House holiday rentals in Highlands

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Popular amenities for house rentals in Highlands

House rentals with a pool

Guest favourite
Home in Stormville
4.94 out of 5 average rating, 183 reviews

Private Hudson Valley Country Retreat

ElodieRating, 5 stars1 week ago
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!
Top guest favourite
Home in New Paltz
4.98 out of 5 average rating, 490 reviews

midcentury mod * POOL * walk out trail to mohonk

ArielRating, 5 stars2 weeks ago
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!
Guest favourite
Home in Stamford
4.96 out of 5 average rating, 251 reviews

Midcentury Modern ZenHouse Sculptor Studio

EamonRating, 5 stars2 weeks ago
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.
Guest favourite
Home in Commack
4.99 out of 5 average rating, 140 reviews

GOOD VIBEZ HOUSE! Mini Golf-Pool-Hot Tub-GameRoom!

AliceRating, 5 stars1 month ago
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!
Top guest favourite
Home in Pound Ridge
5 out of 5 average rating, 165 reviews

Peaceful Light-Filled Guesthouse 1 Hour From NYC

MeredithRating, 5 stars6 days ago
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!
Superhost
Home in Kerhonkson
4.93 out of 5 average rating, 118 reviews

Modern Lux 5-Bed, Pool Open! Dogs Welcome

KimRating, 5 stars6 days ago
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.
Guest favourite
Home in Narrowsburg
4.95 out of 5 average rating, 202 reviews

Modern House with Private Pool, Hot-Tub, Fireplace

AlexandraRating, 5 stars3 weeks ago
It was a beautiful stay and everything were just like the photos! We enjoyed our stayed!
Superhost
Home in Beacon
4.92 out of 5 average rating, 134 reviews

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town

SelenaRating, 5 stars2 weeks ago
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

Top guest favourite
Home in Cornwall
4.98 out of 5 average rating, 44 reviews

Sunset House: near West Point, Hiking & Woodbury

CamilleRating, 5 stars1 month ago
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!
Superhost
Home in Philipstown
4.73 out of 5 average rating, 152 reviews

Bungalow near West Point on Hudson River

RobinRating, 5 stars1 week ago
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!!
Top guest favourite
Home in Highland Falls
5 out of 5 average rating, 69 reviews

Modern Usma Home, Walk to West Point

LynnRating, 5 stars1 week ago
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!
Guest favourite
Home in Cold Spring
4.95 out of 5 average rating, 324 reviews

Hilltop Hideaway Forest Villa on 13 acres!

RebeccaRating, 5 stars3 weeks ago
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!
Guest favourite
Home in Chester
4.95 out of 5 average rating, 128 reviews

Millionaire Mansion Countryside Stay w/ Lrg Hottub

KeleshaRating, 5 stars6 days ago
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!
Superhost
Home in Greenwood Lake
4.86 out of 5 average rating, 156 reviews

Aster Place

BenRating, 5 stars4 days ago
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.
Guest favourite
Home in Fort Montgomery
4.92 out of 5 average rating, 37 reviews

West Point Cottage

SamanthaRating, 5 stars4 weeks ago
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.
Guest favourite
Home in Highland Falls
5 out of 5 average rating, 13 reviews

Sleek Escape: Modern 3 BR- 4 Min from West Point !

JulieRating, 5 stars2 weeks ago
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

Guest favourite
Home in Cold Spring
4.91 out of 5 average rating, 55 reviews

Summer Adventures in Cold Spring at Gilbo's

BillRating, 5 stars4 weeks ago
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.
Top guest favourite
Home in Putnam Valley
5 out of 5 average rating, 10 reviews

Dr. Ruth’s Serene Lake Retreat

EvanRating, 5 stars5 months ago
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.
Top guest favourite
Home in Mohegan Lake
4.95 out of 5 average rating, 57 reviews

A nice place to getaway

LizRating, 5 stars2 months ago
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!
Top guest favourite
Home in Cold Spring
5 out of 5 average rating, 38 reviews

Home in Cold Spring- Farm Stay!

AishaRating, 5 stars5 days ago
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!
Guest favourite
Home in Putnam Valley
4.97 out of 5 average rating, 68 reviews

Waterfront Lake House

ConorRating, 5 stars3 days ago
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!
Guest favourite
Home in Cornwall
4.89 out of 5 average rating, 9 reviews

Hudson Valley Hideaway: 10 Minutes to Storm King!

DeeRating, 5 stars2 months ago
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.
Guest favourite
Home in Philipstown
5 out of 5 average rating, 14 reviews

Charming contemporary cottage with lap pool

MikeRating, 5 stars1 month ago
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.
Superhost
Home in Philipstown
4.86 out of 5 average rating, 36 reviews

Crystal Cottage Retreat

VivienRating, 5 stars2 months ago
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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