Search Winchester Villa Rentals from CA $89

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Find vacation rentals that suit your style

cabin image
Cabins
Cabins
Cottage image
Cottages
Cottages

Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3
No exact matches found, but these alternatives could be just right

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

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,444 reviews)
"Perfect accommodation- great breakfast and attentive gracious staff"
United States
Kathleen
The price is CA $115
CA $128 total
includes taxes & fees
Nov 15 - Nov 16
Microtel Inn & Suites by Wyndham Winchester
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

Spark by Hilton Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (1,006 reviews)
"Clean room, great staff, good parking and free breakfast"
United States
Albert
The price is CA $92
CA $104 total
includes taxes & fees
Nov 15 - Nov 16
Spark by Hilton Winchester
A Comfort Inn & Suites building with a modern design, featuring a prominent logo on the facade, a covered entrance, and multiple windows.

3. Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.6 out of 10, Exceptional, (1,151 reviews)
"Convenient to the highway and reasonably priced."
United States
Donna S.
The price is CA $140
CA $156 total
includes taxes & fees
Nov 29 - Nov 30
Comfort Inn & Suites Winchester
A modern hotel with a flat facade, multiple windows, and a well-lit entrance.

4. 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, (2,266 reviews)
"Great place to stay the night after a long drive"
United States
lucy
The price is CA $146
CA $163 total
includes taxes & fees
Nov 15 - Nov 16
La Quinta Inn & Suites by Wyndham Winchester
A modern hotel building with a prominent 'TRU by Hilton' sign, multiple floors, and a parking lot in front.

5. TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,002 reviews)
"Hotel was very clean and breakfast was delicious with a lot of options"
United States
Kailyn
The price is CA $115
CA $128 total
includes taxes & fees
Nov 15 - Nov 16
TRU By Hilton Winchester
A Country Inn & Suites by Radisson building with a covered entrance and multiple windows.

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

Country Inn & Suites by Radisson, Winchester, VA
3.0 star property
Winchester
8.8 out of 10, Excellent, (1,003 reviews)
"This hotel is worth the stay!"
United States
David
The price is CA $121
CA $134 total
includes taxes & fees
Dec 6 - Dec 7
Country Inn & Suites by Radisson, Winchester, VA
Exterior

7. Quality Inn Winchester

Quality Inn Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1,003 reviews)
"Welcoming Staff, clean room at a good price."
United States
DARLA
The price is CA $110
CA $122 total
includes taxes & fees
Nov 15 - Nov 16
Quality Inn Winchester
A Fairfield by Marriott hotel with a modern entrance, stone pillars, and a well-lit facade.

8. Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (971 reviews)
"Great place to stay in Winchester."
United States
Thomas
The price is CA $130
CA $145 total
includes taxes & fees
Nov 10 - Nov 11
Fairfield Inn & Suites by Marriott Winchester
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

The George Washington Hotel, A Wyndham Grand Hotel
3.5 star property
Old Town Winchester
9.4 out of 10, Exceptional, (1,005 reviews)
"Always great place and the old nostalgic look is the best"
United States
Christophe
The price is CA $184
CA $209 total
includes taxes & fees
Nov 19 - Nov 20
The George Washington Hotel, A Wyndham Grand Hotel
A Holiday Inn hotel with a modern design, featuring a covered entrance and multiple floors.

10. 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, (1,006 reviews)
"Great hotel."
United States
Nicholas
The price is CA $133
CA $152 total
includes taxes & fees
Dec 6 - Dec 7
Holiday Inn Winchester Se-Historic Gateway by IHG
A Hampton Inn by Hilton hotel with a clear sky and sunset.

11. Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area
2.5 star property
Winchester
9.0 out of 10, Wonderful, (1,000 reviews)
"I like the cleanliness of the room and the breakfast options."
United States
Henedina
The price is CA $129
CA $146 total
includes taxes & fees
Dec 6 - Dec 7
Hampton Inn Winchester-University/Mall Area
A hotel entrance with a covered waiting area, brick facade, and a clear sky.

12. Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester
2.5 star property
Winchester
8.6 out of 10, Excellent, (1,075 reviews)
"Clean room, good staff, good location"
United States
Gregory
The price is CA $98
CA $108 total
includes taxes & fees
Dec 6 - Dec 7
Travelodge by Wyndham Winchester
An outdoor seating area with tables and chairs, a potted plant with flowers, and a view of the street.

13. 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, (871 reviews)
"Very clean comfortable bed good breakfast"
United States
David
The price is CA $155
CA $173 total
includes taxes & fees
Dec 6 - Dec 7
Holiday Inn Express Hotel & Suites Winchester by IHG
A modern hotel with a covered entrance, a sign reading "SPRINGHILL SUITES BY MARRIOTT," and a landscaped area with plants.

14. SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (915 reviews)
"Clean, receptive staff, great breakfast."
United States
Michael
The price is CA $160
CA $179 total
includes taxes & fees
Nov 22 - Nov 23
SpringHill Suites by Marriott Winchester
A Courtyard by Marriott hotel with a covered entrance, multiple floors, and a brick facade.

15. Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1,002 reviews)
"We had an amazing stay and will be back! The rooms were clean and comfy and staff were very helpful."
United States
Jessica
The price is CA $150
CA $167 total
includes taxes & fees
Dec 7 - Dec 8
Courtyard by Marriott Winchester
An outdoor patio with a grill, seating, and string lights.

16. Home2 Suites By Hilton Winchester

Home2 Suites By Hilton Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (51 reviews)
"Clean rooms , friendly staff."
United States
Jean
The price is CA $125
CA $142 total
includes taxes & fees
Nov 15 - Nov 16
Home2 Suites By Hilton Winchester
A large brick building with a central entrance, multiple windows, and a covered walkway.

17. Wayside Inn

Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (465 reviews)
"We enjoyed our short stay at Wayside. We were greeted by Amanda with a very warm and friendly welcome. She kindly let us check in early and gave us a few ideas to explore."
United States
Gerry
The price is CA $90
CA $113 total
includes taxes & fees
Dec 8 - Dec 9
Wayside Inn
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.

18. Candlewood Suites Winchester by IHG

Candlewood Suites Winchester by IHG
2.5 star property
Winchester
8.8 out of 10, Excellent, (657 reviews)
"Nice place to stay. Convenient for our travels."
United States
marilyn
The price is CA $112
CA $125 total
includes taxes & fees
Dec 6 - Dec 7
Candlewood Suites Winchester by IHG
A Sleep Inn hotel with a stone facade, multiple balconies, and a parking lot with several cars.

19. Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University
2.5 star property
Winchester
7.6 out of 10, Good, (1,005 reviews)
"I had a good stay and staff was friendly"
United States
Leah
The price is CA $89
CA $99 total
includes taxes & fees
Dec 6 - Dec 7
Sleep Inn & Suites Winchester near University
A multi-story hotel with a sign reading "Towneplace Suites by Marriott."

20. TownePlace Suites by Marriott Winchester

TownePlace Suites by Marriott Winchester
3.0 star property
Winchester
8.8 out of 10, Excellent, (534 reviews)
"Always a great place to land!! Love the location!! Great walking areas, a grocery store and lots of restaurants within walking distance!! Many many good wineries as well!!"
United States
Lori
The price is CA $158
CA $176 total
includes taxes & fees
Nov 17 - Nov 18
TownePlace Suites by Marriott 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.
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 Comfort Inn & Suites building with a modern design, featuring a prominent logo on the facade, a covered entrance, and multiple windows.
Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
Winchester

10/10 Excellent

Nice quiet clean
Canada
Fay
Reviewed February 8, 2024
Comfort Inn & Suites Winchester

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.

Explore a world of travel with Expedia