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Find hotels in Middletown, VA from ฿2,324

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22 Dec - 23 Dec
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26 Dec - 28 Dec
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Our top choices for Middletown hotels

Dining
Wayside Inn

Wayside Inn

Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (417)
"Historic inn. "
United States
David
The price is ฿2,261
฿2,808 total
includes taxes & fees
23 Dec - 24 Dec
Wayside Inn
Breakfast area
Econo Lodge Inn & Suites Middletown - Winchester South

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 Theatre 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 ฿2,120
฿2,338 total
includes taxes & fees
29 Dec - 30 Dec
Econo Lodge Inn & Suites Middletown - Winchester South
Free daily continental breakfast
Quality Inn Stephens City - Winchester South

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, (632)
Set in charming Stephens City, this hotel offers a serene atmosphere and fitness centre. Guests praise the helpful staff, while free breakfast, WiFi, and parking enhance the value. Valerie Hill Winery and local attractions await just minutes away.
"Good variety at breakfast and courteous staff."
Canada
Madonna
The price is ฿2,317
฿2,521 total
includes taxes & fees
11 Jan - 12 Jan 2026
Quality Inn Stephens City - Winchester South
Exterior
Holiday Inn Express Winchester South-Stephens City by IHG

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, (806)
"Clean room, nice staff, simple but good breakfast, fresh ground coffee machine was really nice. "
United States
Rose
The price is ฿2,261
฿2,460 total
includes taxes & fees
2 Jan - 3 Jan 2026
Holiday Inn Express Winchester South-Stephens City by IHG
Lobby
Travelodge by Wyndham Winchester

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.
"Clean rooms, easy check in"
United States
Leslie
The price is ฿2,136
฿2,324 total
includes taxes & fees
14 Jan - 15 Jan 2026
Travelodge by Wyndham Winchester
Exterior
ANS Inn & Suites

ANS Inn & Suites

ANS Inn & Suites
2.0 star property
Winchester
7.4 out of 10, Good, (67)
This welcoming motel offers free WiFi and parking, with daily housekeeping for a comfortable stay. Located near The Kernstown Battlefield and Apple Blossom Mall, it's a convenient base for Winchester adventures.
"Everyone here was so friendly. The cats in the lobby to greet guests was awesome."
United States
Dinesh
The price is ฿2,104
฿2,510 total
includes taxes & fees
2 Jan - 3 Jan 2026
ANS Inn & Suites
Snack bar
TRU By Hilton Winchester

TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
Winchester
9.0 out of 10, Wonderful, (772)
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.
"Very nice room and common spaces. Breakfast was good and the price was very fair."
United States
Joseph
The price is ฿2,292
฿2,494 total
includes taxes & fees
5 Jan - 6 Jan 2026
TRU By Hilton Winchester
Exterior
Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1089)
Near Appleland Sports Centre and Kernstown Battlefield, this hotel offers a 24-hour fitness centre 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 ฿3,049
฿3,317 total
includes taxes & fees
5 Jan - 6 Jan 2026
Comfort Inn & Suites Winchester
Lobby lounge
Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley
2.5 star property
Strasburg
9.0 out of 10, Wonderful, (1001)
"Great stay."
United States
Kenneth
The price is ฿3,177
฿3,536 total
includes taxes & fees
29 Dec - 30 Dec
Fairfield Inn & Suites Strasburg Shenandoah Valley
Lobby
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley
2.5 star property
Strasburg
8.4 out of 10, Very good, (1006)
Savour Civil War history at this Strasburg retreat with fitness centre 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.
"Breakfast was delicious "
United States
Robert
The price is ฿2,243
฿2,496 total
includes taxes & fees
1 Jan - 2 Jan 2026
Ramada by Wyndham Strasburg/Shenandoah Valley
Pool
APM Inn & Suites

APM Inn & Suites

APM Inn & Suites
2.0 star property
Winchester
6.6 out of 10, (348)
This quiet retreat offers free WiFi and self parking, perfect for exploring nearby Eastgate Plaza Shopping Centre and Nalls Farm Market. Travellers consistently praise the helpful hotel staff and convenient laundry facilities.
"Room was quite nice for the price, and check in lady was very nice "
United States
Glen
The price is ฿1,696
฿1,922 total
includes taxes & fees
25 Dec - 26 Dec
APM Inn & Suites
Premier Villa, 1 King Bed, Mountain View | Terrace/patio
White Moose Inn

White Moose Inn

White Moose Inn
4.0 star property
Washington
9.8 out of 10, Exceptional, (148)
Just 15 minutes from Shenandoah National Park, this inviting inn provides free breakfast, WiFi, and bike rentals for mountain exploration. Discover nearby hiking trails, relax in the garden, or visit charming local attractions like R.H. Ballard Gallery.
"Staff is wonderful. The whole 1st floor would make Marie Kondo proud! Breakfast is excellent. "
United States
Judy
White Moose Inn
Porch
Gay Street Inn

