Luxury Winchester Villas for 2026

A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

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Recommended hotels in Winchester

1. Comfort Inn & Suites Winchester

Winchester

John

includes taxes & fees

18 Oct - 19 Oct

A large brick building with a classic facade, a central entrance with a decorative arch, and a sign reading "The George Washington Hotel."

2. The George Washington Hotel, A Wyndham Grand Hotel

Old Town Winchester

Carol

includes taxes & fees

5 Nov - 6 Nov

A modern hotel building with a prominent 'TRU by Hilton' sign, multiple floors, and a parking lot in front.

3. TRU By Hilton Winchester

Winchester

includes taxes & fees

1 Nov - 2 Nov

A modern hotel with a flat facade, multiple windows, and a well-lit entrance.

4. La Quinta Inn & Suites by Wyndham Winchester

Winchester

includes taxes & fees

11 Oct - 12 Oct

A modern Microtel hotel by Wyndham with a blue and gray exterior, multiple windows, and a parking lot.

5. Microtel Inn & Suites by Wyndham Winchester

Winchester

includes taxes & fees

1 Nov - 2 Nov

A Fairfield by Marriott hotel with a modern entrance, stone pillars, and a well-lit facade.

6. Fairfield Inn & Suites by Marriott Winchester

Winchester

Thomas

includes taxes & fees

1 Nov - 2 Nov

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

7. Quality Inn Winchester

Winchester

Joseph

includes taxes & fees

8 Nov - 9 Nov

A hotel with a modern design, featuring a prominent 'spark by Hilton' sign, a well-lit entrance, and a landscaped front yard.

8. Spark by Hilton Winchester

Winchester

carrie

includes taxes & fees

2 Nov - 3 Nov

A Country Inn & Suites by Radisson building with a covered entrance and multiple windows.

Middletown

includes taxes & fees

19 Oct - 20 Oct

A modern hotel with a covered entrance, a sign reading "SPRINGHILL SUITES BY MARRIOTT," and a landscaped area with plants.

15. SpringHill Suites by Marriott Winchester

Winchester

Michael

includes taxes & fees

8 Nov - 9 Nov

A hotel with a parking lot, multiple vehicles, and a clear sky.

16. Candlewood Suites Winchester by IHG

Winchester

marilyn

includes taxes & fees

2 Nov - 3 Nov

A Holiday Inn Express & Suites building with a covered entrance, large windows, and a fire lane.

17. Holiday Inn Express Hotel & Suites Winchester by IHG

Winchester

Gregory.

includes taxes & fees

8 Nov - 9 Nov

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

18. Holiday Inn Winchester Se-Historic Gateway by IHG

Winchester

Jeffrey

includes taxes & fees

8 Nov - 9 Nov

A multi-story hotel with a sign reading "Towneplace Suites by Marriott."

19. TownePlace Suites by Marriott Winchester

Winchester

anna

includes taxes & fees

13 Oct - 14 Oct

A terrace with tables set for a wedding, overlooking a golf course and a body of water.

20. DoubleTree by Hilton Front Royal Blue Ridge Shadows

Front Royal

Brian

includes taxes & fees

8 Nov - 9 Nov

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Top 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."

Find out more about Winchester

Winchester Villas information

Number of reviews	13,723
Accommodation	3 Villas
Lowest Price	S$100
Highest Price	S$189

Frequently asked questions

Why book your villa in Winchester with Expedia?

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How can I find cheap villas in Winchester?

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What is there to do near my villa in Winchester?

Whatever you love doing, Winchester has plenty of things to keep you on the move. Rock Harbour Golf Course, The Kernstown Battlefield and Museum of the Shenandoah Valley are on many visitors' lists. Don't head home without exploring Apple Blossom Mall, Jim Barnett Park and Handley Regional Library either. With Expedia's Winchester hotel deals, you'll be able to discover even more renowned attractions like these with the money you save.

Villas in Winchester

Change your mind

Treat yourself

Be picky

Check prices for these dates

Recommended hotels in Winchester

1. Comfort Inn & Suites Winchester

2. The George Washington Hotel, A Wyndham Grand Hotel

3. TRU By Hilton Winchester

4. La Quinta Inn & Suites by Wyndham Winchester

5. Microtel Inn & Suites by Wyndham Winchester

6. Fairfield Inn & Suites by Marriott Winchester

7. Quality Inn Winchester

8. Spark by Hilton Winchester

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

10. Travelodge by Wyndham Winchester

11. Home2 Suites By Hilton Winchester

12. Courtyard by Marriott Winchester

13. Hampton Inn Winchester-University/Mall Area

14. Wayside Inn

15. SpringHill Suites by Marriott Winchester

16. Candlewood Suites Winchester by IHG

17. Holiday Inn Express Hotel & Suites Winchester by IHG

18. Holiday Inn Winchester Se-Historic Gateway by IHG

19. TownePlace Suites by Marriott Winchester

20. DoubleTree by Hilton Front Royal Blue Ridge Shadows

Find holiday rentals that suit your style

Top Winchester Hotel Reviews

La Quinta Inn & Suites by Wyndham Winchester

Find out more about Winchester

Winchester Villas information

Frequently asked questions

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