Photo by Samantha Keyes

Middletown Hotels

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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, (419)
"Historic inn. "
United States
Anonymous traveler
The price is P4,238
P5,263 total
includes taxes & fees
Jan 6 - Jan 7
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)
Situated near Wayside Theater and Cedar Creek National Historical Park, this hotel offers complimentary WiFi and parking. The 24-hour front desk ensures your needs are met anytime during your stay in this convenient Middletown location.

"I loved staying here!"
United States
Whitney
The price is P3,655
P4,032 total
includes taxes & fees
Jan 11 - Jan 12
Econo Lodge Inn & Suites Middletown - Winchester South

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, (2246)
Located near Apple Blossom Mall and R-C Track, this hotel offers comfortable beds praised by travelers. Enjoy complimentary breakfast, WiFi, and parking while business amenities and helpful staff ensure a pleasant stay.

"Staff is very pleasant and personable. "
United States
Julie
The price is P5,816
P6,327 total
includes taxes & fees
Jan 7 - Jan 8
La Quinta Inn & Suites by Wyndham Winchester

Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley
2.5 star property
Strasburg
8.4 out of 10, Very Good, (1008)
Savor Civil War history at this Strasburg retreat with fitness center and restaurant. Located near Hupp's Hill Civil War Park and Strasburg Museum, this hotel offers complimentary breakfast, WiFi, and parking that guests consistently praise.

"The complimentary breakfast was good. But the authentic Mexican restaurant on the premises was awesome."
United States
Robert
The price is P4,303
P4,789 total
includes taxes & fees
Jan 13 - Jan 14
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, (782)
Minutes from Rutherford Crossing, this modern hotel features an inviting indoor pool and health club. Fuel your adventures with free breakfast before exploring nearby Star Fort Civil War Battlefield with helpful staff recommendations.

"Clean rooms, courteous staff"
United States
Holly
The price is P4,360
P4,744 total
includes taxes & fees
Jan 26 - Jan 27
TRU By Hilton Winchester

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1423)
Enjoy a comfortable stay at this Winchester hotel with an indoor pool and fitness center. Clean rooms feature cozy beds, while free breakfast, WiFi, and parking add value. Nearby attractions include Rutherford Crossing and Northside Station Shopping Center.

"Clean room and bathroom, friendly staff, helpful."
United States
Thomas
The price is P4,662
P5,072 total
includes taxes & fees
Jan 13 - Jan 14
Microtel Inn & Suites by Wyndham Winchester

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1099)
Near Appleland Sports Center and Kernstown Battlefield, this hotel offers a 24-hour fitness center and complimentary WiFi. Guests praise the comfortable beds, helpful staff, and daily breakfast served from 6:00 AM on weekdays.

"We have stayed here many times on our way to Massachusetts and find it perfect every time."
United States
Patsy
The price is P5,684
P6,184 total
includes taxes & fees
Jan 25 - Jan 26
Comfort Inn & Suites Winchester

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, (1003)
Scenic Front Royal hotel with an 18-hole golf course just 15 minutes from Shenandoah National Park. Unwind in the indoor pool after a day outdoors, enjoy American cuisine at Houlihan's Restaurant, or relax at the bar. Free WiFi and parking add convenience.

"Clean rooms and property. Staff was amazing. Hot tub and pool area were great and clean. Very comfortable stay. Only issue was shower was very slow to drain but confident staff will fix it for next"
United States
Edward
The price is P5,744
P6,335 total
includes taxes & fees
Jan 11 - Jan 12
DoubleTree by Hilton Front Royal Blue Ridge Shadows

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, (1007)
"Clean efficient room with good front desk service. Convienence to Highway 81 and eateries."
United States
Chris
The price is P4,886
P5,315 total
includes taxes & fees
Feb 1 - Feb 2
Country Inn & Suites by Radisson, Winchester, VA

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (794)
Experience comfort at this Winchester hotel with a 24-hour fitness center and inviting indoor pool. Near Rutherford Crossing and Frederick County Fairgrounds, guests enjoy free breakfast, WiFi, and parking with attentive staff service.

"Great stay!"
United States
Rene
The price is P6,304
P6,859 total
includes taxes & fees
Jan 18 - Jan 19
SpringHill Suites by Marriott Winchester

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, (1001)
Refresh in the indoor pool at this Winchester hotel after shopping at nearby Apple Blossom Mall. Comfortable beds, refrigerators and microwaves await in each room, with Kems Restaurant and a bar for evening relaxation.

