Middletown, VA
Travel Guide
Visit Middletown
Wayside Inn
7783 Main St Middletown VA
$89 nightly
The price is $98 total per night from Mar 30 to Mar 31
$98 total
Mar 30 - Mar 31
Total with taxes and fees
Stay at this hotel in Middletown. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Cedar ...
9.2/10 Wonderful! (426 reviews)
Nostalgia and history are prime attractions of this lovely inn. The barkeep Justin was friendly and helpful
Reviewed on Mar 16, 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
$91 nightly
The price is $99 total per night from Apr 5 to Apr 6
$99 total
Apr 5 - Apr 6
Total with taxes and fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
9/10 Wonderful! (1,001 reviews)
Clean room, friendly staff, good location. Only cons were hallway carpet is rippled and no free breakfast
Reviewed on Mar 27, 2026
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
$107 nightly
The price is $117 total per night from Mar 30 to Mar 31
$117 total
Mar 30 - Mar 31
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! (2,274 reviews)
Love this property. Will stay again! Beautiful rooms
Reviewed on Mar 28, 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.
Falling Leaf Cabin Rustic Charm With Modern Decor! Newly Renovated Kitchen!
Rileyville VA
Book a stay at this family-friendly cabin in Rileyville. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Chalybeate Spring and Fort Valley ...
9.8/10 Exceptional! (308 reviews)
The cabin was cozy and warm in this wintry weather. The host was easy to communicate with and everything went smoothly.
Reviewed on Feb 18, 2026
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo
Front Royal VA
Stay at this cabin in Front Royal. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Glen Manor Vineyards and Shenandoah River State Park ...
9.6/10 Exceptional! (343 reviews)
The space was cozy and nice. The view of the river was absolutely breathtaking from the back porch! Quiet and relaxing.
Reviewed on Mar 23, 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 ...
9.8/10 Exceptional! (181 reviews)
Host was very responsive and helpful. House was very clean. Loved the layout and decor. It was wonderful being right in the mountains in such a sweet, secluded and very homie, comfortable place. We will definitely try to book again in the future!
Reviewed on Mar 5, 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
3.5/5(3 reviews)
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.
Jackson's Chase Golf Course
Enjoy a round of golf in Middletown at Jackson's Chase Golf Course. Amble around this vibrant area's riverfront, or seek out the hiking trails.
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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
- Strasburg Hotels
- Hotels near Strasburg Museum
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- Hotels near Blue Ridge Shadows Golf Club
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- Car rentals near Strasburg
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- Car rentals near Canterburg
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- Belle Grove Plantation
- Cedar Creek and Belle Grove National Historical Park
- Jackson's Chase Golf Course
- Cedar Creek Battlefield Foundation
- Shenandoah National Park
- Front Royal Entrance Shenandoah National Park
- George Washington National Forest
- Shenandoah River
- Shenandoah University
- ValleyHealth Winchester Medical Center
- Skyline Caverns
- Shenandoah County Fairgrounds
- Shenandoah River State Park
- Museum of the Shenandoah Valley
- Apple Blossom Mall
- Shenandoah Valley Discovery Museum
- Patsy Cline Historic House
- Sky Meadows State Park
- Front Royal Visitor's Center
- Dinosaur Land
- Rock Harbor Golf Course
- RdV Vineyards
- Linden Vineyards
- Bright Box Theater
- Lost River
- Naked Mountain Winery & Vineyards
- Dickey Ridge Visitor Center
- Secret Passage Ranch
- Jim Barnett Park