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
Jan 27 – Feb 3
Home in Cheshire
5.0 out of 5 average rating, 118 reviewsPool House
Apr 1 – 8
Home in Cold Spring
4.95 out of 5 average rating, 152 reviewsCozy, Modern Retreat in the Woods of Cold Spring
Sep 21 – 28
Home in Manorville
4.99 out of 5 average rating, 200 reviewsUltimate House with Heated Pool, Hot Tub and Sauna
Oct 13 – 20
Home in Putnam Valley
4.93 out of 5 average rating, 182 reviewsPutnam Valley Escape
Oct 1 – 8
Home in Yorktown Heights
4.88 out of 5 average rating, 119 reviewsCozy winter getaway 1 hr from NYC!
Sep 19 – 26
Home in Mastic Beach
4.93 out of 5 average rating, 107 reviewsGorgeous Waterfront and Indoor Pool Family Oasis!
Jan 16 – 23
Home in Cutchogue
4.96 out of 5 average rating, 190 reviewsStunning Vinyard Views - Spring Special $475/Nt!
Apr 6 – 13
Weekly house rentals
Home in Westport
4.89 out of 5 average rating, 46 reviewsWestport/Saugatuck super spot
Sep 25 – Oct 2
Home in Westport
4.92 out of 5 average rating, 38 reviewsGorgeous, luxury Cape in Westport!
Sep 19 – 26
Home in Westport
5.0 out of 5 average rating, 4 reviewsWestport:Private Fire Pit Hideaway 5 min to Town
Aug 29 – Sep 5
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, 9 reviewsFarmhouse 1899: Westport, CT
Aug 10 – 17
Home in Norwalk
5.0 out of 5 average rating, 34 reviews❤️ Your Silvermine Hideaway, nestled in nature.
Apr 22 – 29
Home in Fairfield
5.0 out of 5 average rating, 64 reviewsFairfield Cottage: Near Beach, Great for Families
Feb 2 – 9
Home in Westport
4.8 out of 5 average rating, 20 reviewsCustom Westport Home, perfect for families
Jan 6 – 13
Private house rentals
Home in Fairfield
5.0 out of 5 average rating, 15 reviews5 Minute Walk to Beach & Downtown Fairfield
Sep 16 – 23
Home in Fairfield
5.0 out of 5 average rating, 6 reviews4BR/2.5BA Refuge Near University, Downtown & Beach
Jul 12 – 19
Home in Fairfield
5.0 out of 5 average rating, 11 reviewsRemodeled Cozy Country Cape
Apr 23 – 30
Home in Westport
4.93 out of 5 average rating, 14 reviewsBeautiful Brand New Inviting Farmhouse
Jan 19 – 26
Home in Fairfield
5.0 out of 5 average rating, 19 reviewsFairfield! 5 bedroom, 3.5 bath on cul-de-sac
Nov 20 – 27
Home in Norwalk
4.94 out of 5 average rating, 35 reviewsModern Nature Retreat
Sep 16 – 23
Home in Redding
5.0 out of 5 average rating, 17 reviewsQuiet and Cozy Cottage near NYC with a Pond
Mar 26 – Apr 2
Home in Norwalk
5.0 out of 5 average rating, 3 reviewsGreatly located SoNo 2 bedroom apartment
Oct 22 – 29
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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- Family travel hub Tips and inspiration
- Family budget travel Get there for less
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- 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