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
Sep 17 – 24
Home in Shelter Island
4.97 out of 5 average rating, 194 reviewsHuge Island Getaway Pool HotTub Walk To Beach
Feb 6 – 13
Home in Pound Ridge
5.0 out of 5 average rating, 126 reviewsPeaceful Light-Filled Guesthouse 1 Hour From NYC
Sep 18 – 25
Home in Manorville
4.98 out of 5 average rating, 199 reviewsUltimate House with Heated Pool, Hot Tub and Sauna
Oct 3 – 10
Home in Montville
4.96 out of 5 average rating, 106 reviewsCasino Stay & Play House
May 16 – 23
Home in Sag Harbor
4.85 out of 5 average rating, 250 reviewsExclusive Sag Harbor Compound
Dec 4 – 11
Home in East Hampton
4.93 out of 5 average rating, 140 reviews1800 Historical East Hampton Home, 1 Mile to Town!
Sep 30 – Oct 7
Home in Hampton Bays
4.98 out of 5 average rating, 112 reviewsBeach House Feel - newly renovated backyard Oasis
Oct 25 – Nov 1
Weekly house rentals
Home in North Haven
5.0 out of 5 average rating, 123 reviewsLuxury Stay in Expansive Historical Home
Mar 15 – 22
Home in Greenport
4.92 out of 5 average rating, 423 reviewsBlue Bay Dream
Jan 16 – 23
Home in Madison
5.0 out of 5 average rating, 21 reviewsWriter's Retreat & Explorer's Adventure!
Dec 24 – 31
Home in Guilford
4.95 out of 5 average rating, 19 reviewsTiny home one block from the town green.
Mar 27 – Apr 3
Home in Madison
4.8 out of 5 average rating, 15 reviewsCharming beach cottage in Madison, CT
Jun 16 – 23
Home in Guilford
4.89 out of 5 average rating, 38 reviewsGuilford cozy in-law apt with private entrance
Aug 26 – Sep 2
Home in Haddam
5.0 out of 5 average rating, 78 reviewsCozy Comforts!
Aug 18 – 25
Home in Madison
4.91 out of 5 average rating, 34 reviewsCoastal getaway with water views in every room
Jun 21 – 28
Private house rentals
Home in Clinton
5.0 out of 5 average rating, 18 reviewsSoundscape Beachfront House!
May 1 – 8
Home in Madison
5.0 out of 5 average rating, 9 reviewsMadison Riverside Retreat
Jul 14 – 21
Home in Guilford
5.0 out of 5 average rating, 7 reviewsCoast and Country Private Estate
Oct 3 – 10
Home in Westbrook
5.0 out of 5 average rating, 27 reviewsSea Salt Air Changes Everything
Dec 21 – 28
Home in Guilford
5.0 out of 5 average rating, 46 reviewsField of Dreams Hot Tub - Fire Pit Retreat
Dec 9 – 16
Home in Guilford
5.0 out of 5 average rating, 36 reviewsCoastal Farmhouse walking distance to town
Jul 26 – Aug 2
Home in Madison
5.0 out of 5 average rating, 35 reviewsSpacious Newly Furnished 4 BR Near Beach and Town
May 19 – 24
Home in Milford
4.98 out of 5 average rating, 64 reviews2 Bedroom with sweeping views of Long Island Sound
May 8 – 15
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
- Beach house rentals New York
- Guesthouse rentals New York
- Lakehouse rentals New York
- Tiny house rentals New York
- House rentals New York
- Guesthouse rentals United States
- Townhouse rentals United States
- Lighthouse rentals United States
- House rentals United States
- Earth house rentals United States
- Townhouse rentals Manhattan
- House rentals Manhattan
- Guesthouse rentals Manhattan
- Guesthouse rentals Brooklyn
- Townhouse rentals Brooklyn
- House rentals Brooklyn
- Guesthouse rentals Connecticut
- Lakehouse rentals Connecticut
- House rentals Connecticut
- Townhouse rentals Connecticut
- Tiny house rentals Connecticut
- Beach house rentals Connecticut
- Rentals with a fire pit Madison
- Waterfront rentals Madison
- Family-friendly rentals Madison
- Rentals with outdoor seating Madison
- Pet-friendly rentals Madison
- Rentals with beach access Madison
- Rentals with a washer and dryer Madison
- Cottage rentals Madison
- Monthly Rentals Madison
- Rentals with a fireplace Madison
- Rentals with a patio Madison
- Kid-friendly rentals Madison
- Guesthouse rentals New Haven County
- House rentals New Haven County
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- 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
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes