Photo by Stephanie Sutton

Hotels in Middletown

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Tonight
Sep 5 - Sep 6
Tomorrow
Sep 6 - Sep 7
Next weekend
Sep 11 - Sep 13
In two weeks
Sep 18 - Sep 20

Where to stay in Middletown?

A dining area with a high ceiling, wooden beams, and a chandelier. There is a painting on the wall and an American flag. Tables and chairs are arranged for dining.
A Pepsi vending machine in a hallway with tiled flooring and a door in the background.
A hotel entrance with a covered walkway, a parking lot, and a building with a grey roof.
A hotel room with a green sofa, two beds, a desk, and a window with curtains.

Econo Lodge Inn & Suites Middletown - Winchester South

Econo Lodge Inn & Suites Middletown - Winchester South
Middletown
$65
$71 total
includes taxes & fees
Sep 27 - Sep 28
Econo Lodge Inn & Suites Middletown - Winchester South
A rustic interior with wooden tables and chairs, a brick floor, and a wooden ceiling.
A large brick building with a central entrance, multiple windows, and a covered walkway.
A room with wooden flooring, two leather chairs, a wooden table with a green felt top, a brass lamp, and a large mirror on the wall.

Wayside Inn

Wayside Inn
Middletown
$122
$144 total
includes taxes & fees
Sep 6 - Sep 7
Wayside Inn
A hotel lobby with a reception desk, seating area with a round table, and a bar.
A hotel reception desk with a computer, two chairs, and a large mirror.
A swimming pool with a tiled deck, chairs, and a sign indicating no lifeguard on duty.
A multi-story hotel with a prominent sign for Marriott.

Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley
Strasburg
$123
$136 total
includes taxes & fees
Sep 16 - Sep 17
Fairfield Inn & Suites Strasburg Shenandoah Valley
A hotel lobby with a reception desk, a check-in counter, a seating area with chairs, and a dining area in the background.
A hotel lobby with a polished tile floor, a reception desk, and seating area with white chairs.
A modern hotel lobby with a clear exit sign, a reception desk, and a seating area with red chairs.
A hotel room with two beds, a nightstand with a lamp, a desk with a chair, a window with curtains, and a wall-mounted air conditioner.

Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley
Strasburg
$78
$87 total
includes taxes & fees
Sep 13 - Sep 14
Ramada by Wyndham Strasburg/Shenandoah Valley
A Comfort Inn & Suites building with a modern design, featuring a prominent logo on the facade, a covered entrance, and multiple windows.
A hotel room with a television, desk, chair, sofa, and kitchenette.
A hotel dining area with multiple tables and chairs, large windows, and a television screen.

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
Winchester
$93
$103 total
includes taxes & fees
Oct 4 - Oct 5
Comfort Inn & Suites Winchester
A modern hotel lobby with a green sofa, blue chairs, a dining table, and large windows offering a view of the outdoors.
A rectangular swimming pool with a brick wall and trees in the background.
A hotel reception desk with a blue accent, a Holiday Inn Express sign, and a coffee station.
A modern breakfast area with seating, a counter for hot food, and a view of the outdoors.

Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG
Stephens City
$88
$98 total
includes taxes & fees
Sep 13 - Sep 14
Holiday Inn Express Winchester South-Stephens City by IHG
A restaurant with wooden tables and red cushioned chairs, a kitchen area with a coffee machine, and a large window.
A gym with an elliptical, dumbbells, a treadmill, and a wall-mounted phone.
A two-story building with a brick facade and a beige exterior.
A hotel room with two beds, a desk, a television, and a window with curtains.

Quality Inn Stephens City - Winchester South

Quality Inn Stephens City - Winchester South
Stephens City
$80
$89 total
includes taxes & fees
Sep 27 - Sep 28
Quality Inn Stephens City - Winchester South
An indoor swimming pool with clear blue water, surrounded by large windows offering views of greenery.
A modern dining area with tables and chairs, large windows, and a flat-screen TV on the wall.
A hotel room with a gray sofa, a bed with a blue headboard, a painting of a landscape, and a lamp on the nightstand.
A gym with weightlifting equipment, including dumbbells and a bench.

Hampton Inn Front Royal

Hampton Inn Front Royal
Front Royal
$122
$136 total
includes taxes & fees
Sep 29 - Sep 30
Hampton Inn Front Royal
A spacious living room with a fireplace, wooden staircase, and a bookshelf.
A hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.
A Country Inn & Suites by Radisson building with a covered entrance and multiple windows.
A poolside area with lounge chairs and a stack of towels on a table.

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
Winchester
$99
$111 total
includes taxes & fees
Sep 27 - Sep 28
Country Inn & Suites by Radisson, Winchester, VA
A restaurant interior with a bar area, seating, and artwork on the walls.
A spacious lobby with a stone fireplace, blue upholstered sofas, and a chandelier.
A hotel lobby with a reception desk, a minibar, a seating area, and a clothing rack.
A spacious lobby with a reception desk, seating area with sofas, and a chandelier.

