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Chalets in Town of Highland

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Top Cities in Town of Highland

A solitary tree in a misty field with a backdrop of a cloudy sky and dense forest.
ChaletsChalets

Eldred

Eldred
A calm lake surrounded by dense green forest under a partly cloudy sky.
ChaletsChalets

Barryville

Barryville

Our top choices for Town of Highland chalets

A wooden deck with a table and chairs, a red chair, and a lantern.

1. The Fairway Lodge Game Room Fire Pit Tee Tim

The Fairway Lodge Game Room Fire Pit Tee Tim
Lake Ariel
9.4 out of 10, Exceptional, (3 reviews)
"Our trip to Lake Ariel was wonderful! The property was exceptionally clean, spacious, and perfect for our large family. There was plenty of room for everyone, and I highly recommend it for a family getaway.The kids loved the pool table, air hockey, games, CDs, and DVDs—we actually got to introduce them to CDs and DVDs, which they had basically never seen before! We also really appreciated the beach chairs and paddleboard. If you have younger kids, I recommend bringing sand toys for the beach.A...
United States
Jennifer L.
The Fairway Lodge Game Room Fire Pit Tee Tim
A two-story cabin with a deck, surrounded by trees with autumn foliage.

2. Villa MiaNova: A Modern Hideout in the Woods.

Villa MiaNova: A Modern Hideout in the Woods.
Lake Ariel
9.6 out of 10, Exceptional, (21 reviews)
"Great stay - exactly as pictured"
United States
Lori S.
Villa MiaNova: A Modern Hideout in the Woods.
A wooden deck with a railing overlooking a lake, surrounded by trees.

3. Modern Chalet with Hot Tub and Lake Access

Modern Chalet with Hot Tub and Lake Access
Thompson
9.6 out of 10, Exceptional, (8 reviews)
"The property is very cool and secluded. We had a nice, relaxing time!"
United States
Ben N.
Modern Chalet with Hot Tub and Lake Access
A hammock overlooking a pond with a waterfall, surrounded by trees.

4. ★★ - Highly Rated Waterfront: Hot Tub, Fireplace, Pet Friendly! -★★

★★ - Highly Rated Waterfront: Hot Tub, Fireplace, Pet Friendly! -★★
Wallenpaupauk Lake Estates
9.8 out of 10, Exceptional, (318 reviews)
"It was a beautiful property, cozy, inviting, and was a plus we were able to bring our fur babies!"
United States
Nicole T.
The price is CA $270
CA $687 total
includes taxes & fees
Oct 19 - Oct 20
★★ - Highly Rated Waterfront: Hot Tub, Fireplace, Pet Friendly! -★★
A two-story house with a red roof, surrounded by a well-maintained garden and trees.

5. Giant chalet with private lake access. Hot tub. pet friendly. ultimate game room

Giant chalet with private lake access. Hot tub. pet friendly. ultimate game room
Glen Spey
9.8 out of 10, Exceptional, (21 reviews)
"Great property and great home. Enough room and amenities for my whole family. Host was so attentive to all our questions and needs. Lake was beautiful and so serene. I would stay again and recommend to anyone who is looking to get peaceful time away."
United States
Victor S.
Giant chalet with private lake access. Hot tub. pet friendly. ultimate game room
A deck with wicker furniture and a stone wall.

6. Winter Wonderland Chalet wArcades, Pool Table, Fire pit, Lake, Pools & Ski Lifts

Winter Wonderland Chalet wArcades, Pool Table, Fire pit, Lake, Pools & Ski Lifts
Lackawaxen
9.8 out of 10, Exceptional, (18 reviews)
"Great community and the property had a good amount of privacy from neighbors. "
United States
Ryan Carlo
Winter Wonderland Chalet wArcades, Pool Table, Fire pit, Lake, Pools & Ski Lifts
A rustic cabin with a porch, outdoor seating, and a forest backdrop.

7. Family Fun in The Poconos at The Rosewood Hideout

Family Fun in The Poconos at The Rosewood Hideout
Lake Ariel
9.6 out of 10, Exceptional, (34 reviews)
"My family and I had a wonderful stay! The house was clean and comfortable. The kids had a lot of fun in the game room and snow tubing. We would stay there again!"
United States
Jessica C.
Family Fun in The Poconos at The Rosewood Hideout
A deck with outdoor seating, a stone fireplace, and a view of a forested area.

8. Luxury 5BR Chalet with Lake, Pool, Ski, Game Room, 2 Decks and Sleeps 14

Luxury 5BR Chalet with Lake, Pool, Ski, Game Room, 2 Decks and Sleeps 14
Lackawaxen
10.0 out of 10, Exceptional, (3 reviews)
"Communication with the owner was excellent. The home was very clean and well stocked to make our stay very trouble free. The family, all twelve of us, enjoyed the activities available in the community. We recommend this home for any family gathering. Thank you."
United States
Jack F.
Luxury 5BR Chalet with Lake, Pool, Ski, Game Room, 2 Decks and Sleeps 14
An outdoor dining area with a glass table, wooden chairs, and a variety of food items.

9. 4BDRM Games Family Friendly Fire Pit Masthope

4BDRM Games Family Friendly Fire Pit Masthope
Lackawaxen
9.8 out of 10, Exceptional, (28 reviews)
"Family friendly, good location."
United States
James L.
4BDRM Games Family Friendly Fire Pit Masthope
Balcony

10. Chic Chalet River Views & Access

Chic Chalet River Views & Access
Montague
7.6 out of 10, Good, (5 reviews)
"The place was perfect for us"
United States
Chris G.
The price is CA $215
CA $302 total
includes taxes & fees
Oct 19 - Oct 20
Chic Chalet River Views & Access
A two-story house with a stone pathway leading to the entrance, surrounded by lush greenery and trees.

