Chalets in Middletown
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A stone tower with a staircase leading up to it.

Search Chalets in Middletown from CA $253

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your current months are November, 2026 and December, 2026.

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Our top choices for Middletown chalets

A hot tub on a wooden deck with a white railing, surrounded by trees.

A wooden ceiling, a dining table with chairs, a kitchen counter, and a view of the outdoors through a window.

A modern kitchen with wooden cabinets, a central island, and a dining area with chairs.

A cozy living room with a fireplace, wooden ceiling, and a dining area with a kitchen in the background.

1. Forest chalet w/ hot tub & BBQ grill

Forest chalet w/ hot tub & BBQ grill

Harpers Ferry

9.2 out of 10, Wonderful, (35 reviews)

9.2/10

Wonderful

(35 reviews)

"The cabin was perfect for a quick get away from the city for my husband and me. The hot tub was excellent, and the deck up in the trees made for an enjoyable afternoon of reading, working a puzzle, and revisiting the hot tub! It was so cozy that we decided not to leave for dinner. Just stayed at the cabin and relaxed."

LeAnn H.

The price is CA $315

CA $315

CA $625 total

includes taxes & fees

Nov 17 - Nov 18

Forest chalet w/ hot tub & BBQ grill

A wooden porch with a bench and a table, a 'HELLO' sign, and a 'WELCOME' sign.

A rustic cabin interior with a wooden interior, a central island with stools, a window with a view, and a ladder.

A cozy cabin interior with a leather sofa, a wooden coffee table, and shelves with various items.

A cozy cabin interior with a wooden deck, a cushioned bench, a small table with a plant, and a welcome sign.

2. Cozy w/Fire Pit, Grill, Screened Porch & WiFi

Cozy w/Fire Pit, Grill, Screened Porch & WiFi

Harpers Ferry

9.8 out of 10, Exceptional, (7 reviews)

9.8/10

Exceptional

(7 reviews)

"The host was very communicative and the place was very clean. "

Christopher M.

The price is CA $254

CA $254

CA $501 total

includes taxes & fees

Nov 17 - Nov 18

Cozy w/Fire Pit, Grill, Screened Porch & WiFi

A hot tub with a wooden deck and railing, surrounded by trees and a grassy area.

A modern kitchen with white cabinets, stainless steel appliances, and a wooden ceiling.

A bedroom with a bed, a wooden dresser, two bedside tables, and a bench.

A spacious living area with a stone fireplace, a dining table with chairs, a white sofa, and a ceiling fan.

3. Modern Harpers Ferry Cabin w Hot Tub, Deck, WiFi!

Modern Harpers Ferry Cabin w Hot Tub, Deck, WiFi!

Harpers Ferry

9.2 out of 10, Wonderful, (23 reviews)

9.2/10

Wonderful

(23 reviews)

"Beautiful property with plenty of open space. Cozy living room and open kitchen concept. Nice little dining area. The bedrooms and bathrooms were spacious and comfortable."

Elizabeth U.

The price is CA $476

CA $476

CA $833 total

includes taxes & fees

Nov 17 - Nov 18

Modern Harpers Ferry Cabin w Hot Tub, Deck, WiFi!

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

Learn more about Middletown

Nestled in the scenic Middletown Valley, this historic town offers charming Main Street shops and the annual Middletown Heritage Festival each September. Outdoor enthusiasts can explore nearby South Mountain State Park's hiking trails or visit local wineries for tastings with spectacular valley views.

See all hotels in Middletown

Top reviews in Middletown

A rooftop terrace with outdoor seating, a fire pit, and a view of the sunset over a mountainous landscape.

A bar area with multiple seating options, a television, and a variety of bottles on shelves.

A hotel room with two beds, a desk, a chair, a sofa, and a large mirror.

A modern hotel with a prominent sign reading "Springhill Suites by Marriott." It features a multi-story structure with a flat roof and a well-lit entrance.

SpringHill Suites by Marriott Frederick

Frederick

10/10 Excellent

The room was clean, the beds comfortable and the staff

Allanah

Reviewed May 16, 2026Reviewed May 16, 2026

SpringHill Suites by Marriott Frederick

A Hampton Inn & Suites hotel with a modern facade, large columns, and a well-lit entrance.

A hotel room with a bed, a desk with a lamp, a grey sofa, a TV, and a framed picture on the wall.

A hotel bathroom with a large mirror, a sink, and a toilet.

A spacious hotel lobby with multiple seating areas, a bar, and large windows offering views of the outdoors.

Hampton Inn & Suites Frederick-Fort Detrick

Frederick

10/10 Excellent

Oleksandr

Reviewed April 1, 2026Reviewed April 1, 2026

Hampton Inn & Suites Frederick-Fort Detrick

A Best Western hotel entrance at dusk with a covered parking area, outdoor seating, and well-maintained landscaping.

A swimming pool with lounge chairs and umbrellas, surrounded by a fence and greenery.

A hotel restaurant with a counter, seating area, and various food and drink stations.

A hotel room with two beds, a desk, a television, and a window with patterned curtains.

Best Western Historic Frederick

Frederick

10/10 Excellent

The room was very comfortable and the members of the personnel were very accommodating. Would stay there again should I return to Frederick. Thank you

Louise

Reviewed October 30, 2026Reviewed October 30, 2026

Best Western Historic Frederick

A Comfort Inn hotel entrance with a covered parking area, clear signage, and a flagpole with an American flag.

A hotel lobby with seating areas, a fireplace, and a reception desk.

A spacious dining area with multiple tables and chairs, a kitchen area with various appliances, and a clean, well-lit environment.

A hotel lobby with a stone fireplace, red and blue seating, a flat-screen TV, and a large window offering a city view.

