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

Holiday Homes in Highland

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Highland holiday homes

A spacious living area with a staircase, a dining table, and a sofa.

1. 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 NZ$1,189
includes taxes & fees
27 Oct - 28 Oct
Our home is perfect for relaxing and having lots of fun, with near by activity’s
A modern kitchen with a granite countertop, a built-in stove, and a dining area with a glass table and chairs.

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

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Poughkeepsie
9.8 out of 10, Exceptional, (6 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 NZ$741
includes taxes & fees
26 Oct - 27 Oct
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
A two-story house with a front porch and a landscaped garden.

3. A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail

A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
Wallkill
9.2 out of 10, Wonderful, (18 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
The price is NZ$250
includes taxes & fees
28 Oct - 29 Oct
A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
A bedroom with a bed, a TV mounted on the wall, a window with a view of greenery, and a small seating area with a table and chairs.

4. 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, (46 reviews)
"Great property in a serene setting. We enjoyed it very much!"
United States
John M.
The price is NZ$473
includes taxes & fees
26 Oct - 27 Oct
The Studio at the Inn at High Falls
A tent with a central pole, a view of the forest through the entrance, and a bed with patterned bedding.

5. 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 NZ$266
includes taxes & fees
26 Oct - 27 Oct
Glamping Tent & Campsite by Minnewaska State Park
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

6. 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, (7 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 NZ$421
includes taxes & fees
2 Nov - 3 Nov
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

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

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (33 reviews)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
The price is NZ$432
includes taxes & fees
3 Nov - 4 Nov
Campfire Cottage: Fireplace, fire pit & no chores!
A hot tub on a wooden deck with a view of a river and trees.

8. Welcome to The Boathouse! Waterfront/Boats/Hot tub

Welcome to The Boathouse! Waterfront/Boats/Hot tub
New Paltz
9.6 out of 10, Exceptional, (12 reviews)
"We enjoyed our stay very much! Everything was as described, inside was very clean, host was excellent with communication. Scenic, serene spot!"
United States
Jessica B.
The price is NZ$729
includes taxes & fees
5 Nov - 6 Nov
Welcome to The Boathouse! Waterfront/Boats/Hot tub
A living room with a sofa, a coffee table, a wooden chair, a striped rug, and a wall-mounted wreath.

9. The DeVita House Est. 1900

The DeVita House Est. 1900
Gardiner
10.0 out of 10, Exceptional, (44 reviews)
"We really enjoyed a second stay at the De Vita House. The place is so clean and comfortable, and the location is great. Karin is a great host--she immediately dropped off a couple kitchen items we thought we needed--wasn't even an emergency or anything! Absolutely recommend."
United States
Natalie R.
The price is NZ$761
includes taxes & fees
27 Oct - 28 Oct
The DeVita House Est. 1900
A wooden deck with a wood-burning stove and a door leading to an outdoor area with chairs.

10. 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, (6 reviews)
"Great tastefully kept property. Our family including the 8 year felt we should have stayed here longer."
United States
Tarun
The price is NZ$373
includes taxes & fees
1 Nov - 2 Nov
Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet
A covered outdoor area with a barbecue grill and a hot tub.

11. Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
New Paltz
9.6 out of 10, Exceptional, (42 reviews)
"Really nice, house. Location was great. There were 8 of us there for a girls weekend. Plenty of room for all.Clean, attentive host, kitchen was well stocked for our needs. Hot tub was great."
United States
Shirley A.
The price is NZ$777
includes taxes & fees
3 Nov - 4 Nov
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
A neatly made bed with white bedding and a few colorful pillows, a wooden headboard, and a wall-mounted light fixture.

12. 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 NZ$517
includes taxes & fees
17 Nov - 18 Nov
Retro Retreat: renovated 2BR, desk, no chore list!
A kitchen with wooden shelves, a window with a view of trees, and a vase with flowers on the windowsill.

