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Top Middletown hotels deals

Wayside Inn

Wayside Inn

3.5 out of 5
7783 Main St, Middletown, VA
The price is CA $134 per night
CA $134
CA $162 total
includes taxes & fees
9 Dec - 10 Dec
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 Wayside Theater and Cedar Creek and Belle Grove National Historical Park are located nearby.
Parking included
Free WiFi
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

2.5 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Free cancellation
Reserve now, pay when you stay
The price is CA $133 per night
CA $133
CA $145 total
includes taxes & fees
16 Dec - 17 Dec
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Apple Blossom Mall and Abram's Delight are located nearby.
Pool
Breakfast included
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
The price is CA $89 per night
CA $89
CA $96 total
includes taxes & fees
28 Nov - 29 Nov
Book a stay at this business-friendly motel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Apple Blossom Mall and Abram's Delight are located nearby.
Pool
Pet-friendly
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 CA $106 per night
CA $106
CA $115 total
includes taxes & fees
1 Dec - 2 Dec
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rutherford Crossing and Northside Station Shopping Center are located nearby.
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
The price is CA $177 per night
CA $177
CA $201 total
includes taxes & fees
24 Nov - 25 Nov
Stay at this 3.5-star spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Old Court House Civil War Museum and Bright Box Theater are located nearby.
Spa
Free WiFi
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 CA $98 per night
CA $98
CA $109 total
includes taxes & fees
26 Nov - 27 Nov
Book a stay at this business-friendly hotel in Strasburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Hupp's Hill Civil War Park and Strasburg Museum are located nearby.
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.

Popular places to visit

Belle Grove Plantation

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 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

Wayside Theater

Get tickets for a show at Wayside Theater, a storied theater in Middletown. Amble around this vibrant area's riverfront or experience its entertainment venues.

Wayside Theater

Middletown Vacations

A little bit of planning and research can mean the difference between a good vacation and a magnificent one! Wander wisely in Middletown by learning the essentials about it before you set off.

You'll find this Winchester neighborhood 12 miles (19 kilometers) to the southwest of the downtown action.

Visitors to Winchester will be rubbing shoulders with roughly 26,000 residents.

Places to visit in Middletown

It's not easy to see how people in the past survived at home without all the appliances we have these days. Step over the threshold into Belle Grove Plantation and learn how they did. And that's not all there is. Spending time in nature has been shown to lift both your psychological and physical well-being. Take a trip to Cedar Creek and Belle Grove National Historical Park and feel the benefits of connecting with our natural environment.

Where do you fly into for Middletown?

Flying into Washington Dulles International Airport (IAD)? Middletown is only 45 miles (72 kilometers) from here. Grab some nibbles, hail a cab and you'll be there before you know it!

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 105 kilometers from Middletown.
Which airport is best for Middletown?
Washington Dulles Intl. Airport (IAD) is popular. It’s situated approximately 72 kilometers east of Middletown. Your other options are Charlottesville-Albemarle Airport (CHO) (97 kilometers away from central Middletown) and Hagerstown Regional Airport (HGR) (88 kilometers 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