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.

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Check prices for these dates

Next weekend
17 Jul - 19 Jul
In two weeks
24 Jul - 26 Jul
In one month
7 Aug - 9 Aug
In two months
4 Sep - 6 Sep
No exact matches found, but these alternatives could be just right

Recommended hotels in Winchester

Exterior

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (820 reviews)
"Great beds and friendly staff"
United States
Tiffany
The price is AED 278
AED 306 total
includes taxes & fees
12 Jul - 13 Jul
Baymont by Wyndham Winchester
Exterior

Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very Good, (1,007 reviews)
"Good place to stay at"
United States
douglas
The price is AED 314
AED 346 total
includes taxes & fees
26 Jul - 27 Jul
Best Western Winchester Hotel
Front of property - evening/night

Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG
2.5 star property
Winchester
9.2 out of 10, Wonderful, (577 reviews)
"Great hotel, and reasonably priced. Difficult to access and navigate at night, however."
United States
Carl
The price is AED 346
AED 382 total
includes taxes & fees
19 Jul - 20 Jul
Holiday Inn Express Lexington East - Winchester by IHG
Exterior

Value Stay

Value Stay
2.0 star property
Winchester
7.6 out of 10, Good, (161 reviews)
"It was an inexpensive stay and provided a basic but clean and comfortable room."
United States
Robert
The price is AED 217
AED 239 total
includes taxes & fees
2 Aug - 3 Aug
Value Stay
Exterior

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (473 reviews)
The price is AED 479
AED 528 total
includes taxes & fees
18 Jul - 19 Jul
Hampton Inn Winchester
Exterior

Comfort Inn Winchester

Comfort Inn Winchester
2.5 star property
Winchester
7.0 out of 10, Good, (372 reviews)
"CLOSED"
United States
alene
The price is AED 239
AED 264 total
includes taxes & fees
2 Aug - 3 Aug
Comfort Inn Winchester
Exterior

Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.

Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.
Winchester
10.0 out of 10, Exceptional, (46 reviews)
The price is AED 944
AED 1,284 total
includes taxes & fees
17 Jul - 18 Jul
Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.
Exterior

The Winchester

The Winchester
Winchester
8.6 out of 10, Excellent, (8 reviews)
"I rented this house for my bridesmaids. It was a great location and house. The owner was accommodating and replied quickly "
United States
Karissa A.
The price is AED 545
AED 1,144 total
includes taxes & fees
12 Jul - 13 Jul
The Winchester
Exterior

4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
Winchester
9.8 out of 10, Exceptional, (11 reviews)
"Very homey place to stay! Nice neighborhood!"
United States
Tim T.
The price is AED 606
AED 1,227 total
includes taxes & fees
8 Aug - 9 Aug
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
Exterior

River Relaxation - Calm Riverfront Home in Winchester Kentucky

River Relaxation - Calm Riverfront Home in Winchester Kentucky
Winchester
7.6 out of 10, Good, (5 reviews)
"We loved the house, the hosts were great and super communicative! The house is also close to Lexington and Winchester so we had plenty to do and places to eat out! "
United States
Maeve R.
River Relaxation - Calm Riverfront Home in Winchester Kentucky
Exterior

Holiday Inn Express Lexington - Horse Park Area by IHG

Holiday Inn Express Lexington - Horse Park Area by IHG
3.0 star property
Lexington
9.4 out of 10, Exceptional, (2,203 reviews)
"This place was great!"
United States
Jarrod
The price is AED 302
AED 350 total
includes taxes & fees
22 Jul - 23 Jul
Holiday Inn Express Lexington - Horse Park Area by IHG
Exterior

Super 8 by Wyndham Richmond

Super 8 by Wyndham Richmond
2.0 star property
Richmond
7.8 out of 10, Good, (1,005 reviews)
"Nice hotel, conveniently located, friendly staff, very clean rooms"
United States
Anonymous traveler
The price is AED 203
AED 224 total
includes taxes & fees
12 Jul - 13 Jul
Super 8 by Wyndham Richmond
Exterior

Tru By Hilton Lexington Hamburg

Tru By Hilton Lexington Hamburg
2.5 star property
Liberty Area
9.4 out of 10, Exceptional, (244 reviews)
"Great place to stay"
United States
Sharon
The price is AED 313
AED 364 total
includes taxes & fees
22 Jul - 23 Jul
Tru By Hilton Lexington Hamburg
Cabin, 2 Bedrooms, Kitchen | Terrace/patio

Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1,948 reviews)
"Great area Nice place to stay"
United States
Julie
The price is AED 400
AED 441 total
includes taxes & fees
2 Aug - 3 Aug
Natural Bridge State Resort Park
Exterior

BEST CABIN EVER!-IN THE WOODS-SUPER CLEAN-HOT TUB-PAVED ROAD-NATURAL BRIDGE PARK

BEST CABIN EVER!-IN THE WOODS-SUPER CLEAN-HOT TUB-PAVED ROAD-NATURAL BRIDGE PARK
Stanton
10.0 out of 10, Exceptional, (326 reviews)
"Wonderful place to stay. We loved it!"
United States
Jamie B.
The price is AED 659
AED 1,156 total
includes taxes & fees
14 Jul - 15 Jul
BEST CABIN EVER!-IN THE WOODS-SUPER CLEAN-HOT TUB-PAVED ROAD-NATURAL BRIDGE PARK
Exterior

Country Inn & Suites by Radisson, Georgetown, KY

Country Inn & Suites by Radisson, Georgetown, KY
3.0 star property
Georgetown
8.8 out of 10, Excellent, (1,015 reviews)
"Friendly staff, clean property, good breakfast, and love that it was pet friendly for MINIMAL cost ."
United States
James
The price is AED 288
AED 318 total
includes taxes & fees
10 Aug - 11 Aug
Country Inn & Suites by Radisson, Georgetown, KY
Aerial view

Comfort Suites Richmond

Comfort Suites Richmond
2.5 star property
Richmond
7.4 out of 10, Good, (764 reviews)
"Front desk staff were great."
United States
Amy
The price is AED 188
AED 208 total
includes taxes & fees
28 Jul - 29 Jul
Comfort Suites Richmond
Exterior

Quality Inn Richmond

Quality Inn Richmond
2.5 star property
Richmond
9.0 out of 10, Wonderful, (1,004 reviews)
"Was a great stay."
United States
Christopher
The price is AED 382
AED 421 total
includes taxes & fees
12 Jul - 13 Jul
Quality Inn Richmond
Exterior

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
3.0 star property
Lexington
8.8 out of 10, Excellent, (1,182 reviews)
"Fantastic will stay again, great staff, helpful! Beautiful hotel"
United States
Jolene
The price is AED 332
AED 386 total
includes taxes & fees
21 Jul - 22 Jul
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Exterior

Home2 Suites Lexington Keeneland Airport, KY

Home2 Suites Lexington Keeneland Airport, KY
3.0 star property
Beaumont Residential
9.8 out of 10, Exceptional, (376 reviews)
The price is AED 327
AED 379 total
includes taxes & fees
18 Jul - 19 Jul
Home2 Suites Lexington Keeneland Airport, KY
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

Holiday Inn Express Lexington Horse Park Area by IHG

Holiday Inn Express Lexington Horse Park Area by IHG

10/10 Excellent
"Super nice front desk attendant! Clean and comfortable stay. Highly recommend"
Adam 1-night trip
Posted 3 hours ago
Holiday Inn Express Lexington Horse Park Area by IHG