
House holiday rentals in Philipstown
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Top-rated house rentals in Philipstown
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Popular amenities for house rentals in Philipstown
House rentals with a pool

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.

Scenic River View Escape | New Paltz
I spent my birthday at this beautiful house and couldn’t have asked for a better experience. The place was spotless and full of natural light, with lovely views that made the stay even more special. The atmosphere was peaceful and clean, and the house had everything we needed for cooking and relaxing. I truly felt at home and appreciated all the thoughtful touches. Highly recommend for anyone looking for a cozy, well-equipped getaway!

Midcentury Modern ZenHouse Sculptor Studio
Truly one of a kind property. Relaxing, calm, extremely responsive and helpful host. If you are looking to get out of the city or just need some time away to think, look no further. 10/10.

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!

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!

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town
This place has everything we were looking for - pool, hot tub, and a yard for our dogs. This is the second time we stayed here, and it was perfect once again!
Beautiful Salt Water Pool & Fully Fenced 10 Acres
We had a beautiful stay in Kerhonkson for a relaxing bachelorette weekend! Lillian’s place is absolutely beautiful and was so comfortable for my friends and I. Everything was as described, extremely clean, plenty of linens and had everything we needed in the kitchen to cook a few meals. We enjoyed sitting by the pool when it was sunny. Lillian was very communicative and flexible with check in time. Thank you!

Lakefront/Legoland/HotTub/Heated Pool 1 hr to NYC!
We had a wonderful stay at this spacious and kid-friendly home in Monroe. The place was exactly what we imagined—comfortable, peaceful, and perfect for a family getaway. We especially enjoyed relaxing on the beautiful deck, taking a dip in the pool, and kayaking at dawn and dusk. Highly recommend for anyone looking for a serene and scenic escape!
Weekly house rentals

Cold Spring Modern Country House
We had a group of family and friends for my daughter's West Point graduation. It was about a 30 minute drive to West Point, but well worth it. Unique home in a rural setting but near enough to Cold Spring and amenities. Expensive, but worth it. We felt right at home!

Tranquil Hudson Valley Retreat with Cedar Hot Tub
Great place to stay for a family trip. Beautiful surroundings and a great modern touch up kitchen.

Bungalow near West Point on Hudson River
Loved being on the river. Cute bungalow. Easy to get around Hudson Valley sites. Near cute Cold Spring. A/C worked well. Loved having BBQ and eating out in the backyard by the Hudson River. Also watching the boats go by! Thanks much!!

Dr. Ruth’s Serene Lake Retreat
After using Airbnb for years now no other place was a perfect 10. The lake house was simply great. Not only the physical status but the follow up and generosity of the hosts where beyond. We didn’t want to leave.

Home in Cold Spring- Farm Stay!
This was honestly one of our favorite Airbnbs. The house was comfortable, very clean, stylish, and well-stocked (cooking basics, extra phone chargers, etc.) The property is very serene and quiet and my kids loved visiting the animals. Cheryl and Jamie even provided us with carrots to feed them. They also welcomed us with snacks and a bottle of wine. It’s a great spot!

Gorgeous Garrison Gem: Pool, Sauna, Hot Tub & More
Claudine was there when we needed an awesome last-minute family escape. Super helpful and communicative. The home, well, felt like *home.* Would absolutely stay again. Our party was myself, my wife, a preschooler, an infant and a big dopey dog. We had a friend from Peekskill stop by for the day and the kids played in the pool. Would absolutely stay here again.

Charming Retreat 3B/3B Garrison, 2 Fireplaces
There were 5 of us, with another 6 staying in another nearby air bnb. We had Thanksgiving in our house and found everything we needed to cook. Seating was a bit challenging, but we made it work and it was very comfortable. The location is in the woods with lots of boulders and rocks, which we all loved. We found the place easily using GPS. Everyone’s bed was comfy. Close enough to what we wanted, just far enough away to make it an adventure. Because it was so cold and grey, we didn’t hike, but saw plenty of opportunities (maybe next time?!)

Mountain Top Retreat
Very comfy bed… great shower- lots of hot water and good water pressure. The bottled water, oatmeal and snack bars were appreciated. The home was clean and spacious. Back deck was a perfect spot to unwind. Andre and his wife were very helpful.
Private house rentals

Crystal Wave LakeHouse
This is one of the best places I've been! The surroundings are beautiful, the house is in a perfect location on the lake. Communication with the owner is easy and fast

Cottage in the village of Cold Spring
Ann’s place was just perfect for our weekend trip to the area. Super responsive host, unbeatable location steps to Main Street and all the amenities you’d need in a house. Highly recommend!

Cabin with a View
Ellen’s place was beautiful and cozy. The kitchen worked perfectly and even though it was April it was still a bit chilly so the wood stove was a welcome amenity. The shower was great and there was a soaking tub. It was quiet and beautiful. We like all the art and it was very homey.

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.

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

Sunny house on Lake Oscawana
Gaby's place was perfect for our weeklong family stay in early June. The setting is beautiful and quiet with the croaks of frogs greeting us in the evening and song birds in the morning. The natural light, stunning views of the lake and hills, and the uniqueness of each of the rooms added to the feeling of being on retreat. The kitchen was stocked with every item we would stock in our own home making it a breeze to cook meals for the whole family. The bedrooms are spacious, comfortable and private. We loved hanging on the dock with our kids and paddling on the lake with the provided paddle boards and kayaks. Oh... and the sauna was an added treat. We were very appreciative of Gaby's hospitality and quick response to questions. We will recommend her place to friends and hope to stay again in the coming years.

Boulder Tree House
Tranquil place if looking for a peaceful getaway. Was a prefect place to come back to relax at after a wonderful dinner in Rhinebeck.

Accord River House
This was hands-down, my favorite. Air B&B ever! We hope to return and spend more time on our next visit. We were literally immersed in and surrounded by nature and it was so beautiful and peaceful. It also felt like home the minute we stepped in… like going to a friend’s “country weekend” place where the books, puzzles, games, records, artwork, handcrafted pottery, electric blankets, dog beds and more (!) just make you feel at ease and in comfort. This place is so loved and it shares that love with its visitors. Thank you to the owners for sharing such a special place!
Quick stats about house rentals in Philipstown
Total rentals
200 properties
Total number of reviews
7.5K reviews
Family-friendly rentals
170 properties are a good fit for families
Pet-friendly rentals
70 properties allow pets
Rentals with a pool
30 properties have a pool
Rentals with dedicated workspaces
120 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