4/5 - Good
Verified traveler
Cute historic town!
Visit Middletown
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
$82 nightly
The price is $89 total per night from Jan 26 to Jan 27
$89 total
Jan 26 - Jan 27
Total with taxes and fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,428 reviews)
This is our number one spot to stay in in Winchester. The location is perfect. Rooms are clean and modern.
Reviewed on Jan 14, 2026
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
$92 nightly
The price is $100 total per night from Jan 18 to Jan 19
$100 total
Jan 18 - Jan 19
Total with taxes and fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (2,243 reviews)
yes, room was spotless very nice place to stay
Reviewed on Jan 13, 2026
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
$127 nightly
The price is $143 total per night from Jan 25 to Jan 26
$143 total
Jan 25 - Jan 26
Total with taxes and fees
Book a stay at this spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
9.2/10 Wonderful! (1,003 reviews)
Staff was amazing! Benjamin and Carla are two of the kindest people ever!
Reviewed on Jan 4, 2026
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.
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
Rileyville VA
Stay at this cabin in Rileyville. Enjoy free WiFi, a garden, and laundry facilities. Our guests praise the property condition in our reviews. Popular attractions ...
9.8/10 Exceptional! (332 reviews)
Very clean and beautiful views
Reviewed on Jan 16, 2026
Secluded River Cabin Getaway (Masten Cabin)
Strasburg VA
Stay at this vacation home in Strasburg. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Secret Passage Ranch and Strasburg Museum are located ...
9.6/10 Exceptional! (174 reviews)
We had an amazing mountain stay! The views were absolutely breathtaking, and the peaceful surroundings made it the perfect getaway. The place was clean, cozy, and well equipped with everything we needed. Waking up to the fresh mountain air was unforgettable. We would definitely stay here again and ...
Reviewed on Jan 2, 2026
Star view cabin-Riverfront
Rileyville VA
Stay at this cabin in Rileyville. Enjoy laundry facilities, tennis courts, and patios. Our guests praise the property condition in our reviews. Popular attractions ...
9.6/10 Exceptional! (310 reviews)
Excellent location, wonderful home and view. How was very responsive, no service/wifi was tough
Reviewed on Jan 6, 2026
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.
Popular places to visit
Belle Grove Plantation
Learn about the local history of Middletown when you spend time at Belle Grove Plantation. Wander the riverfront or discover the mountain views in this vibrant area.
Cedar Creek and Belle Grove National Historical Park
Explore the great outdoors at Cedar Creek and Belle Grove National Historical Park, a lovely green space in Middletown. Stroll along the riverfront or experience the area's entertainment venues.
Cedar Creek Battlefield Foundation
You can find out 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.
Reviews of Middletown
4
Top Destination
4/5 - Good
M.
Not a lot to do but a good base to visit the park and wineries.
4/5 - Good
Verified traveler
Very nice Irish Pub (Nana's) near the Inn
4/5 - Good
Verified traveler
Didn’t spend much time in Middletown other than when we were at the inn
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- Hotels near Wayside Theater
- Hotels near Cedar Creek and Belle Grove National Historical Park
- Hotels near Cedar Creek Battlefield Foundation
- Hotels near Belle Grove Plantation
- Hotels near Hupp's Hill Civil War Park
- Hotels near Valerie Hill Winery
- Hotels near Jackson's Chase Golf Course
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- Belle Grove Plantation
- Cedar Creek and Belle Grove National Historical Park
- Cedar Creek Battlefield Foundation
- Jackson's Chase Golf Course
- Wayside Theater
- Shenandoah National Park
- Shenandoah University
- Front Royal Entrance Shenandoah National Park
- Shenandoah River
- George Washington National Forest
- ValleyHealth Winchester Medical Center
- Skyline Caverns
- Apple Blossom Mall
- Shenandoah River State Park
- Museum of the Shenandoah Valley
- Shenandoah Valley Discovery Museum
- Shenandoah County Fairgrounds
- Sky Meadows State Park
- Dinosaur Land
- Mackintosh Fruit Farm
- Bright Box Theater
- Lost River
- Linden Vineyards
- Rock Harbor Golf Course
- RdV Vineyards
- Front Royal Visitor's Center
- Glen Manor Vineyards
- Naked Mountain Winery & Vineyards
- Belle Boyd Cottage
