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Top Middletown hotels deals

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
Free Cancellation
Reserve now, pay when you stay
$109 nightly
The price is $119 total per night
$119 total
Mar 1 - Mar 2
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
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
Free Cancellation
Reserve now, pay when you stay
$122 nightly
The price is $138 total per night
$138 total
Mar 5 - Mar 6
Total with taxes and fees
A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and laundry facilities.
Pool
Spa
Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University

2.5 out of 5
140 Costello Dr Winchester VA
Free Cancellation
$80 nightly
The price is $87 total per night
$87 total
Mar 19 - Mar 20
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's a gym on site, and a 24-hour front desk and dry cleaning are also provided.
Breakfast included
Parking included
Falling Leaf Cabin - Rustic Charm With Modern Decor!

Falling Leaf Cabin - Rustic Charm With Modern Decor!

Rileyville VA
Get rates
A hot tub is featured at this cabin, along with laundry facilities and barbecue grills.
Hot Tub
Kitchen
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
Free Cancellation
$86 nightly
The price is $94 total per night
$94 total
Mar 6 - Mar 7
Total with taxes and fees
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Pool
Parking included
Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

3 out of 5
300 Marriott Drive Winchester VA
Free Cancellation
Reserve now, pay when you stay
$107 nightly
The price is $116 total per night
$116 total
Mar 5 - Mar 6
Total with taxes and fees
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Pool
Parking included
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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

Beautiful drive up to this plantation. You can take a tour of it as well.

Belle Grove Plantation

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.

Belle Grove Plantation

Cedar Creek and Belle Grove National Historical Park

Explore the great outdoors at Cedar Creek and Belle Grove National Historical Park, a lovely green space in Middletown. Stroll along the riverfront or experience the area's entertainment venues.

Cedar Creek and Belle Grove National Historical Park

Cedar Creek Battlefield Foundation

You can find out about the history of Middletown with a visit to Cedar Creek Battlefield Foundation. Stroll along the riverfront or experience the entertainment venues in this vibrant area.

Cedar Creek Battlefield Foundation

Frequently asked questions

How much are vacation packages to Middletown?
Packages, which include hotels and flights in Middletown, start from just . Make your travel dreams come true and secure your dream vacation with Travelocity today.
Where can I get the best vacation package deals for Middletown?
There are exciting Middletown package deals to be scored with Travelocity. Did you know we partner with as many as 400 airlines and 1,000,000 properties worldwide? Keep that in mind the next time you're ready to check another destination off your list.
Why should I book my Middletown vacation bundle with Travelocity?
Whether you're on the hunt for the ultimate unplugged vacation or you crave the hustle and bustle of a towering metropolis, booking everything with Travelocity saves you time, money and hassle. No need to comb through hundreds of websites to find the best deal — our Price Match Guarantee ensures you'll always get the lowest possible price, and our team of customer service experts are available 24/7.
Can I save on my Middletown car rental if I book it with my hotel or flight?
Absolutely — bundle your car, flight and hotel into a Middletown vacation package and you'll save a tidy sum. With so much to see in the Middletown area, having your own ride will more than come in handy. Once you're in the driver's seat, crank up the music and cruise toward White House, a well-known sight approximately 65 mi from Middletown.
Which airport is best for Middletown?
Washington Dulles Intl. Airport (IAD) is popular. It's situated approximately 45 mi east of Middletown. Your other options are Charlottesville-Albemarle Airport (CHO) (60 mi away from central Middletown) and Hagerstown Regional Airport (HGR) (55 mi away from central Middletown).
What is there to do in Middletown?
You'll notice an undeniable magic as you stroll through the streets of Middletown. Belle Grove Plantation and Jackson's Chase Golf Course are just a couple of famous sights that make this city so popular, so add them to your must-see list.
Where should I stay when visiting Middletown?
If you're after a place to spend your nights, check out the Wayside Inn. It's the top choice for many travelers.

Photos of local treasures

Browse Middletown vacation photos for more inspiration

Beautiful drive up to this plantation. You can take a tour of it as well.
Beautiful drive up to this plantation. You can take a tour of it as well.