Deals on vacations and trips to Middletown

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Wayside Inn

Wayside Inn

3.5 out of 5
Price was $359, price is now $344 per person
$344
per person
Oct 31 - Nov 3
found 9 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Martinsburg (MRB)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Free parking, a terrace, and a garden are also offered.
Canal Cabins

Canal Cabins

3 out of 5
Price was $391, price is now $365 per person
$365
per person
Oct 31 - Nov 3
found 9 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Martinsburg (MRB)
This cabin doesn't skimp on freebies - guests receive free WiFi and free self parking. A picnic area, express check-out, and luggage storage are also on offer.

Top Middletown hotels deals

Wayside Inn

Wayside Inn

3.5 out of 5
7783 Main St, Middletown, VA
The price is $120 total per night
$120 total
per night
Oct 28 - Oct 29
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Free parking, a terrace, and a garden are also offered.
Parking included
Free WiFi
Econo Lodge Inn & Suites

Econo Lodge Inn & Suites

2 out of 5
91 Reliance Road, Middletown, VA
Free Cancellation
Reserve now, pay when you stay
The price is $78 total per night
$78 total
per night
Oct 5 - Oct 6
A bar/lounge and a 24-hour front desk are featured at this hotel, along with free self parking. WiFi in public areas is free. Laundry facilities are provided for your convenience.
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
The price is $118 total per night
$118 total
per night
Oct 5 - Oct 6
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
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 out of 5
150 Faraday Plaza, Winchester, VA
Free Cancellation
Reserve now, pay when you stay
The price is $91 total per night
$91 total
per night
Oct 26 - Oct 27
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Breakfast included
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 out of 5
21 Signal Knob Dr, GPS: 35 Brandy court, Strasburg, VA
Free Cancellation
Reserve now, pay when you stay
The price is $84 total per night
$84 total
per night
Oct 5 - Oct 6
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like daily breakfast and free self parking.
Breakfast included
Pet friendly
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
The price is $104 total per night
$104 total
per night
Oct 27 - Oct 28
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
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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

3.5/5(3 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.

Belle Grove Plantation

Cedar Creek Battlefield Foundation

4.5/5(2 reviews)

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

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

Frequently asked questions

How much are vacation packages to Middletown?
Packages, which include hotels and flights in Middletown, start from just $344. 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

Photo by Stephanie Sutton
Photo by Stephanie Sutton
Photo by Samantha Keyes
Photo by Samantha Keyes