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Vacation Rentals in Town of Highland

Top Cities in Town of Highland

A calm lake surrounded by dense green forest under a partly cloudy sky.
Vacation RentalsVacation Rentals

Barryville

Barryville

Our top choices for Town of Highland vacation rentals

A living room with a fireplace, sofa, TV, and a wooden table with baskets.

1. 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
$305 nightly
The price is $308
Oct 19 - Oct 20
Total with taxes and fees
Bright, Spotless Cottage Near Bethel Woods
A backyard with a fire pit, outdoor furniture, and a deck.

2. Retro Countryside Cabin | Cozy Upstate NY Private Retreat!

Retro Countryside Cabin | Cozy Upstate NY Private Retreat!
Eldred
9.6 out of 10, Exceptional, (5 reviews)
"The place is exactly as described. Very comfortable and had everything we needed to enjoy our stay. Private and quiet. Bed was very comfortable. Pecks market close by. Will stay again."
United States
Robert R.
$435 nightly
The price is $488
Oct 15 - Oct 16
Total with taxes and fees
Retro Countryside Cabin | Cozy Upstate NY Private Retreat!
An indoor water park with a large water slide, inflatable tubes, and lush greenery.

3. 2 Lake Cabins Pool+hottub Game Room 23acs

2 Lake Cabins Pool+hottub Game Room 23acs
2.0 star property
Highland Lake
$1,028 nightly
The price is $1,162
Oct 22 - Oct 23
Total with taxes and fees
2 Lake Cabins Pool+hottub Game Room 23acs
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.
$391 nightly
The price is $440
Oct 15 - Oct 16
Total with taxes and fees
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.
$619 nightly
The price is $696
Nov 4 - Nov 5
Total with taxes and fees
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
$165 nightly
The price is $180
Oct 20 - Oct 21
Total with taxes and fees
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
9.4 out of 10, Exceptional, (33 reviews)
"Would recommend and certainly stay again!"
United States
Jessica
$206 nightly
The price is $225
Oct 28 - Oct 29
Total with taxes and fees
The Rex Hotel
A window with a view of a green, leafy outdoor area, possibly a garden or park.

8. Trails Head Tiny House

Trails Head Tiny House
Rock Hill
9.0 out of 10, Wonderful, (21 reviews)
"Host was very friendly and helpful. "
United States
Michael R.
$111 nightly
The price is $125
Oct 15 - Oct 16
Total with taxes and fees
Trails Head Tiny House
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, (122 reviews)
"Great location being right at the trailhead for hiking."
United States
Tonne
$196 nightly
The price is $220
Oct 20 - Oct 21
Total with taxes and fees
Trails Head Cabin
A wooden staircase with a railing leading to an upper floor. A painting of flowers hangs on the wall above the staircase.

10. Upper floor of charming 2 story house in central Hawley with WiFi

Upper floor of charming 2 story house in central Hawley with WiFi
Hawley
8.8 out of 10, Excellent, (3 reviews)
"Property was as advertised. Simple accommodations and a great price for the area. I did have to reach out to the host for check-in details rather than being sent them ahead of time as usually happens but she responded very quickly. It was nice that they had a bunch of streaming services available on the tv too."
United States
Tara K.
$246 nightly
The price is $268
Oct 15 - Oct 16
Total with taxes and fees
Upper floor of charming 2 story house in central Hawley with WiFi
A living room with a wooden floor, a sofa, a dining table with chairs, and a door leading outside.

11. 5 minutes from original Woodstock site.

5 minutes from original Woodstock site.
Mongaup Valley
9.8 out of 10, Exceptional, (76 reviews)
"The house was really nice. Decorated in line with the area. Plus, Bruce was a great host."
United States
Robert
$308 nightly
The price is $347
Oct 15 - Oct 16
Total with taxes and fees
5 minutes from original Woodstock site.
A wooden interior with a staircase, a cozy seating area, and a kitchen.

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

Cozy Cabin with Fireplace, Firepit, Close to Lake
Hawley
10.0 out of 10, Exceptional, (26 reviews)
"Our stay was amazing. The house is so cozy and welcoming!"
United States
Kenzie F.
$292 nightly
The price is $317
Oct 18 - Oct 19
Total with taxes and fees
Cozy Cabin with Fireplace, Firepit, Close to Lake
A cabin with a wooden deck and a staircase leading to a second-story balcony.

13. 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, (165 reviews)
"Such a beautiful place to stay and explore with my pup!"
United States
Alison H.
$238 nightly
The price is $268
Oct 19 - Oct 20
Total with taxes and fees
Peaceful woodsy retreat with stream and hiking on property / near Bethel Woods
A cozy living room with a fireplace, a sofa, and a green accent wall.

