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)
Amazing hotel with lovely rooms, easy parking, near (walking distance ) great restaurants and shops. Highly recommend spa in building.

Reviewed on Oct 23, 2025

The George Washington Hotel, A Wyndham Grand Hotel
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 a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.4/10 Very Good! (1,110 reviews)
Stayed for a night on my way through town. Not a bad spot, clean and quiet. Staff was great. Lots of food delivery options around.

Reviewed on Oct 25, 2025

Travelodge by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
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 ...
9.2/10 Wonderful! (2,186 reviews)
We had a pleasant stay, staff was really nice and the room was spotless. Easy check in, the breakfast in the morning was enjoyable.

Reviewed on Oct 29, 2025

La Quinta Inn & Suites by Wyndham Winchester
Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

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! (1,049 reviews)
Everything you look for in a hotel. Would stay here again if ever in the area.

Reviewed on Oct 28, 2025

Comfort Inn & Suites 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! (1,350 reviews)
Friendly staff, super clean hotel.

Reviewed on Oct 28, 2025

Microtel Inn & Suites by Wyndham Winchester
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! (1,004 reviews)
Very courteous. Only problem is lack of outlets near the bed.

Reviewed on Oct 31, 2025

Country Inn & Suites by Radisson, Winchester, VA
Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area

2.5 out of 5
640 East Jubal Early Drive, 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! (1,004 reviews)
bed was not comfortable

Reviewed on Oct 25, 2025

Hampton Inn Winchester-University/Mall Area
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! (1,002 reviews)
All in all, the stay was good and I would stay there again.The location was close to the Village of Appomatox. The rooms were clean except for stains on the floor and chairs. The breakfast that was advertised wasn't fantastic. It was cold cereal and a bit of fruit.

Reviewed on Oct 26, 2025

Days Inn by Wyndham Charles Town/Harpers Ferry
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

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! (1,000 reviews)
Good

Reviewed on Oct 24, 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
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! (1,003 reviews)
Good Stay
Good stay for an overnight trip. Kumar treated us like very special people! Clean and very comfortable. Only problem - ADA shower very difficult to use for someone less then 5’4. Reaching the shower head was impossible. Would not recommend this place for special needs.

Reviewed on Oct 22, 2025

Red Roof Inn Winchester, VA
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! (1,028 reviews)
The staff was amazing! As we zipped in and out we were always welcomed or wished a good day. Big smiles and just super nice! Loved the coffee/tea area. Talk about coming home. My one comment would be that the trash cans were never emptied in our room or bathroom. And because the cans are so small ...

Reviewed on Oct 28, 2025

Hampton Inn Front Royal
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! (1,001 reviews)
Staff were great. Beautiful property. Registration process was hampered by slow computers. Breakfast service was really slow at Houlihans

Reviewed on Oct 29, 2025

DoubleTree by Hilton Front Royal Blue Ridge Shadows
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.