Photo by Vincent Ramundo

Search Chalets in Middletown

    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
9 Jum. I - 11 Jum. I
In two weeks
16 Jum. I - 18 Jum. I
In one month
30 Jum. I - 1 Jum. II
In two months
27 Jum. II - 29 Jum. II

Compare 12 Chalets in Middletown with updated reviews, rates, and availability.

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, (53)
"Nice property, good location, great communication with host. Check in process was a breeze."
The price is SAR 1,004
SAR 2,076 total
includes taxes & fees
4 May - 5 May
Luxe 10 guest Ski Chalet /Skiing/Pools/Tennis/Gym/Golf/Hiking
Catskills Lakefront Escape with Hot Tub
Exterior

Catskills Lakefront Escape with Hot Tub

10.0 out of 10, Exceptional, (17)
"Everyone had a place to sleep! Very clean! Great hot tub! "
Catskills Lakefront Escape with Hot Tub
★Chic Chalet River Views & Access★
Miscellaneous

★Chic Chalet River Views & Access★

4.0 out of 10, (1)
"Dirty. Ants. Not well stocked."
The price is SAR 450
SAR 854 total
includes taxes & fees
5 May - 6 May
★Chic Chalet River Views & Access★
Luxury Ski In-Out ● Mountain Creek ● Hot Tub ● Golf
Terrace/patio

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

9.8 out of 10, Exceptional, (9)
"Beautiful house with amazing views and responsive hosts. Excellent for kids. Plenty of space and comfortable beds. Would definitely stay again!"
Luxury Ski In-Out ● Mountain Creek ● Hot Tub ● Golf
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, (24)
"We had a beautiful time thank you"
Private Chalet with Mtn views, Pool, Hot Tub, Fire Pits, Game Room & Gym
Giant chalet with private lake access. Hot tub. pet friendly. ultimate game room
Property grounds

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

10.0 out of 10, Exceptional, (16)
"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
Ski House - ON THE SLOPE w/ hot tub
Interior

Ski House - ON THE SLOPE w/ hot tub

10.0 out of 10, Exceptional, (18)
" The house was in Exceptional condition upon entering. The Host Brian was very friendly, and available for any and all concerns! We’ll be back for certain"
The price is SAR 4,463
SAR 6,005 total
includes taxes & fees
5 May - 6 May
Ski House - ON THE SLOPE w/ hot tub
Modern Chalet with Hot Tub and Lake Access
Miscellaneous

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!
Beach

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!
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!
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
Modern Zen Chalet at the Foot of Gunks w Mt. View
Terrace/patio

Modern Zen Chalet at the Foot of Gunks w Mt. View

2.0 star property
The price is SAR 615
SAR 1,006 total
includes taxes & fees
21 May - 22 May
Modern Zen Chalet at the Foot of Gunks w Mt. View
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.
Don't see what you're looking for?
See all available properties in Middletown
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Middletown

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!
5 bedrooms, desk, iron/ironing board, free WiFi

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

9.0 out of 10, Wonderful, (73)
"Celebrated my husbands 50th birthday and the property was perfect!"
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (109)
"Great place and host!"
The price is SAR 630
SAR 1,044 total
includes taxes & fees
4 May - 5 May
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Cozy Cabin with Sauna & Firepit!
Outdoor dining

Cozy Cabin with Sauna & Firepit!

9.6 out of 10, Exceptional, (25)
"Excellent "
Cozy Cabin with Sauna & Firepit!
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.