11. Welcome to beautiful Masthope Mountain Community in the Poconos!

Welcome to beautiful Masthope Mountain Community in the Poconos!
Lackawaxen
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful 3 night stay! The home was very clean & well equipped.The community has great amenities & the host was very receptive."
United States
Frances R.
Welcome to beautiful Masthope Mountain Community in the Poconos!
A Clubhouse Tenth Hole Pub with a stone facade, wooden deck, and landscaped garden.

12. The Fawn Château w/ Game Room & sauna

The Fawn Château w/ Game Room & sauna
Lake Ariel
9.8 out of 10, Exceptional, (27 reviews)
"Home was beautiful! Very comfortable! "
United States
Karen G.
The Fawn Château w/ Game Room & sauna
Property grounds

13. The Gray Chalet - Dog Friendly • Near Lake Wallenpaupack

The Gray Chalet - Dog Friendly • Near Lake Wallenpaupack
Hawley
9.8 out of 10, Exceptional, (36 reviews)
"The house was perfect for a girls book club weekend. The set up was cozy and relaxing. Well appointed. Would book again! "
United States
Melissa W.
The Gray Chalet - Dog Friendly • Near Lake Wallenpaupack
A living room with a sectional sofa, a coffee table, a fireplace, and a ceiling fan.

14. Cozy 4-bedroom chalet in serene Hawley with cool AC

Cozy 4-bedroom chalet in serene Hawley with cool AC
Hawley
8.0 out of 10, Very good, (1 review)
"The host was great! The house was also great for our big family. IT was close to the lake and close to everything!"
United States
Karen S.
Cozy 4-bedroom chalet in serene Hawley with cool AC
A modern building with large glass windows and a well-lit entrance.

15. The Lookout * Lake * Masthope * Firepit * Arcade

The Lookout * Lake * Masthope * Firepit * Arcade
Lackawaxen
9.6 out of 10, Exceptional, (24 reviews)
"A very nice stay in a clean, well kept, nicely appointed home. Good timely communication with host, clear instructions, and no issues before, during, or after our stay. We’re appreciative of the memories made."
United States
Matthew M.
The Lookout * Lake * Masthope * Firepit * Arcade
A log cabin with a porch and a dining area.

16. Masthope modern log-cabin sided retreat!

Masthope modern log-cabin sided retreat!
Lackawaxen
9.8 out of 10, Exceptional, (120 reviews)
"Good location. "
United States
Stefano C.
Masthope modern log-cabin sided retreat!
A wooden deck with outdoor seating and a view of a lake.

17. Masthope Mountain Retreat Hot Tub, Game Room, Lake Access, 5 Min to Ski Big Bear

Masthope Mountain Retreat Hot Tub, Game Room, Lake Access, 5 Min to Ski Big Bear
Lackawaxen
10.0 out of 10, Exceptional, (17 reviews)
"Great location and amazing owner !"
United States
Jill
Masthope Mountain Retreat Hot Tub, Game Room, Lake Access, 5 Min to Ski Big Bear
A wooden deck with two chairs and a table overlooking a lake.

18. Serenity at Lake Joseph | Lakefront•Hot Tub•Ski

Serenity at Lake Joseph | Lakefront•Hot Tub•Ski
Forestburgh
9.6 out of 10, Exceptional, (5 reviews)
"This property has an amazing location with plenty of space in the home! Loved the open kitchen with plenty of seating. Great place to stay if you have children. "
United States
Erin R.
Serenity at Lake Joseph | Lakefront•Hot Tub•Ski
A two-story house with a stone foundation, a covered porch, and a staircase leading to the upper level.

19. Welcome to On the Rocks a charming retreat located near Lake Wallenpaupack

Welcome to On the Rocks a charming retreat located near Lake Wallenpaupack
Wallenpaupauk Lake Estates
10.0 out of 10, Exceptional, (5 reviews)
"My experience at this house was fantastic. The cleanliness and layout were impressive, making it a comfortable stay. The location offered both convenience and privacy, which I truly appreciated. Additionally, it was well-stocked with toiletries. I would absolutely choose to stay here again."
United States
Anonymous traveller
Welcome to On the Rocks a charming retreat located near Lake Wallenpaupack
A two-story cabin with a balcony, surrounded by a forest.

20. Luxury Pocono Chalet • Hot Tub • Ski Hill • Game Room • Golf • Beaches • Dog OK

Luxury Pocono Chalet • Hot Tub • Ski Hill • Game Room • Golf • Beaches • Dog OK
Lake Ariel
10.0 out of 10, Exceptional, (12 reviews)
"Amazing experience house was stocked with everything we needed and the host was a pleasure. Very clean and great place to make memories would definitely book again. Lake Life!!!"
United States
Robert B.
Luxury Pocono Chalet • Hot Tub • Ski Hill • Game Room • Golf • Beaches • Dog OK
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

Resorts World Catskills Casino

Resorts World Catskills Casino

8/10 Good
"Needs improvement"
Wan 1-night trip
Posted 6 hours ago
Resorts World Catskills Casino

Find out more about Town of Highland

Town of Highland Chalets information

Number of reviews
651
Accommodation
54 Chalets
Lowest Price
CA $302
Highest Price
CA $687

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