Winchester Villas from CA $89

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Recommended hotels in Winchester

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

1. Microtel Inn & Suites by Wyndham Winchester

Winchester

Kathleen

CA $124 total

includes taxes & fees

Nov 15 - Nov 16

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

2. Spark by Hilton Winchester

Winchester

Albert

CA $104 total

includes taxes & fees

Nov 29 - Nov 30

3. Comfort Inn & Suites Winchester

Winchester

Donna S.

CA $137 total

includes taxes & fees

Dec 1 - Dec 2

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

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

Winchester

Zohair

CA $132 total

includes taxes & fees

Dec 1 - Dec 2

A hotel with a covered outdoor area, a parking lot, and well-maintained landscaping.

5. Quality Inn Winchester

Winchester

james

CA $114 total

includes taxes & fees

Nov 17 - Nov 18

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

6. La Quinta Inn & Suites by Wyndham Winchester

Winchester

lucy

CA $163 total

includes taxes & fees

Nov 15 - Nov 16

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

7. TRU By Hilton Winchester

Winchester

Jesse

CA $128 total

includes taxes & fees

Nov 29 - Nov 30

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

8. Fairfield Inn & Suites by Marriott Winchester

Winchester

Thomas

CA $146 total

includes taxes & fees

Nov 15 - Nov 16

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

9. The George Washington Hotel, A Wyndham Grand Hotel

Old Town Winchester

Christophe

CA $209 total

includes taxes & fees

Nov 19 - Nov 20

A Hampton Inn by Hilton hotel with a clear sky and sunset.

10. Hampton Inn Winchester-University/Mall Area

Winchester

Henedina

CA $147 total

includes taxes & fees

Dec 6 - Dec 7

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

11. Holiday Inn Winchester Se-Historic Gateway by IHG

Winchester

Nicholas

CA $160 total

includes taxes & fees

Dec 10 - Dec 11

A hotel entrance with a covered waiting area, brick facade, and a clear sky.

12. Travelodge by Wyndham Winchester

Winchester

Gregory

CA $109 total

includes taxes & fees

Dec 1 - Dec 2

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

Winchester

marilyn

CA $126 total

includes taxes & fees

Nov 15 - Nov 16

An outdoor seating area with tables and chairs, a potted plant with flowers, and a view of the street.

14. Holiday Inn Express Hotel & Suites Winchester by IHG

Winchester

David

CA $179 total

includes taxes & fees

Dec 10 - Dec 11

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

15. Courtyard by Marriott Winchester

Winchester

Jessica

CA $168 total

includes taxes & fees

Nov 17 - Nov 18

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

16. SpringHill Suites by Marriott Winchester

Winchester

Roy

CA $178 total

includes taxes & fees

Nov 23 - Nov 24

A Sleep Inn hotel with a stone facade, multiple balconies, and a parking lot with several cars.

17. Sleep Inn & Suites Winchester near University

Winchester

Leah

CA $100 total

includes taxes & fees

Dec 6 - Dec 7

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

18. Home2 Suites By Hilton Winchester

Winchester

Jean

CA $141 total

includes taxes & fees

Nov 29 - Nov 30

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

19. TownePlace Suites by Marriott Winchester

Winchester

Lori

CA $178 total

includes taxes & fees

Nov 15 - Nov 16

A Hampton Inn hotel with a modern facade, multiple windows, and a welcoming entrance.

20. Hampton Inn Winchester N/Conference Center, VA

Winchester

Elizabeth

CA $169 total

includes taxes & fees

Nov 17 - Nov 18

View all properties

Winchester and related destinations

Stroll through the charming pedestrian mall in the historic district, where shops and excellent restaurants await. Delve into local culture at the Museum of the Shenandoah Valley or catch a show at the Bright Box Theatre.

See all hotels in Winchester

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

Top reviews in Winchester

A multi-story hotel with a swimming pool, parking lot, and a landscaped area.

TownePlace Suites by Marriott Front Royal

Front Royal

10/10 Excellent

Bruce

An outdoor patio area with a long wooden table and chairs, a red umbrella, and a grill station.

Home2 Suites by Hilton Martinsburg, WV

Martinsburg

10/10 Excellent

Gary

The George Washington Hotel, A Wyndham Grand Hotel

Old Town Winchester

10/10 Excellent

Pauline

La Quinta Inn & Suites by Wyndham Winchester

Winchester

10/10 Excellent

Jean-Pierre

Fairfield Inn & Suites by Marriott Winchester

Winchester

10/10 Excellent

Jean-Francois

Microtel Inn & Suites by Wyndham Winchester

Winchester

10/10 Excellent

Mark

Hampton Inn Winchester N/Conference Center, VA

Winchester

10/10 Excellent

Dean

A Hampton Inn with a covered entrance and a parking lot.

Hampton Inn Front Royal

Front Royal

10/10 Excellent

Gurpreet

A large brick building with a central entrance, multiple windows, and a covered walkway.

Wayside Inn

Middletown

10/10 Excellent

Shelley

Hampton Inn Winchester-University/Mall Area

Winchester

10/10 Excellent

Kimberly

Frequently Asked Questions

Why book your villa in Winchester with Expedia?

With Expedia, it's easy to find your ideal villa in Winchester. Vacationing with the family? Take advantage of our filters to look for stays with amenities like a pool. If you're sticking to a budget, click on how much you want to spend and your preferred star rating. We'll help you find the right stay that gels with your taste and style.

How can I find cheap villas in Winchester?

With Expedia's filter tool, comparing cheap villas in Winchester has never been easier. To find properties that give you the most bang for your buck, narrow your search by budget, star rating and amenities.

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 Harbor 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.

Search Winchester Villa Rentals from CA $89

Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Recommended hotels in Winchester

1. Microtel Inn & Suites by Wyndham Winchester

2. Spark by Hilton Winchester

3. Comfort Inn & Suites Winchester

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

5. Quality Inn Winchester

6. La Quinta Inn & Suites by Wyndham Winchester

7. TRU By Hilton Winchester

8. Fairfield Inn & Suites by Marriott Winchester

9. The George Washington Hotel, A Wyndham Grand Hotel

10. Hampton Inn Winchester-University/Mall Area

11. Holiday Inn Winchester Se-Historic Gateway by IHG

12. Travelodge by Wyndham Winchester

13. Candlewood Suites Winchester by IHG

14. Holiday Inn Express Hotel & Suites Winchester by IHG

15. Courtyard by Marriott Winchester

16. SpringHill Suites by Marriott Winchester

17. Sleep Inn & Suites Winchester near University

18. Home2 Suites By Hilton Winchester

19. TownePlace Suites by Marriott Winchester

20. Hampton Inn Winchester N/Conference Center, VA

Winchester and related destinations

Top reviews in Winchester

TownePlace Suites by Marriott Front Royal

10/10 Excellent

Frequently Asked Questions

Why book your villa in Winchester with Expedia?

How can I find cheap villas in Winchester?

What is there to do near my villa in Winchester?

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