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Find hotels in Middletown, VA from 1.609.515 ₫

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Our top choices for Middletown hotels

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 1.633.665 ₫
1.801.934 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Econo Lodge Inn & Suites Middletown - Winchester South

Wayside Inn

Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (416)
"Historic inn. "
United States
David
The price is 1.894.104 ₫
2.352.003 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Wayside Inn

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 1.762.569 ₫
2.102.745 ₫ total
includes taxes & fees
20 Dec - 21 Dec
ANS 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 1.420.578 ₫
1.609.515 ₫ total
includes taxes & fees
15 Dec - 16 Dec
APM Inn & Suites

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 1.762.569 ₫
1.917.780 ₫ total
includes taxes & fees
13 Jan - 14 Jan 2026
Super 8 by Wyndham Winchester VA

Motel 6 Winchester, VA

Motel 6 Winchester, VA
2.0 star property
Winchester
8.2 out of 10, Very good, (1003)
This peaceful Motel 6 in Winchester offers free WiFi and parking. Located near Kernstown Battlefield and Apple Blossom Mall, guests praise the helpful staff and clean rooms that ensure a restful night's sleep.

"Very good and convenient budget motel in Winchester, happy to recommend."
United States
Jane
The price is 1.788.613 ₫
2.026.428 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Motel 6 Winchester, VA

Red Roof Inn Winchester, VA

Red Roof Inn Winchester, VA
2.0 star property
Winchester
7.4 out of 10, Good, (1002)
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 1.591.310 ₫
1.731.345 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Red Roof Inn Winchester, VA

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester
2.5 star property
Winchester
8.6 out of 10, Excellent, (1085)
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 1.788.876 ₫
1.946.192 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Travelodge by Wyndham Winchester

L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant
4.0 star property
Boyce
9.6 out of 10, Exceptional, (174)
Savour local cuisine at La Table Provencale after swimming in the seasonal outdoor pool. This business-friendly inn provides spa services, complimentary breakfast, and free parking. Enjoy easy access to White Post Village Park while receiving attentive service from the staff.

"This B&B has been by far the loveliest, friendliest, cleanest with staff so eager to please. The rural area was so peaceful and relaxing with views of black angus in the fields. Winchester close with quaint shops. The food at the Inn was excellent. "
United States
DONNA
The price is 7.865.793 ₫
8.675.970 ₫ total
includes taxes & fees
15 Dec - 16 Dec
L'Auberge Provencale Inn & Restaurant

Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley
2.5 star property
Strasburg
9.0 out of 10, Wonderful, (1002)
"Great stay."
United States
Kenneth
The price is 2.972.691 ₫
3.308.605 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Fairfield Inn & Suites Strasburg Shenandoah Valley

Days Inn by Wyndham Winchester

Days Inn by Wyndham Winchester
2.0 star property
Winchester
6.6 out of 10, (482)
Quiet rooms offer a restful retreat in Winchester. Enjoy daily on-the-go breakfast and complimentary parking. Near Rutherford Crossing and Star Fort Civil War Battlefield, this hotel provides clean accommodation with free WiFi.

"Very comfortable stay"
United States
Jose David
The price is 1.704.694 ₫
1.854.907 ₫ total
includes taxes & fees
13 Jan - 14 Jan 2026
Days Inn by Wyndham Winchester

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 9.444.213 ₫
10.180.862 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Gay Street Inn

Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley
2.5 star property
Strasburg
8.2 out of 10, Very good, (1005)
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 1.878.320 ₫
2.090.570 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Ramada by Wyndham Strasburg/Shenandoah Valley

White Moose Inn

White Moose Inn
4.0 star property
Washington
9.8 out of 10, Exceptional, (147)
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.

"Amazing trip! "
United States
Rebecca
White Moose Inn

Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University
2.5 star property
Winchester
7.8 out of 10, Good, (1003)
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 1.795.716 ₫
1.953.739 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Sleep Inn & Suites Winchester near University

TownePlace Suites by Marriott Winchester

TownePlace Suites by Marriott Winchester
3.0 star property
Winchester
8.8 out of 10, Excellent, (479)
Splash into the refreshing outdoor pool at this Winchester retreat. Located near Winchester Gateway, the hotel offers free breakfast and parking. Rooms feature microwaves and refrigerators, while the fitness centre and coffee shop energise your stay.

"Nice place to stay. Great staff and breakfast."
United States
Stormy
The price is 2.817.480 ₫
3.065.418 ₫ total
includes taxes & fees
15 Dec - 16 Dec
TownePlace Suites by Marriott Winchester

Hilton Garden Inn Winchester

Hilton Garden Inn Winchester
3.0 star property
Winchester
8.8 out of 10, Excellent, (509)
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 2.511.792 ₫
2.845.861 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Hilton Garden Inn Winchester

Candlewood Suites Winchester by IHG

Candlewood Suites Winchester by IHG
2.5 star property
Winchester
8.8 out of 10, Excellent, (544)
Travellers appreciate the comfortable accommodation with easy access to R-C Track and Apple Blossom Mall. This hotel offers free WiFi, parking, and a fitness centre, perfect for both business and outdoor enthusiasts.

"Very clean room, excellent staff!!!"
United States
James
The price is 2.051.946 ₫
2.232.516 ₫ total
includes taxes & fees
3 Jan - 4 Jan 2026
Candlewood Suites Winchester by IHG

TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
Winchester
9.0 out of 10, Wonderful, (766)
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.

"The hotel was clean and the staff was pleasant."
United States
Sherri
The price is 1.873.058 ₫
2.037.887 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
TRU 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.

"Great location close to restaurants "
United States
SILVIA
The price is 1.978.286 ₫
2.241.356 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Spark by Hilton 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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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.

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

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Frequently asked questions

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.

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