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

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Highland vacation homes

A modern kitchen with white cabinets, a built-in toaster, a blender, and a window with a view of trees.

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

Amazing 3-bedroom house with AC in adorable Highland
Highland
The price is ￥41,803
￥84,028 total
includes taxes & fees
Sep 29 - Sep 30
Amazing 3-bedroom house with AC in adorable Highland
A spacious living area with a staircase, a dining table, and a sofa.

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 ￥38,175
￥114,548 total
includes taxes & fees
Sep 29 - Sep 30
Our home is perfect for relaxing and having lots of fun, with near by activity’s

3. Hudson Escape W/ Hot Tub + Bridge View

Hudson Escape W/ Hot Tub + Bridge View
Highland
The price is ￥81,480
￥143,459 total
includes taxes & fees
Oct 1 - Oct 2
Hudson Escape W/ Hot Tub + Bridge View
A rural landscape with a barn, a silo, and a bridge with rocks and purple flowers in the foreground.

4. 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 ￥10,770
￥21,763 total
includes taxes & fees
Sep 29 - Sep 30
A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
A modern kitchen with a granite countertop, a built-in stove, and a dining area with a glass table and chairs.

5. 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 ￥29,758
￥73,767 total
includes taxes & fees
Oct 6 - Oct 7
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
A wooden deck with a wood-burning stove and a door leading to an outdoor area with chairs.

6. 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 ￥11,501
￥30,082 total
includes taxes & fees
Sep 28 - Sep 29
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.

7. 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 ￥17,713
￥42,587 total
includes taxes & fees
Oct 4 - Oct 5
The Studio at the Inn at High Falls
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 ￥13,462
￥23,895 total
includes taxes & fees
Oct 4 - Oct 5
Glamping Tent & Campsite by Minnewaska State Park
A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

9. 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 ￥13,611
￥42,011 total
includes taxes & fees
Sep 28 - Sep 29
Campfire Cottage: Fireplace, fire pit & no chores!
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

10. 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 ￥12,911
￥41,265 total
includes taxes & fees
Oct 14 - Oct 15
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
A living room with a sofa, a coffee table, a wooden chair, a striped rug, and a wall-mounted wreath.

11. The DeVita House Est. 1900

The DeVita House Est. 1900
Gardiner
10.0 out of 10, Exceptional, (40 reviews)
"Great house, well equipped, very accommodating hosts!"
United States
Christopher T.
The price is ￥23,618
￥69,656 total
includes taxes & fees
Oct 5 - Oct 6
The DeVita House Est. 1900
A covered outdoor area with a barbecue grill and a hot tub.

12. 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 ￥45,873
￥75,583 total
includes taxes & fees
Sep 27 - Sep 28
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
A kitchen with grey cabinets, a stone floor, and a view of a garden through an open door.

13. 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 ￥21,130
￥75,269 total
includes taxes & fees
Sep 29 - Sep 30
Historic Cottage * Steam Shower * Chef’s Kitchen
A fireplace with logs, a vase with flowers, and candles on a woven mat.

14. 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 ￥17,351
￥31,112 total
includes taxes & fees
Oct 7 - Oct 8
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.

15. Zen House at the Mountain Ridge

Zen House at the Mountain Ridge
Gardiner
9.8 out of 10, Exceptional, (9 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 ￥24,628
￥40,575 total
includes taxes & fees
Oct 1 - Oct 2
Zen House at the Mountain Ridge
A hot tub on a wooden deck with a view of a river and trees.

16. 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 ￥41,724
￥68,069 total
includes taxes & fees
Sep 28 - Sep 29
Welcome to The Boathouse! Waterfront/Boats/Hot tub
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, (101 reviews)
The price is ￥26,924
￥41,088 total
includes taxes & fees
Sep 27 - Sep 28
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
A fire pit with four Adirondack chairs arranged around it, set on a gravel surface with a lake and trees in the background.

18. 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)
"Had a wonderful time! Loved our stay at this beautiful river front property!"
United States
Debbie M.
The price is ￥29,771
￥61,349 total
includes taxes & fees
Oct 19 - Oct 20
Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
A living room with a fireplace, sofas, a bookshelf, and a decorative wall.

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 ￥27,711
￥131,918 total
includes taxes & fees
Oct 6 - Oct 7
NEW: Family Retreat * Fireplace * Spa Bathroom
A deck with wicker furniture and a view of a lake at sunset.

20. Many perfect sunsets at the magical house on the lake

Many perfect sunsets at the magical house on the lake
Ulster Park
9.8 out of 10, Exceptional, (156 reviews)
"Highly recommend!"
United States
Seth M.
The price is ￥46,763
￥92,581 total
includes taxes & fees
Oct 1 - Oct 2
Many perfect sunsets at the magical house on the lake
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

Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

10/10 Excellent
"Peaceful clean good breakfast loved the front desk people. I’m so glad I chose this property. Would 10 out of 10 stay here again"
Cecilia 2-night trip
Posted 12 hours ago
Hampton Inn & Suites Poughkeepsie

Find out more about Highland

Highland Vacation Homes information

Number of reviews
547
Accommodation
528 Vacation Homes
Lowest Price
￥21,763
Highest Price
￥143,459