Book Cheap Hotels in Winchester

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Check prices in Winchester for tonight, Dec 24 - Dec 25
Dec 24 - Dec 25
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Check prices in Winchester for this weekend, Dec 26 - Dec 28
Dec 26 - Dec 28
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Jan 2 - Jan 4

Most frequently booked Winchester hotels

Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG

2.5 out of 5
100 Winchester Plaza Winchester KY
Free cancellation
3.61 km from city centre
The price is CA $133 per night
CA $133
CA $147 total
Jan 5 - Jan 6, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Wiseman Park and Community Park are located nearby.
Pool
Breakfast included
Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 out of 5
1307 W Lexington Ave Winchester KY
Free cancellation
Reserve now, pay when you stay
2.41 km from city centre
The price is CA $105 per night
CA $105
CA $116 total
Dec 28 - Dec 29
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Wiseman Park and Community Park are located nearby.
Pool
Breakfast included
Hilton Lexington/Downtown

Hilton Lexington/Downtown

3.5 out of 5
369 West Vine Street Lexington KY
Free cancellation
Reserve now, pay when you stay
28.83 km from city centre
The price is CA $167 per night
CA $167
CA $194 total
Jan 19 - Jan 20, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in Lexington. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Kroger Field and Keeneland Racing Course are located nearby.
Pool
Free airport shuttle
Motel 6 Lexington, KY - Airport

Motel 6 Lexington, KY - Airport

2 out of 5
750 Newtown Court Lexington KY
Free cancellation
29.15 km from city centre
The price is CA $70 per night
CA $70
CA $82 total
Dec 26 - Dec 27
includes taxes & fees
Stay at this motel in Lexington. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Red Mile Racetrack and Kroger Field are located nearby.
Pet-friendly
Parking included
Candlewood Suites Lexington Medical District by IHG

Candlewood Suites Lexington Medical District by IHG

2.5 out of 5
501 Waller Avenue Lexington KY
Free cancellation
30.36 km from city centre
The price is CA $102 per night
CA $102
CA $118 total
Dec 27 - Dec 28
includes taxes & fees
Book a stay at this business-friendly hotel in Lexington. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Red Mile Racetrack and Kroger Field are located nearby.
Pet-friendly
Parking included
The Manchester

The Manchester

4 out of 5
941 Manchester St Lexington KY
Free cancellation
Reserve now, pay when you stay
29.79 km from city centre
The price is CA $210 per night
CA $210
CA $267 total
Jan 4 - Jan 5, 2026
includes taxes & fees
Stay at this hotel in Lexington. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Red Mile Racetrack and Kroger Field are located nearby.
Pet-friendly
Free WiFi
GuestHouse Lexington

GuestHouse Lexington

2.5 out of 5
2261 Elkhorn Road Lexington KY
Free cancellation
Reserve now, pay when you stay
22.14 km from city centre
The price is CA $92 per night
CA $92
CA $107 total
Jan 14 - Jan 15, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Kroger Field and Red Mile Racetrack are located nearby.
Pool
Breakfast included
Hyatt Regency Lexington

Hyatt Regency Lexington

3.5 out of 5
401 W High St Lexington KY
Free cancellation
Reserve now, pay when you stay
28.93 km from city centre
The price is CA $168 per night
CA $168
CA $195 total
Dec 30 - Dec 31
includes taxes & fees
Book a stay at this business-friendly hotel in Lexington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Kroger Field and Keeneland Racing Course are located nearby.
Pool
Free airport shuttle
Staybridge Suites Lexington S Medical Ctr Area by IHG

Staybridge Suites Lexington S Medical Ctr Area by IHG

3 out of 5
209 RUCCIO WAY Lexington KY
Free cancellation
30.6 km from city centre
The price is CA $133 per night
CA $133
CA $154 total
Jan 18 - Jan 19, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Kroger Field and Red Mile Racetrack are located nearby.
Pool
Breakfast included
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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.

Top family friendly Winchester hotel deals

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

960 Interstate Dr Winchester KY
The price is CA $112 per night from Jan 19 to Jan 20
CA $112
CA $124 total
Jan 19 - Jan 20, 2026
includes taxes & fees
7/10 Good! (771 reviews)

Top cheap Winchester hotel deals

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

960 Interstate Dr Winchester KY
The price is CA $112 per night from Jan 19 to Jan 20
CA $112
CA $124 total
Jan 19 - Jan 20, 2026
includes taxes & fees
7/10 Good! (771 reviews)

Winchester hotels essential information

Accommodation
1,188 hotels
Lowest Price
CA $82
Highest Price
CA $267
Popular hotels
Holiday Inn Express Lexington East - Winchester by IHG, Best Western Winchester Hotel, Hilton Lexington/Downtown, Motel 6 Lexington, KY - Airport, Candlewood Suites Lexington Medical District by IHG, The Manchester , GuestHouse Lexington, Hyatt Regency Lexington, Staybridge Suites Lexington S Medical Ctr Area by IHG

Frequently asked questions

What are the top kid-friendly hotels in Winchester?
Family vacations are where amazing memories are made, but traveling with children can be tricky. These kid-friendly Winchester hotels offer perks designed to keep travelers of all ages comfortable and happy: Your gang will enjoy staying at 2nd Story Historic Downtown 2BR with Modern Amenities. Pet-friendly facilities and free WiFi are among the things that help make this property an attractive option. Otherwise, spend your nights in Winchester at This house is a 3 bedroom(s), 2 bathrooms, located in Winchester, KY.. Take advantage of a king bed, pet-friendly facilities and more here.
Where can I find cheap hotels in Winchester?
At Travelocity you'll find really nice hotels in Winchester at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Winchester rather than in Winchester. We may find you even better rates, too.
How do I find the best Winchester hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Winchester then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Winchester?
The cheapest hotel in Winchester is CA $82 This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Winchester?
There are 1,188 hotels in Winchester on Travelocity.
What are the best hotels in Winchester?
Winchester has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Winchester for you!
When is the best time to visit Winchester?
If you want the joy of a fun-filled trip in peak season, visit Winchester during May, August and October. If you'd prefer the peace of off-season, book a stay during quieter months, such as December, January and February.
When is the cheapest time to stay in Winchester?
Based on historic data is usually the cheapest month to visit Winchester. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Winchester?
There are multiple hotels in Winchester that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Winchester. We have plenty of kid-friendly hotels in Winchester to choose from on Travelocity!
Why book a hotel in Winchester through Travelocity?
Because we have the top hotels in Winchester! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Winchester on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Winchester hotel reviews by fellow wanderers

Candlewood Suites Lexington Medical District by IHG

Candlewood Suites Lexington Medical District by IHG

5 out of 5
Posted 2 days ago
Travelocity Verified Review
"Everything was amazing, everyone was super nice, the room was very clean and comfy close to the hospital because we had to be there at 5:30am… it was also my birthday so… I was so happy with my stay! "
A verified traveller stayed at Candlewood Suites Lexington Medical District by IHG
Candlewood Suites Lexington Medical District by IHG

Types of hotels

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Areas of Winchester