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Search Chalets in Middletown from CA $225

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Check prices for these dates

Next weekend
Aug 8 - Aug 10
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Aug 15 - Aug 17
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Aug 29 - Aug 31
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Sep 26 - Sep 28

Browse Select Middletown Chalets

Luxury Ski In-Out ● Mountain Creek ● Hot Tub ● Golf
Outdoor dining

Luxury Ski In-Out ● Mountain Creek ● Hot Tub ● Golf

9.8 out of 10, Exceptional, (10)
"Clean, comfortable beds and cozy"
Luxury Ski In-Out ● Mountain Creek ● Hot Tub ● Golf
Catskills Lakefront Escape with Hot Tub
Escape to a serene lakeside retreat with a cozy main building and dock.

Catskills Lakefront Escape with Hot Tub

9.8 out of 10, Exceptional, (18)
"Everyone had a place to sleep! Very clean! Great hot tub! "
Catskills Lakefront Escape with Hot Tub
★Chic Chalet River Views & Access★
Enjoy cooking in this well-equipped kitchen with a range hood, microwave, double oven, and ample workspace.

★Chic Chalet River Views & Access★

7.4 out of 10, Good, (3)
"Dirty. Ants. Not well stocked."
The price is CA $225
CA $402 total
includes taxes & fees
Aug 4 - Aug 5
★Chic Chalet River Views & Access★
Luxe 10 guest Ski Chalet /Skiing/Pools/Tennis/Gym/Golf/Hiking
Guests can enjoy a refreshing swim in the pool surrounded by a building with a sleek design.

Luxe 10 guest Ski Chalet /Skiing/Pools/Tennis/Gym/Golf/Hiking

9.4 out of 10, Exceptional, (55)
"Nice property, good location, great communication with host. Check in process was a breeze."
The price is CA $345
CA $748 total
includes taxes & fees
Aug 6 - Aug 7
Luxe 10 guest Ski Chalet /Skiing/Pools/Tennis/Gym/Golf/Hiking
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
Relax by the fire pit in a serene outdoor setting surrounded by a mix of sofas and chairs.

Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna

2.0 star property
10.0 out of 10, Exceptional, (2)
The price is CA $321
CA $483 total
includes taxes & fees
Aug 13 - Aug 14
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
Giant chalet with private lake access. Hot tub. pet friendly. ultimate game room
Set amidst lush greenery, this charming house features a front porch and a staircase leading to the entrance.

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

9.8 out of 10, Exceptional, (19)
"Our family enjoyed a wonderful stay. The lake was beautiful and peaceful. We spent our days kayaking and swimming. The large dining area was perfect for family dinners. The kids had a great time playing with the games in the game room. The house had everything that we needed and our host was so lovely to work with!"
Giant chalet with private lake access. Hot tub. pet friendly. ultimate game room
ABomb! Adorable 2-bdrm Chalet with Lots of Room!
Cozy cabin nestled among the trees, offering a peaceful retreat with a single window and a charming entrance.

ABomb! Adorable 2-bdrm Chalet with Lots of Room!

9.6 out of 10, Exceptional, (4)
"Was the perfect spot to come back too after a long day in the sun. The campfire was welcoming and the house its self was just beautiful. Wish we didnt have to leave! Was the perfect girls trip spot and wohld recommend this to anyone ♥️♥️"
ABomb! Adorable 2-bdrm Chalet with Lots of Room!
Chic Mountain Creek Chalet
Enjoy cooking in this well-lit kitchen with a central island stove, large island, and bar stools.

Chic Mountain Creek Chalet

3.0 star property
Chic Mountain Creek Chalet
Ski House - ON THE SLOPE w/ hot tub
Stunning interior with a high ceiling, wooden staircase, and exposed beams, offering a spacious seating and dining area with large windows and outdoor views.

Ski House - ON THE SLOPE w/ hot tub

10.0 out of 10, Exceptional, (19)
"Great location and great host."
The price is CA $1,641
CA $2,216 total
includes taxes & fees
Aug 4 - Aug 5
Ski House - ON THE SLOPE w/ hot tub
Serenity at Lake Joseph | Lakefront•Hot Tub•Ski
Enjoy cooking in this well-lit kitchen with a large island and a view of the outdoors.

Serenity at Lake Joseph | Lakefront•Hot Tub•Ski

9.4 out of 10, Exceptional, (3)
"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. "
Serenity at Lake Joseph | Lakefront•Hot Tub•Ski
Modern Chalet with Hot Tub and Lake Access
Relax in a hot tub on a landscaped patio surrounded by trees and foliage.

Modern Chalet with Hot Tub and Lake Access

10.0 out of 10, Exceptional, (4)
"The property is very cool and secluded. We had a nice, relaxing time!"
Modern Chalet with Hot Tub and Lake Access
Private Chalet with Mtn views, Pool, Hot Tub, Fire Pits, Game Room & Gym
Relax in the hot tub on the deck, surrounded by a serene forest landscape.

Private Chalet with Mtn views, Pool, Hot Tub, Fire Pits, Game Room & Gym

10.0 out of 10, Exceptional, (26)
"We had a beautiful time thank you"
Private Chalet with Mtn views, Pool, Hot Tub, Fire Pits, Game Room & Gym
Beautiful Chalet with Private Lake Spot Near Popular Resorts - Wurtsboro NY!
Enjoy cooking in this kitchen with a refrigerator, stove, and dishwasher.

Beautiful Chalet with Private Lake Spot Near Popular Resorts - Wurtsboro NY!

9.8 out of 10, Exceptional, (31)
"Everything was great!"
Beautiful Chalet with Private Lake Spot Near Popular Resorts - Wurtsboro NY!
Mountain View Retreat w/ Hot Tub, Theater, and Gym
Terrace/patio

Mountain View Retreat w/ Hot Tub, Theater, and Gym

The price is CA $1,052
CA $1,852 total
includes taxes & fees
Aug 24 - Aug 25
Mountain View Retreat w/ Hot Tub, Theater, and Gym
Serenity in Glen Spey! Charming 3 bedroom Chalet with Hot Tub and more!
Sit comfortably in the serene forest surroundings with three Adirondack chairs arranged around a cozy fire pit.

Serenity in Glen Spey! Charming 3 bedroom Chalet with Hot Tub and more!

Serenity in Glen Spey! Charming 3 bedroom Chalet with Hot Tub and more!
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 Middletown Hotel Reviews

Resorts World Catskills Casino

Resorts World Catskills Casino

10/10 Excellent
"Always a great clean room"
Nicole 1-night trip
Posted 2 days ago
Resorts World Catskills Casino