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Compare Vacation Homes in Highland with updated reviews, rates, and availability.

Beautiful cottage with HOT TUB in Kingston/Woodstock Catskills, Hudson Valley
6.0 out of 10, (2)
"we where on tour with our band. we like to stay a few minutes from the venue. This was the perfect place only a few minutes to downtown woodstock. We would definitely book again, and the host the host are very awesome. That you again Stacey"
The price is $100
$153 total
includes taxes & fees
Jun 16 - Jun 17
Beautiful cottage with HOT TUB in Kingston/Woodstock Catskills, Hudson Valley
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
10.0 out of 10, Exceptional, (153)
"We had a great time, and the space was great. The house is so spacious, and that was perfect for us. We would have liked a few more towels, a bit more soap and shampoo, and the grill didn't get hot enough to cook the steak we had brought. Overall a wonderful time. Thank you very much."
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, (63)
"Stayed for West Point graduation. Beautiful home, scenic views, and everything we needed."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
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Bright Cornwall-On-Hudson Vacation Rental!
10.0 out of 10, Exceptional, (4)
"We thoroughly enjoyed our stay at this beautiful and quaint home in the heart of the Cornwall village. The house was exactly as described, communication with the host was easy and quick, and we enjoyed being so close to everything Cornwall has to offer. We would absolutely recommend this beautiful home for your next visit to the Cornwall area"
Bright Cornwall-On-Hudson Vacation Rental!
The Farm at Hyde Park
9.8 out of 10, Exceptional, (49)
"We needed a central location for my daughter’s bridal shower. We could not have imagined a better place. It is beautiful and so natural. Glen was helpful and welcoming. He even came over to sweep off the expansive patio before our guests arrived and this was after he made sure everyone was awake. The house was well supplied with kitchen and dining items. The grounds were perfect - lawn chairs, picnic table, fire pit and free range chickens whose eggs we were able to enjoy. We would all stay here...
The Farm at Hyde Park
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, (37)
"it was excellent. exactly what I wanted. looking forward to coming back with family. the hot tub could have been slightly cleaner but it's like cold pizza, still good and hits the spot. honestly, a beautiful place. top notch Internet provided."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Renovated 1850's Cottage on Storm King Mountain
9.8 out of 10, Exceptional, (8)
"It was a beautiful setting with water fall. The home itself needs a little work. It is well used and needs some TLC. Photos look much better then actual home."
Renovated 1850's Cottage on Storm King Mountain
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
10.0 out of 10, Exceptional, (66)
"Very relaxing and enjoyable with excellent views and tranquility!"
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
9.0 out of 10, Wonderful, (22)
"This house has an ideal location to see lots of local sites of interest in the Hyde Park and Poughkeepsie area. Easy trip from there to West Point, Hyde Park and the Culinary Institute from the location, and great restaurant, Tiramasu, is very close. The house is immaculate! The beds were very comfortable, linens were provided, the bathrooms were spacious and the five of us had plenty of room for our toiletries. The house has steps to its multiple levels for all essential rooms, not accessible....
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Oversized Country house, Quiet Retreat & Gathering space ~NEW !!!
10.0 out of 10, Exceptional, (13)
"We really enjoyed our stay! We had a large group of 24 friends, and the house met all of our needs. It was very clean, had enough bedrooms for everyone, and a large dining table that accommodated everyone for big dinners. We spent a lot of time throughout the weekend outside playing lawn games and sitting by the fire. The place was close enough to grab amenities or go to a grocery store, but off the beaten path and quiet. It was exactly what was listed and made for a where enjoyable time....
Oversized Country house, Quiet Retreat & Gathering space ~NEW !!!
NEW! Gated 31 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.
9.6 out of 10, Exceptional, (43)
"This house had so much going for it! Great location, huge space, every bell and whistle imaginable. Very well furnished and equipped. We had a lovely time, and I can't imagine a place we'd have enjoyed more."
NEW! Gated 31 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.
The Chapel at Upland, with heated salt water pool and new tennis/bball court
10.0 out of 10, Exceptional, (3)
"The Chapel at Upland was the perfect 2-day getaway for me and my two teenage children! We wanted something tucked away but that also had a pool. The added bonus was the tennis court. Both the pool and tennis court are new and well-tended. Our dog was able to roam the property and get her own little vacation too. The house is cute, good for 4 people. The host, Lisa, is super friendly and helpful. 5 stars!"
