Photo by Vincent Ramundo

Find Ski Hotels in Middletown, NY from CA $121

    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 availability on Middletown Ski Hotels

Top Middletown Ski Hotels

Hampton Inn by Hilton Middletown
Exterior

Hampton Inn by Hilton Middletown

2.5 star property
8.6 out of 10, Excellent, (1003)
"Property was clean and staff was friendly. "
The price is CA $136
CA $161 total
includes taxes & fees
Aug 28 - Aug 29
Hampton Inn by Hilton Middletown
Home2 Suites by Hilton Middletown
Courtyard

Home2 Suites by Hilton Middletown

3.0 star property
9.0 out of 10, Wonderful, (707)
"Been here twice and very family friendly "
The price is CA $192
CA $231 total
includes taxes & fees
Sep 7 - Sep 8
Home2 Suites by Hilton Middletown
Holiday Inn Express West Point by IHG
Free daily full breakfast

Holiday Inn Express West Point by IHG

2.5 star property
9.2 out of 10, Wonderful, (148)
"Staff were very nice and quick check-in. The room was clean and the bed was super comfy!"
The price is CA $192
CA $217 total
includes taxes & fees
Aug 24 - Aug 25
Holiday Inn Express West Point by IHG
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, (119)
"Nice view on the top of the mountain….I admired the river with the bridge and the surroundings until late in the night. The accommodation was excellent, we had everything we needed.… we are thinking of coming back sometime…."
The price is CA $260
CA $416 total
includes taxes & fees
Sep 9 - Sep 10
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
The Perfect Essential Getaway!
Interior

The Perfect Essential Getaway!

9.6 out of 10, Exceptional, (5)
"Owner was very responsive and accommodating on the app when I had questions. Place was great."
The price is CA $1,278
CA $1,762 total
includes taxes & fees
Aug 19 - Aug 20
The Perfect Essential Getaway!
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Property grounds

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

10.0 out of 10, Exceptional, (63)
"Great location, the host was very attentive, beautiful view of the river. Would definitely recommend!"
The price is CA $121
CA $274 total
includes taxes & fees
Aug 24 - Aug 25
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Property grounds

Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!

9.6 out of 10, Exceptional, (54)
"Family REALLY loved our stay here. House was gorgeous and roomy. Backyard was amazing, fire pits and well maintained. Kelly, property management, were attentive and very kind. Saving this on favorites for our next trip"
The price is CA $248
CA $545 total
includes taxes & fees
Aug 18 - Aug 19
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Charming 3-BR house: Lake Views, Firepit, Ping Pong, & Kayaks in Greenwood Lake
Outdoor dining

Charming 3-BR house: Lake Views, Firepit, Ping Pong, & Kayaks in Greenwood Lake

10.0 out of 10, Exceptional, (1)
"The location was fantastic and the place was amazing. Our family enjoyed the great views and the house had all the amenities to spend a relaxing vacation. "
The price is CA $522
CA $1,071 total
includes taxes & fees
Aug 20 - Aug 21
Charming 3-BR house: Lake Views, Firepit, Ping Pong, & Kayaks in Greenwood Lake
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!
Interior

5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!

2.0 star property
The price is CA $269
CA $598 total
includes taxes & fees
Sep 15 - Sep 16
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!
Lakefront Haven • Private Beach • Dock • Fire Pit • Game Room • Boat Rental
Outdoor dining

Lakefront Haven • Private Beach • Dock • Fire Pit • Game Room • Boat Rental

The price is CA $442
CA $862 total
includes taxes & fees
Aug 18 - Aug 19
Lakefront Haven • Private Beach • Dock • Fire Pit • Game Room • Boat Rental
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.

Top Middletown Hotel Reviews

Best Western Hunt's Landing Hotel Matamoras/Milford

Best Western Hunt's Landing Hotel Matamoras/Milford

10/10 Excellent
"Used only to get a couple of hours of sleep; but it was extremely convenient, comfortable, & affordable. Typical continental breakfast. Will definitely keep in mind as a future stopping point between ME & VA."
Anita 1-night trip
Posted 4 days ago
Best Western Hunt's Landing Hotel Matamoras/Milford
Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown

10/10 Excellent
"Great stay friendly staff. Only two towels and all they had were pool towels"
Andrew 1-night trip
Posted 5 days ago
Hampton Inn by Hilton Middletown