Middletown, VA
Travel Guide
Visit Middletown
Wayside Inn
7783 Main St Middletown VA
$117 nightly
The price is $129 total per night from Sep 27 to Sep 28
$129 total
Sep 27 - Sep 28
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)
"Clean room at a reasonable price. Interesting old inn."
Reviewed on Aug 11, 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
$102 nightly
The price is $113 total per night from Sep 27 to Sep 28
$113 total
Sep 27 - Sep 28
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 ...
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
$122 nightly
The price is $138 total per night from Sep 7 to Sep 8
$138 total
Sep 7 - Sep 8
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 ...
9.4/10 Exceptional! (6 reviews)
"Everything was as advertised, amazing view, and clean."
Reviewed on Aug 6, 2026
The Grape Escape - A-Frame Cabin
Linden VA
Stay at this cabin in Linden. Enjoy free WiFi, a garden, and patios. Popular attractions Tuckers Lane Trailhead and Fox Meadow Winery are located nearby.
10/10 Exceptional! (24 reviews)
"Nice and cozy. Can't go wrong with this one. Book it!"
Reviewed on Jul 30, 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 University
- Shenandoah River
- 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
- Watermelon Park Campground
- Dinosaur Land
- Rock Harbor Golf Course
- Museum of the Shenandoah Valley
- Lost River
- Naked Mountain Winery & Vineyards
- RdV Vineyards
- Front Royal Visitor's Center
- Linden Vineyards
- Stonewall Jackson's Headquarters
- Delaplane Cellars
- Valerie Hill Winery
- Little Washington Theatre
