Photo by Samantha Keyes

Find hotels in Middletown, VA from AED 225

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Our top choices for Middletown hotels

Wayside Inn

Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (418)
"Historic inn. "
United States
David
The price is AED 264
AED 328 total
includes taxes & fees
28 Dec - 29 Dec
Wayside Inn

Econo Lodge Inn & Suites Middletown - Winchester South

Econo Lodge Inn & Suites Middletown - Winchester South
2.0 star property
Middletown
5.8 out of 10, (299)
"I loved staying here!"
United States
Whitney
The price is AED 253
AED 280 total
includes taxes & fees
25 Dec - 26 Dec
Econo Lodge Inn & Suites Middletown - Winchester South

Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1002)
"The place is spotless, comfortable and quiet. Very convenient as well, right off of 81"
United States
Michael
The price is AED 283
AED 321 total
includes taxes & fees
11 Jan - 12 January 2026
Spark by Hilton Winchester

Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley
2.5 star property
Strasburg
8.4 out of 10, Very Good, (1000)
"Breakfast was delicious "
United States
Robert
The price is AED 262
AED 292 total
includes taxes & fees
1 Jan - 2 January 2026
Ramada by Wyndham Strasburg/Shenandoah Valley

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1397)
"Clean room great helpful staff good breakfast"
United States
Loretta
The price is AED 291
AED 316 total
includes taxes & fees
29 Dec - 30 Dec
Microtel Inn & Suites by Wyndham Winchester

TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
Winchester
9.0 out of 10, Wonderful, (772)
"Very nice room and common spaces. Breakfast was good and the price was very fair."
United States
Joseph
The price is AED 358
AED 390 total
includes taxes & fees
4 Jan - 5 January 2026
TRU By Hilton Winchester

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
3.0 star property
Winchester
8.8 out of 10, Excellent, (1001)
"Have stayed here multiple times -always good"
United States
Robert
The price is AED 304
AED 331 total
includes taxes & fees
18 Jan - 19 January 2026
Country Inn & Suites by Radisson, Winchester, VA

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1090)
"We have stayed here many times on our way to Massachusetts and find it perfect every time."
United States
Patsy
The price is AED 356
AED 388 total
includes taxes & fees
5 Jan - 6 January 2026
Comfort Inn & Suites Winchester

Quality Inn Winchester

Quality Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1000)
"Great stay"
United States
Jaron
The price is AED 278
AED 302 total
includes taxes & fees
4 Jan - 5 January 2026
Quality Inn Winchester

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester
2.5 star property
Winchester
8.6 out of 10, Excellent, (1085)
"Hotels well Located off 81 for a nice pull Off and overnight stay. Staff is friendly and helpful and rooms comfortable and quiet. "
United States
Stefanie
The price is AED 250
AED 272 total
includes taxes & fees
19 Jan - 20 January 2026
Travelodge by Wyndham Winchester

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
2.5 star property
Winchester
9.0 out of 10, Wonderful, (800)
"Quick check in, clean room, friendly staff."
United States
Darcy
The price is AED 340
AED 370 total
includes taxes & fees
26 Dec - 27 Dec
Fairfield Inn & Suites by Marriott Winchester

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (2239)
"The place was clean, super friendly front desk staff, SO pet friendly with such a reasonable pet fee, and overall reasonable rate. Would 100% stay here again if I came back through this town. "
United States
Jordyn
The price is AED 363
AED 395 total
includes taxes & fees
28 Dec - 29 Dec
La Quinta Inn & Suites by Wyndham Winchester

Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University
2.5 star property
Winchester
7.8 out of 10, Good, (1000)
"great stay with breakfast too"
United States
James
The price is AED 227
AED 247 total
includes taxes & fees
18 Jan - 19 January 2026
Sleep Inn & Suites Winchester near University

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (788)
"Great staff, very clean room with a good breakfast "
United States
Jim
The price is AED 393
AED 428 total
includes taxes & fees
4 Jan - 5 January 2026
SpringHill Suites by Marriott Winchester

Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG
2.5 star property
Stephens City
8.2 out of 10, Very Good, (807)
"Clean room, nice staff, simple but good breakfast, fresh ground coffee machine was really nice. "
United States
Rose
The price is AED 272
AED 296 total
includes taxes & fees
31 Dec - 1 January 2026
Holiday Inn Express Winchester South-Stephens City by IHG

Candlewood Suites Winchester by IHG

Candlewood Suites Winchester by IHG
2.5 star property
Winchester
8.8 out of 10, Excellent, (545)
"Very clean room, excellent staff!!!"
United States
James
The price is AED 286
AED 312 total
includes taxes & fees
3 Jan - 4 January 2026
Candlewood Suites Winchester by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1000)
"Great room cozy bed fabulous restaurant great staff on property"
United States
joyce
The price is AED 301
AED 339 total
includes taxes & fees
1 Jan - 2 January 2026
Holiday Inn Winchester Se-Historic Gateway by IHG

