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17 Jul - 18 Jul
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Top 10 Middletown hotels and places to stay

Holiday Inn Express Winchester South-Stephens City by IHG
Guests can check in at the hotel's prominent entrance, surrounded by ample parking.

Holiday Inn Express Winchester South-Stephens City by IHG

2.5 star property
8.2 out of 10, Very good, (757)
"Always great!"
The price is £64
includes taxes & fees
26 Jul - 27 Jul
Holiday Inn Express Winchester South-Stephens City by IHG
Fairfield Inn & Suites by Marriott Winchester
Welcome to Fairfield by Marriott, where a covered walkway leads to the main entrance.

Fairfield Inn & Suites by Marriott Winchester

2.5 star property
9.0 out of 10, Wonderful, (736)
"Clean and comfortable room, wonderful breakfast, pleasant personnel"
The price is £79
includes taxes & fees
20 Jul - 21 Jul
Fairfield Inn & Suites by Marriott Winchester
Relax Inn Motel
Welcome to Relax Inn, a motel with a brick exterior and upper-floor balcony.

Relax Inn Motel

2.0 star property
8.2 out of 10, Very good, (235)
"Clean, quiet and convenient. Check in process was quick and easy, with the very friendly and helpful staff. I would absolutely stay here again."
The price is £57
includes taxes & fees
18 Jul - 19 Jul
Relax Inn Motel
Wayside Inn
Enjoy a drink at the bar, surrounded by a selection of beverages and rustic charm.

Wayside Inn

3.5 star property
9.2 out of 10, Wonderful, (401)
"We stayed last year on July 4th. ...really liked it...decided to make it an annual event. I like the small town atmosphere. "
The price is £88
includes taxes & fees
21 Jul - 22 Jul
Wayside Inn
Econo Lodge Inn & Suites
Enjoy a warm and elegant dining experience in this inviting space with a high ceiling, chandelier, and comfortable seating.

Econo Lodge Inn & Suites

2.0 star property
5.6 out of 10, (283)
"Great place to sleep and its was very quiet. "
The price is £56
includes taxes & fees
23 Jul - 24 Jul
Econo Lodge Inn & Suites
Quality Inn
Guests can enjoy a covered outdoor seating area with beautiful landscaping and a paved pathway to the entrance.

Quality Inn

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Great place , great front desk staff, super clean & very quiet"
The price is £75
includes taxes & fees
23 Jul - 24 Jul
Quality Inn
Country Inn & Suites by Radisson, Winchester, VA
Cozy living room with a fireplace, wooden shelves, and a light-colored sofa.

Country Inn & Suites by Radisson, Winchester, VA

3.0 star property
8.8 out of 10, Excellent, (1002)
"Great stay for a great price!"
The price is £79
includes taxes & fees
20 Jul - 21 Jul
Country Inn & Suites by Radisson, Winchester, VA
Super 8 by Wyndham Front Royal
Relax in our welcoming lobby, featuring a reception desk, comfortable seating area, and dining space.

Super 8 by Wyndham Front Royal

2.0 star property
7.4 out of 10, Good, (1007)
"Great place"
The price is £61
includes taxes & fees
21 Jul - 22 Jul
Super 8 by Wyndham Front Royal
Comfort Inn & Suites
Welcome to Comfort Inn & Suites, featuring a modern exterior with a brick and beige facade and a welcoming entrance.

Comfort Inn & Suites

2.5 star property
9.4 out of 10, Exceptional, (1001)
"Would stay again. "
The price is £79
includes taxes & fees
27 Jul - 28 Jul
Comfort Inn & Suites
Motel 6 Winchester, VA
Relax in a cozy seating area with a kitchenette, perfect for a home away from home.

