Hotels Near
Old Town Winchester

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Featured Old Town Winchester Hotels

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 bar and the helpful staff in our ...
9.2/10 Wonderful! (1,000 reviews)
"Lovely stay, staff were kind and helpful, parking was easy and plenty of cool places to dine within walking distance. We love coming here."

Reviewed on Dec 16, 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 breakfast and the helpful ...
9/10 Wonderful! (1,758 reviews)
"Excellent customer service"

Reviewed on Dec 20, 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 ...
9/10 Wonderful! (1,077 reviews)
Great place
"Nice place"

Reviewed on Dec 20, 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 ...
9.2/10 Wonderful! (1,005 reviews)
"Rooms nice. Staff very helpful."

Reviewed on Dec 21, 2024

Comfort Inn & Suites
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 clean rooms in our reviews. Popular attractions ...
7.4/10 Good! (1,001 reviews)
"Nice, clean, easy"

Reviewed on Dec 9, 2024

Red Roof Inn Winchester, VA
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)
"It was very comfortable and quiet."

Reviewed on Dec 8, 2024

Country Inn & Suites by Radisson, 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
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 ...
7.8/10 Good! (1,000 reviews)
"Front desk was great. Room was good. I would stay here again."

Reviewed on Dec 13, 2024

Ramada by Wyndham Strasburg/Shenandoah Valley
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! (428 reviews)
Best Racetrack View room- Especially for $100
"Could not have been better!"

Reviewed on Dec 2, 2024

The Inn at Charles Town
Sleep Inn & Suites
Sleep Inn & Suites
2.5 out of 5
140 Costello Dr, 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 ...
8/10 Very Good! (1,002 reviews)
"Great hotel"

Reviewed on Dec 10, 2024

Sleep 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 motel in Winchester. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
8.2/10 Very Good! (1,116 reviews)
Comfortable place to stop for a noght
"Have stayed in this hotel many times during our trips to and from Florida from Canada. It has always been the courteous service, cleanliness and comfort which is often lacking in other locals."

Reviewed on Dec 19, 2024

Travelodge by Wyndham Winchester
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! (1,002 reviews)
"Staff was excellent and friendly. The breakfast area was very clean and well stocked. Plus, the Christmas decorations were abundant and beautiful!"

Reviewed on Dec 21, 2024

Spark by Hilton Winchester
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! (657 reviews)
Such great staff!
"I’ve stayed at most of the hotels in this part of Winchester and Fairfield is absolutely the best. Wonderful people and great rooms."

Reviewed on Dec 18, 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 $65
  • 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.