Middletown Travel Guide

Tourist Guide

Photo by Stephanie Sutton
Photo by Samantha Keyes
Wayside Inn

Wayside Inn

3.5 out of 5
7783 Main St, Middletown, VA
The price is NZ$188 per night from 17 Aug to 18 Aug
NZ$188
17 Aug - 18 Aug
includes taxes & 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 Wayside ...
9.2/10 Wonderful! (392 reviews)
"We stayed last year on July 4th. ...really liked it...decided to make it an annual event. I like the small town atmosphere."

Reviewed on 7 Jul. 2025

Wayside Inn
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
The price is NZ$189 per night from 1 Sept to 2 Sept
NZ$189
1 Sept - 2 Sept
includes taxes & fees
Stay at this 3-star 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! (2,122 reviews)
"Great place to stay . Clean , spacious and allow pets to stay ."

Reviewed on 14 Aug. 2025

La Quinta Inn & Suites by Wyndham Winchester
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

3 out of 5
333 Front Royal Pike, Winchester, VA
The price is NZ$163 per night from 24 Aug to 25 Aug
NZ$163
24 Aug - 25 Aug
includes taxes & fees
Stay at this 3-star 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)
"Bed comfort"

Reviewed on 12 Aug. 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
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.
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

Edinburg
Stay at this vacation home in Woodstock. Enjoy a garden, laundry facilities, and patios. Popular attractions Shenandoah Vineyards and Edinburg Mill Museum are ...
9.8/10 Exceptional! (322 reviews)
"Lovely cabin in the woods perfect for our family for a relaxing vacation enjoying nature. Beautiful place to view the sunset from the porch."

Reviewed on 10 Aug. 2025

Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub

"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub

Rileyville
Stay at this cabin in Rileyville. Enjoy free WiFi, a garden, and laundry facilities. Our guests praise the property condition in our reviews. Popular attractions ...
9.8/10 Exceptional! (313 reviews)
Quiet and comfortable
"Property was clean and well maintained. Plenty of room for the family to spread out. Walk down to the river was easy and path was mowed. Hot tub could use some maintenance, the jets did not seem to be working to full capacity, but it was clean and relaxing."

Reviewed on 29 Jul. 2025

"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
Star view cabin-Riverfront

Star view cabin-Riverfront

Rileyville
Stay at this cabin in Rileyville. Enjoy laundry facilities, tennis courts, and patios. Our guests praise the property condition in our reviews. Popular attractions ...
9.6/10 Exceptional! (293 reviews)
Wonderful, relaxing stay
"The pictures on VRBO do not do this place justice. It is beautiful here. The view from the porch is absolutely amazing. Location is close to anything you need. We kayaked nearby, hiked, ziplined, and fished every night. My kids even braved the dark to try some catfishing! They are HUGE and plentiful ..."

Reviewed on 28 Jul. 2025

Star view cabin-Riverfront
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

Cities near Middletown