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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 $97 per night
CA $97
CA $121 total
Oct 19 - Oct 20
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.
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 $120 per night
CA $120
CA $133 total
Nov 15 - Nov 16
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 Rutherford Crossing and Northside Station Shopping Center are located nearby.
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 $185 per night
CA $185
CA $210 total
Nov 8 - Nov 9
includes taxes & fees
Book a stay at this spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. 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.
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 out of 5
21 Signal Knob Dr Strasburg VA
Free cancellation
Reserve now, pay when you stay
The price is CA $108 per night
CA $108
CA $120 total
Nov 8 - Nov 9
includes taxes & fees
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
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 $121 per night
CA $121
CA $135 total
Nov 8 - Nov 9
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.
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 CA $140 per night
CA $140
CA $155 total
Oct 18 - Oct 19
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 breakfast and the helpful staff in our reviews. Popular attractions Apple Blossom Mall and R-C Track 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 mountainous landscape with autumn foliage, rocky outcrops, and a valley below.
A large house in a field with a cloudy sky.