Photo by Vincent Ramundo

Middletown Chalets

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 13 Chalets in Middletown with updated reviews, rates, and availability.

Interior
Ski House - ON THE SLOPE w/ hot tub
10.0 out of 10, Exceptional, (13)
"My husband and 2 children enjoyed a 3 night bday weekend at this beautiful home. We enjoyed the perfect location to watch skiers and snowboarders glide down the mountain from almost every window. The home was bright, cozy and romantic. The hot tub on the patio is a perfect end to a day of skiiing. It is the perfect ski in and ski out location, especially if you like terrain parks. It is very close to restaurants and is also a simple drive to the other trail lifts. It is a charming home and we...
The price is $650
$919 total
includes taxes & fees
May 27 - May 28
Ski House - ON THE SLOPE w/ hot tub
Exterior
ABomb! Adorable 2-bdrm Chalet with Lots of Room!
ABomb! Adorable 2-bdrm Chalet with Lots of Room!
Property grounds
🞲𝗡𝗘𝗪🞲 Mountain Views ● Luxurious ● Hot Tub ● Golf
10.0 out of 10, Exceptional, (1)
"Clean, comfortable beds and cozy"
🞲𝗡𝗘𝗪🞲 Mountain Views ● Luxurious ● Hot Tub ● Golf
Save an average of 15% on thousands of hotels when you're signed in
Fridge, microwave, oven, stovetop
★Chic Chalet River Views & Access★
The price is $120
$233 total
includes taxes & fees
May 28 - May 29
★Chic Chalet River Views & Access★
Property grounds
Mountain Chalet with views, Hot Tub, Fire Pits, Game Room & Gym
10.0 out of 10, Exceptional, (20)
"House was just as advertised. Hot tub was perfect, inspire of the weather. Would be a great place for fall adventure bcz the view is awesome."
Mountain Chalet with views, Hot Tub, Fire Pits, Game Room & Gym
Beach
Beautiful Chalet with Private Lake Spot Near Popular Resorts - Wurtsboro NY!
9.6 out of 10, Exceptional, (29)
"Everything was great!"
Beautiful Chalet with Private Lake Spot Near Popular Resorts - Wurtsboro NY!
Property grounds
Giant chalet with private lake access. Hot tub. pet friendly. ultimate game room
10.0 out of 10, Exceptional, (11)
"Great property and great home. Enough room and amenities for my whole family. Host was so attentive to all our questions and needs. Lake was beautiful and so serene. I would stay again and recommend to anyone who is looking to get peaceful time away."
Giant chalet with private lake access. Hot tub. pet friendly. ultimate game room
Outdoor spa tub
Modern Chalet with Hot Tub and Lake Access
10.0 out of 10, Exceptional, (3)
"Escaped the city for a five star weekend. The house was fully equipped for preparing group meals, offering plenty of space to enjoy them together. StayBettr was perfectly communicative and provides a guide with everything you need to prepare for your stay. We relaxed in the hot tub and bonded over a private, virtual @journalingclasses session. Don’t forget to stop by Tilly’s diner (15min) drive away for a delicious breakfast or lunch with the most wonderful waitstaff. We hope to come back again!"
Modern Chalet with Hot Tub and Lake Access
Property grounds
Catskills Lakefront Escape with Hot Tub
10.0 out of 10, Exceptional, (15)
"Perfect location for our group who hadn’t seen each other in over a decade. Stayed at the house all weekend, cooking meals, sitting outside by the lake, and evenings by the fire pit. Kitchen was well stocked with cooking equipment which was great for our group. Property management was very responsive to questions and made check in/out a breeze."
Catskills Lakefront Escape with Hot Tub
Fridge, microwave, oven, stovetop
Chic Mountain Creek Chalet – 2 BDR in Great Gorge Village, Amenities Galore!
10.0 out of 10, Exceptional, (1)
"This unit has obviously been remodeled recently. They did a good job on the remodel and the space is well put together. I was impressed by the fact that all rooms have a large screen TV and are setup for streaming. Made for good entertainment when we were home and the rooms were well equiped with bedding and blankets. I was surprised with the price as it clearly has plenty of upgrades and was well done. Would stay here again if in the area. "
Chic Mountain Creek Chalet – 2 BDR in Great Gorge Village, Amenities Galore!
Outdoor dining
Mountain view retreat w/ hot tub, theater, and gym
The price is $728
$1,123 total
includes taxes & fees
May 27 - May 28
Mountain view retreat w/ hot tub, theater, and gym
Chalet, Multiple Beds, Balcony, Mountain View | Private kitchen | Coffee/tea maker
Chic Mountain Creek Chalet
3.0 star property
Chic Mountain Creek Chalet
Smart TV, fireplace
Serene & Bright: Minnewaska Mtn Views ~ Deck ~BBQ
Serene & Bright: Minnewaska Mtn Views ~ Deck ~BBQ
Don't see what you're looking for?
See all available properties in Middletown
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.

Other property types in Middletown

Luxury Studio | Private kitchen | Full-size fridge, microwave, oven, stovetop
Cottage Suites
3.0 star property
The price is $132
$257 total
includes taxes & fees
May 27 - May 28
Cottage Suites
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (96)
"Comfortable apartment with a phenomenal view! The space could use a deep clean and some decluttering, but that view!!! Did I mention that the view was A-mazing?!?"
The price is $184
$264 total
includes taxes & fees
May 27 - May 28
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
1 bedroom, desk, iron/ironing board, travel crib
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, (35)
"This is a cozy property in a very rural setting. The host is extremely responsive and very thorough. It is quiet and private. The furniture and bed are very comfortable. The wood burning stove is a pellet stove which provides enough heat to take the edge off. The hot tub could comfortably fit 4 people. The Village of Cold Spring is less than 10 minutes away, as is the Interstate 84 bridge across the Hudson. If you want to make your own food, bring it. There is no grocery store nearby."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
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.

Middletown Chalets information

Number of reviews
84
Accommodation
13 Chalets
Lowest Price
$120
Highest Price
$728

Recent reviews of Middletown hotels
Expedia verified reviews