Vacation rentals with a pool in Litchfield
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Litchfield
Guests agree: these homes with a pool 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 Litchfield rentals with a pool
House rentals with a pool
Home in Pound Ridge
5.0 out of 5 average rating, 126 reviewsPeaceful Light-Filled Guesthouse 1 Hour From NYC
Dec 14 – 21
Home in Cold Spring
4.95 out of 5 average rating, 152 reviewsCozy, Modern Retreat in the Woods of Cold Spring
Dec 14 – 21
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
Sep 13 – 20
Home in Staatsburg
4.98 out of 5 average rating, 105 reviewsHilltop Escape ~ 25 acre private retreat
Home in Pine Plains
4.95 out of 5 average rating, 131 reviewsStylish, Secluded Getaway with Pool & Fireplace
May 27 – Jun 3
Home in Putnam Valley
4.93 out of 5 average rating, 182 reviewsPutnam Valley Escape
Oct 1 – 8
Home in Rhinebeck
4.96 out of 5 average rating, 164 reviewsOn The Hill in Rhinebeck
Nov 22 – 29
Home in Yorktown Heights
4.88 out of 5 average rating, 119 reviewsCozy winter getaway 1 hr from NYC!
Sep 15 – 22
Condo rentals with a pool
Condo in Danbury
4.82 out of 5 average rating, 11 reviewsQuaint spacious unit,A+ location
Jul 10 – 17
Condo in New Britain
4.85 out of 5 average rating, 40 reviewsBeautiful Space All For You!
Jul 18 – 25
Condo in Fishkill, New York
5.0 out of 5 average rating, 5 reviewsFishkill Living
May 17 – 24
Condo in Farmington, Connecticut
4.8 out of 5 average rating, 50 reviewsFarmington -NEWLY UPDATED NEAR UCONN HC and WEHA
Oct 31 – Nov 7
Condo in Westbrook, Connecticut
Watersedge resort time share Westbrook ct
Jul 24 – 31
Condo in Punta Cana, Dominican Republic
3.75 out of 5 average rating, 4 reviewsBeach apartment in front of Hard Rock Hotel
Mar 26 – Apr 2
Quick stats about vacation rentals with a pool in Litchfield
Total rentals
20 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
780 reviews
Nightly prices starting at
$120 before taxes and fees
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