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 Nov 28 to Nov 29
$104 total
Nov 28 - Nov 29
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! (461 reviews)
"I fully paid for our stay through Expedia and we got charged once more by the lady working downstairs! This is insane. Definitely not going back and I do not recommend staying there, they can’t be trusted."

Reviewed on Nov 3, 2026

Wayside Inn
Econo Lodge Inn & Suites Middletown - Winchester South

Econo Lodge Inn & Suites Middletown - Winchester South

2 out of 5
91 Reliance Road Middletown VA
$63 nightly
The price is $69 total per night from Nov 24 to Nov 25
$69 total
Nov 24 - Nov 25
Total with taxes and fees
Stay at this hotel in Middletown. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Cedar Creek and Belle Grove National Historical ...
Econo Lodge Inn & Suites Middletown - Winchester South
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike Winchester VA
Fully refundableReserve now, pay when you stay
$70 nightly
The price is $77 total per night from Dec 1 to Dec 2
$77 total
Dec 1 - Dec 2
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 ...
8.6/10 Excellent! (1,072 reviews)
"Je remarque que lorsque nous réservons avez Expedia nous avons des chambres médiocres. La salle de bain excessivement petite et très salle. Je ne retournerai plus à cet endroit et je ne réserverai plus avec Expedia"

Reviewed on Nov 3, 2026

Travelodge by Wyndham Winchester
See all 652 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! (390 reviews)
"Second visit to this property and we like it alot. The basics are there but definitely bring other cookware if you are the type of person to cook at home rather then eat out all the time. Overall pleased and have recommended to other friends and family of ours."

Reviewed on Nov 1, 2026

"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA

"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! (345 reviews)
"Beautiful cabin in a private location with a good view. Firewood was provided and grill too. Hot tub was easy and relaxing. Had a great time."

Reviewed on Nov 2, 2026

"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
Adorable river front cabin ,with hot tub on the River

Adorable river front cabin ,with hot tub on the River

Luray VA
Stay at this cabin in Luray. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Chalybeate Spring and Fort Valley Public ...
9.2/10 Wonderful! (28 reviews)
"This cabin was OK, was not river front as posted. Burners on stove top are reversed. Nice to get away"

Reviewed on Oct 28, 2026

Adorable river front cabin ,with hot tub on the River
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.

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