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows
Front Royal
$122
$135 total
includes taxes & fees
Sep 13 - Sep 14
DoubleTree by Hilton Front Royal Blue Ridge Shadows
An outdoor seating area with a fire feature, wicker furniture, and a building with multiple windows.
A modern hotel lobby with seating areas, a reception desk, and large windows offering a view of the outdoors.
A hotel reception area with a counter, a vending machine, and a sign indicating a minibar.
A conference room with a large table and chairs, a TV mounted on the wall, and a vending machine labeled "Towneplace Suites".

TownePlace Suites by Marriott Front Royal

TownePlace Suites by Marriott Front Royal
Front Royal
$139
$155 total
includes taxes & fees
Sep 20 - Sep 21
TownePlace Suites by Marriott Front Royal
A spacious lobby with a checkered floor, yellow chairs, a green carpet, and a wall with the text "It only takes a spark".
An indoor swimming pool with clear glass walls, a tiled floor, and a few lounge chairs.
A modern hotel room with a bed, sofa, and a small table. There are two doors, one blue and one white, and a small table with chairs.
A hotel with a modern design, featuring a prominent 'spark by Hilton' sign, a well-lit entrance, and a landscaped front yard.

Spark by Hilton Winchester

Spark by Hilton Winchester
Winchester
$77
$87 total
includes taxes & fees
Sep 28 - Sep 29
Spark by Hilton Winchester
A swimming pool area with a fence, lounge chairs, and a flag.
A building entrance with a neon 'OPEN' sign, a reception desk, and a clock.
A reception desk with a green wall, a plant, and various informational posters.
A hotel room with two beds, a nightstand with lamps, a vase with flowers, and framed leaf artwork on the walls.

Twi-Lite Inn

Twi-Lite Inn
Front Royal
$82
$91 total
includes taxes & fees
Sep 6 - Sep 7
Twi-Lite Inn
A spacious lobby with a stone fireplace, red chairs, a wooden staircase, and a flat-screen TV mounted on the wall.
A hotel lobby with a wooden railing, a reception desk, a flower vase, and an exit sign.
A stainless steel kitchen with a built-in water dispenser and a window with blinds.
A hotel lobby with a wooden staircase, a reception desk, and red chairs.

Motel 6 Front Royal, VA

Motel 6 Front Royal, VA
Front Royal
$65
$72 total
includes taxes & fees
Oct 1 - Oct 2
Motel 6 Front Royal, VA
A modern hotel lobby with a sofa set, two armchairs, a coffee table, and a reception desk.
A modern restaurant interior with wooden tables and chairs, a green booth area, and artwork on the walls.
A hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.
A Fairfield by Marriott hotel with a modern entrance, stone pillars, and a well-lit facade.

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
Winchester
$93
$103 total
includes taxes & fees
Sep 7 - Sep 8
Fairfield Inn & Suites by Marriott Winchester
A hotel lobby with a reception desk, seating area, and a fireplace.
A Super 8 hotel with a brick facade, multiple windows, and a central entrance.
A hotel room with a red carpet, white sofas, a reception desk, and a large window with blinds.
A hotel room with two beds, a large window with curtains, an air conditioning unit, a nightstand with a phone and clock, and a wall with a waterfall painting.

Super 8 by Wyndham Front Royal Near Shenandoah National Park

Super 8 by Wyndham Front Royal Near Shenandoah National Park
Front Royal
$66
$73 total
includes taxes & fees
Oct 4 - Oct 5
Super 8 by Wyndham Front Royal Near Shenandoah National Park
A hotel room with a large bed, a bathroom with a bathtub, and a framed picture on the wall.
A room with two grey armchairs, a small table with a vase of flowers, a television mounted on the wall, and a desk with a computer.
A multi-story hotel with a courtyard, outdoor seating, and a guest parking area.
A breakfast counter with various food items and a coffee machine.

Baymont by Wyndham Front Royal Near Shenandoah National Park

Baymont by Wyndham Front Royal Near Shenandoah National Park
Front Royal
$62
$69 total
includes taxes & fees
Sep 13 - Sep 14
Baymont by Wyndham Front Royal Near Shenandoah National Park
A covered outdoor area with a table and chairs, a brick wall, and a metal railing.
A sign for a 'Relax Inn' with a clear view of the building in the background.
A hotel room with two beds, a desk, and a chair.
A brick building with a sign reading "Motel" and a neon sign for "Relax Inn" on the right.

Relax Inn Motel

Relax Inn Motel
Front Royal
$64
$71 total
includes taxes & fees
Sep 6 - Sep 7
Relax Inn Motel
An outdoor patio with a grill, seating, and string lights.
A snack kiosk with refrigerated drink dispensers and shelves stocked with snacks.

Home2 Suites By Hilton Winchester

Home2 Suites By Hilton Winchester
Winchester
$98
$111 total
includes taxes & fees
Sep 28 - Sep 29
Home2 Suites By Hilton Winchester
A building with a sign reading "OFFICE" above the entrance.
A small, compact room with a kitchenette, a single bed, a television mounted on the wall, and a mirror above the bed.
A hotel room with two beds, a nightstand, a lamp, a heater, and two framed pictures on the wall.
A small bathroom with a white sink, a toilet, and a wooden shelf above the toilet holding towels.

