Vacation 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.
Vacation 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 Woodstock
4.98 out of 5 average rating, 101 reviewsWoodstock Historic Artist Estate- The Museum House
Sep 6 – 13
Home in West Milford
4.99 out of 5 average rating, 113 reviewsOn The Rocks In The Hot Tub
Oct 11 – 18
Home in Cottekill
4.95 out of 5 average rating, 242 reviewsPeace & Privacy - High Falls (hot tub & salt pool)
Jul 22 – 29
Home in Narrowsburg
4.97 out of 5 average rating, 141 reviewsModern Ranch With Pool & Hot-Tub
Oct 8 – 15
Home in Litchfield
4.93 out of 5 average rating, 163 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
Sep 12 – 19
Home in Middletown
4.94 out of 5 average rating, 100 reviewsSpringtime farm escape with hot tub and amenities
Jan 5 – 12
Home in Philipstown
5.0 out of 5 average rating, 13 reviewsModern Cottage in the Woods, Garrison
May 13 – 20
Home in Philipstown
4.83 out of 5 average rating, 47 reviews*GARRISON GETAWAY*❤️POOL❤️SAUNA,*HOT TUB* STEAM+MORE
Oct 8 – 15
Condo rentals with a pool
Condo in Vernon Township
4.95 out of 5 average rating, 238 reviewsNYC Escape 1 hr away
Aug 13 – 18
Condo in Vernon Township
4.95 out of 5 average rating, 729 reviewsAppalachian Lodge Top Floor w/views
Sep 25 – Oct 2
Condo in Vernon Township
4.97 out of 5 average rating, 222 reviewsAppalachian Mt. View 1 Bdrm Suite 3rd Flr Balcony
Mar 8 – 15
Condo in Vernon Township
4.76 out of 5 average rating, 137 reviews1 Bedroom Condo @ Appalachian Resort Hotel
Sep 25 – Oct 2
Condo in Vernon Township
4.94 out of 5 average rating, 102 reviewsResort Getaway-Mtn Creek Ski/Pool/Hot Tub/Sauna
Nov 27 – Dec 4
Condo in Vernon Township
4.9 out of 5 average rating, 202 reviewsUpscale Condo Ski-In/Out Mountain Creek 1 hr NYC
Aug 28 – Sep 4
Condo in Vernon
4.93 out of 5 average rating, 107 reviewsMtn front Resort Pool Hot Tub Sauna Best View 342
May 29 – Jun 5
Condo in Danbury
4.82 out of 5 average rating, 11 reviewsQuaint spacious unit,A+ location
Jul 2 – 9
Home rentals with a private pool
Home in Kerhonkson
4.94 out of 5 average rating, 325 reviewsCountry House: Rustic Charm With Modern Feel
Sep 17 – 24
Home in Lagrangeville
4.84 out of 5 average rating, 120 reviewsClassic Hudson Valley Farmhouse Nestled in 9 Rolling Acres
Sep 27 – Oct 4
Farm stay in Fleischmanns
4.91 out of 5 average rating, 11 reviewsEscape to a Dreamy 1857 Farmhouse in Fleischmanns
Jan 23 – 30
Home in Woodstock
4.6 out of 5 average rating, 10 reviewsLuxury Retreat in the Catskills
Sep 1 – 8
Home in Lanesville
4.77 out of 5 average rating, 205 reviewsGo Hiking and Skiing from a Family-Friendly Farmhouse
Mar 13 – 20
Home in Rhinebeck
5.0 out of 5 average rating, 65 reviewsRhinebeck Country Living with a Modern Twist
Oct 2 – 9
Quick stats about vacation 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
$70 before taxes and fees
Destinations to explore
- New City Vacation rentals
- Long Island Vacation rentals
- Newark Vacation rentals
- Pocono Mountains Vacation rentals
- Hoboken Vacation rentals
- Washington Vacation rentals
- Philadelphia Vacation rentals
- Jersey City Vacation rentals
- New York Vacation rentals
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Montreal Vacation rentals
- Rentals with pools New York
- Rentals with pools United States
- Rentals with pools Manhattan
- Rentals with pools Brooklyn
- Rentals with pools New York
- Rentals with pools Putnam County
- Rentals with outdoor seating Philipstown
- Rentals with a washer and dryer Philipstown
- Pet-friendly rentals Philipstown
- House rentals Philipstown
- Monthly Rentals Philipstown
- Rentals with beach access Philipstown
- Fitness-friendly rentals Philipstown
- Apartment rentals Philipstown
- Rentals with a hot tub Philipstown
- Rentals with a patio Philipstown
- Waterfront rentals Philipstown
- Rentals with a kayak Philipstown
- Rentals with a fireplace Philipstown
- Rentals with a fire pit Philipstown
- Rentals with breakfast Philipstown
- Kid-friendly rentals Philipstown
- Family-friendly rentals Philipstown
- Rentals with an EV charger Philipstown
- Rentals with lake access Philipstown
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes