A mountainous landscape with autumn foliage, rocky outcrops, and a valley below.

Middletown hotels from RM146

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Check prices for these dates

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24 Oct - 25 Oct
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25 Oct - 26 Oct
Next weekend
30 Oct - 1 Nov
In two weeks
6 Nov - 8 Nov

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Our top choices for Middletown hotels

A cozy living room with a fireplace, patterned chairs, and a dining area with wooden furniture.
A rustic interior with wooden tables and chairs, a brick floor, and a wooden ceiling.
Bar (on property)
A large brick building with a central entrance, multiple windows, and a covered walkway.

1. Wayside Inn

Wayside Inn
Middletown
United States
David
RM441
RM527 total
includes taxes & fees
8 Nov - 9 Nov
Wayside Inn
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 reception area with a wooden counter, a clock, framed pictures, and a glass door leading outside.
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.

2. Econo Lodge Inn & Suites Middletown - Winchester South

Econo Lodge Inn & Suites Middletown - Winchester South
Middletown
United States
Craig
RM264
RM291 total
includes taxes & fees
15 Nov - 16 Nov
Econo Lodge Inn & Suites Middletown - Winchester South
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 multi-story hotel with a prominent sign for Marriott.
A swimming pool with a tiled deck, chairs, and a sign indicating no lifeguard on duty.

3. Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley
Strasburg
United States
Patrick
RM413
RM460 total
includes taxes & fees
8 Nov - 9 Nov
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 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.
A modern hotel lobby with a clear exit sign, a reception desk, and a seating area with red chairs.

4. Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley
Strasburg
United States
Glenn
RM309
RM344 total
includes taxes & fees
1 Nov - 2 Nov
Ramada by Wyndham Strasburg/Shenandoah Valley
A modern hotel lobby with a green sofa, blue chairs, a dining table, and large windows offering a view of the outdoors.
A workspace with two desks, chairs, a computer, a printer, and a window with a view of a green landscape and buildings.
A modern breakfast area with seating, a counter for hot food, and a view of the outdoors.
A hotel room with two beds, a wooden headboard, a nightstand, a lamp, and a framed picture on the wall.

5. Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG
Stephens City
United States
Michael
RM131
RM146 total
includes taxes & fees
21 Nov - 22 Nov
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 reception area with a marble counter, a desk, and a framed picture on the wall.
A gym with an elliptical, dumbbells, a treadmill, and a wall-mounted phone.
A hotel room with two beds, a desk, a television, and a window with curtains.

6. Quality Inn Stephens City - Winchester South

Quality Inn Stephens City - Winchester South
Stephens City
United States
Jeanne
RM335
RM373 total
includes taxes & fees
22 Nov - 23 Nov
Quality Inn Stephens City - Winchester South
An outdoor seating area with a fire feature, wicker furniture, and a building with multiple windows.
A conference room with a large table and chairs, a TV mounted on the wall, and a vending machine labeled "Towneplace Suites".
A multi-story hotel with a swimming pool, parking lot, and a landscaped area.
A modern hotel lobby with seating areas, a reception desk, and large windows offering a view of the outdoors.

7. TownePlace Suites by Marriott Front Royal

TownePlace Suites by Marriott Front Royal
Front Royal
United States
JoEllen
RM568
RM634 total
includes taxes & fees
9 Nov - 10 Nov
TownePlace Suites by Marriott Front Royal
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 two beds, a desk with a TV, a lamp, and a view of the outdoors.
A hotel dining area with multiple tables and chairs, large windows, and a television screen.
A hotel room with a television, desk, chair, sofa, and kitchenette.

8. Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
Winchester
United States
Kenneth
RM409
RM455 total
includes taxes & fees
15 Nov - 16 Nov
Comfort Inn & Suites Winchester
A spacious lobby with a stone fireplace, blue upholstered sofas, and a chandelier.
A restaurant interior with a bar area, seating, and artwork on the walls.
A hotel lobby with a reception desk, a minibar, a seating area, and a clothing rack.
An indoor swimming pool with a hot tub, lounge chairs, and a view of the outdoors.

9. DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows
Front Royal
United States
Jeffrey
RM520
RM573 total
includes taxes & fees
11 Nov - 12 Nov
DoubleTree by Hilton Front Royal Blue Ridge Shadows
A modern indoor space with a dining area, a clock, and a view into a gym area.
A gym with a rack of dumbbells, kettlebells, and exercise balls.
A reception desk with a 'Welcome to the Mother of States' sign, a wooden panel design, and a digital kiosk.
A hotel room with a gray sofa, a bed with a blue headboard, a painting of a landscape, and a lamp on the nightstand.

10. Hampton Inn Front Royal

Hampton Inn Front Royal
Front Royal
United States
Grace
RM483
RM537 total
includes taxes & fees
18 Nov - 19 Nov
Hampton Inn Front Royal
A modern dining area with a high ceiling, recessed lighting, and a large window providing natural light.
An indoor swimming pool with clear water, blue lounge chairs, and a wooden ceiling.
A modern lounge area with a sofa, chairs, and tables, featuring a patterned carpet and a decorative ceiling light.
A gym with treadmills, elliptical machines, and dumbbells.

11. La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
Winchester
United States
lucy
RM419
RM467 total
includes taxes & fees
25 Oct - 26 Oct
La Quinta Inn & Suites by Wyndham Winchester
A spacious living room with a fireplace, wooden staircase, and a bookshelf.
A woman using a stationary bike in a gym with red walls and multiple exercise machines.
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.

12. Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
Winchester
United States
Zohair
RM357
RM398 total
includes taxes & fees
22 Nov - 23 Nov
Country Inn & Suites by Radisson, Winchester, VA
A modern hotel lobby with a sofa set, two armchairs, a coffee table, and a reception desk.
A hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.
A modern restaurant interior with wooden tables and chairs, a green booth area, and artwork on the walls.
A coffee station with multiple coffee dispensers and a sign above.

13. Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
Winchester
United States
Thomas
RM379
RM421 total
includes taxes & fees
1 Nov - 2 Nov
Fairfield Inn & Suites by Marriott Winchester
A spacious lobby with a checkered floor, yellow chairs, a green carpet, and a wall with the text "It only takes a spark".
A hotel with a modern design, featuring a prominent 'spark by Hilton' sign, a well-lit entrance, and a landscaped front yard.
A modern indoor space with a long wooden table and benches, surrounded by chairs and a green carpet.
An indoor swimming pool with clear glass walls, a tiled floor, and a few lounge chairs.

14. Spark by Hilton Winchester

Spark by Hilton Winchester
Winchester
United States
carrie
RM265
RM301 total
includes taxes & fees
15 Nov - 16 Nov
Spark by Hilton Winchester
A Holiday Inn hotel with a modern design, featuring a covered entrance and multiple floors.
A swimming pool with lounge chairs and a changing room.
A bar area with a counter, multiple bar stools, and a television screen.
A spacious lobby with a checkered floor, a reception desk, and a seating area with a sofa and chairs.

15. Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
Winchester
United States
Jeffrey
RM388
RM444 total
includes taxes & fees
22 Nov - 23 Nov
Holiday Inn Winchester Se-Historic Gateway by IHG
Pool
A snack kiosk with refrigerated drink dispensers and shelves stocked with snacks.
A modern restaurant with seating arrangements, a counter, and a snack display.
A compact kitchen with a refrigerator, microwave, coffee maker, and dishwasher.

16. Home2 Suites By Hilton Winchester

Home2 Suites By Hilton Winchester
Winchester
United States
Jean
RM361
RM409 total
includes taxes & fees
8 Nov - 9 Nov
Home2 Suites By Hilton Winchester
A spacious restaurant with a central island, seating areas, and a mural on the back wall.
An indoor swimming pool with clear lane markings, a lifeguard chair, and a safety ring on the wall.
A modern lounge area with seating arrangements, including sofas and chairs, and a large window providing a view outside.
A fitness center with a water dispenser, seating area, and exercise machines.

