Hotels Near
Old Town Winchester

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Featured Old Town Winchester Hotels

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! (1,000 reviews)
"Everything ok"

Reviewed on Apr 14, 2024

Ramada by Wyndham Strasburg/Shenandoah Valley
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
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! (1,003 reviews)
"From the moment we arrived the front desk person made us feel very welcome and at home. She was very knowledgeable about the walkable areas and restaurants. The room was excellent and the beds were comfortable. The lounge had an excellent singer that we enjoyed immensely. Would highly recommend this ..."

Reviewed on Apr 18, 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! (1,268 reviews)
"Great price for a one night stop enroute that is clean and convenient"

Reviewed on Apr 18, 2024

La Quinta Inn & Suites by Wyndham Winchester
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! (706 reviews)
"Just an overnight stay both to and from Augusta. Everything was more than fine."

Reviewed on Apr 16, 2024

Microtel Inn & Suites by Wyndham Winchester
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! (1,055 reviews)
"Easy on and off interstate for overnight travel stay."

Reviewed on Apr 19, 2024

Travelodge 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! (886 reviews)
"Excellent location. Terrific staff. Very nice room."

Reviewed on Apr 13, 2024

Comfort Inn & Suites
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! (1,003 reviews)
"Nice property, friendly staff."

Reviewed on Apr 18, 2024

Country Inn & Suites by Radisson, Winchester, VA
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! (1,002 reviews)
"Wonderful staff made for a great stay."

Reviewed on Apr 16, 2024

Holiday Inn Winchester Se-Historic Gateway, an IHG Hotel
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! (318 reviews)
"great area"

Reviewed on Apr 13, 2024

The Inn at Charles Town
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
3 out of 5
5 Caroline Drive, Front Royal, VA
Fully refundableReserve now, pay when you stay
Stay at this 3-star business-friendly hotel in Front Royal. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.4/10 Exceptional! (384 reviews)
"The staff was super friendly and nice. The room was quiet, adequate and clean, but could use some updating. But that is to be expected when you have a dog with you. Hotels prefer not to give their best rooms to dogs, which makes sense. I was disappointed that the room in this multi-story hotel was ..."

Reviewed on Apr 11, 2024

TownePlace Suites by Marriott Front Royal
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! (565 reviews)
"Upgraded rooms are very nice. Slept very well."

Reviewed on Apr 15, 2024

Fairfield Inn & Suites by Marriott Winchester
Rodeway Inn & Suites - Charles Town, WV
Rodeway Inn & Suites - Charles Town, WV
2 out of 5
741 E Washington St, Charles Town, WV
Fully refundableReserve now, pay when you stay
Stay at this business-friendly motel in Charles Town. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.6/10 Excellent! (776 reviews)
"Hotel nice and convenient to the casino but with concerts only lasting 90 minutes and the diner’s decline we’re less likely to return."

Reviewed on Apr 14, 2024

Rodeway Inn & Suites - Charles Town, WV
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 $63
  • 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.