Middletown, VA
Travel Guide
Visit Middletown
Wayside Inn
7783 Main St Middletown VA
$144 nightly
The price is $159 total per night from Aug 9 to Aug 10
$159 total
Aug 9 - Aug 10
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! (444 reviews)
"There was not an elevator. We were not able to stay at the Wayside Inn. We were taken aback when we were informed that the front door would be locked at 9pm. While there is a pad with a code for access, there is no staff on site. It was not what we expected, that is not the fault of staff or management. ..."
Reviewed on Aug 1, 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
$96 nightly
The price is $107 total per night from Aug 9 to Aug 10
$107 total
Aug 9 - Aug 10
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! (1,013 reviews)
"Good location and clean hotel"
Reviewed on Aug 4, 2026
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
$120 nightly
The price is $136 total per night from Aug 23 to Aug 24
$136 total
Aug 23 - Aug 24
Total with taxes and fees
Book a stay at this spa hotel in Winchester. Enjoy a full-service spa, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
9.4/10 Exceptional! (1,008 reviews)
"It's a lovely hotel in a great location to the pedestrian area. Our bed was super comfortable and the towels super soft. Room was clean ..elevator needed vac. Parking should be complimentary. Bar area is beautiful."
Reviewed on Aug 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.
Falling Leaf Cabin Rustic Charm With Modern Decor! Newly Renovated Kitchen!
Rileyville VA
Stay at this cabin in Rileyville. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Chalybeate Spring and Fort Valley Public Library are ...
9.8/10 Exceptional! (318 reviews)
"A must stay. The property is beautiful and absolute perfect for a quiet get away."
Reviewed on Jul 14, 2026
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub
Edinburg VA
Stay at this vacation home in Woodstock. Enjoy a garden, laundry facilities, and patios. Popular attractions Shenandoah Vineyards and Edinburg Mill Museum are ...
10/10 Exceptional! (415 reviews)
"Outstanding Property in Every Possible Way!My husband and I were lucky enough to celebrate our minimoon at Deer Haven and it was exceptional in every way! The pictures don't even do the place justice. The house was spacious, spotless clean, and both decks were incredible. The front deck offered those ..."
Reviewed on Aug 2, 2026
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
Rileyville VA
Stay at this cabin in Rileyville. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Chalybeate Spring and Fort Valley Public Library are located ...
9.8/10 Exceptional! (330 reviews)
"We had an amazing stay. Really enjoyed seeing the sun rising over the mountains through the bedroom window every morning. Perfect location to visit Shenandoah National Park and explore Luray Caverns. Beautiful home and incredible location."
Reviewed on Jul 16, 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.
Stay near popular Middletown attractions
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- Visit Sperryville
- Visit Maurertown
- Visit Marshall
- Hupp's Hill Civil War Park
- Visit Rappahannock County
- Visit Strasburg
- Visit Flint Hill
- Visit Boyce
- Visit Berryville
- Visit Bentonville
- Belle Grove Plantation
- Visit Delaplane
- Visit Old Town Winchester
- Visit Woodstock
- Visit Cross Junction
- Cedar Creek and Belle Grove National Historical Park
- Visit Fort Valley
- Jackson's Chase Golf Course
- Visit Rileyville
- Visit Luray
- Visit Upperville
- Visit Linden
- Visit Millwood
- Visit Winchester
- Visit Front Royal
- Visit Toms Brook
- Visit Star Tannery
- Visit Washington
- Great Falls Park
- Visit Gore
- Valerie Hill Winery
- Visit Stephens City
- Visit Huntly
- Visit Hume
- Visit White Post
- Visit Paris
- Belle Grove Plantation
- Cedar Creek Battlefield Foundation
- Cedar Creek and Belle Grove National Historical Park
- Jackson's Chase Golf Course
- Shenandoah National Park
- Front Royal Entrance Shenandoah National Park
- Shenandoah River
- Shenandoah University
- ValleyHealth Winchester Medical Center
- George Washington National Forest
- Skyline Caverns
- Shenandoah River State Park
- Sky Meadows State Park
- Shenandoah County Fairgrounds
- Dickey Ridge Visitor Center
- Watermelon Park Campground
- Patsy Cline Historic House
- Apple Blossom Mall
- Dinosaur Land
- Museum of the Shenandoah Valley
- Linden Vineyards
- Rock Harbor Golf Course
- Bright Box Theater
- Naked Mountain Winery & Vineyards
- Little Washington Theatre
- Stonewall Jackson's Headquarters
- Front Royal Visitor's Center
- Mackintosh Fruit Farm
- Barrel Oak Winery
- Glen Manor Vineyards
- Delaplane Cellars
