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Compare 439 Vacation Homes in Highland with updated reviews, rates, and availability.

Exterior
Midcentury Modern Cabin Home in the Woods- Under 2 Hrs From NYC!
10.0 out of 10, Exceptional, (103)
"Great comfortable home with all the amenities we could have asked for! Loved the games there to entertain us and the vestigial fireplace to relax at at night. Close by to area hiking and short drive into town!"
Midcentury Modern Cabin Home in the Woods- Under 2 Hrs From NYC!
Dining
The Solarium: Woodstock Retreat w/Hot tub+Stream!
10.0 out of 10, Exceptional, (1)
"This place was a gem to sit back, relax and take in the scenery. The owner was very accommodating. I highly recommend staying."
The Solarium: Woodstock Retreat w/Hot tub+Stream!
Fridge, microwave, oven, stovetop
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
10.0 out of 10, Exceptional, (27)
"Weather was not so great to be outside but the game room made up for it!"
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
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Smart TV, offices
Indulge in an Elegant Upstate Getaway
10.0 out of 10, Exceptional, (39)
"We've stayed at this house 4 times--for several days each time--and it was, as always, incredibly comfortable and lovely. The house is beautiful and always spotless, and the kitchen is a pleasure to use. I would highly recommend. We rent houses in the Rhinebeck area several times throughout the year and this house is always our first choice."
Indulge in an Elegant Upstate Getaway
Fridge, microwave, stovetop, dishwasher
Bright Cornwall-On-Hudson Vacation Rental!
10.0 out of 10, Exceptional, (2)
"We had an enjoyable stay. Easy check in and house was exactly as noted in listing. Super convenient for access to West Point. No issue for my group, but stairs are steep and could be a challenge for some people. We would / will stay again next time in the area."
Bright Cornwall-On-Hudson Vacation Rental!
Property grounds
Beautiful Private Stone Home in the Hudson Valley
10.0 out of 10, Exceptional, (127)
"This was our 2nd stay and even better, as this time we explored the woods behind the house where a brook runs back far enough we never found the end or edge of the property. Great hikes less than 20 min drive away, but honestly exploring the woods and stream was about our speed, with teens who are non-experienced hikers. Used the hot tub every night under the stars, built fires and did s'mores multiple times in the fire pit. Large porch with ping pong, foosball, keyboard and movie watching spot...
Beautiful Private Stone Home in the Hudson Valley
Smart TV, fireplace, table tennis, computer monitors
Private retreat in Woodstock. Cozy cabin surrounded by trees with heated pool.
10.0 out of 10, Exceptional, (11)
"We came for a Fall weekend break - two families with 5 kids and a dog in tow. Plenty of room for everyone - and very comfortable. Just a short drive to both Woodstock and Saugerties (recommend Good Night if you like Asian food!) Missy was communicative and check in was smooth and easy. All good!"
Private retreat in Woodstock. Cozy cabin surrounded by trees with heated pool.
Fridge, microwave, oven, stovetop
Stylish Cozy Home with Gorgeous Views!
10.0 out of 10, Exceptional, (8)
"House is in mint condition, spectacularly clean and extremely comfortable. Host has a fine attention to detail in decorating, communication and hospitality. Would 100% stay here again."
Stylish Cozy Home with Gorgeous Views!
Fridge, microwave, oven, stovetop
Campfire Cottage: Fireplace, fire pit & no chores!
10.0 out of 10, Exceptional, (15)
"Matt is a wonderful host! I was very impressed by the cleanliness of the 1 bedroom cabin and how much thought went into providing guests with everything they need. I stayed for four nights and was very comfortable. The bed was so comfortable I slept great. Kingston is a city so some noise is expected. The neighborhood is very quiet at night and you can hear a little noise occasionally in the distance. Matt provides an adjustable sound machine. I put it on low and slept like a baby. Matt is very...
The price is $71
$194 total
includes taxes & fees
May 15 - May 16
Campfire Cottage: Fireplace, fire pit & no chores!
Exterior
Classic Catskills Estate, Amazing Location!
10.0 out of 10, Exceptional, (87)
"Beautiful location and view, extremely quiet. Room enough for everyone (we had 9 adults and 3 kids). We hosted an Easter dinner for 15, the kitchen and dining room had room to spare. We had beautiful spring weather so most time was spent on the huge porch or around the fire pit."
