House vacation 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.
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
Nov 29 – Dec 6
Home in Montville
4.96 out of 5 average rating, 106 reviewsCasino Stay & Play House
May 31 – Jun 7
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 Sag Harbor
4.89 out of 5 average rating, 167 reviewsKiddo Approved! Heated Pool/Hotub Renovated Home
Oct 24 – 31
Home in Cutchogue
4.96 out of 5 average rating, 190 reviewsPrivate Oasis W/Stunning Vinyard And Pool Views
Mar 9 – 16
Home in Hampton Bays
4.98 out of 5 average rating, 112 reviewsBeach House Feel - newly renovated backyard Oasis
Sep 14 – 21
Home in Litchfield
4.93 out of 5 average rating, 165 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
Sep 4 – 11
Home in Sag Harbor
4.85 out of 5 average rating, 250 reviewsExclusive Sag Harbor Compound
Dec 2 – 9
Weekly house rentals
Home in New Haven
4.97 out of 5 average rating, 126 reviewsWaterviewsTakeWedding pics,CollegeTours Yale&Beach
Aug 30 – Sep 6
Home in Centerport
4.94 out of 5 average rating, 114 reviewsThe Harbor House: Beachfront Home 1 hour from NYC
Aug 14 – 21
Home in East Lyme
4.94 out of 5 average rating, 103 reviewsPRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC
Dec 27 – Jan 3
Home in Chester
4.98 out of 5 average rating, 197 reviewsStunning Artisan Waterfall Escape, Walk Downtown
Feb 6 – 13
Home in Guilford
4.9 out of 5 average rating, 39 reviewsGuilford cozy in-law apt with private entrance
Oct 22 – 29
Home in Guilford
4.95 out of 5 average rating, 19 reviewsTiny home one block from the town green.
Mar 3 – 10
Home in Madison
5.0 out of 5 average rating, 23 reviewsWriter's Retreat & Explorer's Adventure!
Sep 10 – 17
Home in Madison
4.81 out of 5 average rating, 16 reviewsCharming beach cottage in Madison, CT
Oct 21 – 28
Private house rentals
Home in Old Saybrook
4.96 out of 5 average rating, 50 reviewsSteps to Beach! *Cozy Cottage* Pet Friendly
Nov 29 – Dec 6
Home in Madison
4.85 out of 5 average rating, 13 reviews7 Min Walk to Water: Cheerful 4 Bedroom Home
Sep 4 – 11
Home in Clinton
5.0 out of 5 average rating, 18 reviewsSoundscape Beachfront House!
Sep 22 – 29
Home in Madison
5.0 out of 5 average rating, 9 reviewsMadison Riverside Retreat
Sep 2 – 9
Home in Guilford
5.0 out of 5 average rating, 7 reviewsCoast and Country Private Estate
Jan 2 – 9
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, 11 reviewsThe Osprey Nest w/views of Long Island Sound
Oct 31 – Nov 7
Home in Guilford
5.0 out of 5 average rating, 36 reviewsCoastal Farmhouse walking distance to town
Oct 12 – 19
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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