Hotels NearOld Town Winchester
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Featured Old Town Winchester Hotels

The George Washington Hotel, A Wyndham Grand Hotel
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)
"Hotel was very nice. Service was good and it was clean and convenient."
Reviewed on Jul 14, 2025

La Quinta Inn & Suites by Wyndham Winchester
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 ...
9/10 Wonderful! (2,078 reviews)
"Our only complaint was the noise as the hotel is at a busy intersecrion."
Reviewed on Jul 15, 2025

Travelodge by Wyndham Winchester
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! (1,105 reviews)
"The value of this property was great. For the price paid we feel we received a very good room to sleep in for one night on a road trip. Breakfast was better than others in this price range. We drove 1.5 miles to Old Town Winchester for dinner and it was interesting and fun to walk through. The only ..."
Reviewed on Jul 16, 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
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! (1,004 reviews)
"Staff was super nice when checking in!"
Reviewed on Jul 15, 2025

Comfort Inn & Suites
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! (1,008 reviews)
"Excellent place to stay. This is our 2nd time and was great both times. I recommend."
Reviewed on Jul 14, 2025

Microtel Inn & Suites by Wyndham Winchester
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! (1,302 reviews)
"Excellent"
Reviewed on Jul 15, 2025

Days Inn by Wyndham Charles Town/Harpers Ferry
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)
"Very good selection for breakfast. Nice thick white towels. Older building but owners keep up with the maintenance. Staff is friendly and helpful."
Reviewed on Jul 14, 2025

Country Inn & Suites by Radisson, Winchester, VA
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)
"The kitchen staff has been great. 1 of the servers went out of his way to help us when there was 2 minutes until closing. Thank you"
Reviewed on Jul 12, 2025

Ramada by Wyndham Strasburg/Shenandoah Valley
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! (1,002 reviews)
"Great stay overall, the attached Mexican restaurant was great. My only complaint is that while they have a coin operated guest laundry, there's no change machine and they had no quarters at the front desk."
Reviewed on Jul 15, 2025

Baymont by Wyndham Front Royal Near Shenandoah National Park
10 S Commerce Ave, 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 helpful staff in our reviews. ...
6.4/10 (849 reviews)
Close to Shenandoah Park
"Good for a quick overnight stay. Older buildings but they are working on nice upgrades"
Reviewed on Jul 13, 2025

Hampton Inn Front Royal
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! (1,008 reviews)
"Great stay!"
Reviewed on Jul 15, 2025

Spark by Hilton Winchester
150 Wingate Dr, Winchester, VA
Fully refundableReserve now, pay when you stay
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and ...
8.8/10 Excellent! (1,000 reviews)
"We stayed here for the state baseball tournament, so we had a lot of kids in and out. The staff were great and very accommodating. The kids loved the pool. Very clean and updated hotel. Would definitely stay there again."
Reviewed on Jul 8, 2025
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.
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Old Town Winchester Neighborhoods
Top Attractions in Old Town Winchester
- Hotels near Shenandoah Valley Discovery Museum (0.16 mi)
- Hotels near Bright Box Theater (0.02 mi)
- Hotels near Handley Regional Library (0.2 mi)
- Hotels near Old Court House Civil War Museum (0.02 mi)
- Hotels near George Washington's Office (0.17 mi)
- Hotels near Hollywood Casino at Charles Town Races (18.52 mi)
- Hotels near Summit Point Motorsports Park (11.12 mi)
- Hotels near Shenandoah River (16.62 mi)
- Hotels near Shenandoah University (1.24 mi)
- Hotels near Winchester Medical Center (1.75 mi)
- Hotels near George Washington National Forest (90.63 mi)
- Hotels near Bluemont Vineyard (18.67 mi)
- Hotels near Museum of the Shenandoah Valley (0.81 mi)
- Hotels near Apple Blossom Mall (1.67 mi)
- Hotels near Rock Harbor Golf Course (2.19 mi)
- Hotels near Sky Meadows State Park (17.71 mi)
- Hotels near Cedar Creek Battlefield Foundation (13.55 mi)
- Hotels near Lost River (37.83 mi)
- Hotels near Watermelon Park Campground (13.42 mi)
- Hotels near Patsy Cline Historic House (0.43 mi)
Cities near Old Town Winchester
- Berkeley Springs Hotels (30.74 mi)
- Harpers Ferry Hotels (25.15 mi)
- Winchester Hotels (0.01 mi)
- Blue Ridge Mountains Hotels (325.84 mi)
- Front Royal Hotels (18.44 mi)
- Charles Town Hotels (17.89 mi)
- Shenandoah Valley Hotels (60.79 mi)
- Martinsburg Hotels (21.65 mi)
- Appalachian Mountains Hotels (101.75 mi)
- Northern Virginia Hotels (35.96 mi)
- Strasburg Hotels (17.01 mi)
- Boyce Hotels (8.48 mi)
- Hedgesville Hotels (27.07 mi)
- Bluemont Hotels (18.46 mi)
- Stephens City Hotels (7.48 mi)
- Linden Hotels (19.61 mi)
- Berryville Hotels (10.07 mi)
- Paw Paw Hotels (28.65 mi)
- Inwood Hotels (13.74 mi)
- Middletown Hotels (12.44 mi)
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