Book Cheap Hotels in Winchester

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Oct 4 - Oct 5

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Oct 5 - Oct 6

Next weekend

Oct 9 - Oct 11

Most frequently booked Winchester hotels

Comfort Inn Winchester

5250 Revilo Rd Winchester KY

Free cancellation

3.4 km from city centre

CA $111

CA $123 total

Nov 3 - Nov 4

includes taxes & fees

Book a stay at this business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Community Park and Wiseman Park 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 $138

CA $160 total

Nov 3 - Nov 4

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 Rupp Arena are located nearby.

21c Museum Hotel Lexington

167 West Main Street Lexington KY

28.57 km from city centre

CA $195

CA $233 total

Nov 1 - Nov 2

includes taxes & fees

Stay at this hotel in Lexington. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Rupp Arena and Red Mile Racetrack are located nearby.

Marriott Lexington Griffin Gate Golf Resort & Spa

1800 Newtown Pike Lexington KY

Free cancellation

Reserve now, pay when you stay

29.06 km from city centre

CA $158

CA $212 total

Oct 11 - Oct 12

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 Rupp Arena and Red Mile Racetrack are located nearby.

The Manchester

941 Manchester St Lexington KY

Free cancellation

Reserve now, pay when you stay

29.79 km from city centre

CA $267

CA $335 total

Nov 1 - Nov 2

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 Rupp Arena and Red Mile Racetrack are located nearby.

GuestHouse Lexington

2261 Elkhorn Road Lexington KY

Free cancellation

22.14 km from city centre

CA $96

CA $111 total

Oct 5 - Oct 6

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 Rupp Arena and Kroger Field are located nearby.

Origin Lexington a Wyndham Hotel

4174 Rowan Lexington KY

Free cancellation

Reserve now, pay when you stay

30.38 km from city centre

CA $227

CA $264 total

Oct 18 - Oct 19

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 restaurant and the helpful staff in our reviews. Popular attractions Kroger Field and Red Mile Racetrack are located nearby.

Natural Bridge State Resort Park

2135 Natural Bridge Road Slade KY

Free cancellation

Reserve now, pay when you stay

49.76 km from city centre

CA $109

CA $121 total

Nov 4 - Nov 5

includes taxes & fees

Stay at this cabin in Slade. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hoedown Island and Natural Bridge State Park are located nearby.

Microtel Inn by Wyndham Lexington

2240 Buena Vista Rd Lexington KY

Free cancellation

Reserve now, pay when you stay

22.43 km from city centre

CA $92

CA $107 total

Nov 1 - Nov 2

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 Rupp Arena and Kroger Field 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 $122 total

Nov 3 - Nov 4

includes taxes & fees

7.4/10 Good! (853 reviews)

Top cheap Winchester hotel deals

Baymont by Wyndham Winchester

960 Interstate Dr Winchester KY

CA $110

CA $122 total

Nov 3 - Nov 4

includes taxes & fees

7.4/10 Good! (853 reviews)

Winchester hotels essential information

Accommodation	1,238 hotels
Lowest Price	CA $107
Highest Price	CA $335
Popular hotels	Comfort Inn Winchester, Holiday Inn Express Lexington - Horse Park Area by IHG, 21c Museum Hotel Lexington, Marriott Lexington Griffin Gate Golf Resort & Spa, The Manchester , GuestHouse Lexington, Origin Lexington a Wyndham Hotel, Natural Bridge State Resort Park, Microtel Inn by Wyndham 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 $107 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 1,238 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.