A white neoclassical building with columns, an American flag, and a clock tower.

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Check availability on Old Town Winchester Luxury Hotels

Next weekend
30 Oct - 1 Nov
In two weeks
6 Nov - 8 Nov
No exact matches found, but these alternatives could be just right

Recommended hotels in Old Town Winchester

A courtyard with a fountain, tables with white tablecloths, and brick buildings.

1. The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel
3.5 star property
Old Town Winchester
9.4 out of 10, Exceptional, (1,003 reviews)
  • cleanliness
    Historic Georgian hotel offers luxury with spa, indoor pool, and two restaurants in Old Town Winchester.
The price is ฿4,402
฿4,988 total
includes taxes & fees
1 Nov - 2 Nov
The George Washington Hotel, A Wyndham Grand Hotel
A modern dining area with a high ceiling, recessed lighting, and a large window providing natural light.

2. La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (2,273 reviews)
The price is ฿3,616
฿4,025 total
includes taxes & fees
26 Oct - 27 Oct
La Quinta Inn & Suites by Wyndham Winchester
An outdoor seating area with a fire feature, wicker furniture, and a building with multiple windows.

3. TownePlace Suites by Marriott Front Royal

TownePlace Suites by Marriott Front Royal
3.0 star property
Front Royal
9.6 out of 10, Exceptional, (614 reviews)
The price is ฿4,693
฿5,244 total
includes taxes & fees
9 Nov - 10 Nov
TownePlace Suites by Marriott Front Royal
A modern hotel lobby with a central dining area, a reception desk, and a large window providing natural light.

4. Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
2.5 star property
Winchester
9.2 out of 10, Wonderful, (960 reviews)
The price is ฿3,239
฿3,670 total
includes taxes & fees
9 Nov - 10 Nov
Hampton Inn Winchester N/Conference Center, VA
A Courtyard by Marriott hotel with a covered entrance, multiple floors, and a brick facade.

5. Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1,001 reviews)
The price is ฿3,616
฿4,025 total
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Winchester
A modern dining area with tables and chairs, large windows, and a flat-screen TV mounted on the wall.

6. Holiday Inn Express Hotel & Suites Winchester by IHG

Holiday Inn Express Hotel & Suites Winchester by IHG
2.5 star property
Winchester
9.0 out of 10, Wonderful, (869 reviews)
The price is ฿3,714
฿4,134 total
includes taxes & fees
22 Nov - 23 Nov
Holiday Inn Express Hotel & Suites Winchester by IHG
A modern hotel lobby with a sofa set, two armchairs, a coffee table, and a reception desk.

7. Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (957 reviews)
The price is ฿3,128
฿3,482 total
includes taxes & fees
1 Nov - 2 Nov
Fairfield Inn & Suites by Marriott Winchester
A Holiday Inn hotel with a modern design, featuring a covered entrance and multiple floors.

8. Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1,007 reviews)
The price is ฿3,208
฿3,671 total
includes taxes & fees
22 Nov - 23 Nov
Holiday Inn Winchester Se-Historic Gateway by IHG
An outdoor patio with a fire feature, seating, and a covered area.

9. SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (912 reviews)
The price is ฿3,833
฿4,266 total
includes taxes & fees
8 Nov - 9 Nov
SpringHill Suites by Marriott Winchester
A Comfort Inn & Suites building with a modern design, featuring a prominent logo on the facade, a covered entrance, and multiple windows.

10. Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1,141 reviews)
The price is ฿3,378
฿3,759 total
includes taxes & fees
15 Nov - 16 Nov
Comfort Inn & Suites 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.
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Top Old Town Winchester Hotel Reviews

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"I really enjoyed the property. Extremely convenient to downtown attractions while being relatively quiet and nice. Staff was very helpful, room was lovely and clean and the pool was gorgeous."
MARY 1-night trip
Posted 12 hours ago
The George Washington Hotel, A Wyndham Grand Hotel

Frequently asked questions

Are you searching for a great accommodation for your luxury trip to Old Town Winchester?
Let Expedia help you arrange your flight to Martinsburg, WV (MRB-Eastern West Virginia Regional) airport or Washington Dulles International Airport (IAD) airport, and then choose from some places to stay that will deliver the luxury you seek. Amenities are important when you plan a trip, so we make it easy to find what you want to make your stay relaxing and comfortable. If you want an upscale hotel with a spa, an indoor pool or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Old Town Winchester has to offer. During your visit, you might want to enjoy the restaurants and bars which Old Town Winchester is known for.
What's there to see and do in Old Town Winchester?
Enjoy all that Old Town Winchester has to offer when you visit Bright Box Theater, Shenandoah Valley Discovery Museum and Old Court House Civil War Museum. If you have extra time while you're in the area, you might want to stop by Handley Regional Library and George Washington's Office.