Middletown Chalets from CA $164

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Our top choices for Middletown chalets

1. Chic Chalet River Views & Access

Montague

Chris G.

CA $224 total

includes taxes & fees

Dec 1 - Dec 2

A rustic cabin with a large deck and multiple windows, surrounded by dense forest.

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

Warwick

Dorian G.

CA $1,849 total

includes taxes & fees

Nov 8 - Nov 9

A swimming pool surrounded by snow, with people swimming and a building in the background.

3. Luxe 10 Guest Ski Chalet · Mountain Creek · Fire Pit · Spa · Golf · Hiking · Ski

vernon

Kirstin V.

CA $813 total

includes taxes & fees

Nov 9 - Nov 10

A rustic cabin with a green awning, surrounded by autumn foliage.

4. Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna

Gardiner

Bernice

CA $373 total

includes taxes & fees

Nov 19 - Nov 20

A log cabin with a patio area featuring outdoor seating and a hot tub.

5. Ski House - ON THE SLOPE w/ hot tub

Vernon Township

JoeGina M.

CA $1,329 total

includes taxes & fees

Nov 9 - Nov 10

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Learn more about Middletown

Just an hour from NYC, this historic Hudson Valley town offers scenic hikes along the Heritage Trail and apple picking at local orchards. Explore the interactive exhibits at the National Soaring Museum, then catch a performance at the beautifully restored Paramount Theatre built in 1930.

See all hotels in Middletown

A lake surrounded by autumn-colored trees reflecting on the water.

Top reviews in Middletown

La Quinta Inn & Suites by Wyndham Middletown-Goshen

Middletown

10/10 Excellent

Sumaya

A circular outdoor seating area with a fire pit in the center, surrounded by wicker chairs and a small table.

Candlewood Suites Middletown Goshen by IHG

Middletown

8/10 Good

Stamatia

A large, two-story white house with a wrap-around porch and a small front garden.

The Dominion House Bed & Breakfast

Chester

10/10 Excellent

I’m torn between telling everyone about Dominion House and keeping it to myself. What a glorious B&B, with a swimming pool too. Only 3 rooms so you never feel crowded. Kathy was a welcome host and Liane’s breakfasts were amazing. It was really hot over the weekend, but the house was cool so even though it has A/C, I was still able to sleep with the windows open. So quiet and still. A family of deer wandered the lawn. The bed was comfortable, the water pressure was great, the library had tons of...

Susan