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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, (422 reviews)
"Room 14 was great for spirit activity as well as the rest of the property! Highly recommend ghost hunters to explore the inn. Food at their Larick’s tavern was delish!! Overall service and staff were knowledgeable and friendly! We had a great experience for our anniversary! "
United States
Megan
The price is SAR 300
SAR 368 total
includes taxes & fees
8 Feb - 9 Feb
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, (300 reviews)
"I loved staying here!"
United States
Whitney
The price is SAR 233
SAR 257 total
includes taxes & fees
15 Feb - 16 Feb
Econo Lodge Inn & Suites Middletown - Winchester South

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester
2.5 star property
Winchester
8.6 out of 10, Excellent, (1,081 reviews)
"Clean place, breakfast ok, warm and comfy, would stay again"
United States
Lyle
The price is SAR 263
SAR 286 total
includes taxes & fees
8 Feb - 9 Feb
Travelodge by Wyndham Winchester

ANS Inn & Suites

ANS Inn & Suites
2.0 star property
Winchester
7.4 out of 10, Good, (67 reviews)
"Everyone here was so friendly. The cats in the lobby to greet guests was awesome."
United States
Dinesh
The price is SAR 236
SAR 282 total
includes taxes & fees
11 Feb - 12 Feb
ANS Inn & Suites

APM Inn & Suites

APM Inn & Suites
2.0 star property
Winchester
6.6 out of 10, (360 reviews)
"Room was quite nice for the price, and check in lady was very nice "
United States
Glen
The price is SAR 206
SAR 234 total
includes taxes & fees
11 Feb - 12 Feb
APM Inn & Suites

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, (637 reviews)
"Spotless room, great staff"
United States
Roy
The price is SAR 268
SAR 291 total
includes taxes & fees
22 Feb - 23 Feb
Quality Inn Stephens City - Winchester South

Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley
2.5 star property
Strasburg
8.4 out of 10, Very Good, (1,001 reviews)
"Great stay everyone friendly will stay again"
United States
Mary K
The price is SAR 284
SAR 316 total
includes taxes & fees
15 Feb - 16 Feb
Ramada by Wyndham Strasburg/Shenandoah Valley

TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
Winchester
9.0 out of 10, Wonderful, (795 reviews)
"Clean room, good breakfast, easy check in/out."
United States
Joseph
The price is SAR 335
SAR 365 total
includes taxes & fees
8 Mar - 9 Mar
TRU By Hilton Winchester

Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley
2.5 star property
Strasburg
9.0 out of 10, Wonderful, (1,000 reviews)
"We stay here every year on our way to NC. Always very nice and helpful staff."
United States
Catherine
The price is SAR 424
SAR 472 total
includes taxes & fees
18 Feb - 19 Feb
Fairfield Inn & Suites Strasburg Shenandoah Valley

Red Roof Inn Winchester, VA

Red Roof Inn Winchester, VA
2.0 star property
Winchester
7.4 out of 10, Good, (1,001 reviews)
"Clean, pet friendly and great check in."
United States
Anita Willsie
The price is SAR 261
SAR 284 total
includes taxes & fees
8 Feb - 9 Feb
Red Roof Inn Winchester, VA

Super 8 by Wyndham Winchester VA

Super 8 by Wyndham Winchester VA
2.0 star property
Winchester
6.2 out of 10, (624 reviews)
"Easy to book."
United States
Maria
The price is SAR 226
SAR 246 total
includes taxes & fees
22 Feb - 23 Feb
Super 8 by Wyndham Winchester VA

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, (819 reviews)
"The room was spotless, staff is excellent. Well, recommend the stay to everyone I know"
United States
Kelso
The price is SAR 315
SAR 343 total
includes taxes & fees
9 Feb - 10 Feb
Holiday Inn Express Winchester South-Stephens City by IHG

Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University
2.5 star property
Winchester
7.8 out of 10, Good, (1,000 reviews)
"great stay with breakfast too"
United States
James
The price is SAR 300
SAR 326 total
includes taxes & fees
10 Mar - 11 Mar
Sleep Inn & Suites Winchester near University

Hilton Garden Inn Winchester

Hilton Garden Inn Winchester
3.0 star property
Winchester
8.8 out of 10, Excellent, (517 reviews)
"Great hotel"
United States
DONNA D
The price is SAR 381
SAR 432 total
includes taxes & fees
1 Mar - 2 Mar
Hilton Garden Inn Winchester

L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant
4.0 star property
Boyce
9.6 out of 10, Exceptional, (175 reviews)
"This B&B has been by far the loveliest, friendliest, cleanest with staff so eager to please. The rural area was so peaceful and relaxing with views of black angus in the fields. Winchester close with quaint shops. The food at the Inn was excellent. "
United States
DONNA
The price is SAR 807
SAR 890 total
includes taxes & fees
8 Feb - 9 Feb
L'Auberge Provencale Inn & Restaurant

Candlewood Suites Winchester by IHG

Candlewood Suites Winchester by IHG
2.5 star property
Winchester
8.8 out of 10, Excellent, (554 reviews)
"The room was just the right temp, check in with my service dog was the most professional I’ve experienced! "
United States
Shenandoah
The price is SAR 330
SAR 359 total
includes taxes & fees
9 Feb - 10 Feb
Candlewood Suites Winchester by IHG

Motel 6 Winchester, VA

Motel 6 Winchester, VA
2.0 star property
Winchester
8.2 out of 10, Very Good, (1,001 reviews)
"It was clean and in a safe area "
United States
Daryl
The price is SAR 255
SAR 289 total
includes taxes & fees
9 Feb - 10 Feb
Motel 6 Winchester, VA

The Foster Harris House

The Foster Harris House
2.0 star property
Washington
10.0 out of 10, Exceptional, (4 reviews)
"Lovely inn in a great location three course breakfast with one of the best scones I have eaten "
United States
Mary
The price is SAR 1,871
SAR 2,017 total
includes taxes & fees
19 Feb - 20 Feb
The Foster Harris House

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
2.5 star property
Winchester
9.0 out of 10, Wonderful, (818 reviews)
"We stay here a lot and it is always consistently clean and service is great. "
United States
Kim
The price is SAR 332
SAR 361 total
includes taxes & fees
9 Feb - 10 Feb
Fairfield Inn & Suites by Marriott Winchester

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1,101 reviews)
"Staff was very friendly and room was great! "
United States
Courtney
The price is SAR 370
SAR 402 total
includes taxes & fees
22 Feb - 23 Feb
Comfort Inn & Suites Winchester
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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.

Beautiful drive up to this plantation. You can take a tour of it as well.
Photo by Stephanie Sutton
Open Photo by Stephanie Sutton

Top Middletown Hotel Reviews

More cheap stays in Middletown

Find out more about Middletown

Top reasons to visit Middletown

  • Outdoor Adventures: Middletown is a haven for outdoor enthusiasts, offering stunning scenery for hiking, skiing, and exploring serene rivers.
  • Local Wineries: Enjoy delightful wine tastings at local wineries, perfect for a relaxing afternoon.
  • Historic Exploration: Discover the rich history of Middletown through its charming downtown and historic houses.
  • Live Entertainment: Experience vibrant entertainment venues featuring live music for a lively night out.
  • Diverse Accommodations: Find a range of lodging options, from cozy motels to pet-friendly hotels, catering to all travelers.

Find great hotels near Middletown

Explore a variety of hotel accommodations in Middletown, Virginia, catering to diverse needs and preferences. Whether you're seeking a pet-friendly stay, a business-friendly atmosphere, or an LGBTQIA-welcoming environment, Middletown offers options for every traveler. From cozy motels to comfortable hotels with suites, you'll find the perfect lodging for your vacation. Don't forget to check out hotel reviews to ensure a pleasant experience.

