House holiday rentals in Highland Falls

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Popular amenities for house rentals in Highland Falls

House rentals with a pool

Guest favourite
Home in Rhinebeck
4.89 out of 5 average rating, 145 reviews

4Br Mountain Brook House on 130 acres w/ trails

eveRating, 5 stars2 weeks ago
We were 5 girlfriends staying at this property. Each one of us loved everything about it . Perfect location !
Superhost
Home in New Paltz
4.86 out of 5 average rating, 159 reviews

Scenic River View Escape | New Paltz

TatiaRating, 5 stars3 weeks ago
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!
Guest favourite
Home in Stamford
4.96 out of 5 average rating, 251 reviews

Midcentury Modern ZenHouse Sculptor Studio

EamonRating, 5 stars1 week 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 New Paltz
4.93 out of 5 average rating, 135 reviews

Harrison FieldBook Book6Nights and 7th Night FREE

EmmaRating, 5 stars4 weeks ago
We had a great stay at Nathan’s place. The playroom was great for our kids and we all enjoyed the pool. The view was also beautiful. We will definitely be back!
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 stars4 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 stars4 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.
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!
Guest favourite
Home in Philipstown
5 out of 5 average rating, 14 reviews

Charming contemporary cottage with lap pool

MikeRating, 5 stars4 weeks 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.

Weekly house rentals

Guest favourite
Home in New Paltz
4.95 out of 5 average rating, 147 reviews

New Paltz Guest Cabin Nestled In The Woods

PhilRating, 5 stars2 weeks ago
Beautiful location, peaceful and private. Spacious, modern, comfortable home. Really good advice about places to explore and visit in the surrounding area. This is a place we’d return to in a heartbeat. Just the tonic after a week in Paris and a hectic entry via JFK. Ben’s place is a haven away from the world. We just loved it!
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!
Top guest favourite
Home in Highland Falls
5 out of 5 average rating, 15 reviews

Old Grad House, 850ft from Thayer Gate

DonnaRating, 5 stars6 months ago
Great place to stay for an Army game weekend. Very convenient to Post and West Point decor made it fun and interesting. Very clean, comfortable and well appointed. Robert is very responsive and friendly.
Guest favourite
Home in Highland Falls
4.97 out of 5 average rating, 86 reviews

West Point Mountain House

JasonRating, 5 stars3 weeks ago
The hosts were very responsive. It is a great house, exactly what we wanted and as advertised. There isn't much to do in the immediate area, but there are a few shops and restaurants in the town center. The house is situated in a back lot and shares an access driveway with the house closer to the street, but once you are at the house it is very private. The only issue we ran into is the three season porch hadn't been cleaned and was covered in pollen, so it wasn't very usable. This place is perfect for a large group that mostly wants to stay on site!
Guest favourite
Home in Highland Falls
4.97 out of 5 average rating, 61 reviews

West Point Hudson Valley Getaway

TimRating, 5 stars6 months ago
We stayed at Patrick’s place to attend an Army football game. Everything was perfect and easy. It’s really close to campus/post. It’s a nice little town and close to Cold Spring where we had lunch on Friday. Thanks for a great weekend.
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!
Top guest favourite
Home in Highland Falls
5 out of 5 average rating, 76 reviews

GRAD MOM House Walk to WP King 2 Queen

StephenRating, 5 stars1 month ago
Susan’s house was an absolute gem! It was immaculate and decorated so nicely to honor West Point. The home was so clean, comfortable, with all the amenities - we felt at home. The location is unbeatable- just a short walk to Thayer gate. Highly recommend— we will certainly stay at Susan’s home for our next trip to West Point.

Private 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!
Top guest favourite
Home in Highland Falls
5 out of 5 average rating, 10 reviews

West Point Family Retreat 5 min walk to Thayer

MaraRating, 5 stars3 weeks ago
Very nice location. Spacious. Clean. Would stay there again.
Guest favourite
Home in Newburgh
4.89 out of 5 average rating, 27 reviews

Margaret's Heart

AntRating, 5 stars2 weeks ago
I did not stay but my son did and I got to look at the place I fell in love with it instantly. I felt at home everything was organized and clean. I definitely recommend to book with Rachel.
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 Accord
5 out of 5 average rating, 65 reviews

Accord River House

KacyRating, 5 stars2 weeks ago
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!
Guest favourite
Home in Putnam Valley
4.97 out of 5 average rating, 68 reviews

Waterfront Lake House

ConorRating, 5 stars2 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!
Top guest favourite
Home in Cold Spring
5 out of 5 average rating, 44 reviews

Mountain Top Retreat

RachelRating, 5 starstoday
Andre's place was a beautiful home away from home. Sparkling clean inside and surrounded by serene natural beauty outside. Bring your bug spray if you're going for a hike!
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 Highland Falls

  • Total rentals

    40 properties

  • Nightly prices starting at

    ₹4,319 before taxes and fees

  • Total number of reviews

    1.5K reviews

  • Family-friendly rentals

    30 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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