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, (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 P4,166
P5,173 total
includes taxes & fees
Mar 1 - Mar 2
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 P3,593
P3,963 total
includes taxes & fees
Feb 26 - Feb 27
Econo Lodge Inn & Suites Middletown - Winchester South

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, (1,000 reviews)
"The staff was friendly and attentive. The room was clean. The breakfast was good, with pancakes, toast, cereal, juice, and coffee. Good location for visiting Shenandoah National Park."
United States
Teresa
The price is P3,587
P3,993 total
includes taxes & fees
Feb 21 - Feb 22
Super 8 by Wyndham Front Royal Near Shenandoah National Park

Comfort Inn Woodstock Shenandoah

Comfort Inn Woodstock Shenandoah
2.5 star property
Woodstock
8.8 out of 10, Excellent, (1,001 reviews)
"The staff was helpful and the room was comfortable."
United States
Joseph
The price is P5,156
P5,790 total
includes taxes & fees
Feb 23 - Feb 24
Comfort Inn Woodstock Shenandoah

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (820 reviews)
"We stay here a lot and it is always consistently clean and service is great. "
United States
Kim
The price is P5,361
P5,833 total
includes taxes & fees
Feb 23 - Feb 24
Fairfield Inn & Suites by Marriott Winchester

Quality Inn Winchester

Quality Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,000 reviews)
"Great stay, as usual"
United States
Mary
The price is P4,869
P5,298 total
includes taxes & fees
Feb 26 - Feb 27
Quality Inn Winchester

Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1,002 reviews)
"Rooms was clean, staff friendly all in all great place to stay for price close to all we needed and cozy "
United States
Frederick
The price is P4,934
P5,591 total
includes taxes & fees
Feb 26 - Feb 27
Spark by Hilton 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)
"Courteous staff, clean room. Nice to have free breakfast available."
Canada
Mary
The price is P5,009
P5,449 total
includes taxes & fees
Feb 25 - Feb 26
Country Inn & Suites by Radisson, Winchester, VA

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester
2.5 star property
Winchester
8.6 out of 10, Excellent, (1,086 reviews)
"Clean place, breakfast ok, warm and comfy, would stay again"
United States
Lyle
The price is P4,108
P4,470 total
includes taxes & fees
Feb 20 - Feb 21
Travelodge by Wyndham 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, (1,001 reviews)
"Awesome hotel, highly recommend. Great staff!"
United States
WILLIAM
The price is P4,513
P5,084 total
includes taxes & fees
Mar 22 - Mar 23
Holiday Inn Winchester Se-Historic Gateway by IHG

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 P5,772
P6,280 total
includes taxes & fees
Feb 23 - Feb 24
Comfort Inn & Suites Winchester

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, (2,265 reviews)
"Very Friendly staff and clean rooms! "
United States
Kayla
The price is P6,102
P6,638 total
includes taxes & fees
Feb 23 - Feb 24
La Quinta Inn & Suites 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, (863 reviews)
"The staff was wonderful! "
United States
Jayne
The price is P6,121
P6,935 total
includes taxes & fees
Feb 25 - Feb 26
Hampton Inn Winchester N/Conference Center, 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, (823 reviews)
"The room was spotless, staff is excellent. Well, recommend the stay to everyone I know"
United States
Kelso
The price is P4,583
P4,986 total
includes taxes & fees
Feb 22 - Feb 23
Holiday Inn Express Winchester South-Stephens City by IHG

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 P4,427
P4,927 total
includes taxes & fees
Mar 13 - Mar 14
Ramada by Wyndham Strasburg/Shenandoah Valley

Relax Inn Motel

Relax Inn Motel
2.0 star property
Front Royal
8.2 out of 10, Very Good, (260 reviews)
"Clean, and nice rooms, friendly staff"
United States
James
The price is P3,594
P4,000 total
includes taxes & fees
Feb 20 - Feb 21
Relax Inn Motel

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (812 reviews)
"Great stay!"
United States
Rene
The price is P6,197
P6,742 total
includes taxes & fees
Mar 1 - Mar 2
SpringHill Suites by Marriott Winchester

TownePlace Suites by Marriott Winchester

TownePlace Suites by Marriott Winchester
3.0 star property
Winchester
8.8 out of 10, Excellent, (488 reviews)
"Nice place to stay. Great staff and breakfast."
United States
Stormy
The price is P6,541
P7,117 total
includes taxes & fees
Feb 22 - Feb 23
TownePlace Suites by Marriott Winchester

Twi-Lite Inn

Twi-Lite Inn
2.0 star property
Front Royal
8.2 out of 10, Very Good, (545 reviews)
"Clean, comfortable room. Staff was nice and I really enjoyed my stay. Motel was in a high traffic area, but still a quiet stay"
United States
Daniel
The price is P3,587
P3,993 total
includes taxes & fees
Feb 21 - Feb 22
Twi-Lite Inn

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 P3,934
P4,457 total
includes taxes & fees
Feb 22 - Feb 23
Motel 6 Winchester, VA
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Stay near popular Middletown attractions

Learn more about Middletown

History buffs can explore the Cedar Creek Battlefield and Belle Grove Plantation, where costumed interpreters bring Civil War stories to life. Visit the Wayside Inn, Virginia's oldest continuously operating inn, and ask locals about hidden hiking trails in nearby Shenandoah Valley.

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 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. Additionally, you might want to add Jackson's Chase Golf Course to your itinerary. 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.