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Our top choices for Middletown hotels

1. Wayside Inn

Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (443 reviews)
"Nice historic place"
United States
Donna
The price is AU$206
includes taxes & fees
28 July - 29 July
Wayside Inn

2. Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1,144 reviews)
"Clean room, quiet and Good breakfast"
United States
Richard
The price is AU$157
includes taxes & fees
23 Aug - 24 Aug
Comfort Inn & Suites Winchester

3. 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, (1,005 reviews)
"Always clean and a friendly staff. Breakfast is okay, nothing special, but one of my favorite hotels in the Winchester area."
United States
Josh
The price is AU$139
includes taxes & fees
9 Aug - 10 Aug
Country Inn & Suites by Radisson, Winchester, VA

4. Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
Front Royal
9.2 out of 10, Wonderful, (1,006 reviews)
"Nice room, good breakfast and pool"
United States
Gisely
The price is AU$208
includes taxes & fees
11 Aug - 12 Aug
Hampton Inn Front Royal

5. Quality Inn Winchester

Quality Inn Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1,006 reviews)
"Dated property, but reasonable rates and great staff."
United States
John
The price is AU$162
includes taxes & fees
18 Aug - 19 Aug
Quality Inn Winchester

6. Econo Lodge Inn & Suites Middletown - Winchester South

Econo Lodge Inn & Suites Middletown - Winchester South
2.0 star property
Middletown
5.8 out of 10, (325 reviews)
"Not a bad place if you need a bed to sleep in. "
United States
Nathan
The price is AU$102
includes taxes & fees
17 Aug - 18 Aug
Econo Lodge Inn & Suites Middletown - Winchester South

7. 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, (2,275 reviews)
"It was very quiet and clean, great place to stay!"
United States
Wendy
The price is AU$174
includes taxes & fees
30 July - 31 July
La Quinta Inn & Suites by Wyndham Winchester

8. 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, (877 reviews)
"Very nice good breakfast too!"
United States
Steven
The price is AU$127
includes taxes & fees
23 Aug - 24 Aug
Holiday Inn Express Winchester South-Stephens City by IHG

9. Quality Inn Stephens City - Winchester South

Quality Inn Stephens City - Winchester South
2.5 star property
Stephens City
8.0 out of 10, Very good, (679 reviews)
"Great location safe area clean rooms good price"
United States
Elaine
The price is AU$134
includes taxes & fees
23 Aug - 24 Aug
Quality Inn Stephens City - Winchester South

10. The Carriage Inn B&B

The Carriage Inn B&B
3.5 star property
Charles Town
9.6 out of 10, Exceptional, (453 reviews)
"Amazing place with incredible history!"
United States
Andrea
The price is AU$246
includes taxes & fees
29 July - 30 July
The Carriage Inn B&B

11. Relax Inn Motel

Relax Inn Motel
2.0 star property
Front Royal
8.4 out of 10, Very good, (286 reviews)
"Great"
United States
Jamila
The price is AU$108
includes taxes & fees
28 July - 29 July
Relax Inn Motel

12. TownePlace Suites by Marriott Front Royal

TownePlace Suites by Marriott Front Royal
3.0 star property
Front Royal
9.6 out of 10, Exceptional, (592 reviews)
"Enjoyed our stay."
United States
Natalie
The price is AU$223
includes taxes & fees
2 Aug - 3 Aug
TownePlace Suites by Marriott Front Royal

13. Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley
3.0 star property
Strasburg
9.0 out of 10, Wonderful, (1,003 reviews)
"Very affordable, nice rooms, and conveniently located - greatly enjoyed our stay!"
United States
Patrick
The price is AU$161
includes taxes & fees
9 Aug - 10 Aug
Fairfield Inn & Suites Strasburg Shenandoah Valley

14. Glen Gordon Manor

Glen Gordon Manor
3.5 star property
Huntly
9.8 out of 10, Exceptional, (97 reviews)
"Staff was efficient, professional, personable, thoughtful. Facilities were lovely, Breakfast was excellent."
United States
Alexander and Judith
The price is AU$527
includes taxes & fees
30 July - 31 July
Glen Gordon Manor

15. Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley
2.5 star property
Strasburg
8.2 out of 10, Very good, (1,009 reviews)
"Clean room, breakfast was ok, staff is helpful,"
United States
Viorika
The price is AU$129
includes taxes & fees
12 Aug - 13 Aug
Ramada by Wyndham Strasburg/Shenandoah Valley

16. 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, (1,002 reviews)
"The hospitality was amazing from check-in to check out"
United States
Marcus
The price is AU$180
includes taxes & fees
24 Aug - 25 Aug
DoubleTree by Hilton Front Royal Blue Ridge Shadows

