Hotels Near
Old Town Winchester

Check Last Minute Old Town Winchester Hotel Deals

Tonight Feb 22 - Feb 23Next weekend Feb 28 - Mar 2

You choose what matters — star rating, location, amenities.

We pick the perfect hotel, packed with all your must-haves.

Your hotel is revealed right after booking!


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! (1,001 reviews)
"We loved it. Walkable to restaurant area..nice beds and bathroom. Thank you!"

Reviewed on Feb 13, 2025

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! (1,814 reviews)
"Clean room right off the Interstate with friendly staff and a better than normal breakfast. Perfect for a one night stay while traveling."

Reviewed on Feb 15, 2025

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 parking, and a fitness center. Our guests praise the helpful staff and ...
9/10 Wonderful! (1,135 reviews)
"Great area of Winchester"

Reviewed on Feb 19, 2025

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 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! (1,101 reviews)
"Only stopped here to get off the highway for a little while, place is alright for a roadside motel, no complaints, grandkids loved making their own waffles for breakfast, if you find yourself on a long drive, good place to rest,"

Reviewed on Feb 17, 2025

Travelodge by Wyndham Winchester
SpringHill Suites by Marriott Winchester
SpringHill Suites by Marriott Winchester
2.5 out of 5
280 MARKET STREET, 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! (552 reviews)
"Friendly staff and loved the room."

Reviewed on Feb 19, 2025

SpringHill Suites by Marriott Winchester
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! (1,001 reviews)
"Good value for the price. No complaints to report."

Reviewed on Jan 31, 2025

Sleep Inn & Suites
Days Inn by Wyndham Charles Town/Harpers Ferry
Days Inn by Wyndham Charles Town/Harpers Ferry
2 out of 5
642 E Washington Street, Charles Town, WV
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Charles Town. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8/10 Very Good! (1,000 reviews)
"The front desk people was very kind.and welcoming."

Reviewed on Feb 14, 2025

Days Inn by Wyndham Charles Town/Harpers Ferry
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 helpful staff and the clean rooms in our ...
8.8/10 Excellent! (999 reviews)
"Clean very nice room quite comfortable would definitely stay again"

Reviewed on Feb 17, 2025

DoubleTree by Hilton Front Royal Blue Ridge Shadows
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! (683 reviews)
"Great stay"

Reviewed on Feb 15, 2025

Fairfield Inn & Suites by Marriott 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 helpful ...
8/10 Very Good! (1,000 reviews)
"Excellent service"

Reviewed on Feb 16, 2025

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! (438 reviews)
"it was great loved it"

Reviewed on Feb 19, 2025

The Inn at Charles Town
Hampton Inn Front Royal
Hampton Inn Front Royal
2.5 out of 5
9800 Winchester Rd, Front Royal, VA
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Front Royal. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,000 reviews)
"Easy chk in, no problems, nice stay"

Reviewed on Feb 15, 2025

Hampton Inn Front Royal
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.