Motel 6 Winchester, VA

2.0 star property
8.2 out of 10, Very good, (1000)
"Great for an overnight stay. Clean room. Needs comfortable chairs."
The price is £54
includes taxes & fees
21 Jul - 22 Jul
Motel 6 Winchester, VA
Travelodge by Wyndham Winchester
In-room safe, desk, iron/ironing board, free cots/infant beds

Travelodge by Wyndham Winchester

2.5 star property
8.4 out of 10, Very good, (1107)
"The stay was great for the price."
The price is £56
includes taxes & fees
20 Jul - 21 Jul
Travelodge by Wyndham Winchester
TownePlace Suites by Marriott Winchester
Enjoy meals and relaxation in this compact room with a kitchenette, dining area, and sofa.

TownePlace Suites by Marriott Winchester

3.0 star property
8.8 out of 10, Excellent, (444)
"Staff was amazing! "
The price is £87
includes taxes & fees
20 Jul - 21 Jul
TownePlace Suites by Marriott Winchester
Hampton Inn Winchester N/Conference Center, VA
Welcome to our reception area, featuring a central desk, a refrigerated display case, and a patterned rug.

Hampton Inn Winchester N/Conference Center, VA

2.5 star property
9.2 out of 10, Wonderful, (782)
"Well kept, clean, good breakfast."
The price is £100
includes taxes & fees
24 Jul - 25 Jul
Hampton Inn Winchester N/Conference Center, VA
Microtel Inn & Suites by Wyndham Winchester
Relax in the stylish lobby with sofas, armchairs, and a large window offering a view of the outdoors.

Microtel Inn & Suites by Wyndham Winchester

2.5 star property
9.2 out of 10, Wonderful, (1304)
"Clean comfortable room, friendly staff. "
The price is £71
includes taxes & fees
17 Aug - 18 Aug
Microtel Inn & Suites by Wyndham Winchester
Holiday Inn Express Hotel & Suites Winchester by IHG
Relax by the pool, surrounded by a spacious deck and a clear water's edge.

Holiday Inn Express Hotel & Suites Winchester by IHG

2.5 star property
8.8 out of 10, Excellent, (763)
"Very friendly staff and clean property"
The price is £90
includes taxes & fees
26 Jul - 27 Jul
Holiday Inn Express Hotel & Suites Winchester by IHG
Candlewood Suites Winchester by IHG
Relax in a stylish room with a comfortable bed, sofa, and framed artwork.

Candlewood Suites Winchester by IHG

2.5 star property
8.8 out of 10, Excellent, (478)
"great for overnight stay "
The price is £74
includes taxes & fees
25 Jul - 26 Jul
Candlewood Suites Winchester by IHG
Quality Inn Stephens City - Winchester South
Enjoy a convenient breakfast at the hotel's well-equipped breakfast bar, featuring a juice dispenser, bowls, and a coffee machine.

Quality Inn Stephens City - Winchester South

2.5 star property
8.0 out of 10, Very good, (589)
"Really close to highway, with few good dining options near by, room was clean however it was sligltly outdated, breakfast was decent, eggs were good. "
The price is £65
includes taxes & fees
30 Jul - 31 Jul
Quality Inn Stephens City - Winchester South
Sleep Inn & Suites
Welcome to Sleep Ins Suites, where guests can check in and enjoy a spacious lobby with a curved reception desk and comfortable dining area.

Sleep Inn & Suites

2.5 star property
8.0 out of 10, Very good, (1014)
"Comfortable, well priced, good breakfast "
The price is £58
includes taxes & fees
17 Aug - 18 Aug
Sleep Inn & Suites
Ramada by Wyndham Strasburg/Shenandoah Valley
Welcome to our hotel lobby, featuring a spacious area with a reception desk and comfortable seating.

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 star property
8.2 out of 10, Very good, (1004)
"Great location off the highway, restaurant on site was very good, staff was friendly and quick check in"
The price is £59
includes taxes & fees
27 Jul - 28 Jul
Ramada by Wyndham Strasburg/Shenandoah Valley
SpringHill Suites by Marriott Winchester
Relax in a spacious room with a large bed, desk, and window offering a view of the outdoors.

