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Find hotels in Middletown, VA from NT$2,335

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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, (417)
"Historic inn. "
United States
David
The price is NT$2,272
NT$2,822 total
includes taxes & fees
Dec 22 - Dec 23
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 NT$2,130
NT$2,350 total
includes taxes & fees
Dec 29 - Dec 30
Econo Lodge Inn & Suites Middletown - Winchester South

Quality Inn Stephens City - Winchester South

Quality Inn Stephens City - Winchester South
2.5 star property
Stephens City
8.0 out of 10, Very Good, (631)
"Good variety at breakfast and courteous staff."
Canada
Madonna
The price is NT$2,338
NT$2,544 total
includes taxes & fees
Jan 18 - 2026/1/19
Quality Inn Stephens City - Winchester South

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, (803)
"Nice stay and friendly people "
United States
ALFRED
The price is NT$2,272
NT$2,472 total
includes taxes & fees
Jan 2 - 2026/1/3
Holiday Inn Express Winchester South-Stephens City by IHG

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester
2.5 star property
Winchester
8.6 out of 10, Excellent, (1082)
"Clean rooms, easy check in"
United States
Leslie
The price is NT$2,146
NT$2,335 total
includes taxes & fees
Jan 11 - 2026/1/12
Travelodge by Wyndham Winchester

ANS Inn & Suites

ANS Inn & Suites
2.0 star property
Winchester
7.4 out of 10, Good, (67)
"Everyone here was so friendly. The cats in the lobby to greet guests was awesome."
United States
Dinesh
The price is NT$2,115
NT$2,523 total
includes taxes & fees
Jan 2 - 2026/1/3
ANS Inn & Suites

TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
Winchester
9.0 out of 10, Wonderful, (770)
"Very nice room and common spaces. Breakfast was good and the price was very fair."
United States
Joseph
The price is NT$2,303
NT$2,506 total
includes taxes & fees
Jan 5 - 2026/1/6
TRU By Hilton Winchester

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1084)
"Clean property and rooms, helpful and nice staff."
United States
Heidi
The price is NT$3,091
NT$3,363 total
includes taxes & fees
Dec 29 - Dec 30
Comfort Inn & Suites Winchester

Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley
2.5 star property
Strasburg
9.0 out of 10, Wonderful, (1001)
"Great stay."
United States
Kenneth
The price is NT$3,193
NT$3,553 total
includes taxes & fees
Dec 25 - Dec 26
Fairfield Inn & Suites Strasburg Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley
2.5 star property
Strasburg
8.4 out of 10, Very Good, (1006)
"Breakfast was delicious "
United States
Robert
The price is NT$2,280
NT$2,538 total
includes taxes & fees
Jan 1 - 2026/1/2
Ramada by Wyndham Strasburg/Shenandoah Valley

APM Inn & Suites

APM Inn & Suites
2.0 star property
Winchester
6.6 out of 10, (348)
"Room was quite nice for the price, and check in lady was very nice "
United States
Glen
The price is NT$1,704
NT$1,931 total
includes taxes & fees
Dec 22 - Dec 23
APM Inn & Suites

White Moose Inn

White Moose Inn
4.0 star property
Washington
9.8 out of 10, Exceptional, (148)
"Staff is wonderful. The whole 1st floor would make Marie Kondo proud! Breakfast is excellent. "
United States
Judy
White Moose Inn

Gay Street Inn

Gay Street Inn
3.5 star property
Washington
10.0 out of 10, Exceptional, (34)
"Beautiful historic Inn with incredible owners and service. "
United States
Renee
The price is NT$11,331
NT$12,215 total
includes taxes & fees
Jan 1 - 2026/1/2
Gay Street Inn

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1394)
"Clean room great helpful staff good breakfast"
United States
Loretta
The price is NT$2,348
NT$2,555 total
includes taxes & fees
Jan 4 - 2026/1/5
Microtel 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 NT$1,967
NT$2,140 total
includes taxes & fees
Jan 11 - 2026/1/12
Sleep Inn & Suites Winchester near University

Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1002)
"Great location close to restaurants "
United States
SILVIA
The price is NT$2,433
NT$2,756 total
includes taxes & fees
Jan 4 - 2026/1/5
Spark by Hilton Winchester

Super 8 by Wyndham Winchester VA

Super 8 by Wyndham Winchester VA
2.0 star property
Winchester
6.2 out of 10, (621)
"Very limited, bread , butter , jam"
Canada
Susan
The price is NT$2,115
NT$2,301 total
includes taxes & fees
Jan 1 - 2026/1/2
Super 8 by Wyndham Winchester VA

