Photo by Vincent Ramundo

Search Ski Hotels in Middletown

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check availability on Middletown Ski Hotels

Tonight
21 Dec - 22 Dec
Tomorrow
22 Dec - 23 Dec
Next weekend
26 Dec - 28 Dec
In two weeks
2 Jan - 4 Jan

Our top choices for Middletown ski hotels

Exterior
Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1005)
"Room was clean and staff was great!"
United States
Annemarie
The price is 1.978.888 ₫
2.337.561 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Hampton Inn by Hilton Middletown
Courtyard
Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown
3.0 star property
Middletown
9.0 out of 10, Wonderful, (746)
"Staff was really amazing. They worked hard and were great all week long. "
United States
Joshua
The price is 4.333.554 ₫
5.211.113 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Home2 Suites by Hilton Middletown
Lobby
Hampton Inn Matamoras/Milford

Hampton Inn Matamoras/Milford

Hampton Inn Matamoras/Milford
2.5 star property
Matamoras
8.8 out of 10, Excellent, (1005)
"Love staying here"
United States
Jo-Ann
The price is 2.567.818 ₫
2.798.922 ₫ total
includes taxes & fees
16 Jan - 17 Jan 2026
Hampton Inn Matamoras/Milford
Indoor pool, pool loungers
Best Western Hunt's Landing Hotel Matamoras/Milford

Best Western Hunt's Landing Hotel Matamoras/Milford

Best Western Hunt's Landing Hotel Matamoras/Milford
3.0 star property
Matamoras
8.4 out of 10, Very good, (1003)
"Was clean and staff was courteous "
United States
Oneil
The price is 2.393.349 ₫
2.608.750 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Best Western Hunt's Landing Hotel Matamoras/Milford
Property grounds
Resorts World Catskills Casino

Resorts World Catskills Casino

Resorts World Catskills Casino
4.5 star property
Monticello
8.6 out of 10, Excellent, (1113)
"The staff was very courteous and helpful. "
United States
Odalys
Resorts World Catskills Casino
Reception
Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport
2.5 star property
Newburgh
9.2 out of 10, Wonderful, (979)
"Clean great staff great breakfast pool area warm "
United States
LaRhonda
The price is 2.783.601 ₫
3.288.129 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Hampton Inn & Suites Newburgh Stewart Airport
Free daily full breakfast
Holiday Inn Express West Point by IHG

Holiday Inn Express West Point by IHG

Holiday Inn Express West Point by IHG
2.5 star property
Fort Montgomery
9.2 out of 10, Wonderful, (216)
"Wonderful stay…excellent staff!"
United States
John
The price is 2.947.280 ₫
3.334.111 ₫ total
includes taxes & fees
2 Jan - 3 Jan 2026
Holiday Inn Express West Point by IHG
Lobby
Quality Inn near Mountain Creek

Quality Inn near Mountain Creek

Quality Inn near Mountain Creek
2.5 star property
Vernon
7.6 out of 10, Good, (977)
"Nice hotel. Close to golf,"
United States
Joseph
The price is 2.244.143 ₫
2.572.349 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Quality Inn near Mountain Creek
Exterior detail
Borland House Inn

Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (144)
"Had a great stay at the the Borland House Inn a historical setting in a cute town with wonderful staff and a delicious breakfast"
United States
Deborah
Borland House Inn
Front of property – evening/night
Minnewaska Lodge

Minnewaska Lodge

Minnewaska Lodge
3.0 star property
Gardiner
9.0 out of 10, Wonderful, (525)
"Great peaceful stay. Can’t wait to go back :)"
United States
Makeda
The price is 3.325.163 ₫
4.096.719 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Minnewaska Lodge
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.
View all properties

Top Middletown Hotel Reviews