Photo by Karen Wirtz

Highland Vacation Rentals

Most properties are fully refundable. Because flexibility matters.

Save an average of 15% on thousands of hotels with Expedia Rewards

Search over 2.9 million properties and 550 airlines worldwide

Browse Select Highland Vacation Homes

Luxury Rhinebeck NY Home on 5 Acres w/ NEW Hot Tub. Great for Families & Groups
10.0 out of 10, Exceptional, (85)
"As we drove up the long driveway to this house we quickly felt it was a home for the next few days we stayed there. The space was inviting, comfortable, clean and the decor was beautiful. Our daughter absolutely loved celebrating her 13th birthday at this beautiful home. It was instant relaxation as the surroundings are beautiful and quiet. Gretchen was a lovely host who was very easy to communicate with and provided such helpful information for us during our stay. A few weeks later and we are...
Luxury Rhinebeck NY Home on 5 Acres w/ NEW Hot Tub. Great for Families & Groups
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
10.0 out of 10, Exceptional, (152)
"this was one of the most comfortable, easy to navigate vacation homes we have ever had. we used the grill, kitchen had everything you need, the deep sinks made washing dishes easy, (there was a dishwasher. but we didn't use it), windows allowed a 180 degree view of the back yard and forest beyond, where we saw a family of deer. Everyone slept like babies on mattresses that were heavenly! Or was super available and responsive to questions. A hannaford super market is 2.3 miles away. Bread Alone...
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
10.0 out of 10, Exceptional, (64)
"This is our 4th time staying here! And it won't be the last. Weather perfect for sitting on the deck with coffee and cocktails watching the creek slowly flow by. Beds are super comfortable with the BEST pillows. Everything you need for a relaxing stay. O.J, incredible bread with butter and strawberry preserves to greet you! Only a mile from town. An easy walk. Will see you again soon!"
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
Save an average of 15% on thousands of hotels when you're signed in
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
10.0 out of 10, Exceptional, (29)
"Our stay was wonderful! The house was super clean and just what we needed. The bed was comfortable and the game room even better for the little ones and adults :) thank you so much!"
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
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
Bright Cornwall-On-Hudson Vacation Rental!
10.0 out of 10, Exceptional, (3)
"Excellent location, well-equipped, comfortable and clean. Everything we hoped for!"
Bright Cornwall-On-Hudson Vacation Rental!
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, (61)
"The property and house were beautiful, out of the way but beautiful. The fire pit, sunroom, and porch were amazing. It was great for decompressing after a West Point graduation. Thank you for sharing your little piece of heaven."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
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
5-Star New Barn Home - Music Studio, Views & Hot Tub
10.0 out of 10, Exceptional, (18)
"The house is amazing, it delivers on everything stated in the listing and then some. This was our second time staying at Stephen's place and it just keeps getting better. Can't wait for the next one. If you love to listen and play music, its a must."
5-Star New Barn Home - Music Studio, Views & Hot Tub
Black Walnut Tree Farm: Farmhouse on 50 Acres
10.0 out of 10, Exceptional, (13)
"Four friends had a wonderful time at Black Walnut Tree Farm. The space was amazing! There was plenty of spaces that we could hang out together, but also we each had areas that we could retreat to. The kitchen was well-stocked ands spacious, the large living room had many comfortable seats around the fire, and there was a great sunroom where we could sit and play games. The grounds were huge and one could easily get lost walking around the property. We all loved the place and are collectively...
Black Walnut Tree Farm: Farmhouse on 50 Acres
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
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 CA $866
CA $1,419 total
includes taxes & fees
May 28 - May 29
Dream escape, new modern farmhouse, stunning views, game room & hot tub for 10+!
Brookside Retreat: streamside patio•outdoor fireplace•fenced yard•walk to town!
10.0 out of 10, Exceptional, (82)
"Great country house, well situated near town, with stream in the rear. Would definitely stay here agin. Excellent communication with the owner, whose attention to detail helps to make this a comfortable stay. Well equipped kitchen -- pretty much everything you might need. This is a cozy house, not a fancy house. Very comfortable for a family. Stairs are a bit steep for little kids with kids beds upstairs."
Brookside Retreat: streamside patio•outdoor fireplace•fenced yard•walk to town!
Modern Farmhouse; Quiet, Eclectic,Cozy, Fun, situated on a peaceful Creek.
10.0 out of 10, Exceptional, (13)
"The host was fantastic with details and communication. Can’t wait to stay here again."
Modern Farmhouse; Quiet, Eclectic,Cozy, Fun, situated on a peaceful Creek.
Salt Point Guest House on Working Horse Farm!
10.0 out of 10, Exceptional, (50)
"The property location was so close to everything we had planned for our Hyde Park is it. Rebecca was a marvelous host and the property was everything we expected."
Salt Point Guest House on Working Horse Farm!
The Farm at Hyde Park
9.8 out of 10, Exceptional, (47)
"Very unusual, appealing proportions, well stocked, perfect location"
The Farm at Hyde Park
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, (35)
"This is a cozy property in a very rural setting. The host is extremely responsive and very thorough. It is quiet and private. The furniture and bed are very comfortable. The wood burning stove is a pellet stove which provides enough heat to take the edge off. The hot tub could comfortably fit 4 people. The Village of Cold Spring is less than 10 minutes away, as is the Interstate 84 bridge across the Hudson. If you want to make your own food, bring it. There is no grocery store nearby."
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
Renee's Get-Away New Paltz
9.8 out of 10, Exceptional, (13)
"perfect for what we needed. We only needed a place to sleep since we were visiting our daughter and had several plans throughout the trip. The be was comfortable and it was the perfect size place for my wife and I, as well as my 20yo daughter who stayed 2 nights."
Renee's Get-Away New Paltz
Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz
9.8 out of 10, Exceptional, (18)
"Would have liked to have some live TV instead of just streaming apps. Took a while to figure out how to run coffee pot"
Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz
Don't see what you're looking for?
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

Streamside Cottage Walking Distance to Town of Woodstock
10.0 out of 10, Exceptional, (196)
"My sister and I needed a quick getaway from the world and found refuge in this sweet little cottage that is right on the creek. The cottage was pristine, fully eqipped, quiet and tastefully decorated. My communication with the owner, Jane, was "easy breezy". Our favorite part of our stay were the sights and sounds of the water! It was truly magnificent. We came to the cottage a little tired from the pressures of life but left rejuvenated and filled with peace. Our short stay was delightful. We...
The price is CA $217
CA $437 total
includes taxes & fees
May 16 - May 17
Streamside Cottage Walking Distance to Town of Woodstock
The Farm at Hyde Park
9.8 out of 10, Exceptional, (47)
"Very unusual, appealing proportions, well stocked, perfect location"
The Farm at Hyde Park
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 CA $294
CA $387 total
includes taxes & fees
May 16 - May 17
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
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.