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

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

1. Wayside Inn

Middletown

Luanne

₹6,578

₹8,222 total

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

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

A Pepsi vending machine in a hallway with tiled flooring and a door in the background.

2. Econo Lodge Inn & Suites Middletown - Winchester South

Middletown

Nathan

₹6,249

₹6,893 total

includes taxes & fees

8 Nov - 9 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 modern hotel dining area with a long table, multiple chairs, and a large window providing natural light.

A multi-story hotel with a prominent sign for Marriott.

3. Fairfield Inn & Suites Strasburg Shenandoah Valley

Strasburg

Patrick

₹9,785

₹10,890 total

includes taxes & fees

1 Nov - 2 Nov

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 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.

A hotel with a green roof, a covered entrance, and a sign that reads "RAMADA".

4. Ramada by Wyndham Strasburg/Shenandoah Valley

Strasburg

CHRISTI

₹7,072

₹7,871 total

includes taxes & fees

25 Oct - 26 Oct

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 room with two beds, a wooden headboard, a nightstand, a lamp, and a framed picture on the wall.

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

₹8,513

₹9,475 total

includes taxes & fees

1 Nov - 2 Nov

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.

An indoor swimming pool with a hot tub, lounge chairs, and a view of the outdoors.

A hotel lobby with a reception desk, a minibar, a seating area, and a clothing rack.

6. DoubleTree by Hilton Front Royal Blue Ridge Shadows

Front Royal

Brian

₹11,026

₹12,162 total

includes taxes & fees

1 Nov - 2 Nov

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 modern kitchen with a flat-screen TV, a microwave, and a refrigerator.

A gym with exercise equipment, a mirror, and a window with a view of a snowy landscape.

7. Hampton Inn Front Royal

Front Royal

Grace

₹11,429

₹12,721 total

includes taxes & fees

1 Nov - 2 Nov

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.

8. Comfort Inn & Suites Winchester

Winchester

John

₹9,620

₹10,707 total

includes taxes & fees

18 Oct - 19 Oct

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

9. Quality Inn Stephens City - Winchester South

Stephens City

Jeanne

₹8,140

₹9,060 total

includes taxes & fees

2 Nov - 3 Nov

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 conference room with a large table and chairs, a TV mounted on the wall, and a vending machine labeled "Towneplace Suites".

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

10. TownePlace Suites by Marriott Front Royal

Front Royal

Justin

₹13,446

₹15,025 total

includes taxes & fees

25 Oct - 26 Oct

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

A gym with treadmills, elliptical machines, and dumbbells.

An indoor swimming pool with clear water, blue lounge chairs, and a wooden ceiling.

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

11. La Quinta Inn & Suites by Wyndham Winchester

Winchester

lucy

₹10,447

₹11,628 total

includes taxes & fees

11 Oct - 12 Oct

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 Country Inn & Suites by Radisson building with a covered entrance and multiple windows.

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

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

Winchester

Allen

₹8,873

₹9,875 total

includes taxes & fees

8 Nov - 9 Nov

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 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 modern indoor space with a long wooden table and benches, surrounded by chairs and a green carpet.

13. Spark by Hilton Winchester

Winchester

carrie

₹7,403

₹8,388 total

includes taxes & fees

18 Oct - 19 Oct

A courtyard with a fountain, tables with white tablecloths, and brick buildings.

A bar area with a piano, seating, and a bar counter with bottles.

A spacious lobby with a round table, chairs, a chandelier, and an American flag.

A large brick building with a classic facade, a central entrance with a decorative arch, and a sign reading "The George Washington Hotel."

14. The George Washington Hotel, A Wyndham Grand Hotel

Old Town Winchester

Carol

₹12,612

₹14,290 total

includes taxes & fees

28 Oct - 29 Oct

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.

A Fairfield by Marriott hotel with a modern entrance, stone pillars, and a well-lit facade.

15. Fairfield Inn & Suites by Marriott Winchester

Winchester

Thomas

₹8,963

₹9,975 total

includes taxes & fees

1 Nov - 2 Nov

A modern lobby with a seating area, a flat-screen TV, and a large window offering a view of the outdoors.

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 lounge area with seating, a TV, and a children's play area.

A modern Microtel hotel by Wyndham with a blue and gray exterior, multiple windows, and a parking lot.

16. Microtel Inn & Suites by Wyndham Winchester

Winchester

Marcia

₹8,358

₹9,302 total

includes taxes & fees

8 Nov - 9 Nov

A Holiday Inn hotel with a modern design, featuring a covered entrance and multiple floors.

A bar area with a counter, multiple bar stools, and a television screen.

A hotel room with a bed, a desk with a computer, a chair, and a TV.

A swimming pool with lounge chairs and a changing room.

17. Holiday Inn Winchester Se-Historic Gateway by IHG

Winchester

Jeffrey

₹9,190

₹10,518 total

includes taxes & fees

8 Nov - 9 Nov

A self-service beverage station with a refrigerated drink dispenser, a coffee machine, and a variety of snacks.

A spacious restaurant with a central island, seating areas, and a mural on the back wall.

A fitness center with a water dispenser, seating area, and exercise machines.

An indoor swimming pool with clear lane markings, a lifeguard chair, and a safety ring on the wall.

18. TRU By Hilton Winchester

Winchester

Kailyn

₹8,250

₹9,182 total

includes taxes & fees

1 Nov - 2 Nov

A Courtyard by Marriott hotel with a covered entrance, multiple floors, and a brick facade.

