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Town of Highland Vacation Rentals

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Our top choices for Town of Highland vacation rentals

An indoor water park with a large water slide, inflatable tubes, and lush greenery.

1. 2 Lake Cabins Pool+hottub Game Room 23acs

2 Lake Cabins Pool+hottub Game Room 23acs
2.0 star property
Highland Lake
The price is CA $262
CA $1,444 total
includes taxes & fees
Oct 29 - Oct 30
2 Lake Cabins Pool+hottub Game Room 23acs
An indoor water park with a large water slide, inflatable tubes, and tropical plants.

2. Lakefront | Sport Courts | HotTub | GameRoom

Lakefront | Sport Courts | HotTub | GameRoom
Highland Lake
10.0 out of 10, Exceptional, (33 reviews)
"We had a wonderful time and definitely would recommend!"
United States
Phillip C.
The price is CA $224
CA $1,269 total
includes taxes & fees
Oct 27 - Oct 28
Lakefront | Sport Courts | HotTub | GameRoom
A living room with a fireplace, sofa, TV, and a wooden table with baskets.

3. Bright, Spotless Cottage Near Bethel Woods

Bright, Spotless Cottage Near Bethel Woods
Highland
10.0 out of 10, Exceptional, (7 reviews)
"This was the perfect place for a long weekend where we wanted to be disconnected yet still have modern amenities. Everything was great from the check in process to the place itself and the location. Looking forward to staying here again in the future!"
United States
Chloe
The price is CA $224
CA $462 total
includes taxes & fees
Oct 26 - Oct 27
Bright, Spotless Cottage Near Bethel Woods
A covered porch with wicker furniture and a view of a blue house in the background.

4. Sweet Old Farmhouse in a Tranquil Setting

Sweet Old Farmhouse in a Tranquil Setting
Highland Lake
10.0 out of 10, Exceptional, (4 reviews)
"The property was very easy to access and easy to navigate the area with the location. Also right across from the local yoga studio was a bonus!"
United States
Anne H.
The price is CA $252
CA $614 total
includes taxes & fees
Oct 27 - Oct 28
Sweet Old Farmhouse in a Tranquil Setting
A cabin surrounded by dense forest, with a deck and outdoor seating area.

5. Enchanting River - Waterfront A Frame Cabin

Enchanting River - Waterfront A Frame Cabin
Yulan
10.0 out of 10, Exceptional, (4 reviews)
"I can’t put into words the feel of Enchanting River front. The location is BEAUTIFUL. Being able to fall asleep to the sound of the flowing water was just heaven. John is an incredible host, and I can’t wait for my next visit! "
United States
Britney P.
The price is CA $551
CA $966 total
includes taxes & fees
Nov 19 - Nov 20
Enchanting River - Waterfront A Frame Cabin
A wooden cabin with a circular structure, a wooden bench outside, and a wooden deck.

6. Ferncrest Campground

Ferncrest Campground
3.0 star property
Greentown
9.6 out of 10, Exceptional, (27 reviews)
"Loved this campground!! Being in nature, cooking on the grill, showering outside. A great experience was had, would definitely book again."
United States
Jerelle
The price is CA $242
CA $264 total
includes taxes & fees
Oct 22 - Oct 23
Ferncrest Campground
A bedroom with a large window overlooking a forest, a bed, a plant, and a hanging coat rack.

7. The Rex Hotel

The Rex Hotel
3.5 star property
Greentown
9.6 out of 10, Exceptional, (34 reviews)
"Would recommend and certainly stay again!"
United States
Jessica
The price is CA $290
CA $316 total
includes taxes & fees
Oct 28 - Oct 29
The Rex Hotel
A living room with a wooden floor, a sofa, a dining table with chairs, and a door leading outside.

8. 5 minutes from original Woodstock site.

5 minutes from original Woodstock site.
Mongaup Valley
9.8 out of 10, Exceptional, (77 reviews)
"Great place"
United States
Anonymous traveller
The price is CA $313
CA $538 total
includes taxes & fees
Oct 27 - Oct 28
5 minutes from original Woodstock site.
A room with a wooden floor, a bed, a TV, and a sign with 'CABIN RULES'.

9. Trails Head Cabin

Trails Head Cabin
Rock Hill
9.8 out of 10, Exceptional, (123 reviews)
"Great location being right at the trailhead for hiking."
United States
Tonne
The price is CA $190
CA $329 total
includes taxes & fees
Oct 27 - Oct 28
Trails Head Cabin
A cabin with a wooden deck and a staircase leading to a second-story balcony.

10. Peaceful woodsy retreat with stream and hiking on property / near Bethel Woods

Peaceful woodsy retreat with stream and hiking on property / near Bethel Woods
Narrowsburg
10.0 out of 10, Exceptional, (167 reviews)
"Such a beautiful place to stay and explore with my pup!"
United States
Alison H.
The price is CA $151
CA $447 total
includes taxes & fees
Oct 25 - Oct 26
Peaceful woodsy retreat with stream and hiking on property / near Bethel Woods
A circular outdoor seating area with wooden chairs and a central table, surrounded by a stone-paved circle.

11. In the cloud ~your cozy lake house

In the cloud ~your cozy lake house
Swan Lake
9.6 out of 10, Exceptional, (120 reviews)
"We had a wonderful one night stay!"
United States
Anonymous traveller
The price is CA $251
CA $489 total
includes taxes & fees
Nov 3 - Nov 4
In the cloud ~your cozy lake house
A house with a dock by a lake, surrounded by trees and a clear sky.

