House holiday 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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Westport
House rentals with a pool
Home in Cheshire
5.0 out of 5 average rating, 118 reviewsPool House
21–28 Nov
Home in Stormville
4.94 out of 5 average rating, 156 reviewsPrivate Hudson Valley Country Retreat
20–27 Oct
Home in Cold Spring
4.95 out of 5 average rating, 152 reviewsCozy, Modern Retreat in the Woods of Cold Spring
25 Oct – 1 Nov
Home in Manorville
4.99 out of 5 average rating, 200 reviewsUltimate House with Heated Pool, Hot Tub and Sauna
11–18 Oct
Home in Putnam Valley
4.93 out of 5 average rating, 182 reviewsPutnam Valley Escape
30 Sep – 7 Oct
Home in Yorktown Heights
4.88 out of 5 average rating, 119 reviewsCozy winter getaway 1 hr from NYC!
30 Jul – 6 Aug
Home in North Salem
4.99 out of 5 average rating, 220 reviewsConverted Barn House
14–21 Oct
Home in Redding
4.83 out of 5 average rating, 12 reviewsMeeker Hill House - Country Escape w/ Heated Pool
9–16 Oct
Weekly house rentals
Home in Westport
4.89 out of 5 average rating, 46 reviewsWestport/Saugatuck super spot
30 Nov – 7 Dec
Home in Westport
4.92 out of 5 average rating, 37 reviewsGorgeous, luxury Cape in Westport!
16–23 Jul
Home in Westport
5.0 out of 5 average rating, 4 reviewsWestport:Private Fire Pit Hideaway 5 min to Town
28 Aug – 4 Sep
Home in Westport
5.0 out of 5 average rating, 19 reviewsCharming & Spacious New England Family Home
23–30 Jan
Home in Westport
4.8 out of 5 average rating, 20 reviewsCustom Westport Home, perfect for families
25 Nov – 2 Dec
Home in Norwalk
5.0 out of 5 average rating, 34 reviews❤️ Your Silvermine Hideaway, nestled in nature.
14–21 Dec
Home in Westport
5.0 out of 5 average rating, 9 reviewsFarmhouse 1899: Westport, CT
15–22 Aug
Home in Fairfield
5.0 out of 5 average rating, 63 reviewsFairfield Cottage: Cozy retreat near Universities
12–19 Apr
Private house rentals
Home in Redding
5.0 out of 5 average rating, 17 reviewsQuiet and Cozy Cottage near NYC with a Pond
22–29 Jul
Home in Fairfield
5.0 out of 5 average rating, 11 reviewsRemodeled Cozy Country Cape
2–9 Mar
Home in Fairfield
5.0 out of 5 average rating, 9 reviewsStillson House - Central Cozy Updated Colonial
11–18 Jun
Home in Fairfield
5.0 out of 5 average rating, 11 reviewsWaterlot Cottage
1–8 Jun
Home in Norwalk
5.0 out of 5 average rating, 3 reviewsGreatly located SoNo 2 bedroom apartment
1–8 Oct
Home in Fairfield
5.0 out of 5 average rating, 15 reviews5 Minute Walk to Beach & Downtown Fairfield
10–17 Dec
Home in Westport
4.93 out of 5 average rating, 14 reviewsBeautiful Brand New Inviting Farmhouse
2–9 Aug
Home in Norwalk
4.94 out of 5 average rating, 35 reviewsModern Nature Retreat
14–21 Sep
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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