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

An outdoor seating area with wicker furniture and a small table, surrounded by greenery and a building in the background.

A modern hotel lobby with a curved sofa, a glass coffee table, and a flat-screen TV mounted on the wall.

19. Courtyard by Marriott Winchester

Winchester

John

₹9,785

₹10,890 total

includes taxes & fees

18 Oct - 19 Oct

A gym with treadmills, exercise balls, and a mirrored wall.

A Hampton Inn hotel with a modern facade, a covered entrance, and a landscaped front yard.

A kitchenette with a coffee machine, toaster, and a display case with pastries.

A modern living room with a sofa, chairs, a coffee table, and a TV mounted on the wall.

20. Hampton Inn Winchester-University/Mall Area

Winchester

Henedina

₹9,374

₹10,620 total

includes taxes & fees

1 Nov - 2 Nov

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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

TRU By Hilton Winchester

10/10 Excellent

"Rim was clean, staff was professional and courteous"

Fairfield Inn & Suites by Marriott Winchester

10/10 Excellent

"Everything was fantastic"

Travelodge by Wyndham Winchester

10/10 Excellent

"Staff is always very pleasant to work with."

Ramada by Wyndham Strasburg/Shenandoah Valley

10/10 Excellent

"Helpful, friendly, clean, and a restaurant that is attached but not affiliated with but fabulous!"

Comfort Inn & Suites Winchester

10/10 Excellent

"Only thing was a negative the breakfast was only open til 9 am. 9:30 or 10 am would have been better"

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent

"This facility is excellent. The breakfast was excellent with many extras including honey packets. It has a very good selection 8 plus to add to yogurt, etc. I had a very nice cream cheese bagel with honey drizzled. They also had eggs and sausage. It also has a coffee/herbal tea station in the lobby. The pool was spotless. Perfectly clean. Perfect. The room was spacious. There were plenty of spaces to congregate both inside and outside. The seasonal fall decor was a very nice touch. It was very full and impressive. I very highly reccomend this facility. Superb."

Days Inn by Wyndham Winchester

8/10 Good

"Location is excellent. Lot of places to eat and gas stations nearby. Easy check in and staff was very friendly. Beds were comfortable. Breakfast was disappointing. Not.much to pick from, and coffee pots were both empty."

DoubleTree by Hilton Front Royal Blue Ridge Shadows

10/10 Excellent

"Wry helpful reception. Clean hotel , beautiful golf course With a nice restaurant. Great place"

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"

More cheap stays in Middletown

Travelodge by Wyndham Winchester

160 Front Royal Pike Winchester VA

₹6,868

₹7,575 total

25 Oct - 26 Oct

includes taxes & fees

8.6/10 Excellent! (1,073 reviews)

Ramada by Wyndham Strasburg/Shenandoah Valley

21 Signal Knob Dr Strasburg VA

₹7,072

₹7,871 total

25 Oct - 26 Oct

includes taxes & fees

8.2/10 Very good! (1,020 reviews)

Quality Inn Winchester

1601 Martinsburg Pike Winchester VA

₹8,054

₹8,964 total

8 Nov - 9 Nov

includes taxes & fees

TRU By Hilton Winchester

118 Mercedes Court Winchester VA

₹8,250

₹9,182 total

1 Nov - 2 Nov

includes taxes & fees

9.2/10 Wonderful! (1,002 reviews)

Microtel Inn & Suites by Wyndham Winchester

150 Faraday Plaza Winchester VA

₹8,358

₹9,302 total

8 Nov - 9 Nov

includes taxes & fees

Comfort Inn & Suites Winchester

195 Kernstown Commons Blvd Winchester VA

₹9,620

₹10,707 total

18 Oct - 19 Oct

includes taxes & fees

9.4/10 Exceptional! (1,132 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.

Explore a world of travel with Expedia

Book Hotels in Middletown on Expedia.com

Middletown Hotels from ₹6,296

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. Fairfield Inn & Suites Strasburg Shenandoah Valley

4. Ramada by Wyndham Strasburg/Shenandoah Valley

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

6. DoubleTree by Hilton Front Royal Blue Ridge Shadows

7. Hampton Inn Front Royal

8. Comfort Inn & Suites Winchester

9. Quality Inn Stephens City - Winchester South

10. TownePlace Suites by Marriott Front Royal

11. La Quinta Inn & Suites by Wyndham Winchester

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

13. Spark by Hilton Winchester

14. The George Washington Hotel, A Wyndham Grand Hotel

15. Fairfield Inn & Suites by Marriott Winchester

16. Microtel Inn & Suites by Wyndham Winchester

17. Holiday Inn Winchester Se-Historic Gateway by IHG

18. TRU By Hilton Winchester

19. Courtyard by Marriott Winchester

20. Hampton Inn Winchester-University/Mall Area

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

TRU By Hilton Winchester

Fairfield Inn & Suites by Marriott Winchester

Travelodge by Wyndham Winchester

Ramada by Wyndham Strasburg/Shenandoah Valley

Comfort Inn & Suites Winchester

Country Inn & Suites by Radisson, Winchester, VA

Days Inn by Wyndham Winchester

DoubleTree by Hilton Front Royal Blue Ridge Shadows

Super 8 by Wyndham Front Royal Near Shenandoah National Park

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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