  • Travelodge by Wyndham Winchester: Located 17.7km from Middletown, Travelodge by Wyndham Winchester offers a welcoming atmosphere for travelers seeking a pet-friendly lodging experience. This motel-style property features convenient amenities tailored for those traveling with pets, including service animal accommodations and specific pet policies. Guests can enjoy spacious rooms that provide a comfortable retreat after a day of exploring the local attractions. Ideal for budget-conscious visitors, this property strikes a balance between affordability and essential comforts.
  • Country Inn & Suites by Radisson, Winchester, VA: Situated 12.9km from Middletown, this charming 3-star hotel is perfect for families, business travelers, and pet lovers alike. Country Inn & Suites by Radisson boasts a cozy ambiance with amenities designed for both relaxation and productivity. Families will appreciate the complimentary cribs and pet-friendly policies, while business travelers can take advantage of convenient workspaces. The hotel also provides a complimentary breakfast to start your day off right, making it an ideal choice for your stay in the area.
  • Holiday Inn Winchester Se-Historic Gateway by IHG: Just 17.7km away from Middletown, the Holiday Inn Winchester Se-Historic Gateway promises a delightful blend of comfort and modern amenities. This 3-star hotel is welcoming to families and the LGBTQIA community, providing a friendly environment for all guests. With services tailored for children, including free cribs, the hotel ensures a seamless stay for families. Business travelers will find the location and facilities conducive for work, while the stylish ambiance and attentive service create a memorable experience for every visitor.

Where to stay near Middletown

Middletown, Virginia, offers a delightful mix of outdoor adventures and rich history. Explore the charming downtown area, where you can enjoy local wineries and family-friendly attractions. Just a short drive away, you’ll find picturesque small towns and vibrant neighborhoods that showcase both scenic beauty and urban energy. Whether you’re looking for a historical journey or a relaxing getaway, Middletown and its surroundings provide the perfect backdrop for an unforgettable vacation.

  • Winchester: Located 19.3km from Middletown, Winchester is a charming city that effortlessly blends history with outdoor adventure. Known for its picturesque scenery, visitors flock here for recreational activities and the stunning landscapes of nearby national parks and lakes. The city is rich in historical significance, with landmarks that tell the story of the Civil War. In the summer months, especially from July to August, Winchester comes alive with festivals and outdoor events, making it an excellent time to explore its vibrant community and local attractions.
  • Front Royal: Just 14.5km away from Middletown, Front Royal serves as the gateway to Shenandoah National Park, making it a top destination for outdoor enthusiasts. With its stunning natural beauty, this city draws visitors year-round, peaking during the warmer months of April, July, and September. Front Royal offers a variety of recreational activities, including skiing and hiking, allowing travelers to immerse themselves in nature. The local parks and lakes provide picturesque backdrops for picnics and relaxation, ensuring a memorable travel experience.
  • Strasburg: A mere 8.0km from Middletown, Strasburg is a delightful city that invites adventure seekers and nature lovers alike. Known for its scenic vistas and outdoor activities, this charming destination is particularly popular in the summer months from June to August. Visitors can enjoy skiing at local ski fields or relax in the abundant parks. Strasburg's proximity to national parks and recreational areas makes it an ideal spot for those looking to explore Virginia's beautiful landscapes while enjoying a friendly small-town atmosphere.

Things to do in and around Middletown

Middletown, Virginia, is an ideal destination for outdoor enthusiasts, offering stunning scenery and exciting adventures. Visitors can enjoy recreational areas, skiing, and beautiful ski fields. Wine tastings are a must, along with various entertainment venues featuring live music. Whether you seek thrilling outdoor spots or relaxing moments in nature, Middletown provides a perfect blend of activities for a memorable vacation experience.

Shopping

In Middletown, visit Shen-Val Farm Market, only 12.9km away, for local produce and handmade goods. Natural Art Garden Center, located 14.5km away, offers beautiful plants and garden decor. If you're up for a drive, check out Apple Blossom Mall, 17.7km away, for a wide range of shopping options.

