House holiday rentals in Weston
Find and book unique houses on Airbnb
Top-rated house rentals in Weston
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 Weston
House rentals with a pool
Home in Cheshire
5.0 out of 5 average rating, 117 reviewsPool House
15–22 Apr
Home in Cold Spring
4.95 out of 5 average rating, 152 reviewsCozy, Modern Retreat in the Woods of Cold Spring
3–10 Feb
Home in Putnam Valley
4.93 out of 5 average rating, 182 reviewsPutnam Valley Escape
26 Sept – 3 Oct
Home in Yorktown Heights
4.88 out of 5 average rating, 119 reviewsCozy winter getaway 1 hr from NYC!
12–19 Sept
Home in North Salem
4.99 out of 5 average rating, 220 reviewsConverted Barn House
6–13 Oct
Home in Redding
4.83 out of 5 average rating, 12 reviewsMeeker Hill House - Country Escape w/ Heated Pool
10–17 May
Home in Redding
4.93 out of 5 average rating, 68 reviewsLovely Country Retreat:
25 Jun – 2 Jul
Home in Redding
4.94 out of 5 average rating, 67 reviewsPrivate * Hiking * Swimming * Pool * Steam-room
2–9 Dec
Weekly house rentals
Home in Pawling
5.0 out of 5 average rating, 186 reviewsHobbit House of Pawling
3–10 Aug
Home in Weston
5.0 out of 5 average rating, 36 reviewsGorgeous Weston Retreat with Tennis & Hot Tub
25 May – 1 Jun
Home in Redding
5.0 out of 5 average rating, 17 reviewsQuiet and Cozy Cottage near NYC with a Pond
19–26 Aug
Home in Redding
4.89 out of 5 average rating, 66 reviewsNature Retreat Airbnb
15–22 Dec
Home in Norwalk
5.0 out of 5 average rating, 34 reviews❤️ Your Silvermine Hideaway, nestled in nature.
1–8 Apr
Home in Westport
5.0 out of 5 average rating, 4 reviewsWestport:Private Fire Pit Hideaway 5 min to Town
24–31 Aug
Home in Fairfield
5.0 out of 5 average rating, 62 reviewsFairfield Cottage: Cozy retreat near Universities
15–22 Nov
Home in Westport
5.0 out of 5 average rating, 17 reviewsCharming & Spacious New England Family Home
4–11 Jan
Private house rentals
Home in Fairfield
5.0 out of 5 average rating, 11 reviewsRemodeled Cozy Country Cape
31 Dec – 7 Jan
Home in Westport
5.0 out of 5 average rating, 9 reviewsFarmhouse 1899: Westport, CT
23–30 Sept
Home in Southbury
5.0 out of 5 average rating, 57 reviewsThe Cottage at Cedar Spring Farm
21–28 Jul
Home in Redding
5.0 out of 5 average rating, 35 reviewsModern Farmhouse in Redding - Walk to Metro North
24–29 Jun
Home in Shelton
4.88 out of 5 average rating, 40 reviewsMid-Century Modern House - Ciela Haus
4–11 Nov
Home in Fairfield
5.0 out of 5 average rating, 7 reviewsStillson House - Central Cozy Updated Colonial
11–18 Jun
Home in Westport
4.89 out of 5 average rating, 46 reviewsWestport/Saugatuck super spot
12–19 Jan
Home in Norwalk
4.94 out of 5 average rating, 35 reviewsModern Nature Retreat
11–18 Sept
Quick stats about house rentals in Weston
Total rentals
30 properties
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
380 reviews
Nightly prices starting at
£32 before taxes and fees
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