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Most frequently booked Winchester hotels

The Manchester

941 Manchester St Lexington KY

Free cancellation

Reserve now, pay when you stay

29.79 km from city centre

CA $233

CA $294 total

May 31 - Jun 1

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.

Hotel LEX, Trademark Collection by Wyndham

5532 Athens Boonesboro Rd Lexington KY

Free cancellation

Reserve now, pay when you stay

18.47 km from city centre

CA $122

CA $142 total

Jun 18 - Jun 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 helpful staff and the clean rooms in our reviews. Popular attractions Hamburg Place and Lexington Sporting Club Youth Complex are located nearby.

Holiday Inn Express Lexington Horse Park Area by IHG

1935 Stanton Way, 1935 4 yes Lexington KY

Free cancellation

29.29 km from city centre

CA $158

CA $183 total

May 26 - May 27

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.

Hilton Lexington/Downtown

369 West Vine Street Lexington KY

Free cancellation

Reserve now, pay when you stay

28.83 km from city centre

CA $169

CA $196 total

May 31 - Jun 1

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.

DoubleTree Suites by Hilton Hotel Lexington

2601 Richmond Rd Lexington KY

Free cancellation

Reserve now, pay when you stay

24.23 km from city centre

CA $163

CA $190 total

May 31 - Jun 1

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.

Natural Bridge State Resort Park

2135 Natural Bridge Road Slade KY

49.76 km from city centre

CA $150

CA $165 total

Jun 14 - Jun 15

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 Hoedown Island are located nearby.

Days Inn Lexington SE/Hamburg

5575 Athens Boonesboro Rd Lexington KY

Free cancellation

Reserve now, pay when you stay

18.31 km from city centre

CA $82

CA $95 total

May 25 - May 26

includes taxes & fees

Book a stay at this business-friendly motel 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 Hamburg Place and Lexington Sporting Club Youth Complex are located nearby.

Spark by Hilton Lexington Hamburg

2381 Buena Vista Rd Lexington KY

Free cancellation

Reserve now, pay when you stay

22.03 km from city centre

CA $102

CA $119 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 pool in our reviews. Popular attractions Hamburg Place and Red Mile Racetrack are located nearby.

Elwood Hotel & Suites

444 Parkway Drive Lexington KY

Free cancellation

Reserve now, pay when you stay

30.41 km from city centre

CA $146

CA $169 total

Jun 1 - Jun 2

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 Keeneland Racing Course are located nearby.

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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

960 Interstate Dr Winchester KY

CA $110

CA $121 total

May 31 - Jun 1

includes taxes & fees

7.2/10 Good! (800 reviews)

Top cheap Winchester hotel deals

Baymont by Wyndham Winchester

960 Interstate Dr Winchester KY

CA $110

CA $121 total

May 31 - Jun 1

includes taxes & fees

7.2/10 Good! (800 reviews)

Winchester hotels essential information

Accommodation	1,184 hotels
Lowest Price	CA $95
Highest Price	CA $294
Popular hotels	The Manchester , Hotel LEX, Trademark Collection by Wyndham, Holiday Inn Express Lexington Horse Park Area by IHG, Hilton Lexington/Downtown, DoubleTree Suites by Hilton Hotel Lexington, Natural Bridge State Resort Park, Days Inn Lexington SE/Hamburg, Spark by Hilton Lexington Hamburg, Elwood Hotel & Suites

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 $95 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 1,184 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.