The Chapel at Upland, with heated salt water pool and new tennis/bball court
The Calf Pen
10.0 out of 10, Exceptional, (15)
"Very peaceful place that backs up to a wooded area. The Calf Pen was very clean, plenty of room and has many comforts of home! Glen, the owner, lives on the property but is respectful of your space while being available to answer questions or for a friendly chat. The deck is a wonderful spot to enjoy the sounds of nature and visits from Glen's chickens."
The Calf Pen
Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz
9.8 out of 10, Exceptional, (20)
"Several days with family for my Son’s West Point Graduation! House was perfect , located in a nice neighborhood. Hosts are super friendly and easy to communicate with. Prompt response and helpful information! Highly recommend for groups from 4-8! Thank you !"
Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz
CREATIVES DREAM GETAWAY
10.0 out of 10, Exceptional, (1)
"Our group of 4 adults spent 3 nights in Ezequiel's beautiful property. It was cozy, beautifully decorated, comfortable, and the kitchen had everything you could possibly need. We enjoyed the lovely, tranquil outdoor space, and we had easy access to the attractions we were there to visit (Mohank Nature Preserve, CIA -Culinary Institute of America, Storm King Sculpture Park, etc.). Highly recommend and would definitely stay here again."
CREATIVES DREAM GETAWAY
Pet-Friendly ‘Pond View Loft' w/ Private Pool!
9.6 out of 10, Exceptional, (11)
"Overall, it seemed like the property manager was not ready for guests. The toilet instantly broke, the pool hadn’t been cleaned in probably weeks, and the apartment had stained sheets. It’s a nice place but really not worth the money."
Pet-Friendly ‘Pond View Loft' w/ Private Pool!
Spacious restored Victorian w/ wraparound porch
9.4 out of 10, Exceptional, (10)
"Spacious house, beautiful setting. Perfect set up for a reunion with friends and family. Highlights were spending quality time on the wrap around porch and making s'mores in the fire pit. Kids loved the pool and exploring the property. Host was responsive and helpful. Highly recommend!"
Spacious restored Victorian w/ wraparound porch
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
10.0 out of 10, Exceptional, (18)
"We had a very pleasant stay! We came for our son’s graduation from West Point. Pat was a gracious host and made sure that we had up to date info. There were lots of thoughtful amenities, the beds and couches were very comfortable, we used the grill and sat on the deck which overlooks a wooded hill. The location is peaceful and in the country just down the street from a horse pasture. You can hear the brook bubbling across the way. The WiFi worked great and although there is just a window air...
The price is $176
$321 total
includes taxes & fees
Jun 17 - Jun 18
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
9.6 out of 10, Exceptional, (30)
"This place is wonderful!!!! It was a beautiful stay."
The price is $176
$359 total
includes taxes & fees
Jun 18 - Jun 19
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Historic Kingston 1800s Waterfront Townhouse - / Backyard / BKLYN Loft / Modern
9.8 out of 10, Exceptional, (25)
"Loved everything about the place. Exactly as represented, in a really cool and relatively quiet neighborhood. If stairs bother you then that might be the only downside as the inner staircase is pretty steep but has excellent railings and safety glass."
Historic Kingston 1800s Waterfront Townhouse - / Backyard / BKLYN Loft / Modern
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Highland

Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
9.8 out of 10, Exceptional, (22)
"The backyard was really cool! Great features. Beautiful, peaceful, and private. We did not see or hear anyone else on the property during our stay. The apartment was very nice. Cozy, clean and comfortable, perfect for two. The host, Ryan was extremely responsive and friendly. We had an amazing stay would definitely recommend!"
The price is $215
$285 total
includes taxes & fees
Jun 16 - Jun 17
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
The Scenic Mansion With Breathtaking View
9.4 out of 10, Exceptional, (3)
"We loved staying in this large home for a weekend wedding in the area. All couples had plenty of room, with a bathroom in every bedroom, comfy beds, lots of living spaces, and gorgeous views of the valley below. The fall colors were so pretty!"
The Scenic Mansion With Breathtaking View
The Farm at Hyde Park
9.8 out of 10, Exceptional, (49)
"We needed a central location for my daughter’s bridal shower. We could not have imagined a better place. It is beautiful and so natural. Glen was helpful and welcoming. He even came over to sweep off the expansive patio before our guests arrived and this was after he made sure everyone was awake. The house was well supplied with kitchen and dining items. The grounds were perfect - lawn chairs, picnic table, fire pit and free range chickens whose eggs we were able to enjoy. We would all stay here...
The Farm at Hyde Park
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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