"Great room cozy bed fabulous restaurant great staff on property"
United States
joyce
The price is P4,827
P5,428 total
includes taxes & fees
Jan 25 - Jan 26
Holiday Inn Winchester Se-Historic Gateway by IHG

Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1004)
This quiet hotel offers complimentary continental breakfast and self parking, along with convenient access to Abram's Delight and Apple Blossom Mall. Comfortable rooms and helpful staff ensure a pleasant stay near restaurants, shopping, and highways.

"Enjoyable stay! Courteous staff. Great location central to everything. "
United States
Octavia
The price is P4,537
P5,141 total
includes taxes & fees
Jan 25 - Jan 26
Spark by Hilton Winchester

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, (1011)
Relish this Winchester hotel's Georgian charm, with an indoor pool, full-service spa, and 2 restaurants including Uno's Pizzeria for dinner. The 24-hour fitness center complements the prime location near Old Court House Civil War Museum and Bright Box Theater.

"Great hotel!"
United States
CHARLES
The price is P7,455
P8,446 total
includes taxes & fees
Jan 11 - Jan 12
The George Washington Hotel, A Wyndham Grand Hotel

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, (1001)
Minutes from Shenandoah National Park, this Front Royal hotel offers complimentary WiFi and daily on-the-go breakfast. Guests appreciate the helpful staff and clean rooms. Blue Ridge Arts Council is nearby.

"Good condition "
United States
Phillip
The price is P3,649
P4,062 total
includes taxes & fees
Jan 6 - Jan 7
Super 8 by Wyndham Front Royal Near Shenandoah National Park

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
2.5 star property
Winchester
9.0 out of 10, Wonderful, (810)
This business-friendly hotel sits near Apple Blossom Mall and Abram's Delight. Energize in the fitness center or indoor pool before exploring. Guests rave about the helpful staff and complimentary breakfast, WiFi and parking.

"We stay here a lot and it is always consistently clean and service is great. "
United States
Kim
The price is P5,303
P5,770 total
includes taxes & fees
Jan 7 - Jan 8
Fairfield Inn & Suites by Marriott Winchester

Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
Front Royal
9.0 out of 10, Wonderful, (1005)
Just 15 minutes from Shenandoah National Park, this hotel offers 24-hour fitness facilities and an indoor pool. Guests love the helpful staff, free breakfast, WiFi, and parking, with Shenandoah River nearby.

"Room was spotless, place was quiet and our welcome at the desk was perfect"
United States
Merrill
The price is P6,709
P7,467 total
includes taxes & fees
Jan 11 - Jan 12
Hampton Inn Front Royal

Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University
2.5 star property
Winchester
7.8 out of 10, Good, (1005)
Modern hotel with a convenient location near Apple Blossom Mall and Abram's Delight. Enjoy a complimentary full breakfast, free WiFi, and parking. The fitness center adds value while helpful staff ensure a pleasant stay for business travelers.

"great stay with breakfast too"
United States
James
The price is P4,253
P4,627 total
includes taxes & fees
Jan 26 - Jan 27
Sleep Inn & Suites Winchester near University

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester
2.5 star property
Winchester
8.6 out of 10, Excellent, (1084)
This welcoming motel offers free WiFi and parking with clean, comfortable rooms. Guests praise the helpful staff and quiet atmosphere despite the highway location. Explore nearby shopping and restaurants or take a day trip to Martinsburg.

"Hotels well Located off 81 for a nice pull Off and overnight stay. Staff is friendly and helpful and rooms comfortable and quiet. "
United States
Stefanie
The price is P4,003
P4,355 total
includes taxes & fees
Feb 1 - Feb 2
Travelodge by Wyndham Winchester

Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG
2.5 star property
Stephens City
8.2 out of 10, Very Good, (810)
"Clean room, nice staff, simple but good breakfast, fresh ground coffee machine was really nice. "
United States
Rose
The price is P4,356
P4,739 total
includes taxes & fees
Jan 11 - Jan 12
Holiday Inn Express Winchester South-Stephens City by IHG

Quality Inn Winchester

Quality Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1006)
"Great stay, as usual"
United States
Mary
The price is P4,565
P4,967 total
includes taxes & fees
Jan 18 - Jan 19
Quality Inn 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.

