Middletown, VA

Travel Guide

A mountainous landscape with autumn foliage, rocky outcrops, and a valley below.
A large house in a field with a cloudy sky.
Wayside Inn

Wayside Inn

3.5 out of 5
7783 Main St Middletown VA
$94 nightly
The price is $104 total per night from Oct 19 to Oct 20
$104 total
Oct 19 - Oct 20
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! (452 reviews)
"Wonderful staff and vibe . If you enjoy history then this is a place for you . The rooms are “old school ;so, don’t be prepared for the “newest” amenities . Thus is a place for people who like to “feel” the historic vibe"

Reviewed on Oct 14, 2026

Wayside Inn
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 out of 5
150 Faraday Plaza Winchester VA
$84 nightly
The price is $93 total per night from Nov 15 to Nov 16
$93 total
Nov 15 - Nov 16
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 ...
9.2/10 Wonderful! (1,440 reviews)
"Loved our stay, it was well priced and had everything we needed!"

Reviewed on Oct 16, 2026

Microtel Inn & Suites by Wyndham Winchester
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 out of 5
103 E Piccadilly St Winchester VA
$130 nightly
The price is $148 total per night from Oct 29 to Oct 30
$148 total
Oct 29 - Oct 30
Total with taxes and fees
Book a stay at this spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
The George Washington Hotel, A Wyndham Grand Hotel
See all 660 properties in Middletown
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.

"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! (384 reviews)
"Very nice and clean. Everything you might need in a secluded cabin. The hot tub was perfect! Saw deer each day we were there. Fire ring was nice to have as well."

Reviewed on Oct 16, 2026

"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal

Front Royal VA
Stay at this vacation home in Front Royal. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Shenandoah River and Bing Crosby Stadium are ...
10/10 Exceptional! (46 reviews)
"Very cool, very clean and shiny and interestingly located. Catch a sunset from the front porch. They have everything you may need and everything is top of the line. Wish we could’ve stayed longer than 1 night. Highly recommended!"

Reviewed on Oct 14, 2026

Mountain View Bungalow in Front Royal
"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 VA
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 ...
10/10 Exceptional! (375 reviews)
"The cabin is very secluded and very relaxing. The field with the trails was fantastic nice quiet hang out by the water was beautiful. It's an excellent place to unplug from the world."

Reviewed on Oct 6, 2026

"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
See all properties in Middletown
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

Belle Grove Plantation

8.4/10 (8 reviews)
Learn about the local history of Middletown when you spend time at Belle Grove Plantation. Wander the riverfront or discover the mountain views in this vibrant area.
See properties

Frequently asked questions

Is Middletown worth visiting?
Middletown is worth visiting for its rich history and diverse culinary scene. Travelers can explore significant historical sites such as Belle Grove Plantation and the Cedar Creek Battlefield Foundation, and enjoy a variety of dining options, including delicious Italian and Asian cuisine.
When is the best time to visit Middletown?
The best time to visit Middletown is from May through September, when the climate is generally most pleasant. For fewer crowds and better value, the cooler months of November through February are a good option, offering a different experience with milder temperatures.
What is Middletown known for?
Middletown is known for its rich history, highlighted by significant sites like Belle Grove Plantation and the Cedar Creek Battlefield Foundation. These are key components of the Cedar Creek and Belle Grove National Historical Park. Travelers can also enjoy the local Italian food culture.
What is a good itinerary length for Middletown?
A good itinerary length for Middletown is one to two days to visit key sites like Belle Grove Plantation and the Cedar Creek Battlefield Foundation. For an extended stay of three to four days, travelers can fully explore the Cedar Creek and Belle Grove National Historical Park and enjoy the local Italian, Asian, and North American cuisine.
What are the top things to do in and around Middletown?
Middletown offers a blend of historical sites, natural landscapes, and recreational activities for travelers to enjoy:


How do I plan a trip to Middletown?
To plan your trip to Middletown, search for places to stay and book flights and rental cars in advance. Explore attractions like Belle Grove Plantation, Cedar Creek Battlefield Foundation, and Cedar Creek and Belle Grove National Historical Park. When planning activities, remember to pair outdoor plans with indoor backups for weather flexibility, and enjoy the local Italian, Asian, or North American cuisine.
What cuisines can you find in Middletown?
In Middletown, travelers can find New American cuisine, with options like gourmet burgers, artisanal flatbreads, and creative small plates. The area also offers Italian classics such as pasta and pizza, plus a range of Asian dishes including Chinese, Japanese, and Thai. You'll also find Latin American flavors like Mexican and Caribbean.
Can I book a refundable hotel in Middletown?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Middletown by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Middletown with Expedia?
Expedia makes it easier to plan your Middletown trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Middletown?
The best choice depends on your travel style. Hotels in Middletown can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Middletown trip on Expedia?
Once you've booked your Middletown trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Middletown trip?
Expedia offers customer support before, during, and after your Middletown trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Middletown?
If it's your first trip to Middletown, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Middletown hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Middletown hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Middletown

A mountainous landscape with autumn foliage.

Front Royal

A mountainous landscape with autumn foliage.

Stephens City

An aerial view of a railway station with multiple tracks, a steam locomotive emitting smoke, and a blue train car.

Strasburg

A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

Winchester

Explore a world of travel with Expedia