13. 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, (47 reviews)
"Sweet place, very close to Minnewaska State Park which was great for us"
United States
Sueane
The price is NZ$290
includes taxes & fees
1 Nov - 2 Nov
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
A wooden gate leading to a driveway with a stone pathway, surrounded by greenery and a house in the background.

14. Maple Ridge Modern Rustic Retreat where Modern comfort meets Rustic Charm

Maple Ridge Modern Rustic Retreat where Modern comfort meets Rustic Charm
Ulster Park
9.8 out of 10, Exceptional, (20 reviews)
"Easy access and checkout, extremely clean, accurate pictures, comfy beds, well stocked kitchen. Great for groups. Would gladly stay again!"
United States
Emily F.
The price is NZ$1,412
includes taxes & fees
1 Nov - 2 Nov
Maple Ridge Modern Rustic Retreat where Modern comfort meets Rustic Charm
A kitchen with grey cabinets, a stone floor, and a view of a garden through an open door.

15. Historic Cottage * Steam Shower * Chef’s Kitchen

Historic Cottage * Steam Shower * Chef’s Kitchen
Kingston
10.0 out of 10, Exceptional, (1 review)
"We had a great time staying here! The house is a gorgeous historic house with modern amenities. It was a short drive to Kingston which was super convenient. We loved that we could bring our dog with us as well. It is on a main road, but we didn't find that to be a disturbance at all. I would definitely come back here again!!"
United States
Laura D.
The price is NZ$885
includes taxes & fees
3 Nov - 4 Nov
Historic Cottage * Steam Shower * Chef’s Kitchen
A bedroom with a large bed, multiple windows, a ceiling fan, and a view of trees.

16. The New Paltz Moondance Ridge

The New Paltz Moondance Ridge
New Paltz
The price is NZ$4,748
includes taxes & fees
29 Oct - 30 Oct
The New Paltz Moondance Ridge
A view from a room with a sliding glass door leading to an outdoor deck with a wooden fence, a chair, and a bench.

17. Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!

Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
Kingston
9.6 out of 10, Exceptional, (108 reviews)
"Wonderful stay. Lovely tiny house in a beautiful wooded setting. Woke to the sounds of birds singing. Would stay again"
United States
Nan
The price is NZ$430
includes taxes & fees
9 Nov - 10 Nov
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
A modern living room with a fireplace, a dining area with a wooden table, and a large window with curtains.

18. Zen House at the Mountain Ridge

Zen House at the Mountain Ridge
Gardiner
10.0 out of 10, Exceptional, (12 reviews)
"Great space! Very nicely decorated. Host was very responsive and answered questions quickly. Also close to a great bakery and coffee shop!"
United States
Julie
The price is NZ$502
includes taxes & fees
16 Nov - 17 Nov
Zen House at the Mountain Ridge
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

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

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.4 out of 10, Exceptional, (13 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
The price is NZ$492
includes taxes & fees
26 Oct - 27 Oct
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A spacious room with a high ceiling, large windows, a ceiling fan, and a dining area with a table and chairs.

20. NEW: Family Retreat * Fireplace * Spa Bathroom

NEW: Family Retreat * Fireplace * Spa Bathroom
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 NZ$1,451
includes taxes & fees
26 Oct - 27 Oct
NEW: Family Retreat * Fireplace * Spa Bathroom
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

The Heartwood

The Heartwood

10/10 Excellent
"The staff at the hotel were so amazing and communicative. They were so nice and this was the weekend that I proposed to my now fiancée. Everything was wonderful, the room and bathroom was clean and very spacious and The Salt Line had great breakfast. The bartender was super kind! Absolutely no complaints about this hotel!"
Finley 1-night trip
Posted less than an hour ago
The Heartwood

Find out more about Highland

Highland Holiday Homes information

Number of reviews
435
Accommodation
419 Holiday Homes
Lowest Price
NZ$250
Highest Price
NZ$4,748