What is Old Town Winchester like?

Old Town Winchester is an historic neighbourhood known for its array of dining options. Are you looking for Old Town Winchester travel tips? Make sure that you visit Bright Box Theater and Shenandoah Valley Discovery Museum while you're in the neighbourhood.

Where is the best place to stay in Old Town Winchester?

Based on our traveller data, The George Washington Hotel, A Wyndham Grand Hotel is one of the top choices for your stay in Old Town Winchester. This hotel offers a full-service spa and 2 restaurants.

How many hotels should I expect to find in the Old Town Winchester area?

With 13 Expedia hotels and other accommodation options in Old Town Winchester to choose from, this is a good starting point for exploring the greater Winchester area.

If I need to cancel my hotel reservation in Old Town Winchester, will I receive a refund?

Yes, the majority of room reservations are fully refundable provided that you cancel before the hotel’s cancellation deadline, which often is within 24-48 hours of your scheduled arrival. If you booked a non-refundable reservation, you might be able to still cancel and be given a refund within 24 hours of your booking. Enter dates in and click on "Search", then use the filter option "fully refundable" to review the best deals available in Old Town Winchester.

What is there to do around this Winchester neighbourhood?

Sights like Bright Box Theater and Old Court House Civil War Museum can be part of your cultural tour of Old Town Winchester. Shenandoah Valley Discovery Museum and Handley Regional Library are some other stops worth a visit in the neighbourhood. A few places to visit in the area around Old Town Winchester include George Washington's Office, Mt Hebron Cemetery and Winchester Little Theater. When you're sightseeing in Winchester, Stonewall Jackson's Headquarters and Patsy Cline Historic House are also worth a stop.

Top 10 Old Town Winchester Hotels of 2026

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

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Our top choices for Old Town Winchester hotels

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

1. The George Washington Hotel, A Wyndham Grand Hotel

Old Town Winchester

Carol

includes taxes & fees

5 Nov - 6 Nov

A spacious lobby with a checkered floor, yellow chairs, a green carpet, and a wall with the text "It only takes a spark".

2. Spark by Hilton Winchester

2 km from Old Town Winchester

carrie

includes taxes & fees

2 Nov - 3 Nov

A modern hotel lobby with a sofa set, two armchairs, a coffee table, and a reception desk.

3. Fairfield Inn & Suites by Marriott Winchester

2.9 km from Old Town Winchester

Thomas

includes taxes & fees

1 Nov - 2 Nov

A modern dining area with a high ceiling, recessed lighting, and a large window providing natural light.

4. La Quinta Inn & Suites by Wyndham Winchester

2.9 km from Old Town Winchester

Earl

includes taxes & fees

11 Oct - 12 Oct

A modern hotel lobby with a reception desk, seating area, and a large window providing natural light.

5. Hampton Inn Winchester N/Conference Center, VA

2.1 km from Old Town Winchester

Michael

includes taxes & fees

18 Oct - 19 Oct

A Holiday Inn hotel with a modern design, featuring a covered entrance and multiple floors.

6. Holiday Inn Winchester Se-Historic Gateway by IHG

3.2 km from Old Town Winchester

Jeffrey

includes taxes & fees

8 Nov - 9 Nov

A self-service beverage station with a refrigerated drink dispenser, a coffee machine, and a variety of snacks.

7. TRU By Hilton Winchester

4.4 km from Old Town Winchester

Kailyn

includes taxes & fees

1 Nov - 2 Nov

An outdoor patio with a grill, seating, and string lights.

8. Home2 Suites By Hilton Winchester

3.6 km from Old Town Winchester

Mandy

includes taxes & fees

3 Nov - 4 Nov

A Courtyard by Marriott hotel with a covered entrance, multiple floors, and a brick facade.

9. Courtyard by Marriott Winchester

3.1 km from Old Town Winchester

John

includes taxes & fees

25 Oct - 26 Oct

A modern lobby with a seating area, a flat-screen TV, and a large window offering a view of the outdoors.

10. Microtel Inn & Suites by Wyndham Winchester

4.1 km from Old Town Winchester

Katheryne

includes taxes & fees

1 Nov - 2 Nov

A modern hotel with a covered outdoor area, landscaped gardens, and a parking lot.

11. Quality Inn Winchester

4.3 km from Old Town Winchester

Joseph

includes taxes & fees

8 Nov - 9 Nov

12. Comfort Inn & Suites Winchester

7.8 km from Old Town Winchester

John

includes taxes & fees

18 Oct - 19 Oct

A hotel room with a bed, a brown sofa, a round table, a lamp, a window with a decorative screen, and a framed picture on the wall.

