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Tonight
Check prices in Winchester for tonight, Apr 3 - Apr 4
Apr 3 - Apr 4
Tomorrow night
Check prices in Winchester for tomorrow night, Apr 4 - Apr 5
Apr 4 - Apr 5
This weekend
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Apr 3 - Apr 5

Most frequently booked Winchester hotels

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 $134 per night
CA $134
CA $155 total
Apr 6 - Apr 7
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 $253 per night
CA $253
CA $318 total
May 3 - May 4
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.
Pet-friendly
Free WiFi
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 $148 per night
CA $148
CA $172 total
Apr 26 - Apr 27
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
Spark by Hilton Lexington Hamburg

Spark by Hilton Lexington Hamburg

2.5 out of 5
2381 Buena Vista Rd Lexington KY
Free cancellation
Reserve now, pay when you stay
22.03 km from city centre
The price is CA $102 per night
CA $102
CA $118 total
Apr 26 - Apr 27
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 Red Mile Racetrack and Hamburg Place are located nearby.
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 $207 per night
CA $207
CA $269 total
Apr 5 - Apr 6
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 Red Mile Racetrack and Kentucky Horse Park are located nearby.
Pool
Hot tub
The Campbell House Lexington, Curio Collection by Hilton

The Campbell House Lexington, Curio Collection by Hilton

4 out of 5
1375 South Broadway Lexington KY
Free cancellation
Reserve now, pay when you stay
30.54 km from city centre
The price is CA $191 per night
CA $191
CA $221 total
Apr 5 - Apr 6
includes taxes & fees
Book a stay at this business-friendly hotel in Lexington. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Red Mile Racetrack and Kroger Field are located nearby.
Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North

3 out of 5
2100 Hackney Pl Lexington KY
Free cancellation
Reserve now, pay when you stay
29.16 km from city centre
The price is CA $99 per night
CA $99
CA $115 total
May 3 - May 4
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 Kentucky Horse Park and Red Mile Racetrack are located nearby.
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 $232 per night
CA $232
CA $270 total
Apr 5 - Apr 6
includes taxes & fees
Book a stay at this business-friendly hotel in Lexington. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rupp Arena and Red Mile Racetrack are located nearby.
DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

4 out of 5
2601 Richmond Rd Lexington KY
24.23 km from city centre
The price is CA $164 per night
CA $164
CA $191 total
Apr 26 - Apr 27
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 Rupp Arena 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 $105 per night from Apr 5 to Apr 6
CA $105
CA $116 total
Apr 5 - Apr 6
includes taxes & fees
7.2/10 Good! (780 reviews)

Top cheap Winchester hotel deals

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

960 Interstate Dr Winchester KY
The price is CA $105 per night from Apr 5 to Apr 6
CA $105
CA $116 total
Apr 5 - Apr 6
includes taxes & fees
7.2/10 Good! (780 reviews)

Winchester hotels essential information

Accommodation
1,188 hotels
Lowest Price
CA $103
Highest Price
CA $318
Popular hotels
Holiday Inn Express Lexington Horse Park Area by IHG, The Manchester , Elwood Hotel & Suites, Spark by Hilton Lexington Hamburg, Marriott Lexington Griffin Gate Golf Resort & Spa, The Campbell House Lexington, Curio Collection by Hilton, Fairfield Inn & Suites by Marriott Lexington North, Hyatt Regency Lexington, 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 $103 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

Elwood Hotel & Suites

Elwood Hotel & Suites

5 out of 5
Posted 2 hours ago
Travelocity Verified Review
"Lovely!"
A verified traveller stayed at Elwood Hotel & Suites
Elwood Hotel & Suites