Middletown, VA
Travel Guide
Visit Middletown
Wayside Inn
7783 Main St Middletown VA
$94 nightly
The price is $104 total per night from Oct 15 to Oct 16
$104 total
Oct 15 - Oct 16
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! (447 reviews)
"This is a quaint, historical place to stay with lots of antiques and interesting furnishings. We enjoyed the patio, pub and live music on the night we stayed. We would stay again if we find ourselves in the area."
Reviewed on Sep 17, 2026
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 27 to Sep 28
$148 total
Sep 27 - Sep 28
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 ...
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$69 nightly
The price is $76 total per night from Sep 20 to Sep 21
$76 total
Sep 20 - Sep 21
Total with taxes and fees
Stay at this motel in Winchester. Enjoy free parking, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in ...
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.
"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! (376 reviews)
"Perfect quick getaway"
Reviewed on Sep 9, 2026
Whiskey Hill Cabin a mountain escape in Virginia wine country!
Linden VA
Stay at this cabin in Front Royal. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Deer Lake and George Richard Thompson State Wildlife ...
10/10 Exceptional! (123 reviews)
"Ever clean and welcoming. Would highly recommend this one too anyone."
Reviewed on Aug 16, 2026
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Star Tannery VA
Book a stay at this family-friendly vacation home in Star Tannery. Enjoy free WiFi, a pool table, and patios. Popular attraction J. Allen Hawkins Community Park ...
9.8/10 Exceptional! (269 reviews)
"Very quiet, lovely place out in star tannery with Beautiful views. Clean and well kept. Fun games to play and it was all just very lovely."
Reviewed on Aug 29, 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
- Shenandoah County Fairgrounds
- Apple Blossom Mall
- Sky Meadows State Park
- Patsy Cline Historic House
- Shenandoah Valley Discovery Museum
- Museum of the Shenandoah Valley
- Dinosaur Land
- Lost River
- Dickey Ridge Visitor Center
- Delaplane Cellars
- Rock Harbor Golf Course
- Watermelon Park Campground
- Little Washington Theatre
- Front Royal Visitor's Center
- Linden Vineyards
- Naked Mountain Winery & Vineyards
- Belle Boyd Cottage
- Bright Box Theater
- RdV Vineyards