Classic Catskills Estate, Amazing Location!
Interior
Contemporary art lovers escape nestled, minutes to Fishkill Village and...
10.0 out of 10, Exceptional, (12)
"Clean, well appointed interior. I liked watching the birds cleaning their nest in the tree near the backyard porch."
Contemporary art lovers escape nestled, minutes to Fishkill Village and...
Property grounds
Iconic Woodstock Home - Private, Walk to Town, Family & Pet friendly
10.0 out of 10, Exceptional, (105)
"Great location. Comfortable space. The only drawback was the downstairs bedroom mattress."
Iconic Woodstock Home - Private, Walk to Town, Family & Pet friendly
Exterior
ONE CLOVEWOOD in HIGH FALLS, near Mohonk preserve, mountain bikes included
10.0 out of 10, Exceptional, (136)
"Wonderful Ambience and very accommodating for children and pets. The game room was a bonus and a 'winner' - for us."
ONE CLOVEWOOD in HIGH FALLS, near Mohonk preserve, mountain bikes included
Property grounds
Lake Front Home close to Great Hiking Trails & just 60 minutes from NYC
10.0 out of 10, Exceptional, (3)
"Enjoyed quality time spent with daughter. Cute bungalow house in nice historical neighborhood, safe location and amazing views of the lake. Close to Beacon, New Paltz, Warwick, Walden and other cute little towns. 5 stars 💛"
Lake Front Home close to Great Hiking Trails & just 60 minutes from NYC
Smart TV, fireplace, video games, table tennis
Dream escape, new modern farmhouse, stunning views, game room & hot tub for 10+!
10.0 out of 10, Exceptional, (3)
"Great experience. Liked the location. Only complaint needs more hangers in the closets. Nice stay for big grouos"
The price is $492
$876 total
includes taxes & fees
May 14 - May 15
Dream escape, new modern farmhouse, stunning views, game room & hot tub for 10+!
Interior
Maple Ridge Modern Rustic Retreat where Modern comfort meets Rustic Charm
10.0 out of 10, Exceptional, (5)
"We had a wonderful time. Excellent layout for a large group. I am sure it's beautiful right about now with the budding trees. We had a wonderful stay!"
Maple Ridge Modern Rustic Retreat where Modern comfort meets Rustic Charm
5 bedrooms, desk, iron/ironing board, travel crib
The 212 Escape
10.0 out of 10, Exceptional, (2)
"Super house - very spacious and clean. We had a great stay!"
The 212 Escape
Exterior
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
10.0 out of 10, Exceptional, (27)
"This is our third stay in this property, and each time we had a fabulous time."
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
Fridge, microwave, dishwasher, coffee/tea maker
Beacon Area Vacation Rental with Heated Pool!
10.0 out of 10, Exceptional, (9)
"Myself and some friends stayed at this location for a short weekend away. It was in a quiet neighborhood and provided ample space. Would stay again."
Beacon Area Vacation Rental with Heated Pool!
Private kitchen
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
10.0 out of 10, Exceptional, (10)
"We had a lovely weekend at this updated farm house. The house is a great combination of old comfortable farm house and updated and clean kitchens and bathrooms. We loved having Artie, the kitty, as our welcoming party."
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
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See all available properties in Highland
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

Property grounds
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
9.6 out of 10, Exceptional, (18)
"Wow Ryan, the owner was really nice guy just a great place to relax and enjoy firepit,.mountain views, outdoor sitting with tv, very private!!! I'll give this one 10+ review!!!!!"
The price is $215
$280 total
includes taxes & fees
May 2 - May 3
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
Exterior
The Farm at Hyde Park
9.6 out of 10, Exceptional, (45)
"We booked the Chapel for a quick weekend to check out the FDR Home and other sights around Hyde Park and Dutchess County. The place was perfect for our needs! Glen was very helpful and communication was excellent. We loved that the property has chickens and a wild turkey."
The Farm at Hyde Park
1 bedroom, internet, bed sheets
Hotel Woodstock - Iris suite
9.6 out of 10, Exceptional, (45)
"Cool propertry in a unique town"
The price is $99
$220 total
includes taxes & fees
May 2 - May 3
Hotel Woodstock - Iris suite
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.

Highland Vacation Homes information

Number of reviews
581
Accommodation
439 Vacation Homes
Lowest Price
$71
Highest Price
$492

Recent reviews of Highland hotels
Expedia verified reviews