House holiday rentals in Madison
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Top-rated house rentals in Madison
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Madison
House rentals with a pool
Home in Stamford
4.97 out of 5 average rating, 220 reviewsMidcentury Modern ZenHouse Sculptor Studio
17–24 Sept
Home in Shelter Island
4.97 out of 5 average rating, 194 reviewsHuge Island Getaway Pool HotTub Walk To Beach
6–13 Feb
Home in Pound Ridge
5.0 out of 5 average rating, 126 reviewsPeaceful Light-Filled Guesthouse 1 Hour From NYC
18–25 Sept
Home in Manorville
4.98 out of 5 average rating, 199 reviewsUltimate House with Heated Pool, Hot Tub and Sauna
3–10 Oct
Home in Montville
4.96 out of 5 average rating, 106 reviewsCasino Stay & Play House
16–23 May
Home in Sag Harbor
4.85 out of 5 average rating, 250 reviewsExclusive Sag Harbor Compound
4–11 Dec
Home in East Hampton
4.93 out of 5 average rating, 140 reviews1800 Historical East Hampton Home, 1 Mile to Town!
30 Sept – 7 Oct
Home in Hampton Bays
4.98 out of 5 average rating, 112 reviewsBeach House Feel - newly renovated backyard Oasis
25 Oct – 1 Nov
Weekly house rentals
Home in North Haven
5.0 out of 5 average rating, 123 reviewsLuxury Stay in Expansive Historical Home
15–22 Mar
Home in Greenport
4.92 out of 5 average rating, 423 reviewsBlue Bay Dream
16–23 Jan
Home in Madison
5.0 out of 5 average rating, 20 reviewsWriter's Retreat & Explorer's Adventure!
24–31 Dec
Home in Guilford
4.95 out of 5 average rating, 19 reviewsTiny home one block from the town green.
27 Mar – 3 Apr
Home in Madison
4.8 out of 5 average rating, 15 reviewsCharming beach cottage in Madison, CT
16–23 Jun
Home in Guilford
4.89 out of 5 average rating, 38 reviewsGuilford cozy in-law apt with private entrance
26 Aug – 2 Sept
Home in Haddam
5.0 out of 5 average rating, 78 reviewsCozy Comforts!
18–25 Aug
Home in Madison
4.91 out of 5 average rating, 34 reviewsCoastal getaway with water views in every room
21–28 Jun
Private house rentals
Home in Clinton
5.0 out of 5 average rating, 18 reviewsSoundscape Beachfront House!
1–8 May
Home in Madison
5.0 out of 5 average rating, 9 reviewsMadison Riverside Retreat
14–21 Jul
Home in Guilford
5.0 out of 5 average rating, 7 reviewsCoast and Country Private Estate
3–10 Oct
Home in Westbrook
5.0 out of 5 average rating, 27 reviewsSea Salt Air Changes Everything
21–28 Dec
Home in Guilford
5.0 out of 5 average rating, 46 reviewsField of Dreams Hot Tub - Fire Pit Retreat
9–16 Dec
Home in Guilford
5.0 out of 5 average rating, 36 reviewsCoastal Farmhouse walking distance to town
26 Jul – 2 Aug
Home in Madison
5.0 out of 5 average rating, 35 reviewsSpacious Newly Furnished 4 BR Near Beach and Town
19–24 May
Home in Milford
4.98 out of 5 average rating, 64 reviews2 Bedroom with sweeping views of Long Island Sound
8–15 May
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
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