
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
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Popular amenities for Philipstown rentals with a pool
House rentals with a pool

MCM in the Hudson Valley
We had a fantastic stay at this Airbnb! The place was impeccably clean and incredibly comfortable, making it a perfect retreat. The host was very responsive and helpful, addressing all our needs promptly. Highly recommend!

Summer Retreat! Amazing Pool, Playground, 7 acres!
This property is large and roomy with plenty beds to go around including the basement with the pool and ping pong tables plus a home gym with various equipments. The outdoors were fantastic with a very nice temperature controlled pool, Jacuzzi, swings set for the little ones and enough acreage to have a soccer match. The neighborhood was nice and quiet in a great country setting with lots of wildlife to enjoy to include lots of singing birds. Our family reunion was a great success due in part to the before mentioned surroundings. Douglas was always available to resolve minor issues, very responsive and accommodating, thanks for making our stay at this property a great one.

Summer Adventures in Cold Spring at Gilbo's
We were there for a USMA graduation, and the location / accommodations worked great. Handy having a decent grocery store two blocks away. The walking loop down to the Foundry and Cold Springs Park is delightful. Nice with our house guests (extended family and friends) to be able to spread out in the place. Kitchen was spacious and awesome for family meals. Pool wasn't open yet, but looked inviting to add to the outside BBQ area.

4Br Mountain Brook House on 130 acres w/ trails
It was a fantastic house with a beautiful view. Plenty of space and we really enjoyed our stay. The property itself is absolutely gorgeous. Would definitely come back.

The Barger Wixon House
Stayed for West Point graduation. House was awesome. Hosts were more awsomelierist….. Highly recommend. GO ARMY! BEAT navy!

GOOD VIBEZ HOUSE! Mini Golf-Pool-Hot Tub-GameRoom!
We liked how easy it was to punch the code in to get into the home. Once in the home, it was really nice to see the welcome placard. We enjoyed access to robes, skincare, slippers, towels, etc. The game room was loads of fun. The indoor and outdoor ping pong tables were fun. We enjoyed billiards, arcade games and table games. The icing on the cake were the hot tub, the four mode shower and bidet. The Smart Home technology took a little getting used to, but it was very convenient once we did. We love the quick response time whenever we had a question or concern. This place allowed for a rejuvenating relaxing atmosphere and we are so glad that we chose “The Good Vibes” home for our debut AirBNB experience. Thanks again for hosting us in your charming abode!

Cold Spring Gem
Beautiful, comfortable, well built house with great views of woods and stream, well equipped kitchen. My husband, son and I really enjoyed staying there, while visiting family, even during some of the coldest days of the winter. We would love to come back at a time when we can take advantage of the deck and pool!

Peaceful Light-Filled Guesthouse 1 Hour From NYC
Our family of 5 and pup had the best time on this gorgeous property! The photos do not do the artful design justice, it’s simply stunning and so thoughtful. Our kids swam ever day and loved the pool. We enjoyed Grace Farms, Prospect Movie Thester and a lovely Father’s Day meal at the Inn at Pound Ridge. The kitchen is incredibly well stocked for someone who likes to cook and DoorDash was also easy to use when we didn’t feel like cooking. We will definitely be back! Thank you, RJ and John!
Apartment rentals with a pool

Valley Overlook @ Mtn Creek Resort Park & Play
I had a wonderful stay at this Airbnb in Vernon, New Jersey, right by Mountain Creek. The one-bedroom space was exactly as described in the photos—clean, cozy, and inviting. The accommodations, including the pool and hot tubs, and sauna were fantastic and easily accessible. The host was very responsive to messages, making the whole experience smooth and enjoyable. Highly recommend!

Cozy Retreat | Pool & Hot Tub | Mountain Creek Resort @ Appalachian
We had a fantastic family weekend getaway at Chris’s place. The room was spotless and comfortable, which made us feel right at home. Chris was an outstanding host—very responsive and incredibly informative, providing all the details we needed for a smooth and enjoyable stay. We truly appreciated the extra care he took to ensure we had everything we needed. Highly recommend staying here and would absolutely book again!

Comfy Studio at Mountain Creek Resort
This is a beautiful place. Second time we’ve stayed there and I would like to come again next year!

Appalachian Lodge Top Floor w/views
I enjoyed my stay here! Gorgeous condo with an absolutely breathtaking view. Decided to stay here for my friends wedding and it couldn’t have been a more perfect spot. Thank you to Paul and family for allowing me to stay at your home.

Cozy Condo at the Base of Mountain Creek Resort
Perfect for a quick weekend for a wedding! Comfortable and super easy parking, it’s right by the lot so it’s easy in and out

✰ 255 Mountain Creek Luxury 1 bd Deluxe sleeps 5
Massimo was the absolute best and sweetest, honest, helpful, generous, considerate person I’ve ever worked with on here. His home was so beautiful, clean, and aesthetically pleasing. He even provided snacks, water, and mash mellows and graham crackers along with the sticks if we wanted to use the onsite bonfire. He thought of everything down to little candy in trays, chocolates , probably the best bed I’ve ever slept in. There was not 1 thing about this trip I could complain about. I bragged to my friends who came over how amazing he was even at responding when I got lost. I’ve recommended him to a few people already so I hope he gets an abundance of business. It was worth every penny. He is an exceptional host and person. I will make it back to stay again. If you’re looking for pure comfort and ease don’t waste a burger second and book ! His place is worth it. Thank you so much Massimo you made my birthday amazing!!!!

Modern Ski in/out/waterpark/King Bed/WIFI/Parking
It is a great location, with plenty of things to do in the immediate vicinity. The unit was quiet, clean, comfortable, and provided everything I needed for a week long stay. The owner was very responsive to any query, and I did not have any issues with the unit during my stay. I'd work with Henry again for a future stay in Vernon, NJ.

Appalachian TOP 4TH FLOOR Studio+ w/amazing views!
Great host nice view plenty of things to do in the surrounding area had a great time overall wish I had a longer stay
Quick stats about holiday rentals with a pool in Philipstown
Total rentals
40 properties
Nightly prices starting at
₹6,058 before taxes and fees
Total number of reviews
1.7K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Times Square
- Bryant Park
- Madison Square Garden
- Grand Central Terminal
- Empire State Building
- Columbia University
- Fairfield Beach
- Rye Beach
- Citi Field
- MetLife Stadium
- Yankee Stadium
- Mountain Creek Resort
- United Nations Headquarters
- Central Park Zoo
- USTA Billie Jean King National Tennis Center
- Rockefeller Center
- Radio City Music Hall
- Rye Playland Beach
- Bronx Zoo
- The Metropolitan Museum of Art
- Astoria Park
- Minnewaska State Park Preserve
- One World Trade Center
- Walnut Public Beach