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 Madison house rentals
House rentals with a pool
Home in Stamford
4.97 out of 5 average rating, 220 reviewsMidcentury Modern ZenHouse Sculptor Studio
24–31 Dec
Home in Montville
4.96 out of 5 average rating, 106 reviewsCasino Stay & Play House
3–10 Jun
Home in Pound Ridge
5.0 out of 5 average rating, 126 reviewsPeaceful Light-Filled Guesthouse 1 Hour From NYC
14–21 Dec
Home in Sag Harbor
4.89 out of 5 average rating, 166 reviewsKiddo Approved! Heated Pool/Hotub Renovated Home
24 Sep – 1 Oct
Home in Manorville
4.99 out of 5 average rating, 200 reviewsUltimate House with Heated Pool, Hot Tub and Sauna
13–20 Oct
Home in Litchfield
4.93 out of 5 average rating, 163 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
12–19 Sep
Home in Hampton Bays
4.98 out of 5 average rating, 112 reviewsBeach House Feel - newly renovated backyard Oasis
7–14 Aug
Home in East Hampton
4.97 out of 5 average rating, 116 reviewsExplore the Water & Woods at a Relaxing Retreat
30 Dec – 6 Jan
Weekly house rentals
Home in New Haven
4.97 out of 5 average rating, 125 reviewsWaterviewsTakeWedding pics,CollegeTours Yale&Beach
27 Sep – 4 Oct
Home in Centerport
4.94 out of 5 average rating, 114 reviewsThe Harbor House: Beachfront Home 1 hour from NYC
27 Jul – 3 Aug
Home in North Haven
5.0 out of 5 average rating, 123 reviewsLuxury Stay in Expansive Historical Home
17–24 Apr
Home in Madison
5.0 out of 5 average rating, 22 reviewsWriter's Retreat & Explorer's Adventure!
2–9 Jan
Home in Guilford
4.89 out of 5 average rating, 38 reviewsGuilford cozy in-law apt with private entrance
1–8 Sep
Home in Madison
4.81 out of 5 average rating, 16 reviewsCharming beach cottage in Madison, CT
24 Apr – 1 May
Home in Madison
5.0 out of 5 average rating, 17 reviewsNewly Renovated Beach Cottage!
7–14 Sep
Home in Madison
5.0 out of 5 average rating, 9 reviewsStylish Modern Home, 4-Bedroom, Madison CT
27 Sep – 4 Oct
Private house rentals
Home in Madison
4.85 out of 5 average rating, 13 reviews7 Min Walk to Water: Cheerful 4 Bedroom Home
7–14 Dec
Home in Clinton
5.0 out of 5 average rating, 18 reviewsSoundscape Beachfront House!
25 Sep – 2 Oct
Home in Westbrook
5.0 out of 5 average rating, 27 reviewsSea Salt Air Changes Everything
16–23 Dec
Home in Guilford
5.0 out of 5 average rating, 7 reviewsCoast and Country Private Estate
10–17 Nov
Home in Madison
5.0 out of 5 average rating, 9 reviewsMadison Riverside Retreat
2–9 Oct
Home in Guilford
5.0 out of 5 average rating, 11 reviewsThe Osprey Nest w/views of Long Island Sound
9–16 Sep
Home in Guilford
5.0 out of 5 average rating, 36 reviewsCoastal Farmhouse walking distance to town
12–19 Aug
Home in Guilford
5.0 out of 5 average rating, 46 reviewsField of Dreams Hot Tub - Fire Pit Retreat
21–28 Jun
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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