House vacation rentals in Westport
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Top-rated house rentals in Westport
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 Westport house rentals
House rentals with a pool
Home in Stormville
4.94 out of 5 average rating, 156 reviewsPrivate Hudson Valley Country Retreat
Feb 2 – 9
Home in Cheshire
5.0 out of 5 average rating, 118 reviewsPool House
Nov 5 – 12
Home in Cold Spring
4.95 out of 5 average rating, 152 reviewsCozy, Modern Retreat in the Woods of Cold Spring
Feb 16 – 23
Home in Yorktown Heights
4.88 out of 5 average rating, 119 reviewsCozy winter getaway 1 hr from NYC!
Sep 15 – 22
Home in Cutchogue
4.96 out of 5 average rating, 190 reviewsStunning Vinyard Views - Spring Special $475/Nt!
Mar 6 – 13
Home in Putnam Valley
4.93 out of 5 average rating, 182 reviewsPutnam Valley Escape
Oct 1 – 8
Home in Mastic Beach
4.93 out of 5 average rating, 107 reviewsGorgeous Waterfront and Indoor Pool Family Oasis!
Dec 21 – 28
Home in Westhampton Beach
4.93 out of 5 average rating, 134 reviewsHampton's Haven
Oct 30 – Nov 6
Weekly house rentals
Home in Brookhaven
4.95 out of 5 average rating, 129 reviewsBeautiful & Independent Guest House near the water
Feb 16 – 23
Home in Westport
4.89 out of 5 average rating, 46 reviewsWestport/Saugatuck super spot
Aug 27 – Sep 3
Home in Westport
4.92 out of 5 average rating, 38 reviewsGorgeous, luxury Cape in Westport!
Dec 18 – 25
Home in Norwalk
5.0 out of 5 average rating, 34 reviews❤️ Your Silvermine Hideaway, nestled in nature.
Mar 18 – 25
Home in Westport
5.0 out of 5 average rating, 4 reviewsWestport:Private Fire Pit Hideaway 5 min to Town
Jun 5 – 12
Home in Westport
5.0 out of 5 average rating, 19 reviewsCharming & Spacious New England Family Home
Dec 6 – 13
Home in Westport
5.0 out of 5 average rating, 3 reviewsWestport Beach Town Mid-Century Vibe Retreat - Pet
Nov 10 – 17
Home in Westport
5.0 out of 5 average rating, 9 reviewsFarmhouse 1899: Westport, CT
Sep 18 – 25
Private house rentals
Home in Fairfield
5.0 out of 5 average rating, 9 reviewsStillson House - Central Cozy Updated Colonial
Jun 11 – 18
Home in Fairfield
4.96 out of 5 average rating, 55 reviewsModern Beach Bungalow
Jul 4 – 11
Home in Fairfield
5.0 out of 5 average rating, 11 reviewsRemodeled Cozy Country Cape
Mar 2 – 9
Home in Redding
5.0 out of 5 average rating, 18 reviewsQuiet and Cozy Cottage near NYC with a Pond
Mar 24 – 31
Home in Westport
4.93 out of 5 average rating, 14 reviewsBeautiful Brand New Inviting Farmhouse
Jan 7 – 14
Home in Fairfield
5.0 out of 5 average rating, 16 reviews5 Minute Walk to Beach & Downtown Fairfield
Jan 9 – 16
Home in Fairfield
5.0 out of 5 average rating, 6 reviews4BR/2.5BA Refuge Near University, Downtown & Beach
Sep 18 – 25
Home in Milford
5.0 out of 5 average rating, 14 reviewsLuxe Beach House | 3 Bd-King | 4TV | Chef Kitchen
Sep 8 – 15
Quick stats about house rentals in Westport
Total rentals
90 properties
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Rentals with a pool
20 properties have a pool
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
80 properties are a good fit for families
Total number of reviews
870 reviews
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