Super 8 by Wyndham Front Royal

Super 8 by Wyndham Front Royal
2.0 star property
Front Royal
7.6 out of 10, Good, (1002)
"The staff was friendly and attentive. The room was clean. The breakfast was good, with pancakes, toast, cereal, juice, and coffee. Good location for visiting Shenandoah National Park."
United States
Teresa
The price is AED 228
AED 253 total
includes taxes & fees
25 Dec - 26 Dec
Super 8 by Wyndham Front Royal

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel
3.5 star property
Old Town Winchester
9.4 out of 10, Exceptional, (1004)
"Great hotel!"
United States
CHARLES
The price is AED 465
AED 527 total
includes taxes & fees
30 Dec - 31 Dec
The George Washington Hotel, A Wyndham Grand Hotel

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows
4.0 star property
Front Royal
9.0 out of 10, Wonderful, (1000)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
The price is AED 358
AED 395 total
includes taxes & fees
30 Dec - 31 Dec
DoubleTree by Hilton Front Royal Blue Ridge Shadows
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Stay near popular Middletown attractions

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.

Nana’s Irish Pub was a great and delicious stop off the main road on the way to Asheville, NC.  Super cute redesigned bank. The bank door is still in the corner and is not a closet. Highly suggested for a pit stop!
Photo by Samantha Keyes
Open Photo by Samantha Keyes

Top Middletown Hotel Reviews

More cheap stays in Middletown

Hotels in Middletown with star-rating

Find out more about Middletown

Top reasons to visit Middletown

  • Outdoor Adventures: Middletown offers stunning scenery and a variety of outdoor activities, perfect for adventure seekers.
  • Historical Exploration: Visitors can explore historic sites and houses, immersing themselves in the local culture and history.
  • Local Wine Tastings: Enjoy wine tastings at nearby wineries, highlighting the region's rich viticulture.
  • Family-Friendly Atmosphere: The town is ideal for families, providing a welcoming environment and a range of activities.
  • Vibrant Entertainment: Experience live music and nightlife, adding to Middletown’s lively atmosphere.

Find great hotels near Middletown

Discover a variety of hotel accommodations in Middletown, Virginia, perfect for every traveler. Whether you're seeking pet-friendly options, a welcoming environment for LGBTQIA guests, or facilities tailored for business travel, Middletown has something for everyone. Enjoy a comfortable stay in well-reviewed hotels and suites that cater to your needs, making your vacation experience truly memorable.

  • Travelodge by Wyndham Winchester: Experience a comfortable and budget-friendly stay at Travelodge by Wyndham Winchester, a pet-friendly motel located 17.7km from Middletown. This property is perfect for animal lovers, offering amenities that cater to your furry friends. With a warm and welcoming atmosphere, guests appreciate the convenience of its services, including a pet policy that allows pets on-site. The motel features a cozy environment, making it an ideal choice for those seeking a hassle-free vacation with their pets.
  • Country Inn & Suites by Radisson, Winchester, VA: A family-oriented retreat, Country Inn & Suites by Radisson, located just 12.9km from Middletown, combines comfort with convenience. This 3-star hotel is designed for families, business travelers, and pet owners alike. Amenities for children, such as complimentary cribs, enhance the family-friendly experience. The property also welcomes pets, providing food and water bowls, along with a pet policy that ensures a pleasant stay for all. Guests enjoy a warm, inviting ambiance, making it a home away from home.
  • Holiday Inn Winchester Se-Historic Gateway by IHG: Positioned 17.7km from Middletown, Holiday Inn Winchester Se-Historic Gateway is a welcoming destination for business and family travelers, as well as the LGBTQIA community. This 3-star hotel stands out for its commitment to inclusivity and provides amenities tailored for children, including complimentary cribs. Guests appreciate its modern facilities and convenient location, making it an excellent choice for those looking to explore the historic area while enjoying top-notch service and comfort.

Where to stay near Middletown

Discover the charm of Middletown, Virginia, where outdoor adventures await amidst breathtaking scenery. Stroll through the downtown area, explore historical sites, and savor local wines at nearby wineries. This small town offers a family-friendly atmosphere, perfect for a relaxing getaway. Venture into the surrounding region to enjoy the blend of urban vibrancy and rich history, making Middletown a delightful destination for every traveler.