17. 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, (1,008 reviews)
"Very clean and nicely decorated property"
United States
shayla
The price is AU$137
includes taxes & fees
16 Aug - 17 Aug
Holiday Inn Winchester Se-Historic Gateway by IHG

18. SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (879 reviews)
"Comfortable for my family of 6. Great breakfast."
United States
Julianne
The price is AU$181
includes taxes & fees
3 Aug - 4 Aug
SpringHill Suites by Marriott Winchester

19. Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (901 reviews)
"Breakfast was great and very good price.would very much stay again."
United States
george
The price is AU$148
includes taxes & fees
10 Aug - 11 Aug
Fairfield Inn & Suites by Marriott Winchester

20. Blue Ridge Motel

Blue Ridge Motel
2.0 star property
Front Royal
7.0 out of 10, Good, (141 reviews)
"Convenient cheap"
United States
ElizaBeth
The price is AU$100
includes taxes & fees
28 July - 29 July
Blue Ridge Motel
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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.

A large house in a field with a cloudy sky.
Photo by Stephanie Sutton
Open Photo by Stephanie Sutton

Top Middletown Hotel Reviews

Recent Reviews in Middletown

More cheap accommodation in Middletown

Find out more about Middletown

Top reasons to visit Middletown

  • Outdoor Adventures: Middletown boasts scenic golf courses and recreational areas, perfect for nature enthusiasts.
  • Cultural Exploration: Discover historic houses and captivating caves that offer rich cultural experiences.
  • Delightful Wine Tastings: Enjoy the local wineries and indulge in exquisite wine tastings.
  • Charming Accommodations: Choose from a variety of welcoming hotels, including pet-friendly options and historic inns.
  • Nearby Attractions: Explore the picturesque town of Winchester for family-friendly activities and delightful scenery.

Find great hotels near Middletown

Explore a range of delightful hotel accommodations in Middletown, Virginia, tailored to suit various traveller needs. Whether you're seeking a pet-friendly option, a historic inn, or spacious suites, Middletown offers friendly and welcoming establishments perfect for both leisure and business trips. Discover the charming Wayside Inn and other welcoming hotels that embrace diversity, ensuring an enjoyable stay for everyone.

  • Travelodge by Wyndham Winchester: Located 18km from Middletown, Travelodge by Wyndham Winchester offers a comfortable and budget-friendly stay with a guest rating of 8.6. This motel is an excellent choice for pet owners, featuring a pet-friendly policy that includes on-site accommodation for pets, subject to certain restrictions and fees. Guests appreciate the straightforward amenities and welcoming atmosphere, making it an ideal stop for those seeking a relaxed environment while exploring the surrounding area.
  • Country Inn & Suites by Radisson, Winchester, VA: Situated 13km from Middletown, this hotel boasts a commendable guest rating of 8.8 and caters to families, business travellers, and pet lovers alike. The property offers complimentary cribs for young children and a range of facilities that ensure a comfortable stay for guests of all ages. With its pet-friendly policy, which permits pets in rooms, Country Inn & Suites provides a warm and inviting atmosphere, making it a versatile choice for various travel needs.
  • Ramada by Wyndham Strasburg/Shenandoah Valley: Just 6km from Middletown, Ramada by Wyndham Strasburg/Shenandoah Valley holds a guest rating of 8.4, appealing particularly to those on business trips or travelling with pets. The hotel welcomes pets with specific weight restrictions and fees, ensuring that furry companions can join in the adventure. Guests enjoy comfortable accommodations and convenient access to local attractions, providing a pleasant and practical lodging experience.

Where to stay near Middletown

Middletown, Virginia, offers a delightful blend of outdoor adventures and historical exploration. Just a stone's throw away is Winchester, where you can immerse yourself in family-friendly activities and charming scenery. The area's romantic getaways and cosy hotels make it perfect for a memorable holiday. With upcoming local festivities to enjoy, your stay in Middletown promises to be filled with diverse experiences, from serene landscapes to vibrant urban atmospheres.

