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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, (428 reviews)
"Old building but clean and very comfortable. Perfect spot and price."
United States
Caroline
The price is CA $166
CA $196 total
includes taxes & fees
May 10 - May 11
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, (306 reviews)
"Clean rooms"
United States
Robbie
The price is CA $85
CA $93 total
includes taxes & fees
May 19 - May 20
Econo Lodge Inn & Suites Middletown - Winchester South

Relax Inn Motel

Relax Inn Motel
2.0 star property
Front Royal
8.2 out of 10, Very good, (269 reviews)
"On my way back from shenendoah and Luray to dc place was fine "
United States
tara
The price is CA $89
CA $99 total
includes taxes & fees
May 10 - May 11
Relax Inn Motel

Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1,027 reviews)
"Great location, clean rooms and friendly staff."
United States
Daniel
The price is CA $114
CA $129 total
includes taxes & fees
May 31 - Jun 1
Spark by Hilton Winchester

Super 8 by Wyndham Front Royal Near Shenandoah National Park

Super 8 by Wyndham Front Royal Near Shenandoah National Park
2.0 star property
Front Royal
7.6 out of 10, Good, (1,004 reviews)
"Location is right across the road from Spelunker's, the best casual restaurant in Virginia."
United States
Rachel
The price is CA $100
CA $111 total
includes taxes & fees
May 10 - May 11
Super 8 by Wyndham Front Royal Near Shenandoah National Park

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester
2.5 star property
Winchester
8.6 out of 10, Excellent, (1,058 reviews)
"Very clean and great rates will stay again if in the area "
United States
Cindi
The price is CA $97
CA $105 total
includes taxes & fees
May 12 - May 13
Travelodge by Wyndham Winchester

Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
2.5 star property
Winchester
9.2 out of 10, Wonderful, (888 reviews)
"Location was excellent"
United States
Jennie
The price is CA $146
CA $166 total
includes taxes & fees
May 25 - May 26
Hampton Inn Winchester N/Conference Center, VA

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (851 reviews)
"great rooms!"
United States
Justine Patrick E.F.
The price is CA $126
CA $137 total
includes taxes & fees
May 24 - May 25
Fairfield Inn & Suites by Marriott 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, (1,002 reviews)
"Staff are so nice and everything was good"
United States
Osama
The price is CA $128
CA $140 total
includes taxes & fees
Jun 8 - Jun 9
Country Inn & Suites by Radisson, Winchester, VA

Blue Ridge Motel

Blue Ridge Motel
2.0 star property
Front Royal
7.0 out of 10, Good, (134 reviews)
"Great lady that works there had a great time thanks again !!! Definitely will be back "
United States
William
The price is CA $80
CA $89 total
includes taxes & fees
May 10 - May 11
Blue Ridge Motel

Motel 6 Winchester, VA

Motel 6 Winchester, VA
2.0 star property
Winchester
8.0 out of 10, Very good, (1,004 reviews)
"Very good and convenient budget motel in Winchester, happy to recommend."
United States
Jane
The price is CA $93
CA $105 total
includes taxes & fees
May 10 - May 11
Motel 6 Winchester, VA

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1,108 reviews)
"Neat place and excellent stay"
United States
Anoop
The price is CA $142
CA $155 total
includes taxes & fees
Jun 8 - Jun 9
Comfort Inn & Suites Winchester

Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (972 reviews)
"Beautiful hotel!"
United States
David
The price is CA $146
CA $159 total
includes taxes & fees
May 19 - May 20
Courtyard by Marriott Winchester

Twi-Lite Inn

Twi-Lite Inn
2.0 star property
Front Royal
8.2 out of 10, Very good, (552 reviews)
"Great location and clean room! Would stay again"
United States
Brent
The price is CA $115
CA $127 total
includes taxes & fees
May 12 - May 13
Twi-Lite Inn

TownePlace Suites by Marriott Winchester

TownePlace Suites by Marriott Winchester
3.0 star property
Winchester
8.8 out of 10, Excellent, (500 reviews)
"IMO the breakfast buffet should be available later than 09:30am on the weekend."
United States
Anthony
The price is CA $154
CA $168 total
includes taxes & fees
May 10 - May 11
TownePlace Suites by Marriott Winchester

Quality Inn Winchester

Quality Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,006 reviews)
"Great breakfast. Very clean. Parking was safe and easy. Staff was excellent!"
United States
Diane
The price is CA $122
CA $133 total
includes taxes & fees
May 25 - May 26
Quality Inn Winchester

Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
Front Royal
9.0 out of 10, Wonderful, (1,006 reviews)
"Friendly staff clean and comfy"
United Kingdom
Helen
The price is CA $172
CA $191 total
includes taxes & fees
May 17 - May 18
Hampton Inn Front Royal

