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Tonight
Check prices in Winchester for tonight, Jun 14 - Jun 15
Jun 14 - Jun 15
Tomorrow night
Check prices in Winchester for tomorrow night, Jun 15 - Jun 16
Jun 15 - Jun 16
Next weekend
Check prices in Winchester for next weekend, Jun 19 - Jun 21
Jun 19 - Jun 21

Most frequently booked Winchester hotels

Value Stay

Value Stay

2 out of 5
5100 Revilo Rd Winchester KY
Free cancellation
Reserve now, pay when you stay
3.33 km from city centre
The price is CA $91 per night
CA $91
CA $100 total
Jun 15 - Jun 16
includes taxes & fees
Stay at this motel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Community Park and Wiseman Park are located nearby.
Pet-friendly
Parking included
Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

2.5 out of 5
960 Interstate Dr Winchester KY
Free cancellation
Reserve now, pay when you stay
2.38 km from city centre
The price is CA $118 per night
CA $118
CA $130 total
Jul 12 - Jul 13
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 clean rooms in our reviews. Popular attractions The Holler and Lykins Park are located nearby.
Pool
Breakfast included
Holiday Inn Express Lexington Horse Park Area by IHG

Holiday Inn Express Lexington Horse Park Area by IHG

3 out of 5
1935 Stanton Way, 1935 4 yes Lexington KY
Free cancellation
29.29 km from city centre
The price is CA $130 per night
CA $130
CA $151 total
Jul 2 - Jul 3
includes taxes & fees
Stay at this hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Kentucky Horse Park and Red Mile Racetrack are located nearby.
Pool
Breakfast 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 $215 per night
CA $215
CA $274 total
Jul 2 - Jul 3
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 Hamburg Place are located nearby.
Pet-friendly
Free WiFi
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 $171 per night
CA $171
CA $198 total
Jul 1 - Jul 2
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 Red Mile Racetrack and Hamburg Place are located nearby.
Pool
Free airport shuttle
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

3 out of 5
100 Canebrake Drive Lexington KY
Free cancellation
Reserve now, pay when you stay
18.22 km from city centre
The price is CA $127 per night
CA $127
CA $147 total
Jun 16 - Jun 17
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 Hamburg Place and Lexington Sporting Club Youth Complex are located nearby.
Pool
Breakfast included
Marriott Lexington Griffin Gate Golf Resort & Spa

Marriott Lexington Griffin Gate Golf Resort & Spa

4.5 out of 5
1800 Newtown Pike Lexington KY
Free cancellation
Reserve now, pay when you stay
29.06 km from city centre
The price is CA $144 per night
CA $144
CA $196 total
Jun 21 - Jun 22
includes taxes & fees
Book a stay at this luxury resort in Lexington. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Kentucky Horse Park and Red Mile Racetrack are located nearby.
Pool
Hot tub
DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

4 out of 5
2601 Richmond Rd Lexington KY
Free cancellation
Reserve now, pay when you stay
24.23 km from city centre
The price is CA $139 per night
CA $139
CA $161 total
Jun 28 - Jun 29
includes taxes & fees
Stay at this hotel in Lexington. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Hamburg Place and Red Mile Racetrack are located nearby.
Pool
Free airport shuttle
Natural Bridge State Resort Park

Natural Bridge State Resort Park

3.5 out of 5
2135 Natural Bridge Road Slade KY
Free cancellation
Reserve now, pay when you stay
49.76 km from city centre
The price is CA $177 per night
CA $177
CA $196 total
Jul 5 - Jul 6
includes taxes & fees
Stay at this cabin in Slade. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Natural Bridge State Park and Red River Gorge Geological Area 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 $118 per night from Jul 12 to Jul 13
CA $118
CA $130 total
Jul 12 - Jul 13
includes taxes & fees
7.2/10 Good! (808 reviews)

Top cheap Winchester hotel deals

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

960 Interstate Dr Winchester KY
The price is CA $118 per night from Jul 12 to Jul 13
CA $118
CA $130 total
Jul 12 - Jul 13
includes taxes & fees
7.2/10 Good! (808 reviews)

Winchester hotels essential information

Accommodation
1,203 hotels
Lowest Price
CA $100
Highest Price
CA $274
Popular hotels
Value Stay, Baymont by Wyndham Winchester, Holiday Inn Express Lexington Horse Park Area by IHG, The Manchester , Hilton Lexington/Downtown, La Quinta Inn & Suites by Wyndham Lexington South / Hamburg, Marriott Lexington Griffin Gate Golf Resort & Spa, DoubleTree Suites by Hilton Hotel Lexington, Natural Bridge State Resort Park

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 $100 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 1,203 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

Value Stay

Value Stay

4 out of 5
Posted 12 hours ago
Travelocity Verified Review
"While the room was clean and maintained, the only grip I had was its location and the road you had to travel to reach the hotels. A sign would have been nice so drivers won't get lost on their first time getting to the hotel."
A verified traveller stayed at Value Stay
Value Stay