Search Chalets in Middletown from CA $186

Change your mind

Book hotels with free cancellation

Treat yourself

Be picky

Search almost a million properties worldwide

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Browse Select Middletown Chalets

Relax in a serene outdoor seating area surrounded by a lush hillside and a well-manicured lawn.

"We had a nice stay at this location. The property managers were extremely quick to respond and helpful pointing out must visit locations while at the property."

Enjoy dining or socializing on the deck surrounded by lush greenery and a white-framed window.

"Perfect little cabin for my husband & I with our dog. The bed was very comfortable & house was clean. Easy to find in a peaceful location. "

CA $382 total

includes taxes & fees

Aug 25 - Aug 26

Relax in a tranquil hot tub surrounded by lush forest views.

CA $342 total

includes taxes & fees

Aug 18 - Aug 19

Situated in a forested area, this cabin features a front porch with a railing and chimney, and a small balcony overlooking the surrounding trees.

"Loved the beautiful scenery and location. Very peaceful and relaxing. Just what we were looking for. "

CA $457 total

includes taxes & fees

Sep 2 - Sep 3

Relax on the deck with a comfortable seating area, surrounded by lush greenery and string lights.

"I would recommend this property to anyone looking to visit Virginia wineries with friends, go hiking in the beautiful mountains, or just unwind. It is close to so many wineries, restaurants, hiking trails, and is a quiet spot to just relax. We will definitely be back!"

Relax on the deck with wicker sofas and a small table, perfect for al fresco dining and outdoor cooking.

"This house was new, clean, well stocked in the kitchen and bathrooms with essentials which was very nice. . Quick responses with the owner when I had questions. Enjoyed our stay!!"

Enjoy a romantic dinner on the balcony with a scenic view of rolling hills.

"Really enjoyed our stay and all the little touches - like labeled drawers and clear instructions. Very comfortable beds, pillows, and all the amenities you could want. Perfect for an uninterrupted girls weekend getaway."

Save an average of 15% on thousands of hotels when you're signed in

Top Middletown Hotel Reviews

Comfort Inn & Suites Winchester

10/10 Excellent

"I’ve stayed here before with my two dogs, this time without…..Rooms are very spacious and clean, Staff at desk always friendly and helpful. Breakfast good with friendly staff….Convenient off/on from Highway."