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (850 reviews)
"Great visit! "
United States
Susan
The price is CA $155
CA $168 total
includes taxes & fees
May 26 - May 27
SpringHill Suites by Marriott Winchester

Candlewood Suites Winchester by IHG

Candlewood Suites Winchester by IHG
2.5 star property
Winchester
8.8 out of 10, Excellent, (576 reviews)
"Very comfortable stay"
United States
Jane
The price is CA $120
CA $131 total
includes taxes & fees
May 10 - May 11
Candlewood Suites Winchester by IHG

TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
Winchester
9.0 out of 10, Wonderful, (840 reviews)
"the room was nice as was the breakfast"
United States
Evan
The price is CA $155
CA $169 total
includes taxes & fees
May 24 - May 25
TRU By Hilton 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.

Photo by Stephanie Sutton
Open Photo by Stephanie Sutton

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Find out more about Middletown

Top reasons to visit Middletown

  • Outdoor Adventures: Middletown offers stunning scenery and a variety of activities for outdoor enthusiasts, including hiking, skiing, and exploring beautiful rivers.
  • Charming Atmosphere: Experience the small-town charm with family-friendly neighbourhoods, perfect for relaxation and exploration.
  • Cultural Experiences: Discover local cultural attractions and community events that enrich your visit.
  • Convenient Accommodations: A range of welcoming options, from pet-friendly motels to business hotels, cater to all travellers.
  • Nearby Attractions: Ideal for day trips, Middletown provides easy access to local shopping centres and other exciting destinations.

Find great hotels near Middletown

Explore a range of welcoming accommodations in Middletown, Virginia, ideal for every traveller. From pet-friendly motels to business-themed hotels, you'll find options that cater to diverse needs, including LGBTQIA-friendly facilities. Whether you're seeking a cozy stay or the best hotels in town, Middletown has something to offer for everyone looking to enjoy a memorable vacation experience.

  • Travelodge by Wyndham Winchester: Nestled 17.7km from Middletown, Travelodge by Wyndham Winchester is a charming motel that caters to pet lovers seeking a relaxed getaway. With a pet-friendly policy, guests can enjoy the convenience of travelling with their furry companions. The motel features essential amenities, ensuring a comfortable stay for all. The property’s welcoming atmosphere and emphasis on accessibility make it an ideal choice for those looking for a simple yet enjoyable lodging experience.
  • Country Inn & Suites by Radisson, Winchester, VA: Located 12.9km from Middletown, this cozy 3-star hotel offers a family-friendly atmosphere combined with excellent business amenities. Country Inn & Suites is perfect for both leisure and corporate travellers, featuring accessible business centres, meeting rooms, and a 24-hour conference space. Families can take advantage of complimentary cribs, while pets are also welcome, making it a home away from home. Guests can expect a warm environment complemented by friendly service, ensuring a memorable stay for everyone.
  • Holiday Inn Winchester Se-Historic Gateway by IHG: Just 17.7km from Middletown, the Holiday Inn Winchester Se-Historic Gateway stands out for its commitment to inclusivity and comfort. This 3-star hotel is LGBTQIA welcoming and provides a range of business facilities, including accessible meeting spaces and a dedicated business centre. Families will appreciate the availability of complimentary cribs, making it suitable for guests of all ages. With its modern amenities and friendly atmosphere, this hotel ensures a pleasant and accommodating experience for all visitors.

Where to stay near Middletown

Middletown, Virginia offers a delightful blend of outdoor adventures and rich history, making it an ideal vacation spot for Canadian travellers. Explore the charming small town atmosphere, with its scenic views and family-friendly neighbourhoods. Venture into the city center for a taste of urban life, while enjoying the beauty of the surrounding areas. Don't miss the colder months, when Middletown showcases its unique charm, perfect for memorable experiences.

  • Winchester: Located 19.3km from Middletown, Winchester is a charming city known for its rich history and outdoor adventures. Visitors can immerse themselves in the scenic beauty of nearby national parks and recreational areas. Peak tourist seasons occur in June to July and October when the area's vibrant atmosphere comes alive. Popular activities include skiing, exploring local landmarks, and enjoying the natural landscape around lakes and parks. Winchester offers a blend of education and adventure, making it an ideal spot for outdoor enthusiasts.
  • Front Royal: Just 14.5km away from Middletown, Front Royal is a gateway to outdoor adventures and stunning scenery. With its peak visitor numbers in April, July, and September, this city attracts nature lovers year-round. Front Royal is perfect for those looking to explore national parks and recreational areas, or enjoy skiing in the winter months. The town’s proximity to numerous parks enhances the travel experience, providing ample opportunities for hiking, picnicking, and enjoying the great outdoors.
  • Strasburg: Situated a mere 8.0km from Middletown, Strasburg is a delightful city that captures the essence of outdoor adventure. With peak arrivals in June to August, it offers visitors a chance to embrace the beauty of nature. Activities such as skiing and exploring recreational areas are popular here, set against the backdrop of national parks and tranquil parks. Strasburg’s close-knit community and scenic landscapes make it a perfect stop for anyone looking to unwind and experience the great outdoors.