Recreation

At Jackson's Chase Golf Course, enjoy a round of golf surrounded by beautiful landscapes and outdoor vibes. Just a short drive away, Appleland Sports Center offers wellness and relaxation activities, perfect for rejuvenating your spirit. Meanwhile, Blue Ridge Shadows Golf Club invites you to experience more golfing excitement in a picturesque setting.

Adventure

Embark on the Dickey Ridge Trail for a scenic hike, showcasing the beauty of nature 19.3km from Middletown. Experience thrilling races at Summit Point Motorsports Park, located 35.4km away, and enjoy family-friendly adventures at Yogi Bear's Jellystone Park, situated 40.2km from Middletown.

Nightlife

Experience a vibrant nightlife in Middletown. Catch a show at the Wayside Theater for a mix of romance and culture. Just 19.3km away, Bright Box Theater offers fantastic performances, while the Winchester Little Theater promises an engaging evening filled with entertainment and charm.

*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 from December to February when hotel rates are lower, and aim to book your stay on a Tuesday for the best deals. Utilize Expedia's search tool to filter for budget-friendly accommodations and explore eco-certified hotels. Look for package deals that combine flights, hotels, and activities to maximize savings. Additionally, take advantage of free local attractions and affordable public transport options to further stretch your budget during your visit.

  • 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 enables you to choose your budget, desired location, and additional preferences. You can arrange your search results by price, starting with the most affordable hotels. Additionally, you have the option to refine your selections by hotel type; for instance, by selecting the Eco-certified filter, you’ll discover sustainable and environmentally friendly hotels ready for booking.
  • Consider bundling your trip: You can save money by combining your hotel stay in Middletown with your flights and activities through an Expedia package deal.

Find the best attractions in and around Middletown

Middletown, Virginia, is perfect for outdoor enthusiasts and adventure seekers, offering stunning scenery and a variety of attractions. Visitors can explore local points of interest such as the visitor center, serene rivers, and historic houses. Whether you're looking for cultural experiences or family-friendly activities, Middletown has something for everyone, making it an ideal destination for a memorable vacation.

  • Shenandoah River: Experience the beauty of the Shenandoah River, located 12.9km from Middletown. This stunning river offers outdoor activities like kayaking and fishing, surrounded by picturesque scenery that will leave you in awe.
  • Front Royal Entrance Shenandoah National Park: Just 16.1km away, this visitor center serves as the gateway to adventure. Ideal for families, it provides access to hiking trails and breathtaking views of the Blue Ridge Mountains, perfect for outdoor enthusiasts.
  • Cedar Creek Battlefield Foundation: Situated in Middletown, this historic site immerses you in Civil War history. Explore the rich culture and stories of the battlefield through guided tours and educational exhibits.

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

For your visit to Middletown, Virginia, you can fly into two major airports. Washington Dulles International Airport (IAD) is 72.4km away, with excellent hotel options like the 4-star Hyatt Regency Dulles and The Westin Washington Dulles Airport, both just 1.6km from the airport, offering convenient access. Hilton Washington Dulles Airport is located 3.2km away. Alternatively, Eastern West Virginia Regional Airport (MRB) is 48.3km from Middletown, with nearby accommodations such as the 4-star Hillbrook Inn and the 3-star Hilton Garden Inn Martinsburg, both within 11 and 4.8km, respectively, providing easy access to the airport for travelers.

Frequently asked questions

Where is the best place for a stay in Middletown?
Wayside Inn is a favorite with Expedia customers. This hotel offers free parking and free WiFi. Another top choice for your stay based on traveler reviews is Econo Lodge Inn & Suites Middletown - Winchester South. See all available top hotels, or vacation rentals in Middletown.
What are some of the best vacation home rentals in Middletown?
Secluded River Cabin Getaway (Masten Cabin): Visitors like this Middletown vacation home rental. It is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. 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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