House vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Madison house rentals
House rentals with a pool
Home in Stamford
4.97 out of 5 average rating, 220 reviewsMidcentury Modern ZenHouse Sculptor Studio
Dec 24 – 31
Home in Shelter Island
4.97 out of 5 average rating, 197 reviewsHuge Island Getaway Pool HotTub Walk To Beach
Dec 5 – 12
Home in Montville
4.96 out of 5 average rating, 106 reviewsCasino Stay & Play House
Aug 1 – 8
Home in Sag Harbor
4.89 out of 5 average rating, 166 reviewsKiddo Approved! Heated Pool/Hotub Renovated Home
Oct 18 – 25
Home in Pound Ridge
5.0 out of 5 average rating, 126 reviewsPeaceful Light-Filled Guesthouse 1 Hour From NYC
Dec 14 – 21
Home in Manorville
4.99 out of 5 average rating, 201 reviewsUltimate House with Heated Pool, Hot Tub and Sauna
Oct 20 – 27
Home in Sag Harbor
4.94 out of 5 average rating, 102 reviewsSag Harbor Village Cottage with Pool
Jun 11 – 18
Home in Litchfield
4.93 out of 5 average rating, 163 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
Sep 12 – 19
Weekly house rentals
Home in North Haven
5.0 out of 5 average rating, 123 reviewsLuxury Stay in Expansive Historical Home
Sep 16 – 23
Home in New Haven
4.97 out of 5 average rating, 126 reviewsWaterviewsTakeWedding pics,CollegeTours Yale&Beach
Apr 10 – 17
Home in Madison
5.0 out of 5 average rating, 22 reviewsWriter's Retreat & Explorer's Adventure!
Sep 6 – 13
Home in Guilford
4.89 out of 5 average rating, 38 reviewsGuilford cozy in-law apt with private entrance
Sep 2 – 9
Home in Haddam
5.0 out of 5 average rating, 78 reviewsCozy Comforts!
Jan 20 – 27
Home in Madison
4.81 out of 5 average rating, 16 reviewsCharming beach cottage in Madison, CT
Feb 6 – 13
Home in Madison
4.91 out of 5 average rating, 34 reviewsCoastal getaway with water views in every room
Jun 20 – 27
Home in Madison
5.0 out of 5 average rating, 17 reviewsNewly Renovated Beach Cottage!
Sep 11 – 18
Private house rentals
Home in Madison
4.85 out of 5 average rating, 13 reviews7 Min Walk to Water: Cheerful 4 Bedroom Home
Oct 12 – 19
Home in Madison
5.0 out of 5 average rating, 9 reviewsMadison Riverside Retreat
Jul 20 – 27
Home in Guilford
5.0 out of 5 average rating, 7 reviewsCoast and Country Private Estate
Nov 20 – 27
Home in Guilford
5.0 out of 5 average rating, 36 reviewsCoastal Farmhouse walking distance to town
May 15 – 22
Home in Guilford
5.0 out of 5 average rating, 11 reviewsThe Osprey Nest w/views of Long Island Sound
Sep 11 – 18
Home in Madison
4.87 out of 5 average rating, 15 reviewsHistoric Beachside Glamour
Sep 18 – 25
Home in Guilford
5.0 out of 5 average rating, 46 reviewsField of Dreams Hot Tub - Fire Pit Retreat
Jun 17 – 24
Home in Madison
5.0 out of 5 average rating, 35 reviewsSpacious Newly Furnished 4 BR Near Beach and Town
May 19 – 24
Quick stats about house rentals in Madison
Total rentals
60 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
50 properties are a good fit for families
Total number of reviews
1.5K reviews
Destinations to explore
- New City Vacation rentals
- Long Island Vacation rentals
- Newark Vacation rentals
- Montauk Vacation rentals
- Hoboken Vacation rentals
- Washington Vacation rentals
- Philadelphia Vacation rentals
- Jersey City Vacation rentals
- New York Vacation rentals
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Montreal Vacation rentals
- Townhouse rentals New York
- Guesthouse rentals New York
- Lakehouse rentals New York
- Tiny house rentals New York
- House rentals New York
- Beach house rentals New York
- Earth house rentals United States
- House rentals United States
- Guesthouse rentals United States
- Townhouse rentals United States
- Lighthouse rentals United States
- Guesthouse rentals Manhattan
- House rentals Manhattan
- Townhouse rentals Manhattan
- Townhouse rentals Brooklyn
- House rentals Brooklyn
- Guesthouse rentals Brooklyn
- Guesthouse rentals Connecticut
- Beach house rentals Connecticut
- Tiny house rentals Connecticut
- Townhouse rentals Connecticut
- House rentals Connecticut
- Lakehouse rentals Connecticut
- Monthly Rentals Madison
- Rentals with a fireplace Madison
- Pet-friendly rentals Madison
- Rentals with beach access Madison
- Rentals with a washer and dryer Madison
- Family-friendly rentals Madison
- Rentals with a patio Madison
- Rentals with a fire pit Madison
- Kid-friendly rentals Madison
- Cottage rentals Madison
- Waterfront rentals Madison
- Rentals with outdoor seating Madison
- Guesthouse rentals New Haven County
- House rentals New Haven County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom