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 Pet friendly Hotels

Our top choices for Winchester pet-friendly hotels

Indoor pool, open 5:00 AM to 10:00 PM, pool 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, (2,207 reviews)
"This place was great!"
United States
Jarrod
The price is S$138
includes taxes & fees
22 Jul - 23 Jul
Holiday Inn Express Lexington - Horse Park Area by IHG
Snack bar

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 S$128
includes taxes & fees
22 Jul - 23 Jul
Tru By Hilton Lexington Hamburg
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, (1,015 reviews)
"Pleasant front desk staff, clean and quiet"
United States
LISA
The price is S$106
includes taxes & fees
19 Jul - 20 Jul
Country Inn & Suites by Radisson, Georgetown, KY
Free daily full breakfast

Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very good, (1,007 reviews)
The price is S$122
includes taxes & fees
26 Jul - 27 Jul
Best Western Winchester Hotel
Free WiFi, bed sheets

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 S$78
includes taxes & fees
12 Jul - 13 Jul
Value Stay
Lobby

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (473 reviews)
"Room was nice, hotel is quiet, and breakfast was clean and organized."
United States
Andrew
The price is S$174
includes taxes & fees
19 Jul - 20 Jul
Hampton Inn Winchester
In-room safe, desk, laptop workspace, blackout curtains

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, (579 reviews)
"Great hotel, and reasonably priced. Difficult to access and navigate at night, however."
United States
Carl
The price is S$145
includes taxes & fees
19 Jul - 20 Jul
Holiday Inn Express Lexington East - Winchester by IHG
Indoor pool

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (821 reviews)
"Great beds and friendly staff"
United States
Tiffany
The price is S$108
includes taxes & fees
12 Jul - 13 Jul
Baymont by Wyndham Winchester
Living area

Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1,951 reviews)
"Great area Nice place to stay"
United States
Julie
The price is S$149
includes taxes & fees
11 Aug - 12 Aug
Natural Bridge State Resort Park
Reception

Mountain View Inn Irvine Near Richmond KY

Mountain View Inn Irvine Near Richmond KY
2.5 star property
Irvine
6.0 out of 10, (32 reviews)
"Soft bed but the whole place was falling apart "
United States
James
The price is S$62
includes taxes & fees
12 Jul - 13 Jul
Mountain View Inn Irvine Near Richmond 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

Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

10/10 Excellent
"Great stay. Rooms clean and spacious. Beautiful lobby and very good breakfast. Highly recommend"
norman 1-night trip
Posted 3 hours ago
Embassy Suites by Hilton Lexington/UK Coldstream

Frequently asked questions

What's the best dog-friendly accommodation option in Winchester?
Baymont by Wyndham Winchester is a top dog-friendly hotel, and offers an indoor pool and a fitness centre for its human guests. Two other good options for you and your pet include Value Stay and Best Western Winchester Hotel.
How many dog-friendly hotels can I expect to find in Winchester?
Stay with your furry friend at one of Expedia's 5 Winchester hotels that allow pets.
What's the best time of year to travel to Winchester with my pet?
When you travel with your pet, keeping tabs on the weather can help you make the trip more safe and fun for everyone. The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Winchester is 1426 mm.
What is there to see and do with your pet in Winchester?
Known for its hiking trails and football, Winchester has lots to offer visitors. See the local sights and visit Bluegrass Heritage Museum and Community Park. While you're there, make sure you don't miss Wiseman Park and Lykins Park.

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