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Top Middletown hotels deals

Econo Lodge Inn & Suites Middletown - Winchester South

Econo Lodge Inn & Suites Middletown - Winchester South

2 out of 5
91 Reliance Road Middletown VA
Free cancellation
Reserve now, pay when you stay
The price is CA $97 per night
CA $97
CA $107 total
Jul 19 - Jul 20
includes taxes & 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 Park and Belle Grove Plantation are located nearby.
Pet-friendly
Parking included
Wayside Inn

Wayside Inn

3.5 out of 5
7783 Main St Middletown VA
The price is CA $172 per night
CA $172
CA $204 total
Jul 12 - Jul 13
includes taxes & 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 Creek and Belle Grove National Historical Park and Belle Grove Plantation are located nearby.
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
Free cancellation
Reserve now, pay when you stay
The price is CA $115 per night
CA $115
CA $128 total
Jul 26 - Jul 27
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Rutherford Crossing and Northside Station Shopping Center are located nearby.
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
The price is CA $92 per night
CA $92
CA $104 total
Jul 26 - Jul 27
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Abram's Delight and Apple Blossom Mall are located nearby.
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 CA $118 per night
CA $118
CA $135 total
Aug 2 - Aug 3
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). 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
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
The price is CA $173 per night
CA $173
CA $196 total
Jul 19 - Jul 20
includes taxes & fees
Book a stay at this spa hotel in Winchester. Enjoy a full-service spa, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Old Court House Civil War Museum and Bright Box Theater are located nearby.
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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.
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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

A large house in a field with a cloudy sky.