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Search Chalets in Middletown from CA $205

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Middletown Chalets

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

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!
Luxury Ski In-Out ● Mountain Creek ● Hot Tub ● Golf
Outdoor spa tub

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

10.0 out of 10, Exceptional, (11)
"Clean, comfortable beds and cozy"
Luxury Ski In-Out ● Mountain Creek ● Hot Tub ● Golf
Catskills Lakefront Escape with Hot Tub
Exterior

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★
Property grounds

★Chic Chalet River Views & Access★

7.4 out of 10, Good, (3)
"Dirty. Ants. Not well stocked."
The price is CA $205
CA $376 total
includes taxes & fees
Aug 12 - Aug 13
★Chic Chalet River Views & Access★
Luxe 10 guest Ski Chalet /Skiing/Pools/Tennis/Gym/Golf/Hiking
Indoor pool, outdoor pool

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 $753 total
includes taxes & fees
Aug 12 - Aug 13
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
Exterior detail

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 $300
CA $449 total
includes taxes & fees
Sep 2 - Sep 3
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
Exterior

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

9.8 out of 10, Exceptional, (19)
"Wonderful location for long weekend with family! Loved all of the outdoor spaces this property offers. Kayaks, hot tub, sitting areas, campfire and fenced in yard were all utilized. Appreciated all of the extra amenities (stocked kitchen, shampoo, dog toys, etc) that added to this trip."
Giant chalet with private lake access. Hot tub. pet friendly. ultimate game room
Chic Mountain Creek Chalet
Chalet, Multiple Beds, Balcony, Mountain View | Private kitchen

Chic Mountain Creek Chalet

3.0 star property
Chic Mountain Creek Chalet
Ski House - ON THE SLOPE w/ hot tub
Exterior

Ski House - ON THE SLOPE w/ hot tub

10.0 out of 10, Exceptional, (19)
"Great location and great host."
The price is CA $1,637
CA $2,229 total
includes taxes & fees
Aug 11 - Aug 12
Ski House - ON THE SLOPE w/ hot tub
Serenity at Lake Joseph | Lakefront•Hot Tub•Ski
Outdoor dining

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
Outdoor dining

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
Outdoor spa tub

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!
Outdoor dining

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
Outdoor dining

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

The price is CA $908
CA $1,688 total
includes taxes & fees
Aug 13 - Aug 14
Mountain View Retreat w/ Hot Tub, Theater, and Gym
Serenity in Glen Spey! Charming 3 bedroom Chalet with Hot Tub and more!
Exterior

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

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

10/10 Excellent
"Bed comfort"
Juan 1-night trip
Posted 16 hours ago
La Quinta Inn & Suites by Wyndham Middletown-Goshen