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 availability on Winchester Golf Hotels

Next weekend
10 Jul - 12 Jul
In two weeks
17 Jul - 19 Jul

Our top choices for Winchester hotels with a golf course

Free daily full breakfast

Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very Good, (1,004 reviews)
"Good place to stay at"
United States
douglas
The price is AED 314
AED 346 total
includes taxes & fees
28 Jul - 29 Jul
Best Western Winchester Hotel
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, (46 reviews)
"This home was beautiful and the hosts were overly generous with the amenities at the property. If we’re ever in the area again we will definitely be staying here! "
United States
Josiah C.
The price is AED 816
AED 1,106 total
includes taxes & fees
6 Jul - 7 Jul
Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.
Dining

PRIVATE SHIPPING CONTAINER CABIN IN THE WOODS-RED RIVER GORGE-VERY CLEAN-HOT TUB

PRIVATE SHIPPING CONTAINER CABIN IN THE WOODS-RED RIVER GORGE-VERY CLEAN-HOT TUB
Stanton
10.0 out of 10, Exceptional, (30 reviews)
"Love the area and the stay was great! Thanks for the communication we had a great time. "
United States
Holly,
The price is AED 590
AED 1,047 total
includes taxes & fees
6 Jul - 7 Jul
PRIVATE SHIPPING CONTAINER CABIN IN THE WOODS-RED RIVER GORGE-VERY CLEAN-HOT TUB
Terrace/patio

Mountaintop Cottage

Mountaintop Cottage
Stanton
10.0 out of 10, Exceptional, (38 reviews)
"Great stay! Beautiful property and an awesome donkey"
United States
andymorg
The price is AED 479
AED 694 total
includes taxes & fees
12 Jul - 13 Jul
Mountaintop Cottage
Terrace/patio

Mountain Memories Cabin

Mountain Memories Cabin
Stanton
10.0 out of 10, Exceptional, (79 reviews)
"Would stay again. Responsive host, property was very clean and host had left nice touches / decorations for valentines day weekend visit."
United States
Robert C.
The price is AED 496
AED 709 total
includes taxes & fees
5 Jul - 6 Jul
Mountain Memories Cabin
Fridge, microwave, oven, stovetop

Conveniently Located ~ WiFi ~ Central Heat & Air.

Conveniently Located ~ WiFi ~ Central Heat & Air.
Stanton
9.8 out of 10, Exceptional, (51 reviews)
"A great place to stay while exploring the area"
United States
lisa s.
The price is AED 364
AED 867 total
includes taxes & fees
5 Jul - 6 Jul
Conveniently Located ~ WiFi ~ Central Heat & Air.
Property grounds

Cozy, Bright Home in Historic Downtown

Cozy, Bright Home in Historic Downtown
Mount Sterling
8.4 out of 10, Very Good, (22 reviews)
"Great stay as usual. Owners are super friendly & helpful. This was our 3rd time staying as we've made this our regular when visiting family in the area."
United States
Brittany K.
The price is AED 231
AED 458 total
includes taxes & fees
5 Jul - 6 Jul
Cozy, Bright Home in Historic Downtown
Fridge, microwave, oven, stovetop

Cozy farmhouse family friendly with fire pit and grill, within hour to Keeneland

Cozy farmhouse family friendly with fire pit and grill, within hour to Keeneland
Paris
10.0 out of 10, Exceptional, (21 reviews)
"Such a peaceful, cozy place to stay. "
United States
Ninette W.
The price is AED 463
AED 1,162 total
includes taxes & fees
5 Jul - 6 Jul
Cozy farmhouse family friendly with fire pit and grill, within hour to Keeneland
Property grounds

The Professor's Suite: Classic Historic Stay with a King Bed

The Professor's Suite: Classic Historic Stay with a King Bed
Millersburg
The price is AED 606
AED 764 total
includes taxes & fees
5 Jul - 6 Jul
The Professor's Suite: Classic Historic Stay with a King Bed
Property grounds

The Lieutenant's Suite: Sophisticated & Stylish Stay in Millersburg

The Lieutenant's Suite: Sophisticated & Stylish Stay in Millersburg
Millersburg
The price is AED 606
AED 764 total
includes taxes & fees
5 Jul - 6 Jul
The Lieutenant's Suite: Sophisticated & Stylish Stay in Millersburg
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
"Clean, accessible room did not disappoint"
Aderonke 1-night trip
Posted 3 hours ago
Holiday Inn Express Lexington Horse Park Area by IHG

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Frequently asked questions

Are you looking for a golf hotel in Winchester?
From golf carts to clubhouses to panoramic pools, Expedia is the place to book your golfing weekend. Tee off at Southwind Golf Course and Cassell Creek Golf Course. Enjoy the shopping and many popular restaurants during your vacation.
What should I see and do in Winchester while on a golf vacation?
When you're ready to take a break from the back nine, you'll find that Winchester has lots to offer. Explore the local sights and attractions with a stop at Bluegrass Heritage Museum, Community Park, and The Holler. Also, don't miss Wiseman Park, Winchester Traveling Trail, and Lykins Park.
What is a golf hotel in Winchester like?
Golf hotels in Winchester offer accommodations as well as convenient access to a golf course. On Expedia, you will be able to find golf hotels with either a 9+ hole golf course, or that are located adjacent to an 18+ hole golf course. Golf hotels provide a good choice of services and amenities such as carts, caddies, and shuttles.