Things to do in and around Middletown

Middletown, Virginia, is perfect for outdoor enthusiasts and adventure seekers, offering stunning scenery and various activities. Visitors can enjoy recreational areas, educational experiences, and even skiing. For day trips, explore nearby attractions and local shopping centres, making it an ideal destination for a well-rounded vacation. Whether you're seeking relaxation or adventure, Middletown has something to offer everyone.

Shopping

In Middletown, visit Shen-Val Farm Market for local produce and unique gifts, only 12.9km away. Natural Art Garden Center, 14.5km from town, offers beautiful plants and garden decor. If you're up for a drive, check out Apple Blossom Mall, located 17.7km away, for a wider shopping selection.

Recreation

At Jackson's Chase Golf Course, enjoy a round of golf amidst scenic landscapes, perfect for sports enthusiasts. Just 9.7km away, Blue Ridge Shadows Golf Club offers a similar outdoor experience. For wellness, visit Appleland Sports Center, 11.3km from Middletown, where relaxation and rejuvenation await.

Adventure

Embark on the Dickey Ridge Trail, a scenic hiking experience located 19.3km from Middletown, perfect for outdoor enthusiasts. For adrenaline seekers, the Summit Point Motorsports Park, 35.4km away, offers thrilling motor racing. Alternatively, enjoy family-friendly adventures at Watermelon Park Campground, situated 30.6km from town.

Nightlife

Experience the vibrant nightlife in Middletown by catching a show at the Wayside Theater, where culture and entertainment thrive. For a bit more adventure, head to the Bright Box Theater or Winchester Little Theater, both offering captivating performances just a short drive away.

*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 during your trip to Middletown, Virginia, consider visiting between December and February, when accommodation prices are lower. Tuesdays are the most affordable days to stay, while Saturdays are the priciest. Use Expedia to refine your preferences and find eco-friendly hotels, sorting by price for the best deals. You can also save by bundling your hotel, flights, and activities into one package. Exploring local parks and attractions can offer free or low-cost activities, making your vacation enjoyable 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 the type of accommodation you prefer. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels currently available. 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 reservation with your flights and activities through an Expedia package.

Find the best attractions in and around Middletown

Middletown, Virginia, is an ideal destination for those seeking outdoor adventures and scenic beauty. Visitors can explore various points of interest, including local visitor centres and the beautiful rivers in the area. This charming town offers cultural experiences and family-friendly activities, ensuring a memorable vacation for all types of travellers looking to immerse themselves in nature and community.

  • Shenandoah River: Experience the serene beauty of the Shenandoah River, located a mere 12.9km from Middletown. Enjoy stunning scenery and outdoor activities like kayaking, fishing, or leisurely picnicking along the banks, making it perfect for nature lovers.
  • Front Royal Entrance Shenandoah National Park: Just 16.1km away, this visitor centre offers a gateway to adventure in Shenandoah National Park. Families can explore hiking trails, scenic views, and wildlife encounters, making it an ideal spot for outdoor enthusiasts.
  • Cedar Creek Battlefield Foundation: Situated in Middletown, this historic site immerses visitors in the rich culture and history of the Civil War. Explore informative exhibits and guided tours that bring the past to life.

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

When visiting Middletown, Virginia, you can fly into two major airports. Washington Dulles International Airport (IAD) is situated 72.4km away. Nearby hotel options include the 4-star Hyatt Regency Dulles, located 1.6km from the airport, as well as the Hilton Washington Dulles Airport, which is 3.2km away. Eastern West Virginia Regional Airport (MRB) is 48.3km from Middletown, with accommodations like the 4-star Hillbrook Inn and the 3-star Home2 Suites by Hilton Martinsburg, both situated approximately 11.6kms and 4.8km from the airport, respectively. Each hotel offers convenient access to its respective airport, ensuring a smooth start to your vacation.

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. Find more child-friendly accommodations in Middletown
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. See more pet-friendly hotels in Middletown
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. View all budget hotels in Middletown
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. See all romantic hotels in Middletown
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, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 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 Middletown hotel booking with Expedia?
Members always get our best prices. Find our best Middletown hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Middletown hotel?
Prices for hotels in Middletown often vary, but you can find a great deal from CA $83 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 the cheapest rate.

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