An aerial view of a historic town with a prominent clock tower, narrow streets lined with historic buildings, and a mix of commercial and residential areas.

Villas in Winchester

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Winchester villas

A hotel with a modern design, featuring a large building with multiple balconies and a well-maintained lawn.

1. Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.6 out of 10, Excellent, (1,003 reviews)
"They have a really good Breakfast..."
United States
David
$100 nightly
The price is $110
Oct 18 - Oct 19
Total with taxes and fees
Best Western Winchester Hotel
A Hampton Inn hotel with a large parking lot, a prominent sign, and a clear sky.

2. Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (485 reviews)
"This is one of the NICEST hotels that I have stayed at in a long time. The quality of the furnishings, building materials used in the rooms, comfort of the bed, outstanding breakfast and friendly staff all made our stay wonderful. If I am in the area again in the future, I will definitely stay at this hotel!"
United States
Jacqueline
$110 nightly
The price is $121
Nov 8 - Nov 9
Total with taxes and fees
Hampton Inn Winchester
A Holiday Inn Express building with a modern design, featuring a large entrance and a well-lit facade.

3. Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG
2.5 star property
Winchester
9.4 out of 10, Exceptional, (606 reviews)
"This is one of the nicest and cleanest Holiday Inns I’ve ever been to. Very friendly staff too."
United States
Stephen
$98 nightly
The price is $108
Nov 10 - Nov 11
Total with taxes and fees
Holiday Inn Express Lexington East - Winchester by IHG
A Baymont Inn & Suites building with a 'Newly Renovated' sign, featuring a modern design with large windows and a prominent corner tower.

4. Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.4 out of 10, Good, (853 reviews)
"Room was clean beds were comfortable"
United States
Ronald
$77 nightly
The price is $84
Nov 1 - Nov 2
Total with taxes and fees
Baymont by Wyndham Winchester
A ValueStay hotel entrance with a clear sign, a covered walkway, and a parking lot.

5. Value Stay

Value Stay
2.0 star property
Winchester
7.4 out of 10, Good, (180 reviews)
"Room clean and welcoming staff."
United States
Gayle
$52 nightly
The price is $57
Nov 10 - Nov 11
Total with taxes and fees
Value Stay
A hotel with a central entrance, covered parking, and a building with a beige facade and arched windows.

6. Comfort Inn Winchester

Comfort Inn Winchester
2.5 star property
Winchester
7.0 out of 10, Good, (389 reviews)
"Everyone was super sweet the room was clean and breakfast was decent just wish the pool had been in service"
United States
Brittany
$78 nightly
The price is $86
Nov 2 - Nov 3
Total with taxes and fees
Comfort Inn Winchester
A multi-story hotel with a prominent 'LaQuinta' sign, a covered entrance, and a parking lot.

7. La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
3.0 star property
Lexington
9.0 out of 10, Wonderful, (1,181 reviews)
"Comfy beds, clean, quiet, good breakfast."
United States
Sheila
$87 nightly
The price is $101
Oct 11 - Oct 12
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
A hotel with a lobby, a parking lot, and a building with a brown roof.

8. Days Inn Lexington SE/Hamburg

Days Inn Lexington SE/Hamburg
2.0 star property
Lexington
7.2 out of 10, Good, (1,000 reviews)
"Property was well maintained. Staff were helpful and knowledgeable."
United States
Mohammed
$60 nightly
The price is $70
Oct 13 - Oct 14
Total with taxes and fees
Days Inn Lexington SE/Hamburg
A modern hotel with a prominent red and grey facade, multiple windows, and a well-lit entrance.

9. avid hotel Lexington - Hamburg Area by IHG

avid hotel Lexington - Hamburg Area by IHG
3.0 star property
Lexington
9.2 out of 10, Wonderful, (1,000 reviews)
"Nice hotel."
United States
Beth
$91 nightly
The price is $106
Nov 9 - Nov 10
Total with taxes and fees
avid hotel Lexington - Hamburg Area by IHG
A Comfort Inn hotel with a covered entrance, a parking lot, and a clear sky.

10. Comfort Inn Lexington I-75

Comfort Inn Lexington I-75
2.5 star property
Lexington
7.4 out of 10, Good, (826 reviews)
"Nice place to stay friendly staff!"
United States
Steve
$74 nightly
The price is $86
Oct 19 - Oct 20
Total with taxes and fees
Comfort Inn Lexington I-75
A guesthouse with a covered entrance, a large building with a tower, and a sign indicating an indoor pool.

11. GuestHouse Lexington

GuestHouse Lexington
2.5 star property
Lexington
8.4 out of 10, Very good, (1,678 reviews)
"Friendly staff clean room awesome place to say"
United States
Angela
$67 nightly
The price is $78
Oct 12 - Oct 13
Total with taxes and fees
GuestHouse Lexington
A hotel entrance with a sign reading "HOTEL LEX HOTEL AND CONFERENCE CENTER".

12. Hotel Lex and Conference Center, Trademark Collection

Hotel Lex and Conference Center, Trademark Collection
3.0 star property
Lexington
8.0 out of 10, Very good, (821 reviews)
"Nothing to complain about, great stay! Pool & Arcade were a hit for the kids. Room was clean, beds were comfortable."
United States
Alicia
$89 nightly
The price is $104
Oct 25 - Oct 26
Total with taxes and fees
Hotel Lex and Conference Center, Trademark Collection
A spacious lobby with a modern design, featuring a blue sofa, yellow armchairs, and a dining area with blue chairs.

