Middletown Hotel & Accommodation Deals 2026 from NZ$116 - Fully Refundable Options

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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

NZ$151

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

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

NZ$131

includes taxes & fees

21 Oct - 22 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 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 hotel with a green roof, a covered entrance, and a sign that reads "RAMADA".

3. Ramada by Wyndham Strasburg/Shenandoah Valley

Strasburg

CHRISTI

NZ$157

includes taxes & fees

11 Oct - 12 Oct

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

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.

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

4. Fairfield Inn & Suites Strasburg Shenandoah Valley

Strasburg

Patrick

NZ$233

includes taxes & fees

19 Oct - 20 Oct

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

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

A spacious lobby with a stone fireplace, blue upholstered sofas, and a chandelier.

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

5. DoubleTree by Hilton Front Royal Blue Ridge Shadows

Front Royal

Brian

NZ$208

includes taxes & fees

28 Oct - 29 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 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.

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

Stephens City

Michael

NZ$189

includes taxes & fees

11 Oct - 12 Oct

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.

7. Quality Inn Stephens City - Winchester South

Stephens City

Nancy

NZ$166

includes taxes & fees

25 Oct - 26 Oct

A hotel dining area with multiple tables and chairs, large windows, and a television screen.

A hotel room with two beds, a desk with a TV, a lamp, and a view of the outdoors.

8. Comfort Inn & Suites Winchester

Winchester

John

NZ$201

includes taxes & fees

11 Oct - 12 Oct

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

A gym with weightlifting equipment, including dumbbells and a bench.

A hotel room with a gray sofa, a bed with a blue headboard, a painting of a landscape, and a lamp on the nightstand.

9. Hampton Inn Front Royal

Front Royal

Grace

NZ$241

includes taxes & fees

25 Oct - 26 Oct

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

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.

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

10. TownePlace Suites by Marriott Front Royal

Front Royal

Justin

NZ$276

includes taxes & fees

18 Oct - 19 Oct

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

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.

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

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

Winchester

Allen

NZ$186

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

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.

12. La Quinta Inn & Suites by Wyndham Winchester

Winchester

Earl

NZ$203

includes taxes & fees

4 Oct - 5 Oct

A spacious lobby with a checkered floor, yellow chairs, a green carpet, and a wall with the text "It only takes a spark".

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

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.

An indoor swimming pool with clear glass walls, a tiled floor, and a few lounge chairs.

13. Spark by Hilton Winchester

Winchester

carrie

NZ$163

includes taxes & fees

25 Oct - 26 Oct

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 coffee station with multiple coffee dispensers and a sign above.

A modern restaurant interior with wooden tables and chairs, a green booth area, and artwork on the walls.

14. Fairfield Inn & Suites by Marriott Winchester

Winchester

Dawn

NZ$190

includes taxes & fees

19 Oct - 20 Oct

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

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.

A Super 8 hotel with a brick facade, multiple windows, and a central entrance.

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

Front Royal

Snehil Meet

NZ$143

includes taxes & fees

4 Oct - 5 Oct

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

A snack kiosk with refrigerated drink dispensers and shelves stocked with snacks.

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

16. Home2 Suites By Hilton Winchester

Winchester

Mandy

NZ$187

includes taxes & fees

6 Oct - 7 Oct

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.

A modern lounge area with seating arrangements, including sofas and chairs, and a large window providing a view outside.

17. TRU By Hilton Winchester

Winchester

Kailyn

NZ$184

includes taxes & fees

19 Oct - 20 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 two beds, a wooden headboard, a nightstand with lamps, and a view of the outdoors through the window.

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

18. Travelodge by Wyndham Winchester

Winchester

john

NZ$139

includes taxes & fees

5 Oct - 6 Oct

A modern hotel lobby with a reception desk, seating area, and a large window providing natural light.

A lobby with yellow patterned chairs, a round table, a TV on the wall, and a patterned rug.

A modern kitchen with wooden cabinets, a countertop, and a window with a view.

A hotel room with a large bed, a bedside table with a lamp, a small desk, and a kitchenette area.

19. Hampton Inn Winchester N/Conference Center, VA

Winchester

Michael

NZ$193

includes taxes & fees

19 Oct - 20 Oct

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

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

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.

20. Relax Inn Motel

Front Royal

Jamila

NZ$126

includes taxes & fees

5 Oct - 6 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

Recent Reviews in Middletown

Spark by Hilton Winchester

10/10 Excellent

"Easy check in , clean room , easy checkout what more could you ask for!"

Holiday Inn Express Woodstock-Shenandoah Valley by IHG

10/10 Excellent

"It is always a relief to stay at this chain. Competent, friendly staff, clean rooms, great shower and a terrific mattress. And the breakfast and coffee that is always availible are a plus when having to travel."

Microtel Inn & Suites by Wyndham Winchester

10/10 Excellent

"This hotel is great, the only thing that could be A LOT better is the water pressure from the shower head."

