Middletown, VA
Travel Guide
Visit Middletown
Wayside Inn
7783 Main St Middletown VA
$144 nightly
The price is $159 total per night from Sep 6 to Sep 7
$159 total
Sep 6 - Sep 7
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! (446 reviews)
"It was a very nice room with very comfortable bed. We misplaced the key and they were very helpful getting a replacement after hours. Fortunately, we found the lost key. Staff bwas very pleasant. Air conditioner was a little loud but effective. Did not prevent from sleeping. Would stay again."
Reviewed on Aug 29, 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
$77 nightly
The price is $87 total per night from Sep 13 to Sep 14
$87 total
Sep 13 - Sep 14
Total with taxes and fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and ...
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
$130 nightly
The price is $148 total per night from Sep 8 to Sep 9
$148 total
Sep 8 - Sep 9
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 ...
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.
"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! (333 reviews)
"The property was clean and homie. We immediately felt relaxed as soon as we walked in. We had plenty to do in the house, even with the bit of rain we had - our kids had their pick at board games . Would definitely recommend and book again!"
Reviewed on Aug 9, 2026
Mystic Mountain-Secluded Log Cabin with Pool, Hot Tub & Amazing Views!
Rileyville VA
Stay at this cabin in Rileyville. Enjoy a garden, patios, and air conditioning. Popular attractions Elkwallow Picnic Area and Pass Mountain are located ...
9.6/10 Exceptional! (8 reviews)
"Firstly, the road to get to the property is a little bit rough for the last half mile or so, but thats stated clearly in the listing; If you don't have AWD/4X4 or are NOT familiar with how to drive on slightly rocky/rain-washed backroads with a decent incline , I would avoid. A steady pace & good ..."
Reviewed on Aug 17, 2026
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
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 ...
10/10 Exceptional! (374 reviews)
"We really enjoyed our stay in this one bedroom cabin in the woods!"
Reviewed on Aug 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
- George Washington National Forest
- ValleyHealth Winchester Medical Center
- Skyline Caverns
- Shenandoah River State Park
- Sky Meadows State Park
- Apple Blossom Mall
- Patsy Cline Historic House
- Shenandoah County Fairgrounds
- Shenandoah Valley Discovery Museum
- Dickey Ridge Visitor Center
- Dinosaur Land
- Lost River
- Rock Harbor Golf Course
- Watermelon Park Campground
- Museum of the Shenandoah Valley
- Delaplane Cellars
- Front Royal Visitor's Center
- Naked Mountain Winery & Vineyards
- Bright Box Theater
- Little Washington Theatre
- Linden Vineyards
- Stonewall Jackson's Headquarters