12. Lakeview Cabin Duplex

Lakeview Cabin Duplex
Lake Huntington
9.6 out of 10, Exceptional, (26 reviews)
"Great stay!"
United States
melissa m.
The price is CA $180
CA $326 total
includes taxes & fees
Oct 22 - Oct 23
Lakeview Cabin Duplex
A wooden interior with a staircase, a cozy seating area, and a kitchen.

13. Cozy Cabin with Fireplace, Firepit, Close to Lake

Cozy Cabin with Fireplace, Firepit, Close to Lake
Hawley
10.0 out of 10, Exceptional, (27 reviews)
"Our stay was amazing. The house is so cozy and welcoming!"
United States
Kenzie F.
The price is CA $190
CA $446 total
includes taxes & fees
Oct 22 - Oct 23
Cozy Cabin with Fireplace, Firepit, Close to Lake
A sign with the year 1796 and the word 'MILFORD' along with a lantern icon.

14. Cozy Pocono Barn Loft Apartment

Cozy Pocono Barn Loft Apartment
Milford
10.0 out of 10, Exceptional, (20 reviews)
"Our rooms were clean, comfortable and cozy. Everything we needed was there. We would definitely stay again!"
United States
Thomas
The price is CA $260
CA $454 total
includes taxes & fees
Oct 22 - Oct 23
Cozy Pocono Barn Loft Apartment
A cozy living room with a fireplace, a sofa, and a green accent wall.

15. Bear Haven Cozy Poconos Cabin

Bear Haven Cozy Poconos Cabin
Greentown
10.0 out of 10, Exceptional, (89 reviews)
"Host had great communications, the area is very nice but remote with activities spread around. Property was exceptionally clean, but keep in mind that the rental is on the second floor and the stairs are very steep to access it."
United States
Colin
The price is CA $190
CA $367 total
includes taxes & fees
Oct 22 - Oct 23
Bear Haven Cozy Poconos Cabin
A two-story house with a covered porch, a front door, and a staircase leading to the entrance.

16. Spacious 4 bedroom house with a private pool in a quiet area

Spacious 4 bedroom house with a private pool in a quiet area
Glen Spey
10.0 out of 10, Exceptional, (7 reviews)
"Great place"
United States
Johnny A.
The price is CA $322
CA $684 total
includes taxes & fees
Oct 27 - Oct 28
Spacious 4 bedroom house with a private pool in a quiet area
An outdoor deck with a wooden table and chairs, a grill, and a hot tub.

17. Luxury Retreat w/ Hot Tub - near Bethel Woods!

Luxury Retreat w/ Hot Tub - near Bethel Woods!
Forestburgh
10.0 out of 10, Exceptional, (8 reviews)
"This was an excellent property.It was clean, well stocked and beautiful. The host was attentive and available. It was really a wonderful stay."
United States
mary
The price is CA $429
CA $930 total
includes taxes & fees
Oct 22 - Oct 23
Luxury Retreat w/ Hot Tub - near Bethel Woods!
A spacious living room with a high ceiling, large windows, a flat-screen TV, a grey sofa, a small round table, and a wooden deck visible through the glass door.

18. Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
Westbrookville
The price is CA $298
CA $483 total
includes taxes & fees
Oct 22 - Oct 23
Hike & Fish: Outdoor Retreat Near Trails
A deck with lounge chairs and an umbrella, overlooking a body of water and a building with a blue exterior.

19. Victorian Lake Oasis | Hot Tub | Private Lakefront

Victorian Lake Oasis | Hot Tub | Private Lakefront
Damascus
9.8 out of 10, Exceptional, (10 reviews)
"I was working in the area with two other coworkers and this house was perfect. It had everything we needed and was walking distance to great restaurants. I would definitely stay again if in the area. "
United States
Dave
The price is CA $166
CA $619 total
includes taxes & fees
Oct 28 - Oct 29
Victorian Lake Oasis | Hot Tub | Private Lakefront
A wooden deck with wicker furniture, a red barn, and a forested landscape in the background.

20. Cozy Catskills Farmhouse with Wood-Fired Hot Tub near Bethel Woods

Cozy Catskills Farmhouse with Wood-Fired Hot Tub near Bethel Woods
Cochecton
10.0 out of 10, Exceptional, (9 reviews)
"This is a great property to stay at. Beautiful views and very comfortable accommodations. It is very close to Bethel Woods and had everything 3 Spartan Racers could want."
United States
Scott D.
The price is CA $283
CA $669 total
includes taxes & fees
Nov 19 - Nov 20
Cozy Catskills Farmhouse with Wood-Fired Hot Tub near Bethel Woods
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 Town of Highland Hotel Reviews

High Point Motel

High Point Motel

10/10 Excellent
"Melanie was exceptional at attending to any questions or needs i had... i was very pleased with my stay... beautiful sunrise"
Linda 1-night trip
Posted 14 hours ago
High Point Motel

Find out more about Town of Highland

Everything you need to know about Town of Highland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Town of Highland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Town of Highland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Town of Highland vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Town of Highland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Town of Highland vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Town of Highland vacation rentals we have selected for you start as low as CA $264 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Town of Highland rentals

At Expedia, we put the best Town of Highland vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Town of Highland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Town of Highland vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Town of Highland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.