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.

Search Inns in Winchester from CA $67

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Check prices for these dates

Next weekend
Jun 26 - Jun 28
In two weeks
Jul 3 - Jul 5
In one month
Jul 17 - Jul 19
In two months
Aug 14 - Aug 16
No exact matches found, but these alternatives could be just right

Recommended hotels in Winchester

Free daily full breakfast

Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very good, (1,002 reviews)
"Good place to stay at"
United States
douglas
The price is CA $128
CA $141 total
includes taxes & fees
Jun 28 - Jun 29
Best Western Winchester Hotel
Suite, 1 King Bed, Hot Tub

Value Stay

Value Stay
2.0 star property
Winchester
7.6 out of 10, Good, (157 reviews)
"The pool was very nice "
United States
Todd
The price is CA $92
CA $101 total
includes taxes & fees
Jun 22 - Jun 23
Value Stay
In-room safe, desk, laptop workspace, blackout drapes

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, (570 reviews)
"Clean room, good breakfast, friendly staff."
United States
Blake
The price is CA $161
CA $178 total
includes taxes & fees
Jul 19 - Jul 20
Holiday Inn Express Lexington East - Winchester by IHG
Pool

Comfort Inn Winchester

Comfort Inn Winchester
2.5 star property
Winchester
7.0 out of 10, Good, (367 reviews)
"CLOSED"
United States
alene
The price is CA $106
CA $117 total
includes taxes & fees
Jul 19 - Jul 20
Comfort Inn Winchester
Lobby

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (471 reviews)
"Room was nice, hotel is quiet, and breakfast was clean and organized."
United States
Andrew
The price is CA $197
CA $217 total
includes taxes & fees
Jun 21 - Jun 22
Hampton Inn Winchester
Indoor pool

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (810 reviews)
"Great beds and friendly staff"
United States
Tiffany
The price is CA $107
CA $118 total
includes taxes & fees
Jun 21 - Jun 22
Baymont by Wyndham Winchester

The Winchester

The Winchester
Winchester
8.4 out of 10, Very good, (7 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 CA $210
CA $442 total
includes taxes & fees
Jun 23 - Jun 24
The Winchester
Combined shower/tub, hair dryer, towels, soap

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, (45 reviews)
"The host was very accomidating and hospitible. It was the perfect location for our trip. "
United States
MacKendrie P.
The price is CA $324
CA $442 total
includes taxes & fees
Jun 22 - Jun 23
Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.
Fridge, microwave, oven, stovetop

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, (9 reviews)
"Very homey place to stay! Nice neighborhood!"
United States
Tim T.
The price is CA $210
CA $442 total
includes taxes & fees
Jun 21 - Jun 22
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.
The price is CA $184
CA $541 total
includes taxes & fees
Jun 21 - Jun 22
River Relaxation - Calm Riverfront Home in Winchester Kentucky
Exterior

Black Bear Lodge Motel

Black Bear Lodge Motel
2.5 star property
Slade
8.0 out of 10, Very good, (677 reviews)
"For the price, it was a great location and would stay there again."
United States
marion
The price is CA $124
CA $137 total
includes taxes & fees
Jul 8 - Jul 9
Black Bear Lodge Motel
Standard Room, 2 Queen Beds

Super 8 by Wyndham Richmond

Super 8 by Wyndham Richmond
2.0 star property
Richmond
7.8 out of 10, Good, (1,000 reviews)
"Nice hotel, conveniently located, friendly staff, very clean rooms"
United States
Aman
The price is CA $78
CA $86 total
includes taxes & fees
Jun 22 - Jun 23
Super 8 by Wyndham Richmond
Snack bar

Tru By Hilton Lexington Hamburg

Tru By Hilton Lexington Hamburg
2.5 star property
Liberty Area
9.4 out of 10, Exceptional, (230 reviews)
"Great place to stay"
United States
Sharon
The price is CA $124
CA $144 total
includes taxes & fees
Jun 28 - Jun 29
Tru By Hilton Lexington Hamburg
Cabin, 2 Bedrooms, Kitchen | Living area

Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1,930 reviews)
"Great area Nice place to stay"
United States
Julie
The price is CA $173
CA $191 total
includes taxes & fees
Jul 19 - Jul 20
Natural Bridge State Resort Park
Property grounds

Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge

Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge
Irvine
10.0 out of 10, Exceptional, (109 reviews)
"This was a wonderful location and a delightfully cozy cabin for a couple or a solo stay. Might very well stay here again in the future."
United States
Jason H.
The price is CA $125
CA $271 total
includes taxes & fees
Jun 21 - Jun 22
Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge
Comfort Single Room | Interior

Hotel Thoroughbred

Hotel Thoroughbred
2.0 star property
Paris
10.0 out of 10, Exceptional, (14 reviews)
"Hotel was everything I had expected. Staff were exceptionally courteous and friendly."
United States
Cynthia
The price is CA $191
CA $211 total
includes taxes & fees
Jun 22 - Jun 23
Hotel Thoroughbred
Interior

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, (324 reviews)
"Great stay! Loved the private driveway. "
United States
Emily N.
The price is CA $267
CA $461 total
includes taxes & fees
Jul 7 - Jul 8
BEST CABIN EVER!-IN THE WOODS-SUPER CLEAN-HOT TUB-PAVED ROAD-NATURAL BRIDGE PARK
Indoor pool, open 5:00 AM to 10:00 PM, sun loungers

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, (2,197 reviews)
"Hotel staff were great, the rooms were clean And the price was reasonable. Would definitely stay again."
United States
Terry
The price is CA $136
CA $158 total
includes taxes & fees
Jun 28 - Jun 29
Holiday Inn Express Lexington Horse Park Area by IHG
Lobby

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, (1,002 reviews)
"Clean and well maintained property. Enjoyed the hotel."
United States
Gabe
The price is CA $105
CA $116 total
includes taxes & fees
Jul 14 - Jul 15
Country Inn & Suites by Radisson, Georgetown, KY
Lobby

Hampton Inn Lexington South-Keeneland/Airport

Hampton Inn Lexington South-Keeneland/Airport
2.5 star property
Beaumont Residential
8.2 out of 10, Very good, (617 reviews)
"The staff were helpful and nice. The breakfast was great. Everything lived up to what you expect from a Hampton Inn."
United States
Gretchen
The price is CA $104
CA $120 total
includes taxes & fees
Jul 4 - Jul 5
Hampton Inn Lexington South-Keeneland/Airport
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

The Manchester

The Manchester

10/10 Excellent
"Beautiful unique hotel !! Highly recommend!!!"
Angela 2-night trip
Posted 3 hours ago
The Manchester

Find out more about Winchester

Winchester Inns information

Number of reviews
16,470
Accommodation
0 Inns
Lowest Price
CA $67
Highest Price
CA $217

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