A suspension bridge over a river with autumn foliage and distant hills.

Search Holiday Homes in Highland

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Highland holiday homes

Paper towels

1. Amazing 3-bedroom house with AC in adorable Highland

Amazing 3-bedroom house with AC in adorable Highland
Highland
The price is £359
includes taxes & fees
31 Aug - 1 Sept
Amazing 3-bedroom house with AC in adorable Highland
Interior

2. Our home is perfect for relaxing and having lots of fun, with near by activity’s

Our home is perfect for relaxing and having lots of fun, with near by activity’s
Highland
9.6 out of 10, Exceptional, (13 reviews)
"We had was great time and the host Mary was amazing and excellent at communicating. Everything was perfect in the home. Thank you"
United States
Pinal
The price is £535
includes taxes & fees
14 Sept - 15 Sept
Our home is perfect for relaxing and having lots of fun, with near by activity’s
Smart TV

3. The DeVita House Est. 1900

The DeVita House Est. 1900
Gardiner
10.0 out of 10, Exceptional, (37 reviews)
"Great house, well equipped, very accommodating hosts!"
United States
Christopher T.
The price is £326
includes taxes & fees
26 Aug - 27 Aug
The DeVita House Est. 1900
Coffee/tea maker, fridge, microwave, oven

4. NEW: Family Pool Retreat in Stone Ridge

NEW: Family Pool Retreat in Stone Ridge
Cottekill
10.0 out of 10, Exceptional, (1 review)
"Property was great for our girls weekend! Eight of us fit very comfortably. Host was very responsive to all of our needs! We had a great time!"
United States
Shannon M.
The price is £774
includes taxes & fees
15 Sept - 16 Sept
NEW: Family Pool Retreat in Stone Ridge
Miscellaneous

5. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is £502
includes taxes & fees
4 Sept - 5 Sept
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
1 bedroom, free WiFi, bed sheets

6. 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, (41 reviews)
"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!"
United States
Jamie M.
The price is £200
includes taxes & fees
31 Aug - 1 Sept
The Studio at the Inn at High Falls
Interior

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

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Poughkeepsie
9.6 out of 10, Exceptional, (5 reviews)
"Beautiful property with ample space for parking. Host was super nice and met all of our needs!"
United States
Nicole Y.
The price is £442
includes taxes & fees
14 Sept - 15 Sept
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Coffee/tea maker, fridge, microwave, oven

8. 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, (6 reviews)
"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 £185
includes taxes & fees
22 Sept - 23 Sept
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Property grounds

9. Glamping Tent & Campsite by Minnewaska State Park

Glamping Tent & Campsite by Minnewaska State Park
Kerhonkson
9.0 out of 10, Wonderful, (4 reviews)
"This place was amazing and our hosts were as equally as awesome as their campsite. My family highly recommends this place! It's got everything you need and is close to so many beautiful hiking and swimming areas!"
United States
Andie C.
The price is £114
includes taxes & fees
26 Aug - 27 Aug
Glamping Tent & Campsite by Minnewaska State Park
Interior

10. Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (32 reviews)
"The place was amazing! Very easy check in/out process and the host is very responsive. "
United States
Samuel M.
The price is £199
includes taxes & fees
23 Sept - 24 Sept
Campfire Cottage: Fireplace, fire pit & no chores!
Exterior

11. Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.2 out of 10, Wonderful, (12 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
The price is £150
includes taxes & fees
30 Aug - 31 Aug
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
2 bedrooms, iron/ironing board, free WiFi, bed sheets

12. Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet

Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet
Stone Ridge
10.0 out of 10, Exceptional, (3 reviews)
"Great tastefully kept property. Our family including the 8 year felt we should have stayed here longer."
United States
Tarun
The price is £190
includes taxes & fees
7 Sept - 8 Sept
Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet
1 bedroom, free WiFi, bed sheets

13. Totally secluded Yurt surrounded by waterfalls, brooks, cliffs and forest

Totally secluded Yurt surrounded by waterfalls, brooks, cliffs and forest
Ulster Park
10.0 out of 10, Exceptional, (110 reviews)
"Always love the yurt "
United States
Curt B.
The price is £365
includes taxes & fees
27 Aug - 28 Aug
Totally secluded Yurt surrounded by waterfalls, brooks, cliffs and forest
Interior

14. Breezy Days Hiking, Quiet Yard, an Easy Escape Near New Paltz

Breezy Days Hiking, Quiet Yard, an Easy Escape Near New Paltz
New Paltz
10.0 out of 10, Exceptional, (8 reviews)
"Superb property - comfortable, spotless, all the amenities you could need, and lots of space. "
United States
Thomas B.
The price is £439
includes taxes & fees
26 Aug - 27 Aug
Breezy Days Hiking, Quiet Yard, an Easy Escape Near New Paltz
Interior

15. 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, (15 reviews)
"It was great! "It's about a whale"."
United States
jwinegra W.
The price is £154
includes taxes & fees
13 Sept - 14 Sept
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
Interior

16. 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, (42 reviews)
"Sweet place, very close to Minnewaska State Park which was great for us"
United States
Sueane
The price is £172
includes taxes & fees
13 Sept - 14 Sept
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Smart TV, fireplace, books

17. Zen House at the Mountain Ridge

Zen House at the Mountain Ridge
Gardiner
9.8 out of 10, Exceptional, (8 reviews)
"I have been sharing with everyone that we found a cabin in the woods with a movie theater. Our boys loved it and had a fantastic time."
United States
Sumit S.
The price is £225
includes taxes & fees
30 Aug - 31 Aug
Zen House at the Mountain Ridge
2 bedrooms, desk, free WiFi, bed sheets

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

Retro Retreat: renovated 2BR, desk, no chore list!
Kingston
9.6 out of 10, Exceptional, (15 reviews)
"Great, easy, full of everything you’d need. Stayed with 2 others for a work trip and it was perfect! "
United States
Kelley Marie
The price is £249
includes taxes & fees
22 Sept - 23 Sept
Retro Retreat: renovated 2BR, desk, no chore list!
Outdoor dining

19. Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.2 out of 10, Wonderful, (74 reviews)
"Great spot! Very unique, has lots of charm!"
United States
Brian
The price is £246
includes taxes & fees
31 Aug - 1 Sept
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Property grounds

20. Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz

Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
wallkill
9.8 out of 10, Exceptional, (60 reviews)
"We had a lovely time and the host had lots of great communication!"
United States
Amanda S.
The price is £324
includes taxes & fees
9 Sept - 10 Sept
Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
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
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

DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center

8/10 Good
"First-class hotel, except for the breakfast. My spouse and child waited for 40 minutes to be fed until they gave up and left. They observed other patrons not getting any breakfast, either. Probably just as well, as the prices were outrageously high (even if the service had been even remotely competent). The drive-thru window at Dunkin' Donuts provided better service and at much more reasonable prices. I would stay at the Doubletree again, but I would plan to avoid their restaurant at all costs."
Robert 1-night trip
Posted 4 hours ago
DoubleTree by Hilton Poughkeepsie Convention Center

Find out more about Highland

Highland Holiday Homes information

Number of reviews
473
Accommodation
532 Holiday Homes
Lowest Price
£114
Highest Price
£774