A mountainous landscape with autumn foliage, rocky outcrops, and a valley below.

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Our top choices for Middletown hotels

1. Wayside Inn

Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (461 reviews)
"We very much enjoyed our night at the Inn. Historic, charming, unique. The people we met were attentive and friendly. Our room was clean and quiet throughout the night. The onsite restaurant served delicious food both at dinner and breakfast."
United States
Susan
The price is NT$2,216
NT$2,769 total
includes taxes & fees
Nov 28 - Nov 29
Wayside Inn

2. Econo Lodge Inn & Suites Middletown - Winchester South

Econo Lodge Inn & Suites Middletown - Winchester South
2.0 star property
Middletown
5.8 out of 10, (332 reviews)
"Place is in poor repair."
United States
Craig
The price is NT$2,049
NT$2,261 total
includes taxes & fees
Nov 24 - Nov 25
Econo Lodge Inn & Suites Middletown - Winchester South

3. Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley
3.0 star property
Strasburg
9.0 out of 10, Wonderful, (1,002 reviews)
"Very clean room and property. Staff was great. Breakfast was good."
United States
Kayla
The price is NT$3,930
NT$4,374 total
includes taxes & fees
Nov 15 - Nov 16
Fairfield Inn & Suites Strasburg Shenandoah Valley

4. Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley
2.5 star property
Strasburg
8.2 out of 10, Very good, (1,024 reviews)
"A really great hotel for the price"
United States
Glenn
The price is NT$2,465
NT$2,743 total
includes taxes & fees
Nov 10 - Nov 11
Ramada by Wyndham Strasburg/Shenandoah Valley

5. 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, (922 reviews)
"Great hotel"
United States
Michael
The price is NT$2,575
NT$2,866 total
includes taxes & fees
Nov 13 - Nov 14
Holiday Inn Express Winchester South-Stephens City by IHG

6. Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
Front Royal
9.2 out of 10, Wonderful, (1,001 reviews)
"The hotel was really well maintained inside and out! Room was super-clean."
United States
Tammy
The price is NT$3,713
NT$4,132 total
includes taxes & fees
Dec 3 - Dec 4
Hampton Inn Front Royal

7. TownePlace Suites by Marriott Front Royal

TownePlace Suites by Marriott Front Royal
3.0 star property
Front Royal
9.6 out of 10, Exceptional, (615 reviews)
"Cleaned, maintained hotel near many conveniences."
United States
JoEllen
The price is NT$4,399
NT$4,917 total
includes taxes & fees
Nov 29 - Nov 30
TownePlace Suites by Marriott Front Royal

8. Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1,146 reviews)
"Nice hotel. I would stay here again."
United States
Kenneth
The price is NT$3,272
NT$3,641 total
includes taxes & fees
Nov 29 - Nov 30
Comfort Inn & Suites Winchester

9. 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, (1,004 reviews)
"It was a nice stay.. third time staying… relaxing and peaceful"
United States
Adrian
The price is NT$4,143
NT$4,570 total
includes taxes & fees
Nov 23 - Nov 24
DoubleTree by Hilton Front Royal Blue Ridge Shadows

10. 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, (723 reviews)
"Rooms were clean and comfortable"
United States
Jeanne
The price is NT$2,548
NT$2,836 total
includes taxes & fees
Nov 30 - Dec 1
Quality Inn Stephens City - Winchester South

11. 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, (2,272 reviews)
"Great place to stay the night after a long drive"
United States
lucy
The price is NT$3,374
NT$3,755 total
includes taxes & fees
Nov 8 - Nov 9
La Quinta Inn & Suites by Wyndham Winchester

12. 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, (1,010 reviews)
"Comfortable bed, friendly staff, and convenient location"
United States
Zohair
The price is NT$2,789
NT$3,104 total
includes taxes & fees
Nov 29 - Nov 30
Country Inn & Suites by Radisson, Winchester, VA

13. Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (967 reviews)
"Great place to stay in Winchester."
United States
Thomas
The price is NT$3,019
NT$3,360 total
includes taxes & fees
Nov 9 - Nov 10
Fairfield Inn & Suites by Marriott Winchester

14. Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,435 reviews)
"Perfect accommodation- great breakfast and attentive gracious staff"
United States
Kathleen
The price is NT$2,685
NT$2,988 total
includes taxes & fees
Nov 8 - Nov 9
Microtel Inn & Suites by Wyndham Winchester

15. 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, (1,007 reviews)
"Great hotel."
United States
Nicholas
The price is NT$3,226
NT$3,688 total
includes taxes & fees
Dec 3 - Dec 4
Holiday Inn Winchester Se-Historic Gateway by IHG

16. Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (1,000 reviews)
"Clean room, great staff, good parking and free breakfast"
United States
Albert
The price is NT$2,117
NT$2,399 total
includes taxes & fees
Nov 22 - Nov 23
Spark by Hilton Winchester

17. TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,006 reviews)
"Hotel was very clean and breakfast was delicious with a lot of options"
United States
Kailyn
The price is NT$2,699
NT$3,003 total
includes taxes & fees
Nov 11 - Nov 12
TRU By Hilton Winchester

18. 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, (1,003 reviews)
"Always great place and the old nostalgic look is the best"
United States
Christophe
The price is NT$4,248
NT$4,813 total
includes taxes & fees
Nov 19 - Nov 20
The George Washington Hotel, A Wyndham Grand Hotel

19. Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area
2.5 star property
Winchester
9.0 out of 10, Wonderful, (1,000 reviews)
"I like the cleanliness of the room and the breakfast options."
United States
Henedina
The price is NT$3,102
NT$3,514 total
includes taxes & fees
Dec 3 - Dec 4
Hampton Inn Winchester-University/Mall Area

20. Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1,002 reviews)
"We had an amazing stay and will be back! The rooms were clean and comfy and staff were very helpful."
United States
Jessica
The price is NT$3,490
NT$3,884 total
includes taxes & fees
Nov 10 - Nov 11
Courtyard by Marriott Winchester
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.

A mountainous landscape with autumn foliage, rocky outcrops, and a valley below.

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, Wayside Inn is one of the top choices for your stay. This hotel offers a restaurant and free parking. Two other choices for your stay in 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, 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 3 hotels and other accommodations to choose from. Find out more about Middletown.
What should I do while I'm visiting 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 agenda are Belle Grove Plantation 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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