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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Vacation Homes in Highland

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

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

Highland Falls
10.0 out of 10, Exceptional, (2)
"Looked like this property was recently renovated. Very clean and nice. "
United States
Ellie M.
The price is AED 345
AED 1,469 total
includes taxes & fees
10 Dec - 11 Dec
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Property grounds
Quaint & Cozy Cottage | Wood Stove, Pet Friendly

Quaint & Cozy Cottage | Wood Stove, Pet Friendly

New Paltz
10.0 out of 10, Exceptional, (3)
"Lovely home in a beautiful area of New York state. Would stay here again! "
United States
Jason W.
The price is AED 601
AED 2,087 total
includes taxes & fees
14 Dec - 15 Dec
Quaint & Cozy Cottage | Wood Stove, Pet Friendly
Fridge, microwave, oven, stovetop
Retro Retreat: renovated 2BR, desk, no chore list!

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

Kingston
9.6 out of 10, Exceptional, (14)
"Great little space. Perfect for two adults. Chill living room and well appointed kitchen. It’s a perfect alternative to a hotel, and reasonably priced for what you get. "
United States
Chris S.
The price is AED 272
AED 1,049 total
includes taxes & fees
10 Dec - 11 Dec
Retro Retreat: renovated 2BR, desk, no chore list!
3 bedrooms, iron/ironing board, travel crib, WiFi
"Country outside the city " 3 bedrooms 2 full bathrooms

"Country outside the city " 3 bedrooms 2 full bathrooms

2.0 star property
Holmes
9.6 out of 10, Exceptional, (4)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
The price is AED 615
AED 1,984 total
includes taxes & fees
15 Dec - 16 Dec
"Country outside the city " 3 bedrooms 2 full bathrooms
Interior
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Kerhonkson
10.0 out of 10, Exceptional, (32)
"I love the place, very comfortable and cozy, Thank you so very much, Enjoyed a lot , Julia"
United States
Julia K.
The price is AED 290
AED 689 total
includes taxes & fees
11 Dec - 12 Dec
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Fridge, microwave, oven, stovetop
Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!

Kingston
10.0 out of 10, Exceptional, (29)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
The price is AED 257
AED 905 total
includes taxes & fees
14 Dec - 15 Dec
Campfire Cottage: Fireplace, fire pit & no chores!
Exterior
The Studio at the Inn at High Falls

The Studio at the Inn at High Falls

High Falls
8.0 out of 10, Very Good, (33)
"Perfect location. Easy access to great surrounding area. Nice space. We had only one night. Wish it was longer!"
United States
loretta p.
The price is AED 413
AED 985 total
includes taxes & fees
10 Dec - 11 Dec
The Studio at the Inn at High Falls
Fridge, microwave, oven, stovetop
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

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

Kingston
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!"
United States
Brendan B.
The price is AED 165
AED 798 total
includes taxes & fees
10 Dec - 11 Dec
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Outdoor dining
Esopus Creek modern Tiny house Retreat!

Esopus Creek modern Tiny house Retreat!

Kingston
9.8 out of 10, Exceptional, (62)
"The property was beautiful. Quiet area but close enough to all the places we wanted to go. Our hosts were very gracious, attentive and friendly. Enjoyed our weekend retreat. "
United States
Rebecca
The price is AED 606
AED 954 total
includes taxes & fees
4 Jan - 5 January 2026
Esopus Creek modern Tiny house Retreat!
Dining
Brand New House with Huge patio overlooks Esopus Creek at Lake Katrine

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

Lake Katrine
10.0 out of 10, Exceptional, (16)
"Perfect getaway!"
United States
Lynn A.
The price is AED 658
AED 1,526 total
includes taxes & fees
22 Dec - 23 Dec
Brand New House with Huge patio overlooks Esopus Creek at Lake Katrine
Exterior detail
Cozy private suite in the heart of beautiful Gardiner.

Cozy private suite in the heart of beautiful Gardiner.

New Paltz
10.0 out of 10, Exceptional, (7)
"Check-in was easy. Hosts very responsive to any questions and helpful to local recommendations. "
United States
Chanah B.
The price is AED 469
AED 941 total
includes taxes & fees
12 Dec - 13 Dec
Cozy private suite in the heart of beautiful Gardiner.
Private kitchen
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

new paltz
9.6 out of 10, Exceptional, (5)
"5 stars!!! 100% recommended and I will be coming back! Host is prompt, attentive, and is great with communication!! No complaints at all!!! "
United States
Fantasia
The price is AED 661
AED 2,608 total
includes taxes & fees
12 Dec - 13 Dec
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
Exterior
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Hopewell Junction
9.0 out of 10, Wonderful, (10)
"We had a great last minute visit to Hopewell Junction and enjoyed a lovely stay at the chapel! It’s a very unique experience and quiet and peaceful. We enjoyed the bbq and an evening fire with smores! "
United States
Esther P.
The price is AED 559
AED 948 total
includes taxes & fees
10 Dec - 11 Dec
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Interior
Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything

Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything

Kerhonkson
9.8 out of 10, Exceptional, (23)
"Comfortable accommodations. Everything you need for a relaxing holiday "
United States
Susan W.
The price is AED 628
AED 1,074 total
includes taxes & fees
11 Dec - 12 Dec
Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything
Fridge, microwave, oven, stovetop
Warm Atomic Ranch - MCM One Level

Warm Atomic Ranch - MCM One Level

Olivebridge
10.0 out of 10, Exceptional, (1)
The price is AED 578
AED 2,092 total
includes taxes & fees
10 Dec - 11 Dec
Warm Atomic Ranch - MCM One Level
Fridge, microwave, oven, stovetop
Double the Fun: Two Houses, Shared Yard & Fire Pit

Double the Fun: Two Houses, Shared Yard & Fire Pit

Kingston
10.0 out of 10, Exceptional, (4)
"Both houses were vey clean and well kept. I would recommend this to anyone. I would stay here again."
United States
Kelly B.
The price is AED 518
AED 1,814 total
includes taxes & fees
14 Dec - 15 Dec
Double the Fun: Two Houses, Shared Yard & Fire Pit
Interior
Lovely 3BR Home with parking-Walk to WP Gate!

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

Highland Falls
10.0 out of 10, Exceptional, (7)
"Convenient location. Nice to have 3 queen beds. One parking space is in a lot, but street for any additional. Plenty of availability though. Excellent washer and dryer, dishwasher. Internet worked well. "
United States
Matt D.
The price is AED 690
AED 1,269 total
includes taxes & fees
5 Jan - 6 January 2026
Lovely 3BR Home with parking-Walk to WP Gate!
Interior
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Poughkeepsie
10.0 out of 10, Exceptional, (2)
"Great host"
United States
Lindsey F.
The price is AED 605
AED 2,133 total
includes taxes & fees
15 Dec - 16 Dec
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Outdoor dining
Huge Private Suite w/ Pool Table, Sauna & Fire Pit

Huge Private Suite w/ Pool Table, Sauna & Fire Pit

2.0 star property
Ellenville
The price is AED 514
AED 723 total
includes taxes & fees
10 Dec - 11 Dec
Huge Private Suite w/ Pool Table, Sauna & Fire Pit
Fridge, microwave, oven, stovetop
Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!

Highland Falls
9.0 out of 10, Wonderful, (4)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is AED 667
AED 1,208 total
includes taxes & fees
5 Jan - 6 January 2026
Fabulous 3bdrm Home w/parking!
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

Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

10/10 Excellent
"The was extremely clean"
Dewayne 1-night trip
Posted 2 days ago
Holiday Inn Express Poughkeepsie by IHG