𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Middletown (2026)

A large house in a field with a cloudy sky.

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Our top choices for Middletown hotels

A rustic interior with wooden tables and chairs, a brick floor, and a wooden ceiling.

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.

A cozy living room with a fireplace, patterned chairs, and a dining area with wooden furniture.

A large brick building with a central entrance, multiple windows, and a covered walkway.

1. Wayside Inn

Middletown

Luanne

S$109

includes taxes & fees

19 Oct - 20 Oct

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 reception area with a wooden counter, a clock, framed pictures, and a glass door leading outside.

2. Econo Lodge Inn & Suites Middletown - Winchester South

Middletown

Nathan

S$95

includes taxes & fees

26 Oct - 27 Oct

A hotel lobby with a reception desk, a check-in counter, a seating area with chairs, and a dining area in the background.

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.

A hotel lobby with a polished tile floor, a reception desk, and seating area with white chairs.

3. Ramada by Wyndham Strasburg/Shenandoah Valley

Strasburg

CHRISTI

S$108

includes taxes & fees

1 Nov - 2 Nov

A hotel lobby with a reception desk, seating area with a round table, and a bar.

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.

A hotel reception desk with a computer, two chairs, and a large mirror.

4. Fairfield Inn & Suites Strasburg Shenandoah Valley

Strasburg

Patrick

S$161

includes taxes & fees

1 Nov - 2 Nov

A modern hotel lobby with a green sofa, blue chairs, a dining table, and large windows offering 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.

A rectangular swimming pool with a brick wall and trees in the background.

A modern breakfast area with seating, a counter for hot food, and a view of the outdoors.

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

Stephens City

Michael

S$118

includes taxes & fees

2 Nov - 3 Nov

A restaurant with wooden tables and red cushioned chairs, a kitchen area with a coffee machine, and a large window.

A two-story building with a brick facade and a beige exterior.

A reception area with a marble counter, a desk, and a framed picture on the wall.

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

6. Quality Inn Stephens City - Winchester South

Stephens City

Nancy

S$120

includes taxes & fees

2 Nov - 3 Nov

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.

7. Comfort Inn & Suites Winchester

Winchester

John

S$140

includes taxes & fees

11 Oct - 12 Oct

A restaurant interior with a bar area, seating, and artwork on the walls.

A spacious lobby with a reception desk, seating area with sofas, and a chandelier.

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.

8. DoubleTree by Hilton Front Royal Blue Ridge Shadows

Front Royal

Brian

S$165

includes taxes & fees

1 Nov - 2 Nov

A swimming pool with clear water, surrounded by large windows offering views of greenery.

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.

9. Hampton Inn Front Royal

Front Royal

Grace

S$168

includes taxes & fees

1 Nov - 2 Nov

A spacious living room with a fireplace, wooden staircase, and a bookshelf.

A poolside area with lounge chairs and a stack of towels on a table.

A woman using a stationary bike in a gym with red walls and multiple exercise machines.

A hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.

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

Winchester

Allen

S$128

includes taxes & fees

25 Oct - 26 Oct

An outdoor seating area with a fire feature, wicker furniture, and a building with multiple windows.

A multi-story hotel with a swimming pool, parking lot, and a landscaped area.

A hotel reception area with a counter, a vending machine, and a sign indicating a minibar.

A modern hotel lobby with seating areas, a reception desk, and large windows offering a view of the outdoors.

11. TownePlace Suites by Marriott Front Royal

Front Royal

Justin

S$199

includes taxes & fees

21 Oct - 22 Oct

An outdoor patio with a grill, seating, and string lights.

A modern breakfast bar with a variety of food items, a coffee machine, and a fruit display.

12. Home2 Suites By Hilton Winchester

Winchester

Mandy

S$133

includes taxes & fees

1 Nov - 2 Nov

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.

13. Spark by Hilton Winchester

Winchester

carrie

S$112

includes taxes & fees

2 Nov - 3 Nov

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 coffee station with multiple coffee dispensers and a sign above.

14. Fairfield Inn & Suites by Marriott Winchester

Winchester

Dawn

S$132

includes taxes & fees

1 Nov - 2 Nov

A modern dining area with a high ceiling, recessed lighting, and a large window providing natural light.

A modern hotel with a flat facade, multiple windows, and a well-lit entrance.

A gym with treadmills, elliptical machines, and dumbbells.

A modern lounge area with a sofa, chairs, and tables, featuring a patterned carpet and a decorative ceiling light.

15. La Quinta Inn & Suites by Wyndham Winchester

Winchester

Earl

S$154

includes taxes & fees

25 Oct - 26 Oct

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 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 hotel room with a red carpet, white sofas, a reception desk, and a large window with blinds.

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

Front Royal

Rosilene

S$91

includes taxes & fees

1 Nov - 2 Nov

A covered outdoor area with a table and chairs, a brick wall, and a metal railing.

A bathroom with a shower, toilet, and a bathtub.

A sign for a 'Relax Inn' with a clear view of the building in the background.

A brick building with a sign reading "Motel" and a neon sign for "Relax Inn" on the right.

17. Relax Inn Motel

Front Royal

Sarah

S$92

includes taxes & fees

6 Oct - 7 Oct

A modern living room with a sofa, armchair, dining table, and chairs. There is a TV mounted on the wall and a small table with a lamp.

A spacious indoor area with a long table and chairs, a statue, and a large window.

A hotel room with a sofa, a desk, a TV, a dresser, and a bed.

A hotel room with two beds, a wooden headboard, a nightstand with lamps, and a view of the outdoors through the window.

