Hotels Near
Old Town Winchester

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Featured Old Town Winchester Hotels

Microtel Inn & Suites by Wyndham Winchester
Microtel Inn & Suites by Wyndham Winchester
2.5 out of 5
150 Faraday Plaza, Winchester, VA
Fully refundableReserve now, pay when you stay
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 ...
8.8/10 Excellent! (733 reviews)
"It’s fairly new facility. Nice. Breakfast could have been a little better, but overall ok."

Reviewed on Apr 26, 2024

Microtel Inn & Suites by Wyndham Winchester
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
Fully refundableReserve now, pay when you stay
Stay at this 3.5-star spa hotel in Winchester. Enjoy free WiFi, 2 restaurants, and a full-service spa. Our guests praise the breakfast and the bar in our reviews. ...
9.2/10 Wonderful! (1,000 reviews)
"Covienience- beauty, decor"

Reviewed on Apr 28, 2024

The George Washington Hotel, A Wyndham Grand Hotel
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
Fully refundableReserve now, pay when you stay
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our ...
8.8/10 Excellent! (1,290 reviews)
Great place to stay
"A very nice place to stay. We loved the fact that it was fast and easy to get checked in and that they welcomed our dog. We have a larger dog, and many hotels won't accept her. The room was great and so was the breakfast the next day. Will definitely stay here again."

Reviewed on Apr 29, 2024

La Quinta Inn & Suites by Wyndham Winchester
Comfort Inn & Suites
Comfort Inn & Suites
2.5 out of 5
195 Kernstown Commons Blvd, Winchester, VA
Fully refundableReserve now, pay when you stay
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 ...
9.4/10 Exceptional! (898 reviews)
"Quick and easy. Room smells fresh"

Reviewed on Apr 28, 2024

Comfort Inn & Suites
Travelodge by Wyndham Winchester
Travelodge by Wyndham Winchester
2.5 out of 5
160 Front Royal Pike, Winchester, VA
Fully refundableReserve now, pay when you stay
Stay at this business-friendly motel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
7.8/10 Good! (1,059 reviews)
"Older motel with good staff and a restful nights sleep. They had a good basic breakfast and overall it was a good for an overnight stop."

Reviewed on Apr 27, 2024

Travelodge by Wyndham Winchester
Red Roof Inn Winchester, VA
Red Roof Inn Winchester, VA
2 out of 5
991 Millwood Pike, Winchester, VA
Fully refundableReserve now, pay when you stay
Stay at this hotel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.2/10 Good! (1,001 reviews)
Well equipped, reasonably priced
"Actually a nice motel. Short drive to many restaurants. Clean, fridge, microwave, even an iron, everything you could need for a short stay. Room is very small but recently updated. Floors are wood vinyl-ish so no fear of things lurking in carpet. It was a bit noisy at night. A guest had tv on full ..."

Reviewed on Apr 17, 2024

Red Roof Inn Winchester, VA
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
Fully refundableReserve now, pay when you stay
Stay at this business-friendly hotel in Strasburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our ...
7.8/10 Good! (1,004 reviews)
"The Ramada was most convenient to get off of I-81 and then to get back on."

Reviewed on Apr 23, 2024

Ramada by Wyndham Strasburg/Shenandoah Valley
Country Inn & Suites by Radisson, Winchester, VA
Country Inn & Suites by Radisson, Winchester, VA
3 out of 5
141 Kernstown Commons Blvd, Winchester, VA
Fully refundable
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (1,001 reviews)
"The shampoo and conditioner made my hair sooooooooo nice, I wish I asked for more and brought home!!!!!!"

Reviewed on Apr 28, 2024

Country Inn & Suites by Radisson, Winchester, VA
Spark by Hilton Winchester
Spark by Hilton Winchester
2.5 out of 5
150 Wingate Dr, Winchester, VA
Fully refundableReserve now, pay when you stay
Stay at this business-friendly hotel in Winchester. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the ...
8.8/10 Excellent! (1,002 reviews)
"Hotel was great, breakfast was average but good, my son left a stuffed animal in the room and the tra ked it down for me and mailed it back to us.. and becasue of that service is 10 outa 5!"

Reviewed on Apr 19, 2024

Spark by Hilton Winchester
The Inn at Charles Town
The Inn at Charles Town
3 out of 5
100 Hollywood Dr, Charles Town, WV
Fully refundableReserve now, pay when you stay
Stay at this 3-star hotel in Charles Town. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
8.4/10 Very Good! (319 reviews)
"Check in was fast, breakfast had plenty of choices. I found the bed to be too soft and I was put off by an unknown amenities fee at checkout"

Reviewed on Apr 24, 2024

The Inn at Charles Town
Holiday Inn Winchester Se-Historic Gateway, an IHG Hotel
Holiday Inn Winchester Se-Historic Gateway, an IHG Hotel
3 out of 5
333 Front Royal Pike, Winchester, VA
Fully refundable
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and breakfast. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (1,001 reviews)
"Nice stay. Wo you led appreciate a buffet breakfast rather than a la carte included. Would be faster"

Reviewed on Apr 19, 2024

Holiday Inn Winchester Se-Historic Gateway, an IHG Hotel
Fairfield Inn & Suites by Marriott Winchester
Fairfield Inn & Suites by Marriott Winchester
2.5 out of 5
250 Front Royal Pike, Winchester, VA
Fully refundableReserve now, pay when you stay
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 ...
8.8/10 Excellent! (573 reviews)
Nice place
"Stayed for a quick night on an 11-hr road trip. Easy to book, comfortable, and affordable."

Reviewed on Apr 24, 2024

Fairfield Inn & Suites by Marriott Winchester
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.

Hotels in Old Town Winchester

Winchester is a city that has a lot going on, but you have your sights set on Old Town Winchester. This part of town is perfect for what you want to be doing, and that is everything that is not on everyone’s radar. For all that Old Town Winchester has going on, you’ll still need a place to crash, eventually. But you don’t want any old shack, you need something that fits the trip. We have a slew of Old Town Winchester hotels that will do the trick.

A beautiful day in the neighborhood

As much as you like getting out there, it’s also good to know a part of Winchester so well you’ll be telling the tourists where to go. Make friends with the concierge or be bold and chat up a local. It’s your trip, so choose your own adventure. And when you get in at night, you’ll have a comfy room and plenty of amenities to help you settle in. Call a friend and spin tales from the Old Town Winchester underground. What’s a journey without a good story to go with it?

Beyond the block

We’re not talking about the Old Town Winchester city block. We’re talking about looking beyond that block of hotels you always focus on. We give you tons of ways to sort our stash of Old Town Winchester cheap hotels. And if you feel like living a little, but not killing your vacation vibes, choose the Hotwire Hot Rate deal. Filter by:

  • Hotwire Hot Rate: Snag some of the best hotels in Old Town Winchester at an almost too good to be true rate. After you book, we’ll reveal the name of the hotel. You can get a luxury hotel at a budget price.
  • Price: You have a price in mind, and we have solutions. Hotels start as low as $70
  • Amenities: Rooftop lounge, designer furniture, 24-7 room service, and everything else you look for to live it up large.

Find the Old Town Winchester hotel you want, book it, and never look back. Because your great escape is ahead of you.