Deals on vacations and trips to Middletown

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Top Middletown hotels deals

Wayside Inn

Wayside Inn

3.5 out of 5
7783 Main St Middletown VA
$144 nightly
The price is $159 total per night
$159 total
Aug 30 - Aug 31
Total with taxes and fees
A restaurant, free parking, and a terrace are among this hotel's amenities. Guests will appreciate free perks like free self parking and WiFi in public areas. A garden, a lobby fireplace, and a library are also on offer.
Pet friendly
Parking included
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
$102 nightly
The price is $113 total per night
$113 total
Sep 27 - Sep 28
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
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
Sep 7 - Sep 8
Total with taxes and fees
A full-service spa, 2 restaurants, and an indoor pool are all featured at this Georgian hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and laundry facilities.
Pool
Spa
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike Winchester VA
Free Cancellation
Reserve now, pay when you stay
$69 nightly
The price is $76 total per night
$76 total
Aug 30 - Aug 31
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. There's express check-out and multilingual staff can provide around-the-clock assistance.
Pet friendly
Parking included
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
$103 nightly
The price is $114 total per night
$114 total
Aug 31 - Sep 1
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
Spark by Hilton Winchester

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr Winchester VA
Free Cancellation
Reserve now, pay when you stay
$77 nightly
The price is $87 total per night
$87 total
Sep 28 - Sep 29
Total with taxes and fees
The hotel doesn't skimp on freebies - guests receive free continental breakfast and free self parking. Traveling for business? Take advantage of the business center, express check-out, and conference space. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Pet friendly
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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.

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

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

A large house in a field with a cloudy sky.