The Best Hotels in Old Town Winchester, Winchester - 2026 Updated Prices

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

Jeanette

Rp2.601.507 total

includes taxes & fees

20 Sept - 21 Sept

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

Peter

Rp1.537.997 total

includes taxes & fees

11 Oct - 12 Oct

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

3. La Quinta Inn & Suites by Wyndham Winchester

2.9 km from Old Town Winchester

Earl

Rp2.271.957 total

includes taxes & fees

27 Sept - 28 Sept

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

4. Hampton Inn Winchester-University/Mall Area

2.1 km from Old Town Winchester

Henedina

Rp2.110.657 total

includes taxes & fees

20 Sept - 21 Sept

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

5. Fairfield Inn & Suites by Marriott Winchester

2.9 km from Old Town Winchester

Michael

Rp1.816.035 total

includes taxes & fees

27 Sept - 28 Sept

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

6. Microtel Inn & Suites by Wyndham Winchester

4.1 km from Old Town Winchester

Katheryne

Rp1.724.891 total

includes taxes & fees

17 Sept - 18 Sept

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

7. Holiday Inn Winchester Se-Historic Gateway by IHG

3.2 km from Old Town Winchester

Jennifer

Rp2.071.740 total

includes taxes & fees

12 Oct - 13 Oct

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

8. Hilton Garden Inn Winchester

2.1 km from Old Town Winchester

Wendy

Rp1.979.763 total

includes taxes & fees

24 Sept - 25 Sept

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.

9. Travelodge by Wyndham Winchester

2.9 km from Old Town Winchester

Pietro

Rp1.340.373 total

includes taxes & fees

15 Sept - 16 Sept

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

10. Quality Inn Winchester

4.3 km from Old Town Winchester

Scott

Rp1.649.428 total

includes taxes & fees

20 Sept - 21 Sept

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

11. Holiday Inn Express Hotel & Suites Winchester by IHG

3.1 km from Old Town Winchester

Gregory.

Rp2.469.730 total

includes taxes & fees

20 Sept - 21 Sept

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

12. Courtyard by Marriott Winchester

3.1 km from Old Town Winchester

Karen

Rp2.099.272 total

includes taxes & fees

20 Sept - 21 Sept

An indoor swimming pool with clear water, surrounded by windows and potted plants.

13. APM Inn & Suites

2.3 km from Old Town Winchester

Edward

Rp1.167.265 total

includes taxes & fees

1 Oct - 2 Oct

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

14. Hampton Inn Winchester N/Conference Center, VA

2.1 km from Old Town Winchester

Jackie

Rp1.914.316 total

includes taxes & fees

5 Oct - 6 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.

15. Candlewood Suites Winchester by IHG

3.1 km from Old Town Winchester

Bridget

Rp1.724.821 total

includes taxes & fees

20 Sept - 21 Sept

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

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

7.5 km from Old Town Winchester

Nancy

Rp1.937.367 total

includes taxes & fees

5 Oct - 6 Oct

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

17. Sleep Inn & Suites Winchester near University

3.1 km from Old Town Winchester

Connor

Rp1.499.480 total

includes taxes & fees

12 Oct - 13 Oct

An outdoor patio with a fire feature, seating, and a covered area.

18. SpringHill Suites by Marriott Winchester

5.3 km from Old Town Winchester

Michael

Rp2.397.600 total

includes taxes & fees

27 Sept - 28 Sept

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

19. TownePlace Suites by Marriott Winchester

3 km from Old Town Winchester

Katherine

Rp2.215.899 total

includes taxes & fees

20 Sept - 21 Sept

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

20. TRU By Hilton Winchester

4.4 km from Old Town Winchester

Gerley

Rp1.832.305 total

includes taxes & fees

27 Sept - 28 Sept

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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

Comfort Inn & Suites Winchester

10/10 Excellent

"All the staff were very friendly and very clean."

Microtel Inn & Suites by Wyndham Winchester

10/10 Excellent

"The property is very clean on the outside. You walk in and you would never know it was a pet friendly hotel. The inside was spotless, as was our room and ding area. Breakfast was good, nothing over the top, pancakes instead of waffles which was different. But hot, fresh and coffee 24 hours a day was a plus for me. The staff is very friendly and eager to help. Shelby at the front desk when we arrived was very helpful with helping us with the air conditioner. Oversight on our part , not the hotel. This was our second stay at this hotel and we will always use this one when we visit our daughter in Winchester. The price was extremely affordable and our king studio room was very spacious. Definitely be back again. Thank you all!"

Hampton Inn Front Royal

10/10 Excellent

"The Hampton in front Royal was a really awesome place to stay very well maintained the staff was very friendly and nice the front desk was very helpful the rooms were clean the grounds were clean food was good I give it five stars all the way. It was easy to get in and out of the town. We highly recommend the Hampton in front Royal has a place to stay"

Frequently asked questions

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.

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.

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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. La Quinta Inn & Suites by Wyndham Winchester

4. Hampton Inn Winchester-University/Mall Area

5. Fairfield Inn & Suites by Marriott Winchester

6. Microtel Inn & Suites by Wyndham Winchester

7. Holiday Inn Winchester Se-Historic Gateway by IHG

8. Hilton Garden Inn Winchester

9. Travelodge by Wyndham Winchester

10. Quality Inn Winchester

11. Holiday Inn Express Hotel & Suites Winchester by IHG

12. Courtyard by Marriott Winchester

13. APM Inn & Suites

14. Hampton Inn Winchester N/Conference Center, VA

15. Candlewood Suites Winchester by IHG

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

17. Sleep Inn & Suites Winchester near University

18. SpringHill Suites by Marriott Winchester

19. TownePlace Suites by Marriott Winchester

20. TRU By Hilton Winchester

Where to stay in Old Town Winchester

Winchester Historic District

Top Old Town Winchester Hotel Reviews

Comfort Inn & Suites Winchester

Frequently asked questions

Explore a world of travel with Expedia