Photo by Karen Wirtz
Highland Vacation Rentals
Most properties are fully refundable. Because flexibility matters.
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Browse Select Highland Vacation Homes
Luxury Rhinebeck NY Home on 5 Acres w/ NEW Hot Tub. Great for Families & Groups
Luxury Rhinebeck NY Home on 5 Acres w/ NEW Hot Tub. Great for Families & Groups
10.0 out of 10, Exceptional, (85)
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
10.0 out of 10, Exceptional, (152)
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
10.0 out of 10, Exceptional, (64)
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Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
10.0 out of 10, Exceptional, (29)
Iconic Woodstock Home - Private, Walk to Town, Family & Pet friendly
Iconic Woodstock Home - Private, Walk to Town, Family & Pet friendly
10.0 out of 10, Exceptional, (105)
Bright Cornwall-On-Hudson Vacation Rental!
Bright Cornwall-On-Hudson Vacation Rental!
10.0 out of 10, Exceptional, (3)
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, (61)
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
10.0 out of 10, Exceptional, (10)
5-Star New Barn Home - Music Studio, Views & Hot Tub
5-Star New Barn Home - Music Studio, Views & Hot Tub
10.0 out of 10, Exceptional, (18)
Black Walnut Tree Farm: Farmhouse on 50 Acres
Black Walnut Tree Farm: Farmhouse on 50 Acres
10.0 out of 10, Exceptional, (13)
ONE CLOVEWOOD in HIGH FALLS, near Mohonk preserve, mountain bikes included
ONE CLOVEWOOD in HIGH FALLS, near Mohonk preserve, mountain bikes included
10.0 out of 10, Exceptional, (136)
Dream escape, new modern farmhouse, stunning views, game room & hot tub for 10+!
Dream escape, new modern farmhouse, stunning views, game room & hot tub for 10+!
10.0 out of 10, Exceptional, (3)
The price is CA $866
CA $1,419 total
includes taxes & fees
May 28 - May 29
Brookside Retreat: streamside patio•outdoor fireplace•fenced yard•walk to town!
Brookside Retreat: streamside patio•outdoor fireplace•fenced yard•walk to town!
10.0 out of 10, Exceptional, (82)
Modern Farmhouse; Quiet, Eclectic,Cozy, Fun, situated on a peaceful Creek.
Modern Farmhouse; Quiet, Eclectic,Cozy, Fun, situated on a peaceful Creek.
10.0 out of 10, Exceptional, (13)
Salt Point Guest House on Working Horse Farm!
Salt Point Guest House on Working Horse Farm!
10.0 out of 10, Exceptional, (50)
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, (35)
Renovated 1850's Cottage on Storm King Mountain
Renovated 1850's Cottage on Storm King Mountain
9.8 out of 10, Exceptional, (8)
Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz
Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz
9.8 out of 10, Exceptional, (18)
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
Streamside Cottage Walking Distance to Town of Woodstock
10.0 out of 10, Exceptional, (196)
The price is CA $217
CA $437 total
includes taxes & fees
May 16 - May 17
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
9.6 out of 10, Exceptional, (18)
The price is CA $294
CA $387 total
includes taxes & fees
May 16 - May 17
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.
Recent Reviews in Highland
Recent Reviews in Highland
5/5 Excellent
"Excellent all around! Highly recommend!"
A verified traveller stayed at Inn at Bellefield / Hyde Park, Residence Inn by Marriott
Posted 11 hours ago
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