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

Holiday Homes in Highland

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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 AU$1,053
includes taxes & fees
6 Oct - 7 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
9.6 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 AU$622
includes taxes & fees
4 Oct - 5 Oct
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
A rural landscape with a barn, a silo, and a bridge with rocks and purple flowers in the foreground.

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, (15 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
The price is AU$198
includes taxes & fees
7 Oct - 8 Oct
A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
A staircase leading to a second floor, a sofa with a throw blanket, a floor lamp, a small table with a vase of sunflowers, and a kitchen area visible through an archway.

4. Chilly Days Hiking, Quiet Yard, an Easy Escape Near New Paltz

Chilly 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 AU$862
includes taxes & fees
5 Oct - 6 Oct
Chilly Days Hiking, Quiet Yard, an Easy Escape Near New Paltz
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.

5. 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)
"The pictures are misleading"
United States
Jia
The price is AU$388
includes taxes & fees
4 Oct - 5 Oct
The Studio at the Inn at High Falls
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, (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 AU$377
includes taxes & fees
27 Oct - 28 Oct
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
A wooden deck with a wood-burning stove and a door leading to an outdoor area with chairs.

7. 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, (5 reviews)
"Great tastefully kept property. Our family including the 8 year felt we should have stayed here longer."
United States
Tarun
The price is AU$384
includes taxes & fees
2 Nov - 3 Nov
Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet
A forest campsite with a tent, a fire pit, and a bench.

8. 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 AU$222
includes taxes & fees
7 Oct - 8 Oct
Glamping Tent & Campsite by Minnewaska State Park
A hot tub on a wooden deck with a view of a river and trees.

9. 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 AU$652
includes taxes & fees
7 Oct - 8 Oct
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.

10. The DeVita House Est. 1900

The DeVita House Est. 1900
Gardiner
10.0 out of 10, Exceptional, (42 reviews)
"Great house, well equipped, very accommodating hosts!"
United States
Christopher T.
The price is AU$634
includes taxes & fees
5 Oct - 6 Oct
The DeVita House Est. 1900
A kitchen with wooden shelves, a window with a view of trees, and a vase with flowers on the windowsill.

11. 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, (45 reviews)
"Sweet place, very close to Minnewaska State Park which was great for us"
United States
Sueane
The price is AU$302
includes taxes & fees
28 Oct - 29 Oct
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

12. 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 AU$425
includes taxes & fees
28 Oct - 29 Oct
Campfire Cottage: Fireplace, fire pit & no chores!
A spacious living area with a high ceiling, wooden beams, two leather sofas, a central rug, and a staircase leading to an upper level.

13. The Loft At The Inn At High Falls

The Loft At The Inn At High Falls
High Falls
9.0 out of 10, Wonderful, (23 reviews)
"this was just a lovely stay all around!! Will absolutely stay there again!"
United States
Inez
The price is AU$507
includes taxes & fees
4 Oct - 5 Oct
The Loft At The Inn At High Falls
A covered outdoor area with a barbecue grill and a hot tub.

14. 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, (40 reviews)
"Exactly as listed, great property and host."
United Kingdom
Neil C.
The price is AU$773
includes taxes & fees
4 Oct - 5 Oct
Scenic New Paltz Escape: River Views, Hot Tub & Deck | 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.

15. 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 AU$1,162
includes taxes & fees
15 Oct - 16 Oct
Maple Ridge Modern Rustic Retreat where Modern comfort meets Rustic Charm
A fireplace with logs, a vase with flowers, and candles on a woven mat.

16. 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 AU$312
includes taxes & fees
2 Nov - 3 Nov
Art Studio Retreat with Sauna Fireplace Forest Views | 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.

17. 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 AU$447
includes taxes & fees
2 Nov - 3 Nov
Retro Retreat: renovated 2BR, desk, no chore list!
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
9.8 out of 10, Exceptional, (10 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 AU$371
includes taxes & fees
6 Oct - 7 Oct
Zen House at the Mountain Ridge
A modern kitchen with granite countertops, dark cabinetry, and a built-in island with bar stools.

19. 3BR Hudson Valley home perfect for families!

3BR Hudson Valley home perfect for families!
Wallkill
10.0 out of 10, Exceptional, (5 reviews)
"A friend and I needed to book a last minute stay. This house exceeded our expectations. It was clean and comfortable and had everything we needed. It was a great location as well!"
United States
Rachel S.
The price is AU$827
includes taxes & fees
6 Oct - 7 Oct
3BR Hudson Valley home perfect for families!
A living room with a stone fireplace, blue sofas, and a bookshelf.

20. The New Paltz Moondance Ridge

The New Paltz Moondance Ridge
New Paltz
The price is AU$4,265
includes taxes & fees
26 Oct - 27 Oct
The New Paltz Moondance Ridge
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

The Thayer Hotel at West Point

The Thayer Hotel at West Point

10/10 Excellent
"Everything was great, and really added a special feeling to the trip"
Joshua 1-night trip
Posted less than an hour ago
The Thayer Hotel at West Point

Find out more about Highland

Highland Holiday Homes information

Number of reviews
349
Accommodation
505 Holiday Homes
Lowest Price
AU$198
Highest Price
AU$4,265