Photo by Vincent Ramundo

Search Chalets in Middletown

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
12 Sep - 14 Sep
In two weeks
19 Sep - 21 Sep
In one month
3 Oct - 5 Oct
In two months
31 Oct - 2 Nov

Chalets in Middletown

Our top choices for Middletown chalets

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, (4)
"Cute house. Nice stay"
The price is AED 643
AED 1,050 total
includes taxes & fees
8 Sep - 9 Sep
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
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, (5)
"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!
Mountain View Retreat w/ Hot Tub, Theater, and Gym
Outdoor dining

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

Mountain View Retreat w/ Hot Tub, Theater, and Gym
Catskills Lakefront Escape with Hot Tub
Exterior

Catskills Lakefront Escape with Hot Tub

9.8 out of 10, Exceptional, (19)
"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 AED 621
AED 1,098 total
includes taxes & fees
4 Sep - 5 Sep
★Chic Chalet River Views & Access★
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
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, (56)
"Nice property, good location, great communication with host. Check in process was a breeze."
The price is AED 816
AED 1,830 total
includes taxes & fees
7 Sep - 8 Sep
Luxe 10 guest Ski Chalet /Skiing/Pools/Tennis/Gym/Golf/Hiking
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

9.6 out of 10, Exceptional, (20)
"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 | Fridge, microwave, oven, stovetop

Chic Mountain Creek Chalet

3.0 star property
Chic Mountain Creek Chalet
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, (27)
"We had a beautiful time thank you"
Private Chalet with Mtn views, Pool, Hot Tub, Fire Pits, Game Room & Gym
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 AED 4,371
AED 5,896 total
includes taxes & fees
3 Sep - 4 Sep
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

9.6 out of 10, Exceptional, (4)
"Cool house in a quiet setting!"
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
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!
Serene & Bright: Minnewaska Mtn Views ~ Deck ~BBQ
Exterior

Serene & Bright: Minnewaska Mtn Views ~ Deck ~BBQ

Serene & Bright: Minnewaska Mtn Views ~ Deck ~BBQ
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middletown Hotel Reviews

The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark

10/10 Excellent
"Very beautiful resort / waterpark, stayed with my husband, two kids under 2 and my mom. We loved it only thing is the food is pricey for something that isn’t as good and also room service should be better as in front desk answering the phones to restock room amenities but other than that staff was great our room wasn’t ready at 4pm which is check in kind of frustrating since we drove over 2 hours, but around 6pm I went to ask and they gave us an upgrade and accommodated us with another beautiful room grand family suite with a balcony. Overall loved it we came here for my sons birthday they both had fun which is all that matters! "
Melissa 2-night trip
Posted 4 days ago
The Kartrite Resort & Indoor Waterpark