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Highland Vacation Rentals

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Check prices for these dates

Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

Browse Select Highland Vacation Homes

Our top choices for Highland vacation homes

Bright Bedroom Near The Forest
Living area

Bright Bedroom Near The Forest

The price is CA $210
CA $282 total
includes taxes & fees
Sep 2 - Sep 3
Bright Bedroom Near The Forest
Hudson Escape W/ Hot Tub + Bridge View
Interior

Hudson Escape W/ Hot Tub + Bridge View

The price is CA $452
CA $917 total
includes taxes & fees
Sep 7 - Sep 8
Hudson Escape W/ Hot Tub + Bridge View
Campfire Cottage: Fireplace, fire pit & no chores!
Fridge, microwave, oven, stovetop

Campfire Cottage: Fireplace, fire pit & no chores!

10.0 out of 10, Exceptional, (26)
"Perfect cozy little spot for 2. Centrally located to explore surrounding areas"
The price is CA $104
CA $344 total
includes taxes & fees
Sep 10 - Sep 11
Campfire Cottage: Fireplace, fire pit & no chores!
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Fridge, microwave, oven, stovetop

Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

10.0 out of 10, Exceptional, (4)
"Beautiful house to stay in, convenient to numerous restaurants and hikes. Our host was very communicative and had great recommendations for the area!"
The price is CA $80
CA $314 total
includes taxes & fees
Sep 10 - Sep 11
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Glamping Tent & Campsite by Minnewaska State Park
Outdoor dining

Glamping Tent & Campsite by Minnewaska State Park

8.8 out of 10, Excellent, (3)
"We had a great time. The tent and toilet were clean. We appreciated the water provided and the cookware. The only thing to note is that there is a bit of walking on a rocky trail before reaching the campsite (not next to the parking spot). The river was fun to explore but can be difficult for younger kids to get to. The campsite is close to Minnewaska State Park, very convenient. "
The price is CA $118
CA $210 total
includes taxes & fees
Aug 25 - Aug 26
Glamping Tent & Campsite by Minnewaska State Park
Retro Retreat: renovated 2BR, desk, no chore list!
Fridge, microwave, oven, stovetop

Retro Retreat: renovated 2BR, desk, no chore list!

9.6 out of 10, Exceptional, (11)
"Very clean and nice inside. Host was very communicative. "
The price is CA $101
CA $382 total
includes taxes & fees
Sep 10 - Sep 11
Retro Retreat: renovated 2BR, desk, no chore list!
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
1 bedroom, desk, free WiFi

THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi

9.6 out of 10, Exceptional, (5)
The price is CA $200
CA $339 total
includes taxes & fees
Aug 26 - Aug 27
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
Dream Art Studio in the Gunks
Interior

Dream Art Studio in the Gunks

10.0 out of 10, Exceptional, (12)
"A quiet, artful place for some peaceful time."
The price is CA $108
CA $229 total
includes taxes & fees
Aug 25 - Aug 26
Dream Art Studio in the Gunks
Cozy Bedroom With Fireplace
Fireplace

Cozy Bedroom With Fireplace

The price is CA $205
CA $280 total
includes taxes & fees
Aug 27 - Aug 28
Cozy Bedroom With Fireplace
The Studio at the Inn at High Falls
Exterior

The Studio at the Inn at High Falls

8.0 out of 10, Very good, (27)
"I had a great stay here, it’s just as listed; simple but has everything that I needed, check in was easy, communication was good, and bed was comfortable!"
The price is CA $156
CA $377 total
includes taxes & fees
Aug 25 - Aug 26
The Studio at the Inn at High Falls
West Wing - a unique private space w/patio
Exterior

West Wing - a unique private space w/patio

9.6 out of 10, Exceptional, (15)
"Very clean house and great service "
The price is CA $174
CA $273 total
includes taxes & fees
Aug 31 - Sep 1
West Wing - a unique private space w/patio
Esopus Creek modern Tiny house Retreat!
Outdoor dining

Esopus Creek modern Tiny house Retreat!