TRU By Hilton Winchester

10/10 Excellent

"Great hotel. Convenient location, friendly staff, clean environment"

Country Inn & Suites by Radisson, Winchester, VA

8/10 Good

"Everything was very good Except the complimentary breakfast. Even if it is free, it should still be tasty. I would rather have to pay and have good food, good coffee and real cream. I wish the local food could be featured."

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent

"Clean room, great shower. A block from the walking mall with lots of food, shopping, and a few breweries. Highly recommend."

Hampton Inn Front Royal

10/10 Excellent

"Really enjoyed our stay at the Hampton Inn, in Front Royal. My wife and I took a trip to do a hiking weekend in Shenandoah National Park. With the hotel being close to the park, as well as just outside a relatively large town, so we'd have stuff to do in the evenings, the location was great. The room was very comfortable, and staff were extremely friendly and helpful. Everything was clean, and they had a great breakfast (which opened early...key for getting a really early start to the day before we hit the trails) The only downside was, we did pick the hotel based off all those factors, but as well as it having an indoor pool. After a day hiking up and down Old Rag, a late afternoon in the pool to decompress and recover was going to be what we needed...unfortunately we did not find out until after we arrived, the pool was out of service. So that was a little disappointing, but we made the best of it."

Super 8 by Wyndham Front Royal Near Shenandoah National Park

8/10 Good

"The hotel is in a great location for access to the Shenandoah National Park and a short walk in to historic Front Royal. Whilst it appears a little tired it was comfortable and had everything we needed. Breakfast was a little basic compared to others but for the price it was good value."

Wayside Inn

10/10 Excellent

"Charmingly beautiful hotel. Like staying in a Civil War museum. Comfortable mattress. Slightly creaky bed. Got to hear the haunted boots on the wooden floor footsteps! Cute coffee shop next door. Will gladly be back!"

More cheap accommodation in Middletown

Travelodge by Wyndham Winchester

160 Front Royal Pike Winchester VA

NZ$139

5 Oct - 6 Oct

includes taxes & fees

Ramada by Wyndham Strasburg/Shenandoah Valley

21 Signal Knob Dr Strasburg VA

NZ$157

11 Oct - 12 Oct

includes taxes & fees

Quality Inn Winchester

1601 Martinsburg Pike Winchester VA

NZ$165

26 Oct - 27 Oct

includes taxes & fees

TRU By Hilton Winchester

118 Mercedes Court Winchester VA

NZ$184

19 Oct - 20 Oct

includes taxes & fees

9.2/10 Wonderful! (1,006 reviews)

Comfort Inn & Suites Winchester

195 Kernstown Commons Blvd Winchester VA

NZ$201

11 Oct - 12 Oct

includes taxes & fees

Microtel Inn & Suites by Wyndham Winchester

150 Faraday Plaza Winchester VA

NZ$201

25 Oct - 26 Oct

includes taxes & fees

9.2/10 Wonderful! (1,461 reviews)

Frequently asked questions

What is the best area to stay in Middletown?

The best area to stay in Middletown is the historic downtown area, particularly around Main Street.This quaint area is the heart of Middletown, offering a relaxed pace with its collection of historic buildings and local businesses. You'll find a few independent shops and eateries dotted along Main Street, providing a pleasant environment for a stroll. The main crossroads of Main Street and Fairfax Street marks the centre of this small but welcoming community.Couples looking for a peaceful getaway will find downtown Middletown perfect. It offers a quiet setting for a romantic break, with the convenience of local dining options within walking distance.

What are the best hotels in Middletown that travellers recommend?

Two of the best hotels in Middletown that receive consistently high recommendations from travellers are the Wayside Inn and the Econo Lodge Inn & Suites.The Wayside Inn, a 3.5-star hotel, has an excellent 9.2 rating. Guests frequently mention the comfortable and clean rooms, the incredible food, and the helpful staff. It also offers evening entertainment and is located just 2.0 km from Cedar Creek and Belle Grove National Historical Park.Another highly recommended option is the Econo Lodge Inn & Suites. This hotel is praised for its clean and spotless rooms and offers convenient amenities such as free accessible parking and RV, bus, and truck parking.

What are the best family hotels in Middletown?

For family-friendly accommodation in Middletown, consider the Wayside Inn or the Econo Lodge Inn & Suites.The 3.5-star Wayside Inn, with an excellent 9.2 rating, is a great choice for families. It offers highchairs for children and free rollaway extra beds, along with early check-in options. Guests frequently mention the comfortable and clean rooms, the incredible food, and the friendly, helpful staff. The hotel is also conveniently located just 2.0 km from Cedar Creek and Belle Grove National Historical Park.Another option is the Econo Lodge Inn & Suites, which provides free cribs and sofa beds, making it suitable for families. Guests appreciate the clean and spotless rooms, and free self-parking and free WiFi are also available.

