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Compare 501 Vacation Homes in Highland with updated reviews, rates, and availability.

The Farm at Hyde Park
Exterior
The Farm at Hyde Park
9.8 out of 10, Exceptional, (63)
"Quiet spot out of the city but not too far from Hudson Valley sites. Large vaulted space, fresh eggs from the hen house next door, sky full of stars at night. Great host!"
The Farm at Hyde Park
Beautiful Private Stone Home in the Hudson Valley
Exterior
Beautiful Private Stone Home in the Hudson Valley
10.0 out of 10, Exceptional, (138)
"home and amenities enjoyed by all age groups. the city-slickers were thrilled by the deer, and visiting the chickens and roosters. the location is beautiful and rural. easy drive from nyc and capital district."
Beautiful Private Stone Home in the Hudson Valley
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
Front of the Red Cottage
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
10.0 out of 10, Exceptional, (33)
"Loved the house. Pictures don’t do it justice. We had a few issues and the property manager was super responsive and had everything corrected. Would stay there again. "
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Interior
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, (74)
"This place was a great place for us to stay on our vacation. Secluded outside of the city, and a short drive down a gravel road, it really feels that you're lost in the woods, but in a good way. If you're up to visit the Gunks, Angry Orchard, the Hudson river, love the beauty of the outdoors, and have other family or friends to visit in the area, definitely consider this home. Host was very responsive and had everything ready for us."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Red Barn Retreat - Shawangunk Mountains Getaway
Property grounds
Red Barn Retreat - Shawangunk Mountains Getaway
10.0 out of 10, Exceptional, (31)
"This was an absolutely amazing stay. My husband and I hand an amazing time with our two dogs celebrating our anniversary. We plan on returning again because we hand such a lovely time. We were greeted by our host who was so kind and helpful. All the recommendations were amazing and really helped us plan out our short time there. I wish we were able to stay longer but again we will be returning in the future!"
Red Barn Retreat - Shawangunk Mountains Getaway
complete privacy vacation home [private pool]
Pool
complete privacy vacation home [private pool]
9.6 out of 10, Exceptional, (4)
"Our family stayed here while visiting a nephew at West Point, around 35 min away. The house was very clean and check-in was flawless. The beds and pillows were comfortable. We spent a lot of time in the game room playing ping pong, air hockey, and pool. We did not swim in the pool but it looked amazing. A perfect place for us and we will definitely return if in the area again."
The price is AED 2,626
AED 4,068 total
includes taxes & fees
11 Nov - 12 Nov
complete privacy vacation home [private pool]
Bright, historic Woodstock home close to town
Exterior
Bright, historic Woodstock home close to town
9.8 out of 10, Exceptional, (6)
"We loved the historic nature of the property. It is in a beautiful setting, just a short walk from downtown Woodstock. Cheryl was very responsive and helpful. Wish we had more time to enjoy the outdoor space!"
Bright, historic Woodstock home close to town
‘A Gathering Den’ 3-bedrm house. Central to Belleayre, Hunter and Windham slopes
Exterior
‘A Gathering Den’ 3-bedrm house. Central to Belleayre, Hunter and Windham slopes
10.0 out of 10, Exceptional, (6)
"My family stayed here while visiting our daughter for parents weekend at Bard College. We have stayed in a number of rentals in the area over the past few years, and this is by far the best! It was perfect in every way: spacious, very clean and comfortable, everything worked well and the hosts were super responsive and kind. We will absolutely want to stay here again! "
‘A Gathering Den’ 3-bedrm house. Central to Belleayre, Hunter and Windham slopes
Hamptons on the Hudson in South Saugerties
Pool
Hamptons on the Hudson in South Saugerties
10.0 out of 10, Exceptional, (12)
"Our group of 7 women had a great time in the house. Beautiful property. Nice view of the Hudson. Lots of amenities. Well stocked kitchen. Cozy and comfortable. We enjoyed the Nespresso machine. Lots of room for us to spread out and to hang out together in the living room and enjoy a meal in the dining room. We would definitely stay again. "
Hamptons on the Hudson in South Saugerties
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Exterior
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
10.0 out of 10, Exceptional, (14)
"The house is best for a small family that can be active and not worry about hurting the interior. The property is pretty especially the open fields across the street where an evening walk is lovely. House was well stocked and comfortable ."
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Eating area leading to one pristeen acre looking out to waterfront
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
9.8 out of 10, Exceptional, (43)
"Wonderful rental, clean, modern, and a beautiful location."
