Photo by Allison Alano Flores

Search Vacation Homes in Highland

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Dec 5 - Dec 7
In two months
Jan 16 - Jan 18
In three months
Feb 13 - Feb 15
In four months
Mar 13 - Mar 15

Vacation Homes in Highland

Property grounds
Hudson Escape W/ Hot Tub + Bridge View

Hudson Escape W/ Hot Tub + Bridge View

Highland
Hudson Escape W/ Hot Tub + Bridge View
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.
$222 nightly
The price is $249
Dec 9 - Dec 10
Total with taxes and fees
Campfire Cottage: Fireplace, fire pit & no chores!
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.
$255 nightly
The price is $286
Dec 9 - Dec 10
Total with taxes and fees
Retro Retreat: renovated 2BR, desk, no chore list!
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, (32)
"We loved our studio — it was cozy, charming, and fit our needs perfectly. Frank went above and beyond to make us feel comfortable, and his hospitality really stood out. Everything was spotless and well-kept, and we had everything we needed for a relaxing stay. The location was convenient, the space felt welcoming, and little touches made it even more enjoyable. We would definitely stay here again and highly recommend it to anyone looking for a comfortable and stress-free getaway!"
United States
Ya-elle G.
$243 nightly
The price is $272
Nov 24 - Nov 25
Total with taxes and fees
The Studio at the Inn at High Falls
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.
$491 nightly
The price is $555
Dec 15 - Dec 16
Total with taxes and fees
"Country outside the city " 3 bedrooms 2 full bathrooms
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, (22)
"Beautiful property on a quiet block. The house is nicely stocked with everything you need and has charming decor elements. "
United States
Julia S.
$263 nightly
The price is $295
Dec 1 - Dec 2
Total with taxes and fees
Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything
Exterior
House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!

Highland Falls
10.0 out of 10, Exceptional, (4)
"Good stay, awesome place"
United States
Scott G.
$374 nightly
The price is $397
Dec 3 - Dec 4
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!
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.
$201 nightly
The price is $225
Dec 9 - Dec 10
Total with taxes and fees
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
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.
$231 nightly
The price is $258
Nov 24 - Nov 25
Total with taxes and fees
Cozy private suite in the heart of beautiful Gardiner.
Interior
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks

Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks

Kerhonkson
10.0 out of 10, Exceptional, (14)
"Can’t emphasize how nice the surrounding area and property itself are. Very relaxing while still being close to several small towns with great restaurants. Communication was excellent, overall a great experience! "
United States
jose f.
$205 nightly
The price is $208
Dec 1 - Dec 2
Total with taxes and fees
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
Outdoor dining
Glamping Tent & Campsite by Minnewaska State Park

Glamping Tent & Campsite by Minnewaska State Park

Kerhonkson
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. "
United States
Angie W.
$136 nightly
The price is $152
Nov 24 - Nov 25
Total with taxes and fees
Glamping Tent & Campsite by Minnewaska State Park
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.
$419 nightly
The price is $424
Nov 24 - Nov 25
Total with taxes and fees
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Fridge, microwave, oven, stovetop
The Meyer: spacious family home with hot tub minutes to downtown New Paltz

The Meyer: spacious family home with hot tub minutes to downtown New Paltz

New Paltz
10.0 out of 10, Exceptional, (9)
"Clean environment, quiet, family friendly and was well equipped. Our family enjoyed staying and the host was available for any questions. "
United States
Awa Malicka B.
$316 nightly
The price is $354
Dec 7 - Dec 8
Total with taxes and fees
The Meyer: spacious family home with hot tub minutes to downtown New Paltz
Property grounds
3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed

Highland Falls
9.0 out of 10, Wonderful, (4)
"Excellent host, house is very clean. The queen and king beds are comfortable. The sound of the brook is relaxing. "
United States
Penny D.
$399 nightly
The price is $451
Dec 1 - Dec 2
Total with taxes and fees
3BR West Point Retreat-3min to Back Gate+ King Bed
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.
$442 nightly
The price is $495
Dec 10 - Dec 11
Total with taxes and fees
Double the Fun: Two Houses, Shared Yard & Fire Pit
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.
$228 nightly
The price is $258
Nov 24 - Nov 25
Total with taxes and fees
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
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, (4)
"Very clean Good communication with host Close to town & hiking Recommend! "
United States
Jennifer E.
$629 nightly
The price is $704
Nov 24 - Nov 25
Total with taxes and fees
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
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.
$371 nightly
The price is $416
Nov 30 - Dec 1
Total with taxes and fees
Brand New House with Huge patio overlooks Esopus Creek at Lake Katrine
Property grounds
Welcome to The Boathouse! Waterfront/Boats/Hot tub

Welcome to The Boathouse! Waterfront/Boats/Hot tub

New Paltz
10.0 out of 10, Exceptional, (3)
"Always love to stay in the New Paltz area. Good for the soul."
United States
Denise C.
$307 nightly
The price is $344
Nov 25 - Nov 26
Total with taxes and fees
Welcome to The Boathouse! Waterfront/Boats/Hot tub
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.
$497 nightly
The price is $582
Nov 24 - Nov 25
Total with taxes and fees
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
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.
View all properties

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Highland Hotel Reviews

Hampton Inn Kingston

Hampton Inn Kingston

10/10 Excellent
"Check-in was a breeze, Aceton and Lovely were friendly welcoming faces after a long day of travel. The room is clean and spacious and the pool is very nice."
Miel 1-night trip
Posted 3 days ago
Hampton Inn Kingston

Find out more about Highland

Highland Vacation Homes information

Number of reviews
Accommodation
 Vacation Homes
Lowest Price
Highest Price

Explore a world of travel with Expedia