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Middletown Hotels

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Oct 4 - Oct 5
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Our top choices for Middletown hotels

1. Wayside Inn

Wayside Inn
Middletown
United States
Luanne
P4,254
P5,317 total
includes taxes & fees
Oct 19 - Oct 20
Wayside Inn

2. Econo Lodge Inn & Suites Middletown - Winchester South

Econo Lodge Inn & Suites Middletown - Winchester South
Middletown
United States
Nathan
P4,200
P4,633 total
includes taxes & fees
Oct 25 - Oct 26
Econo Lodge Inn & Suites Middletown - Winchester South

3. Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley
Strasburg
United States
Patrick
P7,072
P7,871 total
includes taxes & fees
Nov 1 - Nov 2
Fairfield Inn & Suites Strasburg Shenandoah Valley

4. Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley
Strasburg
United States
CHRISTI
P4,732
P5,267 total
includes taxes & fees
Nov 1 - Nov 2
Ramada by Wyndham Strasburg/Shenandoah Valley

5. Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG
Stephens City
United States
Michael
P5,317
P5,918 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn Express Winchester South-Stephens City by IHG

6. Hampton Inn Front Royal

Hampton Inn Front Royal
Front Royal
United States
Grace
P7,391
P8,226 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn Front Royal

7. DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows
Front Royal
United States
Brian
P7,284
P8,034 total
includes taxes & fees
Nov 1 - Nov 2
DoubleTree by Hilton Front Royal Blue Ridge Shadows

8. Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
Winchester
United States
John
P6,168
P6,865 total
includes taxes & fees
Oct 11 - Oct 12
Comfort Inn & Suites Winchester

9. Quality Inn Stephens City - Winchester South

Quality Inn Stephens City - Winchester South
Stephens City
United States
Nancy
P5,264
P5,859 total
includes taxes & fees
Oct 25 - Oct 26
Quality Inn Stephens City - Winchester South

10. TownePlace Suites by Marriott Front Royal

TownePlace Suites by Marriott Front Royal
Front Royal
United States
Justin
P8,695
P9,715 total
includes taxes & fees
Oct 20 - Oct 21
TownePlace Suites by Marriott Front Royal

11. Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
Winchester
United States
Allen
P5,610
P6,244 total
includes taxes & fees
Oct 25 - Oct 26
Country Inn & Suites by Radisson, Winchester, VA

12. La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
Winchester
United States
Earl
P6,756
P7,519 total
includes taxes & fees
Oct 25 - Oct 26
La Quinta Inn & Suites by Wyndham Winchester

13. Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
Winchester
United States
Dawn
P5,795
P6,450 total
includes taxes & fees
Nov 1 - Nov 2
Fairfield Inn & Suites by Marriott Winchester

14. The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel
Old Town Winchester
United States
Carol
P8,156
P9,240 total
includes taxes & fees
Oct 11 - Oct 12
The George Washington Hotel, A Wyndham Grand Hotel

15. Spark by Hilton Winchester

Spark by Hilton Winchester
Winchester
United States
carrie
P4,838
P5,481 total
includes taxes & fees
Nov 2 - Nov 3
Spark by Hilton Winchester

16. Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
Winchester
United States
Jeffrey
P6,193
P7,080 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn Winchester Se-Historic Gateway by IHG

17. Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
Winchester
United States
Katheryne
P5,755
P6,405 total
includes taxes & fees
Nov 1 - Nov 2
Microtel Inn & Suites by Wyndham Winchester

18. TRU By Hilton Winchester

TRU By Hilton Winchester
Winchester
United States
Kailyn
P5,591
P6,223 total
includes taxes & fees
Nov 1 - Nov 2
TRU By Hilton Winchester

19. Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area
Winchester
United States
Henedina
P6,848
P7,759 total
includes taxes & fees
Oct 25 - Oct 26
Hampton Inn Winchester-University/Mall Area

20. Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
Winchester
United States
John
P6,327
P7,042 total
includes taxes & fees
Oct 18 - Oct 19
Courtyard by Marriott Winchester
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Stay near popular Middletown attractions

Belle Grove Plantation

8.4/10 (8 reviews)
This Jeffersonian-inspired Manor House showcases antebellum plantation life and Civil War history. Explore the heritage apple orchard and original outbuildings while enjoying panoramic mountain views.
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Cedar Creek Battlefield Foundation

8.6/10 (7 reviews)
The Cedar Creek Battlefield Foundation preserves this pivotal 1864 Civil War site through exhibits and trails. Experience history during October's annual reenactment featuring authentic battle scenarios.
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Cedar Creek and Belle Grove National Historical Park

9.0/10 (6 reviews)
Explore the pivotal Civil War battlefield where Union forces secured the Shenandoah Valley in 1864. Tour the elegant Belle Grove Manor House and follow interpretive trails detailing strategic troop movements.
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Jackson's Chase Golf Course

6.0/10 (1 review)
This scenic 18-hole course weaves through the rolling Shenandoah Valley, challenging golfers of all abilities. Enjoy the serene natural setting while navigating its strategically designed par-72 layout.
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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.

See all hotels in Middletown
A large house in a field with a cloudy sky.
Photo by Stephanie Sutton

Top Middletown Hotel Reviews

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

10/10 Excellent
"One of the nicest hotels I’ve ever stayed at. Seems way nicer than you’d expect at of a comfort inn."
Kristen 1-night trip
Posted 10 hours ago
Comfort Inn & Suites Winchester
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

8/10 Good
"Stayed here several times. Clean, good rates and value, never a complaint. The main reason is the really excellent Mexican restaurant attached to the motel. Best Mexican food outside Mexico, try it and see!"
Jonathan 1-night trip
Posted 12 hours ago
Ramada by Wyndham Strasburg/Shenandoah Valley
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

10/10 Excellent
"For the price we could not ask for more......well run hotel.....thanks!"
Jeffrey 1-night trip
Posted 18 hours ago
Holiday Inn Winchester Se-Historic Gateway by IHG
Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

10/10 Excellent
"Very clean, very comfortable beds, generous room good pillow, selection, clean, and roomy bathroom"
John 1-night trip
Posted 22 hours ago
Courtyard by Marriott Winchester
Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

8/10 Good
"The staff is very friendly. The room was clean, comfortable beds. The breakfast could be updated with better pantries. I would stay there again."
Mary Jo 1-night trip
Posted 2 days ago
Country Inn & Suites by Radisson, Winchester, VA
Hampton Inn Front Royal

Hampton Inn Front Royal

10/10 Excellent
"Clean and good breakfast"
Mike 1-night trip
Posted 3 days ago
Hampton Inn Front Royal
Days Inn by Wyndham Winchester

Days Inn by Wyndham Winchester

8/10 Good
"Got in really late Friday night so didnt get to interact with the staff much. great price so I wasn't expecting the Ritz but was surprised by how clean the room was. Would use them again in the future."
JUSTON 2-night trip
Posted 5 days ago
Days Inn by Wyndham Winchester
Wayside Inn

Wayside Inn

10/10 Excellent
"Charmingly beautiful hotel. Like staying in a Civil War museum. Comfortable mattress. Slightly creaky bed. Got to hear the haunted boots on the wooden floor footsteps! Cute coffee shop next door. Will gladly be back!"
Angelica 2-night trip
Posted 7 days ago
Wayside Inn

More cheap stays in Middletown

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

160 Front Royal Pike Winchester VA
P4,441
P4,898 total
Oct 5 - Oct 6
includes taxes & fees
8.6/10 Excellent! (1,073 reviews)
Travelodge by Wyndham Winchester
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

21 Signal Knob Dr Strasburg VA
P4,732
P5,267 total
Nov 1 - Nov 2
includes taxes & fees
8.2/10 Very Good! (1,016 reviews)
Ramada by Wyndham Strasburg/Shenandoah Valley
Quality Inn Winchester

Quality Inn Winchester

1601 Martinsburg Pike Winchester VA
P5,264
P5,859 total
Oct 25 - Oct 26
includes taxes & fees
Quality Inn Winchester
TRU By Hilton Winchester

TRU By Hilton Winchester

118 Mercedes Court Winchester VA
P5,591
P6,223 total
Nov 1 - Nov 2
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
TRU By Hilton Winchester
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

150 Faraday Plaza Winchester VA
P5,755
P6,405 total
Nov 1 - Nov 2
includes taxes & fees
Microtel Inn & Suites by Wyndham Winchester
Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

195 Kernstown Commons Blvd Winchester VA
P6,168
P6,865 total
Oct 11 - Oct 12
includes taxes & fees
9.4/10 Exceptional! (1,134 reviews)
Comfort Inn & Suites Winchester

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?
Based on our traveler data, Wayside Inn is one of the top choices for your stay. This hotel offers a restaurant and free parking. Two other choices for your stay in the area are The George Washington Hotel, A Wyndham Grand Hotel and Travelodge by Wyndham Winchester. See all available top hotels, or vacation rentals in Middletown.
If I need to cancel my hotel reservation in Middletown, will I receive a refund?
Yes, the majority of hotel bookings are fully refundable if you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If you have a reservation that's non-refundable, you might still have the option to cancel and receive a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Middletown.
What's it like to stay in Middletown?
Visitors to Middletown are sure to enjoy the bars and restaurants. Tourists can also enjoy the city's entertainment choices, churches, and theaters. In Middletown, there are 3 hotels and other accommodations to choose from. Find out more about Middletown.
What should I do while I'm visiting Middletown?
The picturesque setting of Shenandoah River and Cedar Creek and Belle Grove National Historical Park exemplify the area's natural beauty. A couple of additional sights to add to your agenda are Belle Grove Plantation and Jackson's Chase Golf Course. Check out what more to see and do in Expedia's Middletown guide.
What's the weather like in Middletown?
The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 36°F. Average annual precipitation for Middletown is 43 inches.

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