The price is AED 584
AED 1,247 total
includes taxes & fees
11 Nov - 12 Nov
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Esopus Creek modern Tiny house Retreat!
Interior
Esopus Creek modern Tiny house Retreat!
9.6 out of 10, Exceptional, (17)
"A great spot close to Woodstock ny"
The price is AED 569
AED 830 total
includes taxes & fees
11 Nov - 12 Nov
Esopus Creek modern Tiny house Retreat!
Cute home in Kerhonkson, NY. This home is minutes to many popular destinations
Schawangunk House
Cute home in Kerhonkson, NY. This home is minutes to many popular destinations
8.8 out of 10, Excellent, (16)
"Close to the trails. Loved the park with the trails. "
Cute home in Kerhonkson, NY. This home is minutes to many popular destinations
New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill
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New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill
10.0 out of 10, Exceptional, (9)
"What a special place. The overlook is gorgeous and the entire home was so relaxing. Perfect stay. "
New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill
Nature Getaway: Charming Villa Near Trails and Parks
Interior
Nature Getaway: Charming Villa Near Trails and Parks
7.2 out of 10, Good, (9)
"Really cool house. We has some issues with our stay. It took a bit to get in touch with the manager to resolve the issues. The next day the brought most if the items needed that the h"
Nature Getaway: Charming Villa Near Trails and Parks
Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything
The open dining and living room area has plenty of comfortable seating.
Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything
10.0 out of 10, Exceptional, (1)
"Host was great! This house has everything you need for a perfect upstate stay. Quiet neighborhood close to all amenities and local attractions. "
The price is AED 569
AED 945 total
includes taxes & fees
13 Nov - 14 Nov
Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything
Pet-Friendly ‘Pond View Loft' w/ Private Pool!
Pine Bush Vacation Rental | 1BR | 1.5BA | Stairs Required for Access | 750 Sq Ft
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!
The Studio at the Inn at High Falls
Exterior
The Studio at the Inn at High Falls
7.8 out of 10, Good, (22)
"Great communication with host. Stayed one night for event at Arrowood Farms (only 10 minutes away). Clean , nicely decorated studio with plenty of light. Lovely yard. Close to all local attractions and dining. Large shower. Great towels and toiletries.TV and A/C worked well. Appreciated the drinking water.Really cozy studio. Has frig, microwave and coffee maker.(also iron and hair dryer). A fabulous stay, although water pressure was a little low, but certainly not a deal breaker. Had people...
The Studio at the Inn at High Falls
The Louie II: Accord Farmhouse near Arrowood w/ Hot Tub & Large Yard
Welcome to the Louie II. A serene setting for your next Hudson Valley getaway.
The Louie II: Accord Farmhouse near Arrowood w/ Hot Tub & Large Yard
9.2 out of 10, Wonderful, (22)
"This property was clean and exactly as described. We were in the area for a family gathering and it allowed us a quiet place to regroup with our dog at night. Highly recommend and are hoping to visit again. "
The Louie II: Accord Farmhouse near Arrowood w/ Hot Tub & Large Yard
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
Exterior
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
9.6 out of 10, Exceptional, (24)
"We enjoyed our stay. The property was very clean and had lots of nice amenities."
The price is AED 676
AED 1,213 total
includes taxes & fees
23 Nov - 24 Nov
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
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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Other property types in Highland

The Scenic Mansion With Breathtaking View
Property grounds
The Scenic Mansion With Breathtaking View
9.4 out of 10, Exceptional, (10)
"Our extended stay has been ideal and the host has been attentive, gracious and welcoming. We will be back in the spring!"
The Scenic Mansion With Breathtaking View
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
Property grounds
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
9.8 out of 10, Exceptional, (26)
"This place was great! The apartment itself is a great size for 2 people. The yard was pretty big with lots of seating, firepit, an awesome guitar shaped chiminea, nice sized pool, outdoor tv in the gazebo. The owner, Ryan, came later at night and left the next morning. He was super nice and very helpful!"
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
Mid-Century DJ’s Dream
Outdoor dining
Mid-Century DJ’s Dream
10.0 out of 10, Exceptional, (21)
"Kevin was great with being flexible about check in time! My sister and I didn't get in until past 9pm and it was no problem! And it's a plus that he's very pet friendly as I had my dog and cat with me!"
The price is AED 364
AED 584 total
includes taxes & fees
21 Nov - 22 Nov
Mid-Century DJ’s Dream
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.