18. Travelodge by Wyndham Winchester

Winchester

john

S$100

includes taxes & fees

11 Oct - 12 Oct

A spacious lobby with a stone fireplace, red chairs, a wooden staircase, and a flat-screen TV mounted on the wall.

A hotel room with a large bed, a ceiling fan, a nightstand, a window with curtains, and a view of the ocean.

A stainless steel kitchen with a built-in water dispenser and a window with blinds.

A hotel lobby with a wooden railing, a reception desk, a flower vase, and an exit sign.

19. Motel 6 Front Royal, VA

Front Royal

James

S$83

includes taxes & fees

4 Nov - 5 Nov

A modern hotel with a covered outdoor area, landscaped gardens, and a parking lot.

A hotel lobby with a blue sofa, red chairs, a patterned rug, and artwork on the walls.

A swimming pool with a metal railing, surrounded by lounge chairs and an umbrella.

A hotel reception area with a black counter, coffee dispensers, a juice dispenser, and a small refrigerator.

20. Quality Inn Winchester

Winchester

Joseph

S$120

includes taxes & fees

25 Oct - 26 Oct

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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.

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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.

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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

Top Middletown Hotel Reviews

Fairfield Inn & Suites by Marriott Winchester

10/10 Excellent

"Great place to stay in Winchester."

Super 8 by Wyndham Front Royal Near Shenandoah National Park

8/10 Good

"Staff were attentive and responsive when my expensive watch was left behind"

Holiday Inn Express Woodstock-Shenandoah Valley by IHG

10/10 Excellent

"My experience was very good"

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent

"Very friendly staff, clean facilities, good breakfast."

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent

"The bed was amazingly comfortable and the room was very clean."

Quality Inn Winchester

8/10 Good

"Great staff Very helpful,friendly Place is quite spartan but well kept Close to highway Great bargain"

Days Inn by Wyndham Winchester

10/10 Excellent

"Staff are friendly and helpful, price is best in the area, the area behind the Dennys has a large number of friendly Groundhogs that the dog really appreciated. Easy access to the north-South skirmish Association's Ft. Shenandoah."

Comfort Inn & Suites Winchester

10/10 Excellent

"One of the nicest hotels I’ve ever stayed at. Seems way nicer than you’d expect at of a comfort inn."

Travelodge by Wyndham Winchester

8/10 Good

"Room was clean and efficient. Good for a bed and shower but the breakfast was toast, dry cereal or a waffle. We went to Cracker Barrel."

More cheap stays in Middletown

Travelodge by Wyndham Winchester

160 Front Royal Pike Winchester VA

S$100

11 Oct - 12 Oct

includes taxes & fees

8.6/10 Excellent! (1,074 reviews)

Ramada by Wyndham Strasburg/Shenandoah Valley

21 Signal Knob Dr Strasburg VA

S$108

1 Nov - 2 Nov

includes taxes & fees

Quality Inn Winchester

1601 Martinsburg Pike Winchester VA

S$120

25 Oct - 26 Oct

includes taxes & fees

9.4/10 Exceptional! (1,005 reviews)

TRU By Hilton Winchester

118 Mercedes Court Winchester VA

S$127

1 Nov - 2 Nov

includes taxes & fees

Microtel Inn & Suites by Wyndham Winchester

150 Faraday Plaza Winchester VA

S$131

1 Nov - 2 Nov

includes taxes & fees

Comfort Inn & Suites Winchester

195 Kernstown Commons Blvd Winchester VA

S$140

11 Oct - 12 Oct

includes taxes & fees

9.4/10 Exceptional! (1,134 reviews)

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 22°C, while the coldest months are January and February, with an average of 2°C. Average annual precipitation for Middletown is 1088 mm.

Middletown Hotels from S$73

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Middletown

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Middletown hotels

1. Wayside Inn

2. Econo Lodge Inn & Suites Middletown - Winchester South

3. Ramada by Wyndham Strasburg/Shenandoah Valley

4. Fairfield Inn & Suites Strasburg Shenandoah Valley

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

6. Quality Inn Stephens City - Winchester South

7. Comfort Inn & Suites Winchester

8. DoubleTree by Hilton Front Royal Blue Ridge Shadows

9. Hampton Inn Front Royal

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

11. TownePlace Suites by Marriott Front Royal

12. Home2 Suites By Hilton Winchester

13. Spark by Hilton Winchester

14. Fairfield Inn & Suites by Marriott Winchester

15. La Quinta Inn & Suites by Wyndham Winchester

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

17. Relax Inn Motel

18. Travelodge by Wyndham Winchester

19. Motel 6 Front Royal, VA

20. Quality Inn Winchester

Stay near popular Middletown attractions

Belle Grove Plantation

Cedar Creek Battlefield Foundation

Cedar Creek and Belle Grove National Historical Park

Jackson's Chase Golf Course

Learn more about Middletown

Top Middletown Hotel Reviews

Fairfield Inn & Suites by Marriott Winchester

Super 8 by Wyndham Front Royal Near Shenandoah National Park

Holiday Inn Express Woodstock-Shenandoah Valley by IHG

Country Inn & Suites by Radisson, Winchester, VA

La Quinta Inn & Suites by Wyndham Winchester

Quality Inn Winchester

Days Inn by Wyndham Winchester

Comfort Inn & Suites Winchester

Travelodge by Wyndham Winchester

More cheap stays in Middletown

Travelodge by Wyndham Winchester

Ramada by Wyndham Strasburg/Shenandoah Valley

Quality Inn Winchester

TRU By Hilton Winchester

Microtel Inn & Suites by Wyndham Winchester

Comfort Inn & Suites Winchester

Frequently asked questions

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