
House holiday rentals in Madison
Find and book unique houses on Airbnb
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 $99 AUD per night before taxes and fees

Verified guest reviews
Over 2,270 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
60 of Madison holiday 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.

The Dragon Fly Garden
The phrase "nestled in nature” is the best way to describe the dragonfly's den. Sitting on the trail head to over 1,000 acres of the Cocaponsette State Forest across from Messerschmidt pond and just three miles from the winding salt water marsh water way you won't find a better mix of activities. Golf & boating are just moments away. Mountain biking & Trail running off the property. This country cottage boasts lake views, wildlife and wandering trails to loose yourself within. 1GB internet

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.

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!

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.

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.

Cozy Comforts!
Keep it simple at this peaceful and centrally-located place. Completely open concept and fully renovated. Country living yet just minutes to downtown Middletown and Wesleyan University. Come stay at our home away from home! We are about 20-25 min from the shoreline or travel in the other direction and you’ll be in our state’s capital, Hartford. We are only about 10-15 min from Wesleyan and downtown Middletown for shopping and great restaurants! You don’t want to miss this one!

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

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.

The Connecticut Cottage | Historic Modern Charm
Welcome to The Connecticut Cottage — a beautifully restored 1790s stone cottage blending historic New England charm with modern comfort. Thoughtfully renovated from top to bottom, this one-of-a-kind home offers the perfect mix of cozy escape and central convenience along the Connecticut shoreline. Whether you're planning a laid-back coastal getaway or exploring some of New England’s most iconic destinations, you’re perfectly positioned!!

Adorable Beach House on LI Sound
Beach House with incredible views of the Thimble Islands - 4 min walk to Restaurants including Lenny’s, Zagat award winner for fresh local seafood - 1 min walk to Bud’s Fish Market - 3 min walk to Indian Neck Liquor - 3 min drive to brewery w/ food trucks & music - 4 min drive to Branford Green w/ specialty stores, coffee & ice cream
Popular amenities for Madison house rentals
House rentals with a pool

Private Oasis W/Stunning Vinyard and Pool Views

Breathtaking home with unforgettable views & pool!

Serene East Hampton Escape - Stars Forest Sauna

Serene w/ large pool ~1 block to waterfront dining

East Hampton Oasis - Pool and Hot Tub

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

Secluded Farmhouse - Studio Apartment Style Unit

Modern farmhouse w/ pool, beach, horses and winery
Weekly house rentals

Historic Coastal Home • Marsh Views • Pet-Friendly

Boulder Lake House Retreat

Guilford Field House

New England shoreline charm, private beach access

Mulberry Seaside Cottage

Fortune Retreat

Remodeled Cottage in a Marina!

Red Bird Waterfront Home. Dock available extra!
Private house rentals

NEW Charming Coastal Bungalow steps from the Beach

Blaisdell Point -Indian River

The Davis House

Coastal Getaway on Marsh Near Beach, Town, Trails

Purple Button Factory Sleeps 8, Walk to Town Green

The Saybrook Point Bungalow, Stroll to Downtown

Field of Dreams Hot Tub - Fire Pit Retreat

Entire home - Cheerful 4 bedroom on the shoreline.
When is the best time to visit Madison?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $433 AUD | $480 AUD | $487 AUD | $494 AUD | $539 AUD | $535 AUD | $618 AUD | $628 AUD | $565 AUD | $539 AUD | $473 AUD | $567 AUD |
| 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
- New York City Holiday rentals
- Montreal Holiday rentals
- Philadelphia Holiday rentals
- Washington Holiday rentals
- Boston Holiday rentals
- Ocean City Holiday rentals
- Portland Holiday rentals
- Jersey City Holiday rentals
- Baltimore Holiday rentals
- Newark Holiday rentals
- Newport Holiday rentals
- Atlantic City Holiday rentals
- Yale University
- Mohegan Sun
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- Fairfield Beach
- Ocean Beach Park
- Charlestown Beach
- Mystic Aquarium
- Mystic Seaport Museum
- Southampton Beach
- Sunken Meadow State Park
- University of Connecticut
- Soundview Beach
- Hammonasset Beach State Park
- Compo Beach
- Powder Ridge Mountain Park & Resort
- Ocean Beach
- Sleeping Giant State Park
- Wölffer Estate Vineyard
- Sherwood Island State Park
- Yale University Art Gallery
- Ski Sundown
- Orient Beach State Park
- Meschutt Beach