14. Bear Haven Cozy Poconos Cabin

Bear Haven Cozy Poconos Cabin
Greentown
10.0 out of 10, Exceptional, (88 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
$239 nightly
The price is $260
Oct 19 - Oct 20
Total with taxes and fees
Bear Haven Cozy Poconos Cabin
A bedroom with a wooden ceiling, a bed with pillows, a sofa with cushions, a wooden bench, and a television on a stand.

15. Cozy Loft Cabin high above Bashakill Wildlife Refuge

Cozy Loft Cabin high above Bashakill Wildlife Refuge
Wurtsboro
9.6 out of 10, Exceptional, (34 reviews)
"Very nice place to spend the weekend with my beautiful wife for our 23rd anniversary! Thank you very much for your hospitality!"
United States
nelu
$198 nightly
The price is $223
Oct 22 - Oct 23
Total with taxes and fees
Cozy Loft Cabin high above Bashakill Wildlife Refuge
A house with a dock by a lake, surrounded by trees and a clear sky.

16. Lakeview Cabin Duplex

Lakeview Cabin Duplex
Lake Huntington
9.6 out of 10, Exceptional, (26 reviews)
"Great stay!"
United States
melissa m.
$208 nightly
The price is $234
Oct 20 - Oct 21
Total with taxes and fees
Lakeview Cabin Duplex
A porch with a bench, a door with a wreath, and a welcome mat.

17. The Little Hayloft - Clean & Bright One Bedroom Loft in Honesdale, PA

The Little Hayloft - Clean & Bright One Bedroom Loft in Honesdale, PA
Honesdale
10.0 out of 10, Exceptional, (62 reviews)
"Amazing property! We were so pleasantly surprised in person how cute, spacious, and clean it was! We were in town for a wedding and had an amazing stay ! "
United States
Victoria N.
$204 nightly
The price is $222
Oct 18 - Oct 19
Total with taxes and fees
The Little Hayloft - Clean & Bright One Bedroom Loft in Honesdale, PA
A restaurant interior with a dining table set for two, featuring a plate of food, a glass of water, and a martini glass.

18. Mountaintop Hideaway ~ Piece of Paradise - Apt

Mountaintop Hideaway ~ Piece of Paradise - Apt
Honesdale
9.0 out of 10, Wonderful, (30 reviews)
"It was a nice"
United States
Olympia B.
$170 nightly
The price is $185
Oct 19 - Oct 20
Total with taxes and fees
Mountaintop Hideaway ~ Piece of Paradise - Apt
A sign with the year 1796 and the word 'MILFORD' along with a lantern icon.

19. 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
$296 nightly
The price is $322
Oct 15 - Oct 16
Total with taxes and fees
Cozy Pocono Barn Loft Apartment
A circular outdoor seating area with wooden chairs and a central table, surrounded by a stone-paved circle.

20. In the cloud ~your cozy lake house

In the cloud ~your cozy lake house
Swan Lake
9.6 out of 10, Exceptional, (119 reviews)
"We had a wonderful one night stay!"
United States
Anonymous traveler
$308 nightly
The price is $347
Oct 15 - Oct 16
Total with taxes and fees
In the cloud ~your cozy lake house
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

Days Inn by Wyndham Liberty/Monticello

Days Inn by Wyndham Liberty/Monticello

8/10 Good
"Hello The staff was friendly. The building is old but they have done a good job maintaining it. The building was clean and the area around the property was maintained . Room was clean, Comfortable, Breakfast was good."
Anthony 2-night trip
Posted 1 hour ago
Days Inn by Wyndham Liberty/Monticello

Find out more about Town of Highland

Discover your perfect Town of Highland vacation rental with Expedia

How many vacation rentals are available in Town of Highland?


Expedia has plenty of vacation rentals to choose from in and around  Town of Highland, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Town of Highland?


The selection of Town of Highland vacation rentals we have selected for you start as low as $180 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Town of Highland?


Vacation rentals in Town of Highland come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Town of Highland vacation rentals to suit everyone. 


Why should I choose a vacation rental in Town of Highland?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. 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. 


How do I find the best deal on a vacation rental in Town of Highland?


Find vacation rentals in Town of Highland by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Town of Highland.  


What amenities are available in a vacation rental in Town of Highland?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Town of Highland vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Town of Highland?   


Everytime is a great time to head to Town of Highland! Staying in a Town of Highland vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Town of Highland. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Town of Highland vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Town of Highland, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Town of Highland vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.