13. Hyatt Place Lexington

Hyatt Place Lexington
3.0 star property
Lexington
8.6 out of 10, Excellent, (1,003 reviews)
"Friendly staff, nice hotel, good selection of breakfast items."
United States
Mark
$86 nightly
The price is $100
Nov 9 - Nov 10
Total with taxes and fees
Hyatt Place Lexington
A hotel with a modern facade, a parking lot with several cars, and an American flag on a flagpole.

14. Hampton Inn I-75 Lexington/Hamburg Area

Hampton Inn I-75 Lexington/Hamburg Area
2.5 star property
Lexington
8.6 out of 10, Excellent, (1,002 reviews)
"Really good stay"
United States
JJ
$88 nightly
The price is $103
Nov 4 - Nov 5
Total with taxes and fees
Hampton Inn I-75 Lexington/Hamburg Area
A modern hotel entrance with a covered walkway, large windows, and landscaped garden areas.

15. Spark by Hilton Lexington Hamburg

Spark by Hilton Lexington Hamburg
2.5 star property
Lexington
8.8 out of 10, Excellent, (613 reviews)
"The staff was friendly and checkin went smoothly. Room was clean. Breakfast and parking was nice!"
United States
John
$76 nightly
The price is $88
Oct 26 - Oct 27
Total with taxes and fees
Spark by Hilton Lexington Hamburg
A multi-story hotel with a modern design, featuring a covered entrance and a parking lot.

16. Fairfield Inn & Suites by Marriott Lexington East/I-75

Fairfield Inn & Suites by Marriott Lexington East/I-75
3.0 star property
Lexington
9.2 out of 10, Wonderful, (844 reviews)
"good convenient hotel on the outskirts of Lexington."
Canada
Dorin
$84 nightly
The price is $98
Oct 18 - Oct 19
Total with taxes and fees
Fairfield Inn & Suites by Marriott Lexington East/I-75
A modern hotel building with a blue and grey facade, multiple windows, and a prominent 'tru by Hilton' sign.

17. Tru By Hilton Lexington Hamburg

Tru By Hilton Lexington Hamburg
2.5 star property
Liberty Area
9.4 out of 10, Exceptional, (290 reviews)
"clean rooms, friendly staff perfect for our travels"
United States
Kristin
$84 nightly
The price is $97
Nov 10 - Nov 11
Total with taxes and fees
Tru By Hilton Lexington Hamburg
A Holiday Inn Express & Suites hotel with a modern design, multiple floors, and a parking lot with various vehicles.

18. Holiday Inn Express & Suites Lexington Midtown - I-75 by IHG

Holiday Inn Express & Suites Lexington Midtown - I-75 by IHG
2.5 star property
Lexington
9.2 out of 10, Wonderful, (693 reviews)
"Clean room near lots of good restaurants"
United States
Tim
$97 nightly
The price is $113
Oct 18 - Oct 19
Total with taxes and fees
Holiday Inn Express & Suites Lexington Midtown - I-75 by IHG
A motel with a 'welcome' sign, a central fountain, and a parking lot with a landscaped garden.

19. Motel 6 Lexington I-75 Hamburg

Motel 6 Lexington I-75 Hamburg
2.0 star property
Lexington
7.2 out of 10, Good, (1,005 reviews)
"Staff was friendly the room was clean and the bed was comfy 😌"
United States
Tonya
$50 nightly
The price is $58
Oct 18 - Oct 19
Total with taxes and fees
Motel 6 Lexington I-75 Hamburg
A Holiday Inn hotel with a brick facade, large windows, and a covered entrance.

20. Holiday Inn Lexington - Hamburg by IHG

Holiday Inn Lexington - Hamburg by IHG
3.0 star property
Lexington
9.0 out of 10, Wonderful, (1,000 reviews)
"Nice stay and good convenient location."
United States
John
$89 nightly
The price is $103
Nov 9 - Nov 10
Total with taxes and fees
Holiday Inn Lexington - Hamburg by IHG
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.
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Top Winchester Hotel Reviews

GuestHouse Lexington

GuestHouse Lexington

10/10 Excellent
"Rooms were very nice,clean,& staff very helpful, friendly. Walking distance to restaurants and covenants stores. Very safe and well lite parking lot. Would definitely stay again"
Robert 1-night trip
Posted 8 hours ago
GuestHouse Lexington

Find out more about Winchester

Winchester Villas information

Number of reviews
13,363
Accommodation
0 Villas
Lowest Price
$57
Highest Price
$121

Frequently asked questions

Why book your villa in Winchester with Expedia?
Use Expedia to find your dream villa in Winchester. Getting away with the kids? Take advantage of our filters to search for stays with amenities like WiFi and a pool. If you have a budget in mind, choose how much you want to spend and your preferred star rating. We'll help you find the perfect stay in tune with your taste and style.
How can I find cheap villas in Winchester?
With Expedia's user-friendly filter tool, booking cheap villas in Winchester has never been easier. To discover accommodations that won't break the bank, refine your search results by star rating, amenities and budget.
What is there to do near my villa in Winchester?
If you want to see the sights of Winchester, don't miss Southwind Golf Course. It's a favorite among locals and visitors alike.

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