13. Candlewood Suites Winchester by IHG

3.1 km from Old Town Winchester

marilyn

includes taxes & fees

2 Nov - 3 Nov

A modern dining area with a large white table, blue chairs, and a flat-screen TV mounted on the wall.

14. Holiday Inn Express Hotel & Suites Winchester by IHG

3.1 km from Old Town Winchester

Gregory.

includes taxes & fees

8 Nov - 9 Nov

A gym with treadmills, exercise balls, and a mirrored wall.

15. Hampton Inn Winchester-University/Mall Area

2.1 km from Old Town Winchester

Henedina

includes taxes & fees

1 Nov - 2 Nov

A modern living room with a sofa, armchair, dining table, and chairs. There is a TV mounted on the wall and a small table with a lamp.

16. Travelodge by Wyndham Winchester

2.9 km from Old Town Winchester

john

includes taxes & fees

18 Oct - 19 Oct

A modern interior with a geometric ceiling design, recessed lighting, and hanging pendant lights.

17. Hilton Garden Inn Winchester

2.1 km from Old Town Winchester

Wendy

includes taxes & fees

31 Oct - 1 Nov

A hotel lobby with seating, a reception desk, and a refrigerated display.

18. TownePlace Suites by Marriott Winchester

3 km from Old Town Winchester

anna

includes taxes & fees

13 Oct - 14 Oct

A spacious living room with a fireplace, wooden staircase, and a bookshelf.

19. Country Inn & Suites by Radisson, Winchester, VA

7.5 km from Old Town Winchester

Allen

includes taxes & fees

8 Nov - 9 Nov

A lobby with a green wall, a reception desk, and seating area with sofas and armchairs.

20. Sleep Inn & Suites Winchester near University

3.1 km from Old Town Winchester

Connor

includes taxes & fees

1 Nov - 2 Nov

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Where to stay in Old Town Winchester

Find the best Old Town Winchester areas for the activities you enjoy most.

Winchester Historic District

A red brick church with a blue door and a clock tower.

Winchester Historic District

While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Shenandoah Valley Discovery Museum.

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Top Old Town Winchester Hotel Reviews

La Quinta Inn & Suites by Wyndham Winchester

8/10 Good

"The room was clean and functional. Turning the light on in the bathroom was disturbing in the bedroom area."

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent

"This facility is excellent. The breakfast was excellent with many extras including honey packets. It has a very good selection 8 plus to add to yogurt, etc. I had a very nice cream cheese bagel with honey drizzled. They also had eggs and sausage. It also has a coffee/herbal tea station in the lobby. The pool was spotless. Perfectly clean. Perfect. The room was spacious. There were plenty of spaces to congregate both inside and outside. The seasonal fall decor was a very nice touch. It was very full and impressive. I very highly reccomend this facility. Superb."

TRU By Hilton Winchester

10/10 Excellent

"The mattress was excellent. I woke up refreshed without a back ache which I came in with due to the long car ride. My room was quiet, and clean. My only complaint is wondering why there is such a strong smell of air deodorizer throughout the hotel. It hits you as you walk in the lobby. The smell lingered on my clothes and inside my suitcases through the next day. I prefer fresh air, not artificial air freshener scents. I don’t believe they are healthy."

Hotels in Old Town Winchester

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Our top choices for Old Town Winchester hotels

1. The George Washington Hotel, A Wyndham Grand Hotel

2. Spark by Hilton Winchester

3. Fairfield Inn & Suites by Marriott Winchester

4. La Quinta Inn & Suites by Wyndham Winchester

5. Hampton Inn Winchester N/Conference Center, VA

6. Holiday Inn Winchester Se-Historic Gateway by IHG

7. TRU By Hilton Winchester

8. Home2 Suites By Hilton Winchester

9. Courtyard by Marriott Winchester

10. Microtel Inn & Suites by Wyndham Winchester

11. Quality Inn Winchester

12. Comfort Inn & Suites Winchester

13. Candlewood Suites Winchester by IHG

14. Holiday Inn Express Hotel & Suites Winchester by IHG

15. Hampton Inn Winchester-University/Mall Area

16. Travelodge by Wyndham Winchester

17. Hilton Garden Inn Winchester

18. TownePlace Suites by Marriott Winchester

19. Country Inn & Suites by Radisson, Winchester, VA

20. Sleep Inn & Suites Winchester near University

Where to stay in Old Town Winchester

Winchester Historic District

Top Old Town Winchester Hotel Reviews

La Quinta Inn & Suites by Wyndham Winchester

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