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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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 $365
CA $1,052 total
includes taxes & fees
Oct 13 - Oct 14
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 CA $229
CA $621 total
includes taxes & fees
Oct 13 - Oct 14
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, (17 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
The price is CA $93
CA $192 total
includes taxes & fees
Nov 3 - Nov 4
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)
"The pictures are misleading"
United States
Jia
The price is CA $160
CA $388 total
includes taxes & fees
Oct 12 - Oct 13
The Studio at the Inn at High Falls
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

5. 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 CA $98
CA $343 total
includes taxes & fees
Nov 3 - Nov 4
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.

6. 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 $122
CA $216 total
includes taxes & fees
Oct 12 - Oct 13
Glamping Tent & Campsite by Minnewaska State Park
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 CA $230
CA $424 total
includes taxes & fees
Nov 1 - Nov 2
Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet
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 $122
CA $378 total
includes taxes & fees
Nov 3 - Nov 4
Campfire Cottage: Fireplace, fire pit & no chores!
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, (42 reviews)
"Great house, well equipped, very accommodating hosts!"
United States
Christopher T.
The price is CA $213
CA $632 total
includes taxes & fees
Oct 25 - Oct 26
The DeVita House Est. 1900
A hot tub on a wooden deck with a view of a river and trees.

10. 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 CA $356
CA $593 total
includes taxes & fees
Nov 3 - Nov 4
Welcome to The Boathouse! Waterfront/Boats/Hot tub
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 CA $211
CA $349 total
includes taxes & fees
Nov 5 - Nov 6
Relaxed Mountain Living Near Minnewaska | 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 CA $134
CA $437 total
includes taxes & fees
Nov 2 - Nov 3
Retro Retreat: renovated 2BR, desk, no chore list!
A stone fireplace with a fire, a dining area with a table and chairs, and large windows with a view of trees.

13. NEW: Oaklands Near Shawangunk Mountains

NEW: Oaklands Near Shawangunk Mountains
New Paltz
The price is CA $248
CA $920 total
includes taxes & fees
Nov 3 - Nov 4
NEW: Oaklands Near Shawangunk Mountains
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 CA $413
CA $1,148 total
includes taxes & fees
Oct 15 - Oct 16
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.

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 CA $160
CA $288 total
includes taxes & fees
Nov 3 - Nov 4
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
A modern living room with a fireplace, a dining area with a wooden table, and a large window with curtains.

16. 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 CA $251
CA $411 total
includes taxes & fees
Nov 2 - Nov 3
Zen House at the Mountain Ridge
A kitchen with grey cabinets, a stone floor, and a view of a garden through an open door.

17. 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 $213
CA $715 total
includes taxes & fees
Nov 4 - Nov 5
Historic Cottage * Steam Shower * Chef’s Kitchen
A swimming pool with a curved edge, surrounded by lush greenery and a house with a deck.

18. 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 $355
CA $1,361 total
includes taxes & fees
Oct 27 - Oct 28
NEW: Family Retreat * Fireplace * Spa Bathroom
A bedroom with a large bed, multiple windows, a ceiling fan, and a view of trees.

19. The New Paltz Moondance Ridge

The New Paltz Moondance Ridge
New Paltz
The price is CA $2,743
CA $4,007 total
includes taxes & fees
Oct 29 - Oct 30
The New Paltz Moondance Ridge
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

20. 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 $240
CA $401 total
includes taxes & fees
Oct 12 - Oct 13
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
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

Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

10/10 Excellent
"Guest room was designed well. Very clean. Comfortable bed. Great shower, strong pressure, like a massage. Breakfast was excellent , fresh and hot. Will be back"
Norman 1-night trip
Posted 9 hours ago
Hyatt Place Poughkeepsie / Hudson Valley

Find out more about Highland

Highland Vacation Homes information

Number of reviews
273
Accommodation
505 Vacation Homes
Lowest Price
CA $192
Highest Price
CA $4,007

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