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

Highland Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Highland vacation 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 CA $315
CA $891 total
includes taxes & fees
Nov 5 - Nov 6
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 CA $250
CA $643 total
includes taxes & fees
Nov 2 - Nov 3
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, (19 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
The price is CA $101
CA $199 total
includes taxes & fees
Nov 1 - Nov 2
A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
A wooden deck with a wood-burning stove and a door leading to an outdoor area with chairs.

4. 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 CA $110
CA $275 total
includes taxes & fees
Nov 1 - Nov 2
Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet
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
8.2 out of 10, Very good, (47 reviews)
"Great property in a serene setting. We enjoyed it very much!"
United States
John M.
The price is CA $157
CA $375 total
includes taxes & fees
Nov 1 - Nov 2
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, (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 CA $105
CA $357 total
includes taxes & fees
Nov 2 - Nov 3
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
A forest campsite with a tent, a fire pit, and a bench.

7. 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 CA $120
CA $212 total
includes taxes & fees
Nov 1 - Nov 2
Glamping Tent & Campsite by Minnewaska State Park
A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

8. 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 CA $105
CA $357 total
includes taxes & fees
Nov 3 - Nov 4
Campfire Cottage: Fireplace, fire pit & no chores!
A covered outdoor area with a barbecue grill and a hot tub.

9. 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 CA $324
CA $571 total
includes taxes & fees
Nov 3 - Nov 4
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
A kitchen with wooden shelves, a window with a view of trees, and a vase with flowers on the windowsill.

10. 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 CA $135
CA $244 total
includes taxes & fees
Nov 5 - Nov 6
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
A hot tub on a wooden deck with a view of a river and trees.

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

Welcome to The Boathouse! Waterfront/Boats/Hot tub
New Paltz
9.6 out of 10, Exceptional, (13 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 CA $350
CA $576 total
includes taxes & fees
Nov 5 - Nov 6
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.

12. The DeVita House Est. 1900

The DeVita House Est. 1900
Gardiner
10.0 out of 10, Exceptional, (45 reviews)
"The house was in a perfect location! Host was very easy to communicate with!"
United States
Matthew
The price is CA $210
CA $619 total
includes taxes & fees
Nov 19 - Nov 20
The DeVita House Est. 1900
A neatly made bed with white bedding and a few colorful pillows, a wooden headboard, and a wall-mounted light fixture.

13. 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 CA $126
CA $428 total
includes taxes & fees
Nov 3 - Nov 4
Retro Retreat: renovated 2BR, desk, no chore list!
A modern kitchen with a central island, built-in appliances, and a stone accent wall.

14. 3BR Hudson Valley home perfect for families!

3BR Hudson Valley home perfect for families!
Wallkill
10.0 out of 10, Exceptional, (6 reviews)
"This property was lovely and peaceful! We enjoyed the stay in the area! Very clean and neat. Easy to use technology and check-in/out."
United States
Cheryl N.
The price is CA $302
CA $783 total
includes taxes & fees
Nov 7 - Nov 8
3BR Hudson Valley home perfect for families!
A bedroom with a large bed, multiple windows, a ceiling fan, and a view of trees.

15. The New Paltz Moondance Ridge

The New Paltz Moondance Ridge
New Paltz
The price is CA $2,997
CA $4,150 total
includes taxes & fees
Nov 5 - Nov 6
The New Paltz Moondance Ridge
A kitchen with grey cabinets, a stone floor, and a view of a garden through an open door.

16. 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 CA $188
CA $670 total
includes taxes & fees
Nov 4 - Nov 5
Historic Cottage * Steam Shower * Chef’s Kitchen
A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

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

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
9.8 out of 10, Exceptional, (16 reviews)
"Host was available and communicated very well. The house was very clean too."
United States
Erika
House on the Babbling Brook- Quiet 2BR + King Bed!
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

18. 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 CA $236
CA $397 total
includes taxes & fees
Nov 1 - Nov 2
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.

19. 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 CA $231
CA $1,188 total
includes taxes & fees
Nov 9 - Nov 10
NEW: Family Retreat * Fireplace * Spa Bathroom
A modern living room with a fireplace, a dining area with a wooden table, and a large window with curtains.

20. Zen House at the Mountain Ridge

Zen House at the Mountain Ridge
Gardiner
10.0 out of 10, Exceptional, (13 reviews)
"The house was perfect and really well decorated. The area it was in, proximity to everything. Couldn't have asked for a better spot."
United States
Theresa
The price is CA $197
CA $346 total
includes taxes & fees
Nov 2 - Nov 3
Zen House at the Mountain 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

DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center

10/10 Excellent
"The area surrounding it has a high population of homeless people."
Kassandra 3-night trip
Posted less than an hour ago
DoubleTree by Hilton Poughkeepsie Convention Center

Find out more about Highland

Highland Vacation Homes information

Number of reviews
287
Accommodation
505 Vacation Homes
Lowest Price
CA $199
Highest Price
CA $4,150

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