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