What are the top pet-friendly hotels in Middletown?

For top pet-friendly accommodation in Middletown, the Econo Lodge Inn & Suites is a great choice.The Econo Lodge Inn & Suites is a practical option for travellers with pets, as pets are permitted at this establishment. Guests have frequently commented on the clean and spotless rooms. The hotel also offers free WiFi and complimentary self-parking, along with free cribs for those travelling with infants.

What are the best budget hotels in Middletown?

For a highly-rated budget option in Middletown, the Econo Lodge Inn & Suites is a good choice.This hotel offers complimentary self-parking and free WiFi. Guests appreciate the clean and spotless rooms, and for those travelling with infants, free cribs are available. Early check-in can also be arranged.

What are the most romantic hotels in Middletown for couples?

For a romantic stay in Middletown, the Wayside Inn is an excellent choice for couples.The Wayside Inn, a 3.5-star hotel with an impressive 9.2 rating, is particularly well-suited for couples, offering a dedicated couples dining experience. Guests frequently highlight the comfortable and clean rooms, incredible food, and the very helpful staff. The hotel also provides free WiFi and free self-parking, and is conveniently located just 2.0 km from Cedar Creek and Belle Grove National Historical Park, making it ideal for exploring local attractions together.

What are the best hotels in Middletown near Cedar Creek and Belle Grove National Historical Park?

For a hotel in Middletown conveniently located near Cedar Creek and Belle Grove National Historical Park, the Wayside Inn is an excellent choice.This 3.5-star hotel, with an impressive 9.2 rating, is situated just 2.0 km from the historical park, making it very accessible for visits. Guests frequently praise the comfortable and clean rooms, as well as the incredible and amazing food. The staff are consistently described as very friendly and helpful. Families will appreciate the availability of highchairs for children and free rollaway extra beds. The hotel also offers early check-in options, which can be convenient for travellers. Its beautiful decor and a great bar further enhance the guest experience.

When is the best time to go to Middletown?

The best time to visit Middletown, Virginia, is during the spring (April to May) and autumn (September to October) months.These seasons offer pleasant weather, with mild temperatures and lower humidity, making it ideal for exploring the area's natural beauty and historical sites. Spring brings blooming flowers and lush greenery, while autumn showcases stunning fall foliage.Couples looking for a romantic getaway will appreciate the comfortable climate for leisurely walks through historic downtown or visits to local vineyards. The picturesque scenery during these months also provides a lovely backdrop for outdoor activities.Families travelling with children will find these seasons superb for enjoying outdoor attractions without the discomfort of extreme heat or cold.

Can I cancel my hotel reservation on Expedia?

You can cancel your hotel reservation on Expedia, although it depends on the cancellation policy of your booking. Most bookings are refundable if cancelled within 24 to 48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to 'My Trips' and selecting your reservation. To find flexible deals, filter your search by 'Fully refundable property' for hotels in Middletown.

How can I save on a hotel booking in Middletown with Expedia?

One Key™—Expedia's free travel rewards program—gives you instant access to discounts with Member Prices on Middletown hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

How much is the nightly rate for a hotel in Middletown?

Prices for hotels in Middletown often vary, but you can find a great deal from NZ$116 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by 'Price: low to high' for our cheapest rates.

Explore a world of travel with Expedia

Book Hotels in Middletown on Expedia.com

Search Middletown hotels

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Middletown

Check prices for these dates

Filter by

Property class

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. DoubleTree by Hilton Front Royal Blue Ridge Shadows

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

7. Quality Inn Stephens City - Winchester South

8. Comfort Inn & Suites Winchester

9. Hampton Inn Front Royal

10. TownePlace Suites by Marriott Front Royal

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

12. La Quinta Inn & Suites by Wyndham Winchester

13. Spark by Hilton Winchester

14. Fairfield Inn & Suites by Marriott Winchester

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

16. Home2 Suites By Hilton Winchester

17. TRU By Hilton Winchester

18. Travelodge by Wyndham Winchester

19. Hampton Inn Winchester N/Conference Center, VA

20. Relax Inn Motel

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

Recent Reviews in Middletown

Spark by Hilton Winchester

Holiday Inn Express Woodstock-Shenandoah Valley by IHG

Microtel Inn & Suites by Wyndham Winchester

TRU By Hilton Winchester

Country Inn & Suites by Radisson, Winchester, VA

The George Washington Hotel, A Wyndham Grand Hotel

Hampton Inn Front Royal

Super 8 by Wyndham Front Royal Near Shenandoah National Park

Wayside Inn

More cheap accommodation in Middletown

Travelodge by Wyndham Winchester

Ramada by Wyndham Strasburg/Shenandoah Valley

Quality Inn Winchester

TRU By Hilton Winchester

Comfort Inn & Suites Winchester

Microtel Inn & Suites by Wyndham Winchester

Frequently asked questions

Explore a world of travel with Expedia

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