Blue Ridge Motel

Blue Ridge Motel
Front Royal
$70
$78 total
includes taxes & fees
Sep 6 - Sep 7
Blue Ridge Motel
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Our prices for hotels in Middletown are cheapest in January
Price trends for hotels in Middletown
Pricing is based on two traveler single night rates
View properties in September
Typical weather for Middletown
September
High 26°C / low 14°C. Sunny most days.
View properties in September
26°
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7°
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-4°
7°
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12°
1°
18°
6°
23°
11°
28°
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Monthly weather averages (˚C)

Top landmarks in Middletown

Belle Grove Plantation

8.4/10 (8 reviews)
If you're planning a bit of sightseeing during your trip, head to Belle Grove Plantation— just one of the landmarks located 1.4 mi (2.2 km) from central Middletown.
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Cedar Creek Battlefield Foundation

8.6/10 (7 reviews)
Cedar Creek Battlefield Foundation is 1.2 mi (1.9 km) from central Middletown, why not stop by during your stay.
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Cedar Creek and Belle Grove National Historical Park

9.0/10 (6 reviews)
Cedar Creek and Belle Grove National Historical Park is 1.1 mi (1.7 km) from central Middletown, why not stop by during your stay. Want to stretch your legs some more? Head to Hupp's Hill Civil War Park, located nearby.
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Jackson's Chase Golf Course

6.0/10 (1 review)
You might want to play some rounds at Jackson's Chase Golf Course, located 4.6 mi (7.4 km) from central Middletown. If Jackson's Chase Golf Course doesn't quite scratch your golfing itch, Blue Ridge Shadows Golf Club is also nearby.
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Learn more about Middletown

Middletown is well-known for its attractions such as Belle Grove Plantation and Shenandoah River. Visitors to this historical city speak highly of the bars whereas sights include Cedar Creek and Belle Grove National Historical Park and Jackson's Chase Golf Course.

See all hotels in Middletown
A large house in a field with a cloudy sky.
Photo by Stephanie Sutton

Check out reviews of Middletown hotels guests love

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

10/10 Excellent
"Friendly greeting, excellent, spacious room, clean, comfortable beds. Breakfast was nice and plenty of parking."
Kathie 1-night trip
Posted 1 hour ago
Comfort Inn & Suites Winchester
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

10/10 Excellent
"Great find! It’s new, it’s clean, great staff! Going again soon a stop on a longer trip into Virginia. It’s right off the highway!"
Lisa 1-night trip
Posted 14 hours ago
Holiday Inn Winchester Se-Historic Gateway by IHG
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

10/10 Excellent
"Very clean and comfortable room."
Dave 1-night trip
Posted 15 hours ago
Ramada by Wyndham Strasburg/Shenandoah Valley
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

10/10 Excellent
"Room fully met my needs and was competitively priced. Great overnight stop for my road trip."
Vic 1-night trip
Posted 19 hours ago
Travelodge by Wyndham Winchester
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"We chose Old Town Winchester and stayed at The George Washington Hotel as our gathering spot for High school girl friends The Hotel was beautiful ,our rooms big enough plus having a sm scale table with 2 chairs ,the bathroom very roomy,beds were very comfortable and the staff very accommodating and welcoming The amenities at the hotel met our needs perfectly ! It was really nice to be in a walkable area with many shops and restaurants ,pubs .No complaints from 5 women in our group 😁"
violet 2-night trip
Posted 21 hours ago
The George Washington Hotel, A Wyndham Grand Hotel
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Clean room quiet front desk employees are always awesome !!"
Renee 1-night trip
Posted 21 hours ago
La Quinta Inn & Suites by Wyndham Winchester
Quality Inn Winchester

Quality Inn Winchester

10/10 Excellent
"Convenient and surprisingly nice for the price"
Amelia 1-night trip
Posted 2 days ago
Quality Inn Winchester
Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

10/10 Excellent
"Excellent"
Marvin 1-night trip
Posted 3 days ago
Courtyard by Marriott Winchester
Days Inn by Wyndham Winchester

Days Inn by Wyndham Winchester

8/10 Good
"Not too shabby. I would stay again"
Jeannie 1-night trip
Posted 5 days ago
Days Inn by Wyndham Winchester

Frequently asked questions

What accommodations do travelers recommend in Middletown?
Guests like Wayside Inn, Ramada by Wyndham Strasburg/Shenandoah Valley and Comfort Inn & Suites Winchester.
Can I book refundable accommodations in Middletown?
If you need the flexibility to change your plans to Middletown, most hotels provide refundable* bookable rates. You can see these properties by searching our site and using the "fully refundable" filter to narrow down the results.
What will the weather in Middletown be like during my visit?
July and August are typically the warmest months in Middletown when the average temp is 72°F. January and February are the coldest months when the average temperature is 36°F. September and May are the months with the most rain.
Why should I book my Middletown hotel with Hotels.com?
There are lots of reasons to book your Middletown trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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