Comfort Inn Frederick - Ballenger Creek

Frederick

10/10 Excellent

clean and has breakfast

Miki

Reviewed July 7, 2026Reviewed July 7, 2026

Comfort Inn Frederick - Ballenger Creek

A Fairfield by Marriott Inn & Suites building with a modern architectural design, featuring a prominent entrance and multiple floors.

A modern living room with a fireplace, wooden ceiling, and a flat-screen TV.

A modern living room with a fireplace, a flat-screen TV, and a dining area with a large window.

A bar area with wooden bar stools, a counter with bottles, and a green cushioned seating area.

Fairfield Inn & Suites by Marriott Hagerstown

Hagerstown

10/10 Excellent

Tout était très bien. Un seul petit,mais très petit commentaire négatif...Il y a une petite lumière dans la chambre dans le compartiment du café qui reste allumée toute la nuit.

Gilles

Reviewed September 26, 2026Reviewed September 26, 2026

Fairfield Inn & Suites by Marriott Hagerstown

A Country Inn & Suites building with a stone entrance, large windows, and a sign above the door.

A modern restaurant with a central dining area, kitchen, and blue cabinets.

A living room with two sofas, a coffee table, a TV mounted on a wooden wall, and shelves with decorative items.

A reception desk with a wooden finish, a clock, and a sign indicating check-out times.

Country Inn & Suites by Radisson, Frederick, MD

Frederick

10/10 Excellent

Location, staff, clean, quiet,

Nick

Reviewed January 29, 2025Reviewed January 29, 2025

Country Inn & Suites by Radisson, Frederick, MD

A modern hotel entrance with a covered parking area, multiple flags, and a well-maintained landscape.

A modern lobby with a blue sofa, round tables, and green chairs.

A patio area with a fire pit, outdoor seating, and a pergola with string lights.

A modern interior with a seating area featuring a blue sofa and wooden tables, a bar area, and a beverage machine.

Hampton Inn Hagerstown

Hagerstown

10/10 Excellent

Staff was very friendly. Room was very clean. Overall a good stay at Hampton Inn again.

Susan

Reviewed May 8, 2026Reviewed May 8, 2026

Hampton Inn Hagerstown

A hotel with multiple buildings, a parking lot, and green lawns.

A modern hotel room with a large flat-screen TV mounted on a wooden panel, a grey sofa, a white armchair, a small wooden coffee table, and a patterned carpet.

A modern living room with two flat-screen TVs on a wall, a wooden cabinet below, and a green cushioned chair.

An outdoor seating area with a fire feature, lounge chairs, and a modern building facade.

Fairfield Inn & Suites by Marriott Frederick

Frederick

10/10 Excellent

Very welcoming, room was very clean and spacious!

Ruby

Reviewed August 26, 2026Reviewed August 26, 2026

Fairfield Inn & Suites by Marriott Frederick

A covered patio with white chairs, a grill, and a view of a residential area.

A hotel room with a bed, a desk, a chair, a small ottoman, a bathroom with a granite countertop sink and mirror.

A diner with a counter, bar stools, and a menu board.

A hotel with a distinctive dome-shaped building, a parking lot, and a sign indicating a restaurant.

Travelodge by Wyndham Brunswick near Frederick

Brunswick

10/10 Excellent

We were looking for a place to stop during the long drive from Myrtle beach to home. While this location was a little off our route it proved to be our best choice as it is nestled in a very quiet community. Rooms were clean and hotel was also quiet.

Martin

Reviewed March 3, 2023Reviewed March 3, 2023

Travelodge by Wyndham Brunswick near Frederick

A hotel with a stone facade, a well-lit entrance, and a sign for Homewood Suites.

A hotel lobby with a reception desk, seating area, and a fireplace.

A modern lounge area with a curved sofa, patterned armchairs, and ottomans.

An indoor swimming pool with clear glass walls, lounge chairs, and a lifeguard station.

Homewood Suites by Hilton Frederick

Frederick

10/10 Excellent

Clean room with lots of room, awesome gym with Peleton and very good breakfast. Many places to eat located very close to this hotel too.

Jo-Anne

Reviewed July 7, 2026Reviewed July 7, 2026

Homewood Suites by Hilton Frederick

An outdoor patio area with wicker furniture, a fire pit, and a view of the parking lot.

A modern hotel room with a kitchenette, a bed, a desk, and a chair.

A hotel with a prominent "HOME" sign, outdoor seating area, and a covered entrance.

A modern kitchen with a refrigerator, microwave, and sink. There is a dining area with a table and chairs, and a small seating area with a lamp.

Home2 Suites by Hilton Charles Town

Charles Town

10/10 Excellent

Very nice hotel for travelling

Michel

Reviewed October 29, 2026Reviewed October 29, 2026

Home2 Suites by Hilton Charles Town

A modern hotel building with a sign reading "HOME 2 Suites by Hilton."

A pool area with red chairs and a person swimming.

An outdoor patio with a fire feature, seating, and a covered area with string lights.

A restaurant with a long counter, red chairs, and a 'Good Morning' sign.

Home2 Suites by Hilton Frederick

Frederick

10/10 Excellent

Great stop for a night with the family.

dave

Reviewed July 18, 2024Reviewed July 18, 2024

Home2 Suites by Hilton Frederick

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Search Chalets in Middletown from CA $253

Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Middletown chalets

1. Forest chalet w/ hot tub & BBQ grill

2. Cozy w/Fire Pit, Grill, Screened Porch & WiFi

3. Modern Harpers Ferry Cabin w Hot Tub, Deck, WiFi!

Learn more about Middletown

Top reviews in Middletown

SpringHill Suites by Marriott Frederick

10/10 Excellent

Explore a world of travel with Expedia