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Tonight
Check prices in Winchester for tonight, Feb 17 - Feb 18
Feb 17 - Feb 18
Tomorrow night
Check prices in Winchester for tomorrow night, Feb 18 - Feb 19
Feb 18 - Feb 19
This weekend
Check prices in Winchester for this weekend, Feb 20 - Feb 22
Feb 20 - Feb 22
Next weekend
Check prices in Winchester for next weekend, Feb 27 - Mar 1
Feb 27 - Mar 1

Most frequently booked Winchester hotels

Hampton Inn Winchester

Hampton Inn Winchester

2.5 out of 5
1025 Early Dr Winchester KY
2.41 km from city centre
The price is CA $162 per night
CA $162
CA $178 total
Feb 21 - Feb 22
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 and the clean rooms in our reviews. Popular attractions The Holler and Lykins Park 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 $261 per night
CA $261
CA $327 total
Feb 22 - Feb 23
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
Hyatt Regency Lexington

Hyatt Regency Lexington

3.5 out of 5
401 W High St Lexington KY
28.93 km from city centre
The price is CA $196 per night
CA $196
CA $228 total
Mar 8 - Mar 9
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
Elwood Hotel & Suites

Elwood Hotel & Suites

4 out of 5
444 Parkway Drive Lexington KY
Free cancellation
Reserve now, pay when you stay
30.41 km from city centre
The price is CA $126 per night
CA $126
CA $146 total
Feb 23 - Feb 24
includes taxes & fees
Stay at this hotel in Lexington. Enjoy free WiFi, free parking, and breakfast (surcharge). 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
Parking included
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 $119 per night
CA $119
CA $138 total
Feb 18 - Feb 19
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 Lexington Sporting Club Youth Complex and Boone Station State Historic Site are located nearby.
Pool
Breakfast included
Home2 Suites by Hilton Lexington Hamburg

Home2 Suites by Hilton Lexington Hamburg

3 out of 5
1750 PLEASANT RIDGE DR Lexington KY
Free cancellation
Reserve now, pay when you stay
20.52 km from city centre
The price is CA $127 per night
CA $127
CA $148 total
Feb 27 - Feb 28
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 helpful staff and the clean rooms in our reviews. Popular attractions Kroger Field and Red Mile Racetrack are located nearby.
Pool
Breakfast included
Embassy Suites by Hilton Lexington Green

Embassy Suites by Hilton Lexington Green

3.5 out of 5
245 Lexington Green Circle Lexington KY
Free cancellation
Reserve now, pay when you stay
30.27 km from city centre
The price is CA $174 per night
CA $174
CA $202 total
Feb 22 - Feb 23
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
Quality Inn Lexington -Horse Park

Quality Inn Lexington -Horse Park

2.5 out of 5
1938 Stanton Way Lexington KY
Free cancellation
Reserve now, pay when you stay
29.26 km from city centre
The price is CA $90 per night
CA $90
CA $104 total
Mar 10 - Mar 11
includes taxes & fees
Book a stay at this golf hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Kentucky Horse Park and Red Mile Racetrack are located nearby.
Breakfast included
Pet-friendly
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 $152 per night
CA $152
CA $176 total
Mar 15 - Mar 16
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 Kroger Field and Red Mile Racetrack are located nearby.
Pool
Free airport shuttle
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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 $109 per night from Feb 23 to Feb 24
CA $109
CA $120 total
Feb 23 - Feb 24
includes taxes & fees
7.2/10 Good! (778 reviews)

Top cheap Winchester hotel deals

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

960 Interstate Dr Winchester KY
The price is CA $109 per night from Feb 23 to Feb 24
CA $109
CA $120 total
Feb 23 - Feb 24
includes taxes & fees
7.2/10 Good! (778 reviews)

Winchester hotels essential information

Accommodation
1,172 hotels
Lowest Price
CA $94
Highest Price
CA $327
Popular hotels
Hampton Inn Winchester, The Manchester , Hyatt Regency Lexington, Elwood Hotel & Suites, La Quinta Inn & Suites by Wyndham Lexington South / Hamburg, Home2 Suites by Hilton Lexington Hamburg, Embassy Suites by Hilton Lexington Green, Quality Inn Lexington -Horse Park, DoubleTree Suites by Hilton Hotel Lexington

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 $94 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 1,172 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

Home2 Suites by Hilton Lexington Hamburg

Home2 Suites by Hilton Lexington Hamburg

5 out of 5
Posted 1 day ago
Travelocity Verified Review
"Staff was extremely friendly. Rooms were clean and spacious. Kids loved the pool. Location was great, right off the interstate, close to shopping and lots of good restaurants. "
A verified traveller stayed at Home2 Suites by Hilton Lexington Hamburg
Home2 Suites by Hilton Lexington Hamburg

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Areas of Winchester