Hilton Garden Inn Winchester

Hilton Garden Inn Winchester
3.0 star property
Winchester
8.8 out of 10, Excellent, (510)
"Great hotel"
United States
DONNA D
The price is NT$3,184
NT$3,607 total
includes taxes & fees
Dec 26 - Dec 27
Hilton Garden Inn Winchester

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
2.5 star property
Winchester
9.0 out of 10, Wonderful, (799)
"Quick check in, clean room, friendly staff."
United States
Darcy
The price is NT$2,924
NT$3,182 total
includes taxes & fees
Dec 24 - Dec 25
Fairfield Inn & Suites by Marriott Winchester

Red Roof Inn Winchester, VA

Red Roof Inn Winchester, VA
2.0 star property
Winchester
7.4 out of 10, Good, (1001)
"Really friendly staff, room was clean and perfect for our family and dog. "
United States
Sabrina
The price is NT$2,177
NT$2,369 total
includes taxes & fees
Dec 22 - Dec 23
Red Roof Inn Winchester, VA
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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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 thrilling activities like skiing and scenic hiking trails, perfect for adventure enthusiasts.
  • Charming Downtown: Explore the picturesque downtown area filled with local shops and eateries, enhancing the small-town experience.
  • Wine Tastings: Enjoy delightful wine tastings at nearby vineyards, showcasing the region's unique flavors.
  • Historic Attractions: Discover local history through visitor centers and historic houses that reflect the area’s rich past.
  • Live Music & Entertainment: Experience vibrant live music events at various venues, adding to the local cultural scene.

Find great hotels near Middletown

Discover a range of hotel accommodations in Middletown, Virginia, perfect for every traveler. Whether you're seeking pet-friendly options, business-friendly amenities, or an LGBTQIA welcoming environment, you'll find hotels and motels that cater to your needs. Explore the best hotels and suites in the area, complete with reviews to help guide your choice for a memorable stay in this charming small town.

  • Travelodge by Wyndham Winchester: Embrace a cozy and budget-friendly stay at Travelodge by Wyndham Winchester, a welcoming motel located 17.7km from Middletown. This property stands out for its pet-friendly policy, making it an ideal choice for travelers who want to bring their furry companions along. Guests appreciate the straightforward amenities, including comfortable rooms and essential services. The property allows pets with certain restrictions, ensuring a hassle-free experience for pet owners. Enjoy the convenience of a home-like atmosphere where you can unwind after a day of exploration.
  • Country Inn & Suites by Radisson, Winchester, VA: Situated just 12.9km from Middletown, Country Inn & Suites by Radisson offers a charming and family-oriented atmosphere. This 3-star hotel is perfect for both business and leisure travelers, featuring amenities tailored for families, such as complimentary cribs. The hotel is also pet-friendly, allowing you to travel with your pets without worry. Guests love the welcoming ambiance, well-appointed rooms, and a variety of services designed to ensure a comfortable stay for everyone in the family. Enjoy a delightful blend of hospitality and convenience at this inviting hotel.
  • Holiday Inn Winchester Se-Historic Gateway by IHG: Positioned 17.7km from Middletown, the Holiday Inn Winchester Se-Historic Gateway is an excellent choice for guests seeking a modern yet family-friendly environment. This 3-star hotel is known for its inclusive atmosphere, welcoming LGBTQIA travelers and providing facilities that cater to all guests. With amenities for children, including free cribs, families can relax knowing they have everything they need for a pleasant stay. The hotel combines comfort with a prime location, making it a perfect base for exploring the region.

Where to stay near Middletown

Middletown, Virginia, offers a delightful blend of historical charm and outdoor adventure. Explore the picturesque downtown area, where local wineries invite you to savor regional flavors. The small-town atmosphere is perfect for family-friendly activities, while nearby neighborhoods present a vibrant urban experience. Whether you're hiking scenic trails or enjoying local cuisine, Middletown promises a memorable vacation filled with diverse vibes and captivating sights.