  • Winchester: Located 19km from Middletown, Winchester is a charming city known for its rich history and vibrant outdoor activities. The city offers various recreational areas and is a gateway to stunning national parks and scenic lakes. Visitors flock here to enjoy the beautiful landscapes, making it perfect for hiking, biking, and exploring nature. Highlights include the historic Old Town, with its quaint shops and restaurants, and the nearby Shenandoah National Park, offering breathtaking views and diverse wildlife. The summer months see a peak in visitor numbers, particularly in July and August, making it an ideal time for outdoor adventures.
  • Front Royal: Just 14km from Middletown, Front Royal is often referred to as the Gateway to the Shenandoah . This picturesque city is famed for its stunning natural scenery and outdoor pursuits. Visitors can explore the nearby national parks and lakes, ideal for hiking, fishing, and picnicking. Front Royal's vibrant atmosphere is enhanced by its charming downtown area, with local shops and eateries. The peak tourist seasons occur in April, July, and September, perfect for those looking to immerse themselves in the great outdoors and enjoy the region's natural beauty.
  • Strasburg: Situated a mere 8km from Middletown, Strasburg is a delightful city that offers a plethora of outdoor adventures and scenic views. The area is renowned for its recreational spaces and proximity to national parks, making it a haven for nature enthusiasts. Visitors can indulge in various activities such as hiking and skiing during the winter months. Strasburg's quaint charm is complemented by its educational attractions and beautiful parks. With peak visitor numbers in June to August, summer is an excellent time to explore this enchanting city and its surroundings.

Things to do near Middletown

Middletown, Virginia, is perfect for outdoor enthusiasts, offering a range of activities such as scenic golf courses and recreational areas. Visitors can indulge in delightful wine tastings and enjoy various entertainment options throughout the town. Whether you're seeking adventure or relaxation, Middletown provides a charming backdrop for an unforgettable holiday experience.

Shopping

The nearest shopping area is the Middletown Shopping Centre, featuring local shops and boutiques. If you're up for a drive, visit the Apple Blossom Mall in Winchester, where you can explore a variety of retail stores, dining options, and entertainment venues to enhance your shopping experience.

Recreation

Explore the serene setting of the Shenandoah Valley at the Natural Bridge Wellness Retreat, where you can indulge in yoga sessions and nature walks. After a day of relaxation, enjoy soothing spa treatments that focus on rejuvenation and holistic well-being amidst picturesque landscapes.

Adventure

At Summit Point Motorsports Park, located 35km from Middletown, experience the thrill of motor racing in a vibrant atmosphere. Engage in exhilarating track days or attend exciting events that showcase high-performance vehicles, making it an ideal spot for adrenaline seekers.

Nightlife

Explore the vibrant nightlife at the Mill Street Grill, where you can savour hearty meals and local brews. For a relaxed evening, visit the Town Hall, offering an array of live performances and events that showcase local talent and culture.

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

Booking tips and Expedia advantages for Middletown

  • 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, desired location, and preferred type of accommodation. To discover the most affordable prices and offers, arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can enjoy potential savings 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 excellent destination for those seeking outdoor adventures and scenic beauty. Visitors can explore attractions like rivers, historic houses, and caves, perfect for cultural and family experiences. For additional leisure, be sure to check out the local movie theatre and friendly attractions nearby. With its diverse offerings, Middletown is sure to delight nature enthusiasts and history buffs alike.

  • Cedar Creek Battlefield Foundation: Immerse yourself in the rich history of the American Civil War at this historic site. The Cedar Creek Battlefield Foundation offers insights into the significant battles fought here, with guided tours that enhance your understanding of the area's cultural heritage.
  • Belle Grove Plantation: Explore this beautifully preserved plantation, which reflects the architectural style and agricultural history of the antebellum South. Belle Grove Plantation features stunning gardens and informative tours that provide a glimpse into the lives of those who lived here.
  • Shenandoah River: Experience the natural beauty of the Shenandoah River, located a mere 13km from Middletown. Ideal for leisurely canoeing or hiking along its banks, this scenic spot offers a tranquil escape amidst picturesque landscapes.

Best time to go to Middletown

The best time to visit Middletown is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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

Accessing Middletown, Virginia, is convenient via several major airports. Washington, DC (DCA-Ronald Reagan Washington National) is situated 109km away, with nearby hotel options such as InterContinental Washington D.C. - The Wharf and Pendry Washington DC - The Wharf, both 3km from the airport. Washington, DC (IAD-Washington Dulles Intl.) lies 72km from Middletown, featuring hotels like Hyatt Regency Dulles International Airport, just 2km away. Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall) is 140km distant, with Four Seasons Hotel Baltimore located 13km from the airport. Each hotel offers various transportation services for seamless access to the respective airports.

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.
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.
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.
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.
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 cancelled 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 hotel booking in Middletown with Expedia?
One Key™—Expedia's free travel rewards program—gives you instant access to discounts with Member Prices on Middletown hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
How much is the nightly rate for a hotel in Middletown?
Prices for hotels in Middletown often vary, but you can find a great deal from AU$102 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 our cheapest rates.

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