  • Winchester: Located 19.3km from Middletown, Winchester is a charming city steeped in history and natural beauty. This destination offers a wealth of outdoor adventures, scenic views, and recreational opportunities. Visitors can explore the nearby national parks and lakes, perfect for hiking, picnicking, and photography. The peak travel months are July to August and October, making it an ideal summer and fall getaway. Don't miss local highlights such as the historic downtown area, where you can find unique shops and delightful eateries, or take a scenic drive through the picturesque countryside.
  • Front Royal: Just 14.5km from Middletown, Front Royal is known as the Gateway to Shenandoah National Park. This vibrant city invites outdoor enthusiasts with its stunning scenery, hiking trails, and recreational areas. Peak travel times are in April, July, and September, ideal for enjoying the area's natural beauty. Front Royal is a haven for adventure seekers with nearby ski resorts and lakes for fishing and boating. Make sure to visit the scenic Skyline Drive for breathtaking views of the Blue Ridge Mountains, and explore the charming downtown, featuring local shops and restaurants.
  • Strasburg: Located a mere 8.0km from Middletown, Strasburg is a quaint city that offers a perfect blend of outdoor adventures and small-town charm. With peak travel times from June to August, visitors flock to enjoy the area's recreational areas and ski fields. The city boasts easy access to national and state parks, making it a great spot for hiking and enjoying nature. Take a leisurely stroll through the historic district, filled with beautifully preserved buildings and delightful shops, or relax in one of the local parks, soaking in the peaceful surroundings.

Things to do in and around Middletown

Middletown, Virginia, is an ideal destination for outdoor enthusiasts and adventure seekers, offering stunning scenery and a range of activities. Visitors can enjoy recreational areas, skiing, and wine tastings, while entertainment venues provide live music and vibrant nightlife. Explore the beautiful outdoor spots and immerse yourself in the local culture for a memorable experience.

Shopping

In Middletown, you can visit Shen-Val Farm Market for local goods, just 12.9km away, or Natural Art Garden Center, located 14.5km from town. If you're up for a drive, check out Apple Blossom Mall, 17.7km away, offering a variety of shops and entertainment options.

Recreation

At Jackson's Chase Golf Course, enjoy a round of golf amidst beautiful outdoor scenery, perfect for sports enthusiasts. Nearby, Appleland Sports Center offers a serene environment for wellness and relaxation activities. Blue Ridge Shadows Golf Club provides another excellent golfing experience, surrounded by picturesque landscapes just 9.7km away.

Adventure

Explore the Dickey Ridge Trail for a rewarding hike with breathtaking scenery, located 19.3km from Middletown. Experience the thrill of racing at Summit Point Motorsports Park, 35.4km away, or enjoy family-friendly outdoor activities at Yogi Bear's Jellystone Park, situated 40.2km from Middletown.

Nightlife

Middletown offers a charming nightlife with venues like Wayside Theater, perfect for romantic and cultural experiences. For more entertainment, Bright Box Theater and Winchester Little Theater, both located 19.3km away, provide captivating performances that enhance the vibrant evening atmosphere.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Middletown

To save money on your trip to Middletown, consider visiting during the off-peak months of December to February, when hotel prices are lower. Tuesdays are typically the least expensive days to book your stay, while Saturdays tend to be the priciest. Use Expedia's search tool to filter for budget-friendly accommodations, including eco-certified options. Additionally, look for package deals that combine flights, hotel stays, and activities for further savings. Don't forget to explore free attractions and local parks to enhance your experience without breaking the bank.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Middletown are December to February, where the prices are slightly lower. This is in comparison to May to June and October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Middletown is Tuesday. The most expensive day to stay in Middletown is Saturday.
  • Find cheap hotels on Expedia: Expedia's search tool lets you choose your budget, ideal location, and additional preferences with ease. You can organize your results to display the lowest prices first, making it simple to find the most affordable hotels. Additionally, you can refine your search by hotel type; for instance, if you select the Eco-certified filter, you'll discover sustainable and environmentally friendly accommodations that you can book.
  • Consider bundling your trip: You can save money by creating a package deal that combines your hotel stay in Middletown with your flights and activities through Expedia.

Find the best attractions in and around Middletown

Middletown, Virginia, offers a perfect blend of outdoor adventure and scenic beauty for tourists. You can explore popular attractions such as visitor centers, rivers, and historic houses that cater to culture enthusiasts and families alike. Whether you’re looking to immerse yourself in local history or enjoy nature, Middletown has something for every kind of traveler seeking an unforgettable experience.

  • Shenandoah River: Experience the serene beauty of the Shenandoah River, located 12.9km from Middletown. With its scenic vistas, this destination offers opportunities for kayaking, fishing, and picnicking along its banks, perfect for outdoor enthusiasts.
  • Front Royal Entrance Shenandoah National Park: Just 16.1km away, this visitor center serves as the gateway to adventure. Families can explore hiking trails, enjoy breathtaking mountain views, and learn about the park's diverse wildlife, making it an ideal spot for outdoor lovers.
  • Cedar Creek Battlefield Foundation: Situated within Middletown, this historic site immerses visitors in the rich cultural heritage of the Civil War. Explore the battlefield and discover its significance in American history through engaging exhibits and tours.