SpringHill Suites by Marriott Winchester

2.5 star property
9.4 out of 10, Exceptional, (655)
"Great clean and modern rooms and nice service, would recommend to anyone looking for a stay in the area."
The price is £94
includes taxes & fees
20 Jul - 21 Jul
SpringHill Suites by Marriott Winchester
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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Learn more about Middletown

Middletown awaits: its entertainment, churches, bars and more!

See all hotels in Middletown
Photo by Stephanie Sutton
Open Photo by Stephanie Sutton

Top Middletown Hotel Reviews

Quality Inn

Quality Inn

10/10 Excellent
"Great place , great front desk staff, super clean & very quiet"
Louise 1-night trip
Posted 2 days ago
Quality Inn

Frequently asked questions

What are the best hotels in Middletown that travellers recommend?
Wayside Inn stands out as a top choice for travellers seeking a great experience in Middletown, boasting a great rating of 9.2. This charming hotel offers an array of amenities that cater to various needs, making it a superb getaway for couples looking to rekindle romance or celebrate special occasions. With its exquisite couples dining options and lively evening entertainment, guests can enjoy intimate moments while savoring delicious meals.
What are the best family hotels in Middletown?
Wayside Inn in Middletown, Virginia, is a charming family-friendly hotel that has earned an excellent review score of 9.2 from travellers. This delightful inn goes above and beyond to cater to families, offering amenities like complimentary rollaway beds and highchairs, ensuring that even the littlest guests are well cared for. Find more child-friendly accommodations in Middletown.
What are the top pet-friendly hotels in Middletown?
Wayside Inn, a charming historic property situated in Middletown, VA, is a top choice for travellers who wish to bring their furry friends along for the adventure. With a customer review rating of 9.2, guests rave about the attentive service and friendly setting that make for a stress-free stay. See more pet-friendly hotels in Middletown.
What are the best budget hotels in Middletown?
The Wayside Inn, a charming historic-style hotel in Middletown, VA, is an excellent choice for budget-conscious travellers seeking quality and convenience. With an impressive guest review rating of 9.2, it offers a warm atmosphere combined with thoughtful amenities that cater to both families and couples alike. View all budget hotels in Middletown.
What are the most romantic hotels in Middletown for couples?
For a romantic escape, the Wayside Inn in Middletown, VA, is a delightful choice, boasting a stellar review score of 9.2. This charming hotel captures the essence of romance with its historic property design and cozy atmosphere, making it a superb retreat for couples. See all romantic hotels in Middletown.
When is the best time to go to Middletown?
The most popular time to visit Middletown is during the summer months, particularly July. At this time, the town is vibrant with events and outdoor activities, with average temperatures around 25°C, creating a delightful atmosphere for exploration. Visitors can enjoy a variety of festivals, farmers' markets, and outdoor concerts that bring the community together and showcase the local culture.

As you navigate through the peak season, which runs from June to August, you'll find the streets bustling with tourists and locals alike. This energetic vibe is superb for those who relish in sightseeing and outdoor pursuits. The warm weather makes it an ideal time for leisurely strolls along the scenic parks, waterfronts, or bike rides through the picturesque countryside surrounding Middletown.

For couples looking for a romantic escape or families seeking fun-filled days, July offers the superb backdrop. The long days allow for extended adventures, whether you're picnicking by the river or enjoying a sunset cruise. Many restaurants also feature outdoor seating, enhancing your dining experience with lovely views and fresh air.

If you're considering a visit that aligns with a more budget-friendly approach, September can be a fantastic alternative. While the summer crowds begin to dwindle, the pleasant weather continues, making it a great time for outdoor activities and sightseeing without the busyness of peak season.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Middletown.
How can I save on a Middletown hotel booking with Expedia?
Members always get our best prices. Find our best Middletown hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Middletown hotel?
Prices for hotels in Middletown often vary, but you can find a great deal from £45 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.