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Chalets in Town of Highland

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sep - 13 Sep
In four months
9 Oct - 11 Oct

Our top choices for Town of Highland chalets

A heated pool

★★ - 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, (312 reviews)
"Lovely clean cabin. Loved the view. Fun and beautiful area to stay in.Loved the hot tub too!"
United States
Anders M.
★★ - Highly Rated Waterfront: Hot Tub, Fireplace, Pet Friendly! -★★
Outdoor dining

4BDRM Games Family Friendly Fire Pit Masthope

4BDRM Games Family Friendly Fire Pit Masthope
Lackawaxen
10.0 out of 10, Exceptional, (24 reviews)
"Family friendly, good location."
United States
James L.
4BDRM Games Family Friendly Fire Pit Masthope
Terrace/patio

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
9.6 out of 10, Exceptional, (15 reviews)
"House was clean and everything was in good condition."
United States
Stephen F.
Winter Wonderland Chalet wArcades, Pool Table, Fire pit, Lake, Pools & Ski Lifts
Exterior

Masthope modern log-cabin sided retreat!

Masthope modern log-cabin sided retreat!
Lackawaxen
9.8 out of 10, Exceptional, (117 reviews)
"Good location. "
United States
Stefano C.
Masthope modern log-cabin sided retreat!
Exterior

Bali's Cottage - Wallenpaupack Lake Estates - Pools, Fireplace, Fire Pit, Marina

Bali's Cottage - Wallenpaupack Lake Estates - Pools, Fireplace, Fire Pit, Marina
Wallenpaupauk Lake Estates
10.0 out of 10, Exceptional, (22 reviews)
"The owners, Lisa and Baker, were very easy to communicate with. They shared all necessary information before arrival. They sent over the paperwork for the rental agreement and car tag with good timing. They also shared clear information on how to check in and check out, along with other useful information. The home was clean and comfortable, stocked with essential cooking equipment. There were clean bath towels. WLE is a great neighborhood with outdoor space for activities like volleyball,...
United States
Diana
Bali's Cottage - Wallenpaupack Lake Estates - Pools, Fireplace, Fire Pit, Marina
Outdoor dining

Briar Hill North Lakefront Contemporary with Private Dock

Briar Hill North Lakefront Contemporary with Private Dock
Lakeville
9.4 out of 10, Exceptional, (54 reviews)
"Nice property and great view of the water."
United States
Cheryl Y.
Briar Hill North Lakefront Contemporary with Private Dock
Exterior

Villa MiaNova: A Modern Hideout in the Woods.

Villa MiaNova: A Modern Hideout in the Woods.
Lake Ariel
9.4 out of 10, Exceptional, (16 reviews)
"My family and I had a great time at this property. "
United States
Tom M.
Villa MiaNova: A Modern Hideout in the Woods.
Outdoor dining

The Fairway Lodge Game Room Fire Pit Tee Tim

The Fairway Lodge Game Room Fire Pit Tee Tim
Lake Ariel
The Fairway Lodge Game Room Fire Pit Tee Tim
Outdoor dining

Serenity at Lake Joseph | Lakefront•Hot Tub•Ski

Serenity at Lake Joseph | Lakefront•Hot Tub•Ski
Forestburgh
9.6 out of 10, Exceptional, (4 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
Exterior

Bella Vista Chalet Poconos -Four Season Resort/Lake/Pool/Ski/Horseback-riding

Bella Vista Chalet Poconos -Four Season Resort/Lake/Pool/Ski/Horseback-riding
Lackawaxen
9.8 out of 10, Exceptional, (9 reviews)
"Another great stay!"
United States
roland w.
Bella Vista Chalet Poconos -Four Season Resort/Lake/Pool/Ski/Horseback-riding
Outdoor dining

Huge 4bd Masthope retreat,hot tub game room,lake access,ski, Rain friendly deck

Huge 4bd Masthope retreat,hot tub game room,lake access,ski, Rain friendly deck
Lackawaxen
10.0 out of 10, Exceptional, (14 reviews)
"Great location and amazing owner !"
United States
Jill
Huge 4bd Masthope retreat,hot tub game room,lake access,ski, Rain friendly deck
Outdoor spa tub

Lakefront on Wallenpaupack with Hot Tub - Pet Friendly

Lakefront on Wallenpaupack with Hot Tub - Pet Friendly
Lakeville
9.4 out of 10, Exceptional, (77 reviews)
"Our family had a wonderful experience here."
United States
Anonymous traveler
Lakefront on Wallenpaupack with Hot Tub - Pet Friendly
Property grounds

The Gray Chalet - private lot close to Lake Wallenpaupack & downtown Hawley

The Gray Chalet - private lot close to Lake Wallenpaupack & downtown Hawley
Hawley
9.6 out of 10, Exceptional, (35 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 - private lot close to Lake Wallenpaupack & downtown Hawley
Property grounds

Chic Chalet River Views & Access

Chic Chalet River Views & Access
Montague
7.6 out of 10, Good, (4 reviews)
"Dirty. Ants. Not well stocked."
United States
odette w.
The price is AED 511
AED 732 total
includes taxes & fees
22 Jun - 23 Jun
Chic Chalet River Views & Access
Outdoor pool, a heated pool

The Fawn Château w/ Game Room & sauna

The Fawn Château w/ Game Room & sauna
Lake Ariel
10.0 out of 10, Exceptional, (26 reviews)
"Home was beautiful! Very comfortable! "
United States
Karen G.
The Fawn Château w/ Game Room & sauna
Exterior

The Lookout * Lake * Masthope * Firepit * Arcade

The Lookout * Lake * Masthope * Firepit * Arcade
Lackawaxen
9.8 out of 10, Exceptional, (20 reviews)
"We have been visit this area every year in October for the last 15 years. This was by far our favorite house we have stayed in. Plenty of space, 3 bathrooms, great location. We will definitely be back!"
United States
Stephan K.
The Lookout * Lake * Masthope * Firepit * Arcade
Exterior

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, (33 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
Exterior

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, (2 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 traveler
Welcome to On the Rocks a charming retreat located near Lake Wallenpaupack
Exterior

HOT TUB, Lakes, Ski Hill, Golf, Game Room & Endless Foliage, Dog friendly

HOT TUB, Lakes, Ski Hill, Golf, Game Room & Endless Foliage, Dog friendly
Lake Ariel
10.0 out of 10, Exceptional, (9 reviews)
"We enjoyed a wonderful long weekend at The Chalet and Loreen is a wonderful host"
United States
Steve L.
HOT TUB, Lakes, Ski Hill, Golf, Game Room & Endless Foliage, Dog friendly
Exterior

The Catskill Getaway • Near Bethel Woods & Hiking & HOT TUB

The Catskill Getaway • Near Bethel Woods & Hiking & HOT TUB
Parksville
10.0 out of 10, Exceptional, (3 reviews)
"Great house, great host and great nature.Everything was great."
United States
Thomas H.
The price is AED 1,249
AED 2,758 total
includes taxes & fees
23 Jun - 24 Jun
The Catskill Getaway • Near Bethel Woods & Hiking & HOT TUB
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

10/10 Excellent
"Excellent"
Louise 1-night trip
Posted 4 hours ago
Resorts World Catskills Casino