 2026: Sept **2027 Summer Available: June - End Sept** 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
FamilyValueComfort
Popular amenities for Madison house rentals
House rentals with a pool

Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton
ValueFamilyWalkability

Breathtaking home with unforgettable views & pool!
ValueLocationIndoor spaces

Serene + chic ~ 8 mins to Main Street + beaches
LocationFamilyWalkability

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

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

Historic Designer Farmhouse - Warm Pool until Nov
ValueLocationPets

Heated Indoor Pool • 4 King Beds • Walk Downtown
FamilyLocationQuiet

Beauty and the Beach!
FamilyValueHeating
Weekly house rentals

Cozy beach cottage close to everthing
LocationFamilyBathroom

Perfect Cape Beach Cottage in Madison CT!
FamilyLocationGetting around

Stylish Modern Home, 4-Bedroom, Madison CT
FamilyLocationBathroom

Coastal getaway with water views in every room
FamilyLocationWalkability

Beach Sanctuary on the Long Island Sound
FamilyLocationOutdoor spaces

The Connecticut Cottage | Historic Modern Charm
FamilyLocationBeach

Historic Beachside Glamour
LocationFamilyQuiet

New England shoreline charm, private beach access
LocationFamilyOutdoor spaces
Private house rentals

Soundscape Beachfront House!
FamilyLocationCleanliness

Beachfront Home with Amazing Views | 5BR Sleeps 11
FamilyComfortAmenities

Remodeled Cottage in a Marina!
FamilyLocationSleep quality

3BR Waterfront Oasis on Joshua Cove, Private Beach
FamilyValueSleep quality

Entire home - Cheerful 4 bedroom on the shoreline.
LocationFamilyNearby

Coastal Farmhouse walking distance to town
FamilyLocationAccuracy

Historic Coastal Home • Marsh Views • Pet-Friendly
FamilyLocationKitchen

Coastal Getaway on Marsh Near Beach, Town, Trails
FamilyLocationAmenities
When is the best time to visit Madison?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$64,231 GYD | G$71,135 GYD | G$72,181 GYD | G$73,227 GYD | G$79,922 GYD | G$79,295 GYD | G$91,639 GYD | G$93,103 GYD | G$83,688 GYD | G$79,922 GYD | G$70,089 GYD | G$84,107 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 |
Destinations to explore
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- Yale University
- Mohegan Sun
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- Fairfield Beach
- Ocean Beach Park
- Charlestown Beach
- Mystic Seaport Museum
- Mystic Aquarium
- Southampton Beach
- University of Connecticut
- Sunken Meadow State Park
- Soundview Beach
- Hammonasset Beach State Park
- Powder Ridge Mountain Park & Resort
- Compo Beach
- Wölffer Estate Vineyard
- Ocean Beach
- Sleeping Giant State Park
- Sherwood Island State Park
- Ski Sundown
- Meschutt Beach
- Orient Beach State Park
- Ditch Plains Beach





