Holiday rentals with a pool in Philipstown
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Philipstown
Guests agree: These homes with a pool 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 Philipstown rentals with a pool
House rentals with a pool
Home in Yorktown Heights
4.88 out of 5 average rating, 119 reviewsCozy winter getaway 1 hr from NYC!
23 – 30 Sept
Home in Woodstock
4.98 out of 5 average rating, 100 reviewsWoodstock Historic Artist Estate- The Museum House
5 – 12 Dec
Home in West Milford
4.99 out of 5 average rating, 113 reviewsOn The Rocks In The Hot Tub
12 – 19 Dec
Home in Cottekill
4.95 out of 5 average rating, 241 reviewsPeace & Privacy - High Falls (hot tub & salt pool)
9 – 16 Sept
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
27 Oct – 3 Nov
Home in Middletown
4.94 out of 5 average rating, 100 reviewsSpringtime farm escape with hot tub and amenities
1 – 8 June
Home in New Paltz
4.93 out of 5 average rating, 121 reviewsHarrison Field Heated Pool Upon Request May 2024
24 Feb – 3 Mar
Home in Philipstown
5.0 out of 5 average rating, 13 reviewsModern Cottage in the Woods, Garrison
17 – 24 June
Condo rentals with a pool
Condo in Vernon Township
4.95 out of 5 average rating, 237 reviewsNYC Escape 1 hr away
30 June – 5 July
Condo in Vernon Township
4.97 out of 5 average rating, 222 reviewsAppalachian Mt. View 1 Bdrm Suite 3rd Flr Balcony
4 – 11 Dec
Condo in Vernon Township
4.95 out of 5 average rating, 727 reviewsAppalachian Lodge Top Floor w/views
13 – 20 Oct
Condo in Vernon Township
4.97 out of 5 average rating, 215 reviewsRustic Chic at Mountain Creek! Pool|Hot Tub|Sauna
9 – 16 Aug
Condo in Vernon Township
4.76 out of 5 average rating, 137 reviews1 Bedroom Condo @ Appalachian Resort Hotel
15 – 22 June
Condo in Vernon
4.94 out of 5 average rating, 162 reviewsMtn front Resort Pool Hot Tub Sauna Best View 324
5 – 12 Dec
Condo in Vernon Township
4.94 out of 5 average rating, 102 reviewsResort Getaway-Mtn Creek Ski/Pool/Hot Tub/Sauna
9 – 16 Aug
Condo in Vernon Township
4.9 out of 5 average rating, 200 reviewsUpscale Condo Ski-In/Out Mountain Creek 1 hr NYC
26 Oct – 2 Nov
Home rentals with a private pool
Home in Kerhonkson
4.94 out of 5 average rating, 325 reviewsCountry House: Rustic Charm With Modern Feel
8 – 15 Sept
Home in Lagrangeville
4.84 out of 5 average rating, 120 reviewsClassic Hudson Valley Farmhouse Nestled in 9 Rolling Acres
23 – 30 Sept
Home in Lanesville
4.77 out of 5 average rating, 205 reviewsGo Hiking and Skiing from a Family-Friendly Farmhouse
7 – 14 Mar
Home in Rhinebeck
5.0 out of 5 average rating, 65 reviewsRhinebeck Country Living with a Modern Twist
7 – 14 Sept
Home in Woodstock
4.6 out of 5 average rating, 10 reviewsLuxury Retreat in the Catskills
25 Aug – 1 Sept
Quick stats about holiday rentals with a pool in Philipstown
Total rentals
50 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
2K reviews
Nightly prices starting at
$107 AUD before taxes and fees
Destinations to explore
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