
House holiday rentals in Highlands
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Top-rated house rentals in Highlands
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House rentals with a pool

Private Hudson Valley Country Retreat
We were absolutely charmed by this stunning house, surrounded by breathtaking nature and offering incredible views—especially over the lake. Every corner is filled with character and warmth, making it feel like a true hidden gem. A huge thank-you to our wonderful host Sandy, who was incredibly thoughtful and proactive throughout our stay. We couldn’t have asked for a better experience. We’ll be back without a doubt!

midcentury mod * POOL * walk out trail to mohonk
This is a lovely house very close to New Paltz. We had a nice long weekend with the kids and loved spending time in the pool. Susan was a great host. No complaints!

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!

Modern Lux 5-Bed, Pool Open! Dogs Welcome
The graves home was very comfortable. It was very accommodating. It had enough room for the whole family. We were not on top of each other. The beds were extremely comfortable. The last place we stayed at the beds were horrible. These were absolutely comfortable. It was very peaceful and quiet no surrounding neighbors. It was wonderful to wake up and see the deer in the backyard every morning while I was drinking my coffee. The host was great. He responded within 5 to 10 minutes every time I had no issues would definitely recommend staying here if you’re looking for a quiet, relaxing family getaway. and the pool is wonderful.

Modern House with Private Pool, Hot-Tub, Fireplace
It was a beautiful stay and everything were just like the photos! We enjoyed our stayed!

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!
Weekly house rentals

Sunset House: near West Point, Hiking & Woodbury
Our family stayed here for my son's West Point graduation. This was our second visit and we were thrilled to be back. This house is well taken care of, clean, and relaxing. It's close to the town of Cornwall, grocery stores, etc so you have access to what you need. The hosts are responsive, helpful and welcoming. Highly recommend!

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!!

Modern Usma Home, Walk to West Point
This house was truly AMAZING! The level of thought that this host put into this home is truly outstanding. This was way more than we ever expected. Modern decor and amenities throughout, and the "backyard" is a true oasis! All the things you might need for relaxing or entertaining! The hot tub was great and provided an amazing view of the mountains. Relaxed by the fire pit for evening drinks. Each bedroom had super comfortable beds and plenty of space to feel at home. Forgot something you might need?? Don't worry this host remembered! If you are a foodie, this kitchen had it all, including a wide variety of coffee and tea options, a few snacks and drinks. We could go on and on, but just know the pictures don't even do this place justice! Also had great host communication!

Hilltop Hideaway Forest Villa on 13 acres!
My family of 8 adults needed a place to stay near a wedding at Glynwood. This wonderful spot was minutes away from the farm and town. The number of bedrooms and bathrooms gave everyone the privacy desired while the well equipped kitchen and living rooms had plenty of space for gathering. The house and land are beautiful, including the trail. Paula was easy to communicate with and my whole family felt comfortable and happy with the spot. Highly recommend!

Millionaire Mansion Countryside Stay w/ Lrg Hottub
I recently had the pleasure of staying at a stunning home in Chester, and it was nothing short of magnificent. Every detail was thoughtfully designed from the cozy yet luxurious interiors to the peaceful surroundings that made it feel like a true escape. The home was immaculately clean, beautifully furnished, and offered the perfect balance of comfort and style. Whether you're looking for a relaxing getaway or a place to feel inspired, this gem in Chester truly delivers. I can’t wait to return!

Aster Place
Fantastic spot with views of the lake from the deck. Easy to walk down to the beach and had fun with the kayaks. Lots of space for the kids to run around and play on the open plan kitchen/lounge. Quick drive into town for great shops and places to eat. A lovely community by the lake.

West Point Cottage
My partner and I booked Philomena and Derek’s place for Memorial Day wknd to attend a wedding at West Point. It was the perfect location and a cute space. We went to dinner at a restaurant nearby called the Bird and Bottle Inn which was also great.

Sleek Escape: Modern 3 BR- 4 Min from West Point !
We loved our time at Jason’s home! Is was easy to communicate with Jason, beautifully decorated and quick to West Point! We loved our week there and will definitely be back!
Private house rentals

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.

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.

A nice place to getaway
We’ve stayed at Filiz’s place a few times and it’s perfect! Quiet, clean, and easy to get to where we needed to be. We’ll be back!

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!

Waterfront Lake House
We had a great long weekend stay at Brian's place with our dog. The view of the lake from the house was incredible. The entrance down the stairs gave us a very private area for us to spend time enjoying the surroundings. The place itself was very clean, had everything we needed and Brian was great at communication the whole time. We couldn't believe this was only an hour or so drive from NYC. We would definitely stay again!

Hudson Valley Hideaway: 10 Minutes to Storm King!
This airbnb is absolutely stunning. It looks even better than the pictures. Though it’s only an hour driving from New York but it’s feels a real disconnect from the city life - very peaceful surroundings. You can over look into the mountain far away and enjoy sunset everyday. The movie room downstairs creates a theater experience. We have painted a wonderful memory over the weekend at this Airbnb - felt sad when we close the door behind us on the last day.

Charming contemporary cottage with lap pool
Jad was an amazing host. Super responsive and always aiming to make us comfortable and make sure our needs or requests were addressed. Clearly, he's put a lot of work into this unique property. It housed our extended family of 8 well. He was super flexible about checking in as we arrived earlier and the property was ready. This made for a much less hectic day on our first day. Highly recommend this cottage. He even had the pool ready for our use, but the unseasonably cold weather prevented us from enjoying the pool. Thanks for being so responsive.

Crystal Cottage Retreat
Our family wanted a last minute Easter getaway in the Cold Spring vicinity and Steve & Mara’s place was a wonderful find. The decor, light filled rooms, and proximity to Beacon and local museums plus restaurants were valuable to our experience. The large dining area was excellent for playing games with the kids or staying in to cook meals. Steve and Mara were great hosts. Very responsive when we needed assistance with the house or suggestions.
Quick stats about house rentals in Highlands
Total rentals
120 properties
Total number of reviews
4.2K reviews
Family-friendly rentals
100 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
60 properties have a dedicated workspace
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- Times Square
- Bryant Park
- Madison Square Garden
- Grand Central Terminal
- Empire State Building
- Columbia University
- Barclays Center
- Fairfield Beach
- Rye Beach
- Citi Field
- MetLife Stadium
- Yankee Stadium
- Mountain Creek Resort
- United Nations Headquarters
- Central Park Zoo
- Statue of Liberty
- USTA Billie Jean King National Tennis Center
- Radio City Music Hall
- Rockefeller Center
- Bronx Zoo
- The Metropolitan Museum of Art
- Rye Playland Beach
- Astoria Park
- Minnewaska State Park Preserve