17. TRU By Hilton Winchester

TRU By Hilton Winchester
Winchester
United States
Kailyn
RM348
RM388 total
includes taxes & fees
1 Nov - 2 Nov
TRU By Hilton Winchester
A modern lobby with a seating area, a flat-screen TV, and a large window offering a view of the outdoors.
A modern lounge area with seating, a TV, and a children's play area.
A hotel reception area with a wooden reception desk, two computers, a map of the USA on the wall, and a small plant on the desk.
A modern Microtel hotel by Wyndham with a blue and gray exterior, multiple windows, and a parking lot.

18. Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
Winchester
United States
Christopher
RM340
RM378 total
includes taxes & fees
22 Nov - 23 Nov
Microtel Inn & Suites by Wyndham Winchester
A hotel lobby with a reception desk, seating area, and a fireplace.
A hotel room with a red carpet, two white armchairs, a black sofa, a flat-screen TV, and two windows 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.
A Super 8 hotel with a brick facade, multiple windows, and a central entrance.

19. Super 8 by Wyndham Front Royal Near Shenandoah National Park

Super 8 by Wyndham Front Royal Near Shenandoah National Park
Front Royal
United States
Amelia
RM261
RM291 total
includes taxes & fees
4 Nov - 5 Nov
Super 8 by Wyndham Front Royal Near Shenandoah National Park
A modern hotel lobby with a central dining area, a reception desk, and a large window providing natural light.
A reception desk with a 'WELCOME TO THE MOTHER OF STATES' sign, a 'Hilton Honors' badge, and a 'STAFF ONLY' door.
A hotel lobby with a snack bar, refrigerated display cases, and a trash bin.
A modern kitchen with a wooden cabinet, a stainless steel range, and a window providing natural light.

20. Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
Winchester
United States
Elizabeth
RM392
RM444 total
includes taxes & fees
9 Nov - 10 Nov
Hampton Inn Winchester N/Conference Center, VA
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Stay near popular Middletown attractions

Belle Grove Plantation

8.4/10 (8 reviews)
This Jeffersonian-inspired Manor House showcases antebellum plantation life and Civil War history. Explore the heritage apple orchard and original outbuildings while enjoying panoramic mountain views.
See properties

Cedar Creek Battlefield Foundation

8.6/10 (7 reviews)
The Cedar Creek Battlefield Foundation preserves this pivotal 1864 Civil War site through exhibits and trails. Experience history during October's annual reenactment featuring authentic battle scenarios.
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Cedar Creek and Belle Grove National Historical Park

9.0/10 (6 reviews)
Explore the pivotal Civil War battlefield where Union forces secured the Shenandoah Valley in 1864. Tour the elegant Belle Grove Manor House and follow interpretive trails detailing strategic troop movements.
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Jackson's Chase Golf Course

6.0/10 (1 review)
This scenic 18-hole course weaves through the rolling Shenandoah Valley, challenging golfers of all abilities. Enjoy the serene natural setting while navigating its strategically designed par-72 layout.
See properties

Learn more about Middletown

History buffs can explore the Cedar Creek Battlefield and Belle Grove Plantation, where costumed interpreters bring Civil War stories to life. Visit the Wayside Inn, Virginia's oldest continuously operating inn, and ask locals about hidden hiking trails in nearby Shenandoah Valley.

See all hotels in Middletown
A mountainous landscape with autumn foliage, rocky outcrops, and a valley below.