  • Winchester: Located 19.3km from Middletown, Winchester is a vibrant city known for its rich history and outdoor adventures. Visitors can explore the scenic beauty of nearby national parks and lakes, making it a perfect spot for hiking, picnicking, and enjoying nature. The city’s recreational areas offer activities suitable for all ages, while educational venues provide insights into the region's heritage. Peak visitor months are July to August and October, making summer and fall ideal times to experience local festivals and events.
  • Front Royal: Just 14.5km from Middletown, Front Royal serves as the gateway to the majestic Shenandoah National Park. This charming city attracts outdoor enthusiasts year-round, with its stunning landscapes and recreational opportunities. Front Royal is particularly popular for skiing in the winter and hiking in the warmer months. Peak travel times occur in April, July, and September, when visitors flock to enjoy the scenic drives and vibrant fall foliage. The local ski resorts also draw adventure seekers looking for winter fun.
  • Strasburg: Only 8.0km away from Middletown, Strasburg is a quaint city that offers a blend of outdoor adventure and picturesque scenery. The area is perfect for hiking and skiing, with numerous recreational areas available for exploration. Visitors can enjoy the natural beauty of national parks and local parks throughout the year, particularly during peak travel months from June to August. Strasburg’s small-town charm provides a peaceful retreat while still being close to exciting outdoor activities.

Things to do in and around Middletown

Middletown, Virginia, is perfect for outdoor and adventure enthusiasts, offering a range of activities like skiing and exploring beautiful recreational areas. Visitors can enjoy wine tastings at local vineyards, experience live music at various entertainment venues, and discover charming outdoor spots. Whether you seek thrilling adventures or laid-back outings, Middletown has something for everyone to enjoy.

Shopping

You can enjoy shopping at Shen-Val Farm Market, located 12.9km from Middletown, offering fresh local produce and unique gifts. If you're up for a drive, visit Apple Blossom Mall, 17.7km away, featuring a variety of stores and family-friendly entertainment options.

Recreation

At Jackson's Chase Golf Course, enjoy a round of golf amidst scenic landscapes, perfect for sports enthusiasts. For relaxation, visit Appleland Sports Center, where wellness programs and rejuvenating activities await. Just a short drive away, Blue Ridge Shadows Golf Club offers another exceptional golfing experience surrounded by beautiful outdoor vibes.

Adventure

Dickey Ridge Trail offers a thrilling hiking experience with stunning scenery, located 19.3km from Middletown. For adrenaline junkies, Summit Point Motorsports Park, 35.4km away, provides exhilarating motor racing. Families can enjoy outdoor adventures at Yogi Bear's Jellystone Park, situated 40.2km from town.

Nightlife

Middletown offers a charming nightlife scene with venues like the Wayside Theater, perfect for a romantic evening filled with culture and entertainment. For more options, Bright Box Theater and Winchester Little Theater, both located 19.3km away, showcase captivating performances in a lively 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, Virginia, consider visiting during the off-peak months from December to February, when accommodation prices are lower. Booking your stay on a Tuesday can also help you save, as Saturday is typically the most expensive day. Use Expedia to compare hotel deals and consider bundling your hotel, flights, and activities for additional savings. Look for minute hotel deals and filter your search by price to find the best options. Enjoy free activities in the area 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: Utilize Expedia's search tool to refine your preferences, such as your budget, desired location, and preferred hotel type. To find the best prices and deals, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your Middletown hotel reservations with your flights and activities through an Expedia package.

Find the best attractions in and around Middletown

Middletown, Virginia, offers an ideal vacation for outdoor enthusiasts and adventure seekers. Visitors can explore a variety of attractions, including visitor centers, scenic rivers, and historic houses. With a focus on culture and family experiences, Middletown promises a memorable getaway for travelers looking to immerse themselves in the area's natural beauty and rich history.

  • Shenandoah River: Experience the serene beauty of the Shenandoah River, only 12.9km from Middletown. Enjoy outdoor activities like kayaking, fishing, or simply relaxing by the water while soaking in the picturesque scenery.
  • Front Royal Entrance Shenandoah National Park: Located 16.1km away, this visitor center is the gateway to adventure. Perfect for families, it offers hiking trails, educational exhibits, and stunning views of the Blue Ridge Mountains, making it an ideal spot for outdoor enthusiasts.
  • Cedar Creek Battlefield Foundation: Situated within Middletown, this historic site provides a cultural experience through its insightful exhibits and reenactments, allowing visitors to explore the rich history of the Civil War.

Best time to go to Middletown

The best time to visit Middletown can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Middletown falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Middletown falls in January, 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

Traveling to Middletown, Virginia, can be easily accomplished by flying into two major airports. Washington Dulles International Airport (IAD) is located 72.4km away and offers several nearby hotels, such as the 4-star Hyatt Regency Dulles and The Westin Washington Dulles Airport, both just 1.6km from the airport. Martinsburg, WV, Eastern West Virginia Regional Airport (MRB) is situated 48.3km away, with charming accommodations like the 4-star Hillbrook Inn and the 3-star Hilton Garden Inn Martinsburg, located 11.6kms and 4.8km from the airport, respectively. Both airports provide convenient access to Middletown, making your travel experience smooth and enjoyable.

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.
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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