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

Find out more about Middletown

Top reasons to visit Middletown

  • Outdoor Adventures: Middletown is perfect for outdoor enthusiasts, offering activities like skiing and scenic hikes.
  • Local Wineries: Discover charming local wineries that provide delightful wine tastings in a picturesque setting.
  • Historical Attractions: Explore historic houses and a visitor centre, rich in cultural experiences.
  • Quaint Downtown: Stroll through the quaint downtown area, featuring unique shops and local eateries.
  • Diverse Accommodation: Enjoy a range of lodging options, from charming motels to pet-friendly hotels.

Find great hotels near Middletown

Explore a range of hotel accommodation options in Middletown, Virginia, catering to diverse preferences. From charming motels to comfortable hotels, you'll find pet-friendly establishments and those welcoming LGBTQIA travellers. Ideal for both leisure and business visits, Middletown offers a selection of suites and well-reviewed options to ensure a pleasant stay. Whether you're seeking the best hotels or convenient amenities, this quaint town has something for everyone.

  • Country Inn & Suites by Radisson, Winchester, VA: Experience a warm and inviting atmosphere at the Country Inn & Suites by Radisson, Winchester. Located 12.9km from Middletown, this 3-star hotel is perfect for families and pets alike, offering a comfortable retreat for both leisure and business travellers. The hotel features free cribs for children and has a pet-friendly policy, making it ideal for those travelling with furry companions. Guests can enjoy convenient amenities like complimentary breakfast, free Wi-Fi, and a fitness centre, ensuring a delightful stay for all.
  • Holiday Inn Winchester Se-Historic Gateway by IHG: Situated 17.7km from Middletown, the Holiday Inn Winchester Se-Historic Gateway is a 3-star establishment that embraces inclusivity and family values. This hotel is LGBTQIA welcoming and caters to both business and leisure visitors. Families will appreciate the availability of free cribs, while all guests can enjoy an on-site restaurant, a fitness centre, and a refreshing outdoor pool. Its strategic location offers easy access to historic sites, making it a great choice for those looking to explore the area.
  • DoubleTree by Hilton Front Royal Blue Ridge Shadows: Nestled just 9.7km from Middletown, the DoubleTree by Hilton Front Royal Blue Ridge Shadows is a luxurious 4-star hotel that combines elegance with family-friendly amenities. This property is also LGBTQIA welcoming, ensuring a comfortable atmosphere for all guests. Families will appreciate the availability of free cribs, while business travellers can take advantage of well-equipped meeting spaces. Guests can indulge in the hotel's fine dining options, relax by the outdoor pool, or enjoy the picturesque views of the Blue Ridge Mountains during their stay.

Where to stay near Middletown

Middletown, Virginia, offers a delightful blend of outdoor adventures and historical charm. Visitors can explore the quaint downtown area, discover local wineries, and relish the family-friendly atmosphere. The surrounding regions provide stunning scenery and a vibrant urban vibe, making it an ideal destination for those seeking both relaxation and exploration. Whether wandering through the city centre or enjoying the quaintness of nearby small towns, Middletown promises a memorable travel experience.

  • Winchester: Located a mere 19.3km from Middletown, Winchester is a vibrant city that enchants visitors with its rich history and stunning outdoor landscapes. Known for its outdoor adventures, this city offers a plethora of recreational areas and educational venues. Nature enthusiasts will delight in the nearby national and state parks, while those seeking fun in the winter can enjoy skiing at local resorts. The peak visiting months are July to August and October, offering a lively atmosphere filled with activities that showcase the area's scenic beauty.
  • Front Royal: Just 14.5km from Middletown, Front Royal is a charming city that serves as a gateway to the Shenandoah National Park. This city is a haven for those looking for outdoor adventures and picturesque scenery. Visitors can explore various recreational areas and ski resorts, making it an ideal spot for both summer hiking and winter sports enthusiasts. Front Royal sees a surge in visitors during April, July, and September, ensuring an exciting experience for everyone who visits.
  • Strasburg: A quaint city located 8.0km away from Middletown, Strasburg is perfect for those who crave outdoor exploration and adventure. With a backdrop of stunning landscapes, recreational areas, and ski fields, there's no shortage of activities to enjoy. The city experiences a peak in visitors from June to August, allowing guests to immerse themselves in the vibrant local culture and natural beauty, including nearby parks and state parks that enhance the area's charm.