Top Middletown Hotel Reviews

Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

8/10 Good
"Ok stay, free breakfast was good ( just there for a transit)."
Maria 1-night trip
Posted 1 hour ago
Ramada by Wyndham Strasburg/Shenandoah Valley
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

8/10 Good
"Hot showers. Good breakfast."
Danette 1-night trip
Posted 1 hour ago
La Quinta Inn & Suites by Wyndham Winchester
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

8/10 Good
"Always great place and the old nostalgic look is the best"
Christophe 1-night trip
Posted 1 hour ago
The George Washington Hotel, A Wyndham Grand Hotel
Holiday Inn Express Woodstock-Shenandoah Valley by IHG

Holiday Inn Express Woodstock-Shenandoah Valley by IHG

10/10 Excellent
"Very good would. Stat there again"
Richard 1-night trip
Posted 2 hours ago
Holiday Inn Express Woodstock-Shenandoah Valley by IHG
Spark by Hilton Winchester

Spark by Hilton Winchester

10/10 Excellent
"Clean room, great staff, good parking and free breakfast"
Albert 1-night trip
Posted 11 hours ago
Spark by Hilton Winchester
Hampton Inn Front Royal

Hampton Inn Front Royal

10/10 Excellent
"The hotel was really well maintained inside and out! Room was super-clean."
Tammy 1-night trip
Posted 13 hours ago
Hampton Inn Front Royal
Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent
"It was close to everything."
Frederick 1-night trip
Posted 20 hours ago
Country Inn & Suites by Radisson, Winchester, VA
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

10/10 Excellent
"Very helpful staff"
David 2-night trip
Posted 1 day ago
Microtel Inn & Suites by Wyndham Winchester
DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows

10/10 Excellent
"Very convenient at the start of skyline drive"
Ann 1-night trip
Posted 1 day ago
DoubleTree by Hilton Front Royal Blue Ridge Shadows

More cheap stays in Middletown

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

160 Front Royal Pike Winchester VA
RM290
RM320 total
26 Oct - 27 Oct
includes taxes & fees
Travelodge by Wyndham Winchester
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

21 Signal Knob Dr Strasburg VA
RM309
RM344 total
1 Nov - 2 Nov
includes taxes & fees
8.2/10 Very good! (1,018 reviews)
Ramada by Wyndham Strasburg/Shenandoah Valley
Quality Inn Winchester

Quality Inn Winchester

1601 Martinsburg Pike Winchester VA
RM319
RM355 total
22 Nov - 23 Nov
includes taxes & fees
Quality Inn Winchester
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

150 Faraday Plaza Winchester VA
RM340
RM378 total
22 Nov - 23 Nov
includes taxes & fees
9.2/10 Wonderful! (1,435 reviews)
Microtel Inn & Suites by Wyndham Winchester
TRU By Hilton Winchester

TRU By Hilton Winchester

118 Mercedes Court Winchester VA
RM348
RM388 total
1 Nov - 2 Nov
includes taxes & fees
TRU By Hilton Winchester
Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

195 Kernstown Commons Blvd Winchester VA
RM409
RM455 total
15 Nov - 16 Nov
includes taxes & fees
Comfort Inn & Suites Winchester

Frequently asked questions

Where is the best place for a stay in Middletown?
Based on our traveller data, Wayside Inn is one of the top choices for your stay. This hotel offers a restaurant and free parking. Two other options for your visit to the area are The George Washington Hotel, A Wyndham Grand Hotel and Travelodge by Wyndham Winchester. See all available top hotels, or vacation rentals in Middletown.
If I need to cancel my hotel reservation in Middletown, will I receive a refund?
Yes, most hotel room reservations are fully refundable if cancelled prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of the scheduled arrival. If you booked a non-refundable reservation, you might be able to cancel it and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Middletown.
What's it like staying in Middletown?
Visitors to Middletown will definitely enjoy the bars and restaurants. Tourists can also enjoy the city's entertainment choices, churches and theatres. In Middletown, there are 3 hotels and other accommodation options to choose from. Find out more about Middletown.
What is there to see in Middletown?
The picturesque setting of Shenandoah River and Cedar Creek and Belle Grove National Historical Park exemplify the area's natural beauty. A couple of additional sights to add to your itinerary are Belle Grove Plantation and Jackson's Chase Golf Course. Take a look at what more there is to see and do in Expedia's Middletown guide.
What's the seasonal weather like in Middletown?
The hottest months are usually July and August, with an average temperature of 22ยฐC, while the coldest months are January and February, with an average of 2ยฐC. Average annual precipitation for Middletown is 1088 mm.

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