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Compare 635 Vacation Homes in Highland with updated reviews, rates, and availability.

Esopus Creek modern Tiny house Retreat!

9.8 out of 10, Exceptional, (23)
"This was our first visit to this property, and we will definitely be back for future visits. The house was immaculate and perfect for our travel needs. The owners were very communicative and responsive, and that made the experience even better."
The price is SAR 581
SAR 847 total
includes taxes & fees
6 Apr - 7 Apr
Esopus Creek modern Tiny house Retreat!

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

9.6 out of 10, Exceptional, (5)
"Plenty of room for my family"
The price is SAR 972
SAR 1,103 total
includes taxes & fees
15 Apr - 16 Apr
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

HOT TUB w/ POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN

10.0 out of 10, Exceptional, (92)
"Great place if you are visiting Woodstock! Bill is a great property manager and makes things easy for you from check in to amenities. 10/10 recommend!"
HOT TUB w/ POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN

Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska

9.8 out of 10, Exceptional, (93)
"We had a wonderful family long weekend at Michele’s beautiful home in the Hudson Valley. We were there to celebrate the birthdays of my husband, son, and grandson. The house was comfortable and well equipped to make meals. Michele the host couldn’t be more responsive. There are many great hikes and wineries close by. This was a 5 star expereince enjoyed by all."
Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska

Spacious New Luxurious holiday house in lovely Hudson Valley

9.8 out of 10, Exceptional, (8)
"The house had room for all of us, spacious and comfortable with modern amenities. We enjoyed the large open kitchen, well equipped for making big meals, and especially loved the walk in pantry with sink, oven and coffee bar. The beds were comfy, the bathrooms deluxe. Large couch and huge TV in living room with cozy gas fireplace for us to gather and relax. Located on a quiet cul de sac, easy to get to local attractions. We enjoyed every minute of our stay."
Spacious New Luxurious holiday house in lovely Hudson Valley

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (16)
"Host was eary to communicate with. My kids enjoyed the games. Great view looking over the Hudson River. Easily accessible to town, Kingston, or Ski areas. Definitely would return!"
Hamptons on the Hudson in South Saugerties

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

9.2 out of 10, Wonderful, (33)
"Perfect spot for a get together with friends... kitchen, dining room and living room all connected so you're always together and not missing out on the fun. Comfy couches and plenty of space for large board games."
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

10.0 out of 10, Exceptional, (46)
"This is the perfect spot for us to stay visiting our West Point cadet. Cozy, clean, well-appointed, & great communication. Thanks for everything! We'll be back! :)"
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

Hidden Charm in Hudson Valley In Dutchess County

2.0 star property
10.0 out of 10, Exceptional, (14)
"We visited here for my wife’s birthday with friends. Great location, while it’s just a 2 hour drive from the city the property is has a great location with its own privacy and wonderful light lit living room. The place is well stocked with utensils and linens. Host was very responsive and kind.Thank you for creating the wonderful time for us"
Hidden Charm in Hudson Valley In Dutchess County

Red Barn Retreat - Shawangunk Mountains Getaway

10.0 out of 10, Exceptional, (36)
"Needed rest and quiet away from the city! Not only was this the perfect location, but William is a fantastic host. Great communication before and after, from directions to access and operation with kindness and generosity of spirit. Will return! "
Red Barn Retreat - Shawangunk Mountains Getaway

Bright Cornwall-On-Hudson Vacation Rental!

9.8 out of 10, Exceptional, (14)
"Nice location. Clean and comfortable. Was very cold inside when we entered (52 degrees) and I could not find an extra blanket anywhere. Everything else was great. "
Bright Cornwall-On-Hudson Vacation Rental!

Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View

10.0 out of 10, Exceptional, (284)
"I visited my college aged son over the weeend for a special event and wanted to stay somewhere with a little something special rather than a hotel. This property exceeded my expectations. Even with winter still lingering, the lake view was spectacular and was highlighted by the home's back wall of windows. Also, Don is a very responsive host and made sure the home had everything you could need - grill, grill tools, pots/pans, appliances, etc. I truly appreciated the hospitality. I hope to stay...
The price is SAR 1,032
SAR 1,226 total
includes taxes & fees
28 Mar - 29 Mar
Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View

Our home is perfect for relaxing and having lots of fun, with near by activity’s

10.0 out of 10, Exceptional, (2)
"We enjoyed our stay. The host is very responsive. The location is 30 minutes from Beacon, 10 minutes from Poughkeepsie and 2 hrs from NYC. The office was a nice feature and the house has great WiFi. "
Our home is perfect for relaxing and having lots of fun, with near by activity’s

Brand New House with Huge patio overlooks Esopus Creek at Lake Katrine

10.0 out of 10, Exceptional, (8)
"My family and I had a lovely stay! The home is beautiful and comfortable with all the amenities that we needed, including a crib as we were traveling with a newborn. Not much in the immediate vicinity but a short drive to Kingston. Smooth communication and easy checkin/checkout process."
The price is SAR 454
SAR 1,159 total
includes taxes & fees
31 Mar - 1 Apr
Brand New House with Huge patio overlooks Esopus Creek at Lake Katrine

Pet-Friendly Beacon Area Vacation Rental: 6 Acres

10.0 out of 10, Exceptional, (12)
"Great place to stay for all ages. Had everything we needed and lots of room to relax. Definitely will stay here again next time we come. Comfy beds, easy to get to, easy check in, everything we needed in the kitchen, lots of books and toys, great outdoor space. Thanks for providing the perfect place to stay with extended family! "
Pet-Friendly Beacon Area Vacation Rental: 6 Acres

Experience Woodstock charm while staying in a cozy cabin in the woods

9.8 out of 10, Exceptional, (24)
"This house was perfect for our girls trip! Clean .. very stocked and super easy to get to!"
Experience Woodstock charm while staying in a cozy cabin in the woods

HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace

10.0 out of 10, Exceptional, (35)
"This house was adorably charming and perfect for a weekend getaway in Woodstock. We loved watching wildlife from the beautiful kitchen windows and the privacy the property provided. Our pup loved the front sun room and keeping an eye on the yard. Thank you for sharing your home!"
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace

Modern Farmhouse on pristine private 12 Acres

9.6 out of 10, Exceptional, (76)
"We had a perfect stay at the beautiful farmhouse with all of the modern amenities.Outdoor space is to die for fenced in for your pup walking trails nature trails water features running streams..Cherry on top is that the listing is very generous with check-in and checkout times you can check in at 3 and you check out at 12. This feature allows for true relaxation!Book it!!"
Modern Farmhouse on pristine private 12 Acres

Lovely 2 queen size bedroom apt one block from Rough Draft and Uptown Kingston

10.0 out of 10, Exceptional, (42)
"Very clean, comfortable and convenient to all restaurants and shops. Spacious,comfortable and large enough to be private or not."
Lovely 2 queen size bedroom apt one block from Rough Draft and Uptown Kingston

Dream House in the Gunks

10.0 out of 10, Exceptional, (24)
"Awesome place, great location. We loved our stay."
The price is SAR 307
SAR 703 total
includes taxes & fees
3 Apr - 4 Apr
Dream House in the Gunks
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 House In Highland- Secluded Retreat

The House In Highland- Secluded Retreat

Our home is perfect for relaxing and having lots of fun, with near by activity’s

10.0 out of 10, Exceptional, (2)
"We enjoyed our stay. The host is very responsive. The location is 30 minutes from Beacon, 10 minutes from Poughkeepsie and 2 hrs from NYC. The office was a nice feature and the house has great WiFi. "
Our home is perfect for relaxing and having lots of fun, with near by activity’s

The Scenic Mansion With Breathtaking View

9.6 out of 10, Exceptional, (13)
"This house is so grand and perfect for a destination wedding, corprate retreat or family reunion. Host was wonderful!"
The Scenic Mansion With Breathtaking View
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.