Things to do in and around Middletown

Middletown, Virginia, is an ideal destination for those seeking outdoor adventures and stunning scenery. Visitors can enjoy a variety of activities, including wine tastings, live music, and entertainment at local venues. The area's recreational options, such as skiing and exploring outdoor spots, provide a perfect backdrop for an enjoyable holiday. Whether you're looking for relaxation or excitement, Middletown offers a delightful blend of activities for every traveller.

Shopping

For shopping in Middletown, visit Shen-Val Farm Market for local produce and gifts, just 12.9km away. If you're up for a drive, head to Apple Blossom Mall, 17.7km away, for a variety of shops and entertainment options, or explore Eastgate Plaza Shopping Center, 20.9km away.

Recreation

Jackson's Chase Golf Course offers a scenic golfing experience with vibrant outdoor vibes, perfect for relaxation and sport. Nearby, Appleland Sports Center provides a tranquil setting for wellness activities, while Shenandoah Valley Golf Club combines stunning views with invigorating play, all just a short drive from Middletown.

Adventure

Experience the thrill of motor racing at Summit Point Motorsports Park, located 35.4km from Middletown, where adrenaline meets speed. For a scenic hike, explore Mary's Rock Summit Trailhead, 41.8km away, offering breathtaking views and a chance to connect with nature. Enjoy family camping adventures at Yogi Bear's Jellystone Park, situated 40.2km from Middletown.

Nightlife

Middletown boasts a vibrant nightlife with venues like the Wayside Theater, offering a blend of romance and culture. Nearby, the Bright Box Theater and Winchester Little Theater also provide captivating performances, creating an enchanting atmosphere for a delightful evening out.

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

Booking tips and Expedia advantages for Middletown

For a budget-friendly visit to Middletown, consider travelling between December and February when prices are lower. Tuesdays offer the best hotel rates, while Saturdays are the most expensive. Use Expedia to refine your search by budget and preferences, and consider eco-certified hotels for sustainable options. Additionally, package deals combining hotels, flights, and activities can lead to significant savings. Explore free local attractions and utilise public transport to minimise expenses, ensuring a memorable yet economical trip.

  • 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: Utilise Expedia’s search tool to refine your preferences, such as your budget, preferred location, and the type of hotel you desire. For instance, selecting the Eco-certified filter will showcase sustainable and eco-friendly hotels currently available. To discover 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 hotel booking in Middletown with your flights and activities through an Expedia package.

Find the best attractions near Middletown

Middletown, Virginia, is an ideal destination for those seeking outdoor adventures and picturesque scenery. Visitors can explore a variety of attractions, including a visitor centre, rivers, and historic houses, all of which provide enriching cultural and family experiences. Whether you’re keen on immersing yourself in history or enjoying the beauty of nature, Middletown offers a delightful mix of activities for every traveller.

  • Front Royal Entrance Shenandoah National Park: This welcoming visitor centre, located 16.1km from Middletown, offers an immersive outdoor experience with family-friendly activities, stunning vistas, and adventurous trails, perfect for nature enthusiasts.
  • Abrams Creek Wetlands Preserve: Situated 17.7km away, this eco-friendly nature reserve is a haven for wildlife and outdoor lovers, featuring serene trails and diverse ecosystems that invite exploration and adventure.
  • Shenandoah River: Just 12.9km from Middletown, the picturesque Shenandoah River provides breathtaking scenery and opportunities for kayaking, fishing, or simply enjoying the tranquil surroundings amidst nature.

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

If you are planning to visit Middletown, Virginia, you have a couple of major airports to choose from. Washington Dulles International Airport (IAD) is approximately 72.4km away, with nearby hotel options such as the 4-star Hyatt Regency Dulles and The Westin Washington Dulles Airport, both just 1.6km from the airport. Another option is Martinsburg, WV (MRB), located 48.3km from Middletown, where you can find accommodations like the 3.5-star Carriage Inn B&B, situated 11.6kms from MRB, and Home2 Suites by Hilton Martinsburg, 4.8km away. Each of these hotels offers convenient access to their respective airports.

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.
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.
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.