Gay Street Inn

Gay Street Inn
3.5 star property
Washington
10.0 out of 10, Exceptional, (34)
Surrounded by lush gardens, this charming B&B offers free WiFi and parking near Little Washington Theatre. The peaceful terrace provides a perfect retreat after exploring nearby Shenandoah National Park.
"Beautiful historic Inn with incredible owners and service. "
United States
Renee
The price is ฿11,275
฿12,155 total
includes taxes & fees
1 Jan - 2 Jan 2026
Gay Street Inn
Lobby
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1395)
Enjoy a comfortable stay at this Winchester hotel with an indoor pool and fitness centre. Clean rooms feature cosy beds, while free breakfast, WiFi, and parking add value. Nearby attractions include Rutherford Crossing and Northside Station Shopping Centre.
"Clean room great helpful staff good breakfast"
United States
Loretta
The price is ฿2,488
฿2,706 total
includes taxes & fees
24 Dec - 25 Dec
Microtel Inn & Suites by Wyndham Winchester
Lobby sitting area
Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University
2.5 star property
Winchester
7.8 out of 10, Good, (1000)
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 centre adds value while helpful staff ensure a pleasant stay for business travellers.
"great stay with breakfast too"
United States
James
The price is ฿1,944
฿2,115 total
includes taxes & fees
18 Jan - 19 Jan 2026
Sleep Inn & Suites Winchester near University
Lobby
Spark by Hilton Winchester

Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1003)
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.
"The place is spotless, comfortable and quiet. Very convenient as well, right off of 81"
United States
Michael
The price is ฿2,421
฿2,743 total
includes taxes & fees
11 Jan - 12 Jan 2026
Spark by Hilton Winchester
Desk, blackout curtains, iron/ironing board, free WiFi
Super 8 by Wyndham Winchester VA

Super 8 by Wyndham Winchester VA

Super 8 by Wyndham Winchester VA
2.0 star property
Winchester
6.2 out of 10, (621)
Located in Winchester with easy access to local attractions, this motel offers complimentary WiFi and on-the-go breakfast. Guests praise the helpful staff and appreciate the free parking when exploring Apple Blossom Mall and R-C Track.
"Very limited, bread , butter , jam"
Canada
Susan
The price is ฿2,104
฿2,290 total
includes taxes & fees
1 Jan - 2 Jan 2026
Super 8 by Wyndham Winchester VA
Interior
Hilton Garden Inn Winchester

Hilton Garden Inn Winchester

Hilton Garden Inn Winchester
3.0 star property
Winchester
8.8 out of 10, Excellent, (511)
Located in Winchester near Abram's Delight and Apple Blossom Mall, this hotel offers an indoor pool and fitness centre. Rooms include convenient sofa beds and refrigerators, while Great American Grill serves American cuisine. Free WiFi and parking enhance your stay.
"Great hotel"
United States
DONNA D
The price is ฿3,168
฿3,589 total
includes taxes & fees
28 Dec - 29 Dec
Hilton Garden Inn Winchester
Lobby
Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
2.5 star property
Winchester
9.0 out of 10, Wonderful, (799)
This business-friendly hotel sits near Apple Blossom Mall and Abram's Delight. Energise in the fitness centre or indoor pool before exploring. Guests rave about the helpful staff and complimentary breakfast, WiFi and parking.
"Quick check in, clean room, friendly staff."
United States
Darcy
The price is ฿2,910
฿3,166 total
includes taxes & fees
25 Dec - 26 Dec
Fairfield Inn & Suites by Marriott Winchester
Desk, blackout curtains, free cots/infant beds, free WiFi
Red Roof Inn Winchester, VA

Red Roof Inn Winchester, VA

Red Roof Inn Winchester, VA
2.0 star property
Winchester
7.4 out of 10, Good, (1003)
Get cosy in clean accommodation close to Apple Blossom Mall. This hotel offers complimentary WiFi and parking, with highway access for easy travel. Near R-C Track and local dining spots, it provides a peaceful retreat after exploring Winchester.
"Really friendly staff, room was clean and perfect for our family and dog. "
United States
Sabrina
The price is ฿2,167
฿2,358 total
includes taxes & fees
28 Dec - 29 Dec
Red Roof Inn 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

Belle Grove Plantation

Find out about the history of Middletown when you spend time at Belle Grove Plantation. Wander the riverfront or discover the mountain views in this vibrant area.
See properties

Cedar Creek Battlefield Foundation

You can learn about the history of Middletown with a visit to Cedar Creek Battlefield Foundation. Stroll along the riverfront or experience the entertainment venues in this vibrant area.
See properties

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
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

Spark by Hilton Winchester

Spark by Hilton Winchester

10/10 Excellent
"good"
bhagavathgeet 1-night trip
Posted 3 weeks ago
Spark by Hilton Winchester

More cheap stays in Middletown

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

160 Front Royal Pike Winchester VA
The price is ฿2,136 per night from 14 Jan to 15 Jan
฿2,136
฿2,324 total
14 Jan - 15 Jan 2026
includes taxes & fees
8.4/10 Very Good! (1,088 reviews)

Frequently asked questions

Where is the best place for a stay in Middletown?
Based on our traveller data, Econo Lodge Inn & Suites Middletown - Winchester South is one of the top choices for your stay. This hotel offers free parking and a bar. Two other options for your visit to the area are Microtel Inn & Suites by Wyndham Winchester and La Quinta Inn & Suites 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, most hotel room reservations are fully refundable if cancelled prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of the scheduled arrival. If you booked a non-refundable reservation, you might be able to cancel it and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Middletown.
What's it like staying in Middletown?
Visitors to Middletown will definitely enjoy the bars and restaurants. Tourists can also enjoy the city's entertainment choices, churches and theatres. In Middletown, there are 4 hotels and other accommodation options to choose from. Find out more about Middletown.
What is there to see in 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 itinerary are Wayside Theater and Jackson's Chase Golf Course. Take a look at what more there is to see and do in Expedia's Middletown guide.
What's the seasonal weather like in Middletown?
The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of 2°C. Average annual precipitation for Middletown is 1088 mm.