9.8 out of 10, Exceptional, (46)
"4 of us stayed for a fishing trip and had a blast. Nice place at a reasonable price. Would stay again. "
The price is CA $205
CA $332 total
includes taxes & fees
Aug 25 - Aug 26
Esopus Creek modern Tiny house Retreat!
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Exterior

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

9.0 out of 10, Wonderful, (10)
"Truly a hidden gem. The property and home were nothing short of extraordinary. For those looking for a great location with access to hiking and a one of a kind experience this is the place."
The price is CA $210
CA $357 total
includes taxes & fees
Aug 25 - Aug 26
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Cozy Escape -Strong Wi-Fi -Prime Location
Fridge, microwave, oven, stovetop

Cozy Escape -Strong Wi-Fi -Prime Location

7.4 out of 10, Good, (3)
"The property was perfect for our little weekend getaway. It was very clean and cozy and the host Christina made it so easy for check in and was available for any questions. We would definitely stay again."
The price is CA $138
CA $460 total
includes taxes & fees
Aug 26 - Aug 27
Cozy Escape -Strong Wi-Fi -Prime Location
King Bed | Private Parking | Strong WiFi
Smart TV

King Bed | Private Parking | Strong WiFi

The price is CA $179
CA $550 total
includes taxes & fees
Aug 27 - Aug 28
King Bed | Private Parking | Strong WiFi
Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit
Exterior

Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit

10.0 out of 10, Exceptional, (1)
"Guido was very responsive and thoughtful! My partner and I stayed with our small dog and it was safe, clean, well stocked and in a beautiful area. Highly recommend to those looking to stay in the area!"
The price is CA $200
CA $320 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Property grounds

Sleek Escape: Modern 3 BR- 4 Min from West Point !

10.0 out of 10, Exceptional, (1)
"Looked like this property was recently renovated. Very clean and nice. "
The price is CA $253
CA $681 total
includes taxes & fees
Sep 15 - Sep 16
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Rustic Cabin in Fishkill!
Exterior

Rustic Cabin in Fishkill!

10.0 out of 10, Exceptional, (1)
"Beautiful property with many different areas to explore. We originally intended to spend more time in beacon but decided it was more fun hanging out here. "
The price is CA $380
CA $583 total
includes taxes & fees
Aug 25 - Aug 26
Rustic Cabin in Fishkill!
Lovely 3BR Home with parking-Walk to WP Gate!
Interior

Lovely 3BR Home with parking-Walk to WP Gate!

10.0 out of 10, Exceptional, (4)
"Easy booking, arrival, and departure. Very nice home. Very Clean and comfortable. Host was very kind and clear on everything for stay. Will book again!"
The price is CA $263
CA $455 total
includes taxes & fees
Sep 10 - Sep 11
Lovely 3BR Home with parking-Walk to WP Gate!
Nature Mountain Retreat with Outdoor Hot Tub and Sauna Spa Experience
Exterior detail

Nature Mountain Retreat with Outdoor Hot Tub and Sauna Spa Experience

10.0 out of 10, Exceptional, (4)
"very relaxing and comfortable place to stay!"
The price is CA $588
CA $1,182 total
includes taxes & fees
Aug 25 - Aug 26
Nature Mountain Retreat with Outdoor Hot Tub and Sauna Spa Experience
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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Top Highland Hotel Reviews

Hampton Inn by Hilton New Paltz

Hampton Inn by Hilton New Paltz

10/10 Excellent
"The room is very clean. Loved that I didn’t find any mustiness at all. The bedding felt very crisp. The free breakfast was simple but good quality foods. There’s waffle station that my friend really enjoyed. Having said the above, that should be the standard because this is not a budget hotel. It is on the pricey side but having vacancies in the short time we had to book the room, we felt it was fair. "
Xiu 2-night trip
Posted 7 hours ago
Hampton Inn by Hilton New Paltz