Best time to go to Middletown

The best time to visit Middletown is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January31.5°F (-0.3°C)Light RainMostly SunnyAverageSlightly Low
February35.1°F (1.7°C)Light RainMostly SunnySlightly LowSlightly Low
March42.6°F (5.9°C)Light RainMostly SunnyAverageAverage
April53.2°F (11.8°C)Light RainMostly SunnyAverageAverage
May62.6°F (17.0°C)Light RainMostly SunnyAverageSlightly High
June70.9°F (21.6°C)Light RainMostly SunnySlightly HighSlightly High
July75.7°F (24.3°C)Light RainMostly SunnySlightly HighAverage
August73.4°F (23.0°C)Light RainMostly SunnyAverageAverage
September66.7°F (19.3°C)Light RainMostly SunnySlightly HighAverage
October55.6°F (13.1°C)Light RainMostly SunnyAverageSlightly High
November43.3°F (6.3°C)Light RainMostly SunnySlightly LowAverage
December36.7°F (2.6°C)Light RainMostly SunnySlightly LowSlightly Low

The nearest major airports for your trip to Middletown

Middletown, Virginia, can be conveniently accessed via two major airports. Washington Dulles International Airport (IAD) is located 72.4km away, with several nearby hotel options such as the 4-star Hyatt Regency Dulles, just 1.6km from the airport, and the Westin Washington Dulles Airport, also 1.6km away. Both hotels offer easy access to the airport. Another option is the Hilton Washington Dulles Airport, located 3.2km from IAD. Alternatively, Eastern West Virginia Regional Airport (MRB) is 48.3km from Middletown, with accommodations like the Hillbrook Inn, a 4-star bed and breakfast 11.6kms away, and the 3-star Hilton Garden Inn Martinsburg, located 4.8km from MRB.

Frequently asked questions

Where is the best place for a stay in Middletown?
Based on our traveler data, Econo Lodge Inn & Suites Middletown - Winchester South is one of the top choices for your stay. This hotel offers free parking and a bar. Two other choices for your stay in the area are Microtel Inn & Suites by Wyndham Winchester and La Quinta Inn & Suites by Wyndham Winchester. See all available top hotels, or vacation rentals in Middletown.
What are some of the best vacation home rentals in Middletown?
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly: Visitors like this Middletown vacation home rental. It is located on a river and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. See all vacation rentals in Middletown.
If I need to cancel my hotel reservation in Middletown, will I receive a refund?
Yes, the majority of hotel bookings are fully refundable if you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If you have a reservation that's non-refundable, you might still have the option to cancel and receive a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Middletown.
Where can I learn more about changing or cancelling my trip to Middletown?
To access more information about changing or cancelling your trip to Middletown, click here.
What's the best hotel to stay with easy access to Cedar Creek and Belle Grove National Historical Park?
Ramada by Wyndham Strasburg is one of the top choices for your stay based on our traveler data, and this hotel offers free breakfast and a restaurant. It's located 3 mi (4.8 km) from Cedar Creek and Belle Grove National Historical Park. Other good options within a few miles include Fairfield Inn & Suites Strasburg Shenandoah Valley and Wayside Inn.
What about the best place to stay close to Wayside Theater?
One of the top choices for your stay is Wayside Inn, located next to Wayside Theater, and this 3.5-star hotel offers free breakfast and a restaurant. Econo Lodge Inn & Suites, located just 0.5 mi (0.8 km) away, is another good choice.
What's the best hotel for staying near Ronald Reagan Washington National Airport (DCA)?
Hyatt Regency Crystal City is a popular 4-star hotel featuring a restaurant and an outdoor pool. It's located a short 0.6 mi (1 km) from Ronald Reagan Washington National Airport. Other options near the airport are Courtyard by Marriott Arlington Crystal City/Reagan National and Hilton Garden Inn Reagan National Airport.
What's it like to stay in Middletown?
Visitors to Middletown are sure to enjoy the bars and restaurants. Tourists can also enjoy the city's entertainment choices, churches, and theaters. In Middletown, there are 4 hotels and other accommodations to choose from. Find out more about Middletown.
What should I do while I'm visiting Middletown?
Landmarks like Belle Grove Plantation and Cedar Creek Battlefield Foundation might be worth a visit. 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 agenda are Wayside Theater and Jackson's Chase Golf Course. Check out what more to see and do in Expedia's Middletown guide.
What's the weather like in Middletown?
The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 36°F. Average annual precipitation for Middletown is 43 inches.

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