Hotels Near
Old Town Winchester

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Featured Old Town Winchester Hotels

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
Book a 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 ...
8/10 Very Good! (1,082 reviews)
"Very clean. Great value. Needs better pillows but bed was comfortable. Comparable to much more expensive stays."

Reviewed on Jun 24, 2024

Travelodge 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, a full-service spa, and 2 restaurants. Our guests praise the breakfast and the bar in our reviews. ...
9.2/10 Wonderful! (1,001 reviews)
"Everyone is always so kind, accommodating and genuine. Always enjoy our visit."

Reviewed on Jun 25, 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
Book a 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 ...
9/10 Wonderful! (1,422 reviews)
"Terrific! Loved the cool pictures of local icon buildings done so tastefully throughout the hotel. Good breakfast. Eggs powdered and bacon undercooked, but it is usual fare. Good to have coffee available, esp decaf. Such a hot temp outside, good to keep the water filled. Good beds, showers, soap ..."

Reviewed on Jun 26, 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
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 ...
8.8/10 Excellent! (843 reviews)
Excellent
"Very nice hotel. Very clean and friendly staff. Bed was comfortable. Easy check in and easy check out."

Reviewed on Jun 25, 2024

Microtel 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
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 ...
9.4/10 Exceptional! (983 reviews)
"Very nice large room!"

Reviewed on Jun 26, 2024

Comfort Inn & Suites
Spark by Hilton Winchester
Spark by Hilton Winchester
3 out of 5
150 Wingate Dr, Winchester, VA
Fully refundableReserve now, pay when you stay
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.8/10 Excellent! (1,001 reviews)
"It was convenient to the highway and there were restaurants all around."

Reviewed on Jun 15, 2024

Spark by Hilton Winchester
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
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 restaurant ...
7.8/10 Good! (1,004 reviews)
"Coffee"

Reviewed on Jun 25, 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! (1,005 reviews)
"Internet was very poor."

Reviewed on Jun 25, 2024

Country Inn & Suites by Radisson, Winchester, VA
DoubleTree by Hilton Front Royal Blue Ridge Shadows
DoubleTree by Hilton Front Royal Blue Ridge Shadows
4 out of 5
111 Hospitality Drive, Front Royal, VA
Fully refundableReserve now, pay when you stay
Stay at this 4-star golf hotel in Front Royal. Enjoy free WiFi, free parking, and a golf course. Our guests praise the pool and the restaurant in our reviews. ...
8.8/10 Excellent! (999 reviews)
"The room is clean. The staff is wonderful."

Reviewed on Jun 25, 2024

DoubleTree by Hilton Front Royal Blue Ridge Shadows
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 business-friendly hotel in Charles Town. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (351 reviews)
Will go back
"Nice hotel, the staff were friendly and helpful."

Reviewed on Jun 25, 2024

The Inn at Charles Town
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
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 ...
8.8/10 Excellent! (606 reviews)
"It was comfortable and clean. But the breakfast coffee labeled “Bold” was horrible. It was watered down nothing. A good cup of coffee is very important and so easy to make. But you must have excellent coffee. This tasted like dish water…"

Reviewed on Jun 19, 2024

Fairfield Inn & Suites by Marriott Winchester
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 (surcharge). Our guests praise the breakfast and the ...
9/10 Wonderful! (1,003 reviews)
"I have no complaints it was clean quiet"

Reviewed on Jun 24, 2024

Holiday Inn Winchester Se-Historic Gateway, an IHG Hotel
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 $66
  • 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.