Photo by Karen Wirtz

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

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
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
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.
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
10.0 out of 10, Exceptional, (30)
"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]
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 SAR 2,686
SAR 4,160 total
includes taxes & fees
7 Nov - 8 Nov
complete privacy vacation home [private pool]
Bright, historic Woodstock home close to town
9.6 out of 10, Exceptional, (5)
"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
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
10.0 out of 10, Exceptional, (12)
"Beautiful home and great location . "
Hamptons on the Hudson in South Saugerties
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!
9.8 out of 10, Exceptional, (43)
"Wonderful rental, clean, modern, and a beautiful location."
The price is SAR 710
SAR 1,407 total
includes taxes & fees
7 Nov - 8 Nov
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Esopus Creek modern Tiny house Retreat!
9.6 out of 10, Exceptional, (17)
"A great spot close to Woodstock ny"
The price is SAR 582
SAR 848 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
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
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
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
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 SAR 582
SAR 959 total
includes taxes & fees
7 Nov - 8 Nov
Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything
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 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
9.6 out of 10, Exceptional, (23)
"We enjoyed our stay. The property was very clean and had lots of nice amenities."
The price is SAR 627
SAR 1,167 total
includes taxes & fees
10 Nov - 11 Nov
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
Midcentury Modern Cabin Home in the Woods- Under 2 Hrs From NYC!
10.0 out of 10, Exceptional, (116)
"The home is nestled in the woods and surrounded by amazing boulders . The mid century home is comfortable and stunning . We stayed at the house for a quiet weekend visiting friends in the area. The home is well equipped and a joy to stay and relax in . The area is a hikers dream and there are many amazing places to explore . The working fireplace adds a magical atmosphere. We hope to visit this property again . "
Midcentury Modern Cabin Home in the Woods- Under 2 Hrs From NYC!
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
9.4 out of 10, Exceptional, (8)
"Property is 2 mins away from numerous farms including DuBois. Pool is well maintained and is massive with great landscape in the backyard for large group to enjoy. Would have liked to have inside bit cleaner but I think it comes being outdoor type property."
The Scenic Mansion With Breathtaking View
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
9.8 out of 10, Exceptional, (25)
"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!"
The price is SAR 808
SAR 1,159 total
includes taxes & fees
30 Nov - 1 Dec
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
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 SAR 372
SAR 597 total
includes taxes & fees
20 Nov - 21 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.