Winchester Vacation Packages

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Your Winchester Vacation

Take away the hard part of organizing your next epic adventure with a Winchester vacation package. Whether you're visiting for its landmarks, food or other highlights, this city offers endless possibilities for fun. Every trip to Winchester needs a well-thought-out itinerary. Fill yours with attractions like Bluegrass Heritage Museum, Lykins Park and Southwind Golf Course. Your ultimate Winchester vacation is just a few clicks away. Browse hotels, airfares and more on Expedia for an adventure that's tailored to suit your travel style.

Top Winchester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
GuestHouse Lexington

GuestHouse Lexington

2.5 out of 5
Price was CA $904, price is now CA $860 per person
CA $860
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Lexington (LEX)
8.4/10 Very Good! (1,590 reviews)
Very nice and clean hotel , good place to stay . And close to a lot of nice place to visit and restraunt to eat .

Reviewed on May 6, 2026

21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
Price was CA $1,051, price is now CA $950 per person
CA $950
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Lexington (LEX)
8.8/10 Excellent! (1,000 reviews)
Awesome location with tons of artistic charm.

Reviewed on May 6, 2026

Holiday Inn Express Lexington Horse Park Area by IHG

Holiday Inn Express Lexington Horse Park Area by IHG

3 out of 5
Price was CA $1,092, price is now CA $1,023 per person
CA $1,023
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Lexington (LEX)
9.4/10 Exceptional! (2,196 reviews)
I really enjoyed the modern look of the room. The pocket bathroom door made the space feel open and spacious, and the layout was thoughtfully designed to maximize every inch of the room. Comfortable, clean, and very well planned overall.

Reviewed on May 7, 2026

The Sire Hotel Lexington, Tapestry Collection by Hilton

The Sire Hotel Lexington, Tapestry Collection by Hilton

3.5 out of 5
Downtown Lexington
Price was CA $1,115, price is now CA $1,045 per person
CA $1,045
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Lexington (LEX)
9.4/10 Exceptional! (881 reviews)
Good location, big room, nice.

Reviewed on May 2, 2026

DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

4 out of 5
Price was CA $1,015, price is now CA $956 per person
CA $956
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Lexington (LEX)
8.8/10 Excellent! (1,003 reviews)
Excellent hotel with exceptional staff!

Reviewed on May 7, 2026

Ready to book your vacation to Winchester?

 

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Winchester Hotel Deals

The Manchester

The Manchester

4 out of 5
941 Manchester St Lexington KY
The price is CA $250 per night from May 31 to Jun 1
CA $250
CA $313 total
May 31 - Jun 1
includes taxes & fees
9.6/10 Exceptional! (1,270 reviews)
Amazing stay!

Reviewed on May 8, 2026

The Manchester
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
Fully refundable
The price is CA $141 per night from May 17 to May 18
CA $141
CA $164 total
May 17 - May 18
includes taxes & fees
9.4/10 Exceptional! (2,204 reviews)
We arrived at this hotel on April 11th and were told upon arrival that they had no hot water and it would not be fixed by morning. We had booked through Hotel’s.com. We could not stay because of the water situation. We have been charged for the room and need to be reimbursed as soon as possible. ...

Reviewed on May 8, 2026

Holiday Inn Express Lexington Horse Park Area by IHG
DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

4 out of 5
2601 Richmond Rd Lexington KY
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from May 24 to May 25
CA $162
CA $188 total
May 24 - May 25
includes taxes & fees
8.8/10 Excellent! (1,008 reviews)
C

Reviewed on May 8, 2026

DoubleTree Suites by Hilton Hotel Lexington
See all 1,199 properties in Winchester
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.
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Discover the most popular places to visit in Winchester

Panorama of an autumn, colorful lawn surrounded by buildings in downtown Lexington, Kentucky

University of Kentucky

4.5/5(8 reviews)

Explore the campus of University of Kentucky, during your travels in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.

University of Kentucky
Fayette Mall

Fayette Mall

4.5/5(12 reviews)

You can find the perfect gifts to bring home at Fayette Mall during your stay in Lexington. Discover the area's acclaimed theater scene, or seek out its horseback riding.

Fayette Mall
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The Kentucky Castle

Enjoy a trip to The Kentucky Castle and popular activities like horseback riding in Versailles. Attend a sporting event or simply enjoy the lively bars while you're in the area.

The Kentucky Castle

What to do in Winchester

Unique Horse Farm Tours with Insider Access to Private Farms

Unique Horse Farm Tours with Insider Access to Private Farms

CA $81
per adult
90% of travellers recommend
Unique Horse Farm Tours with Insider Access to Private Farms
Lexington: Downtown Walking Food & History Tour

Lexington: Downtown Walking Food & History Tour

CA $137
per adult
Lexington: Downtown Walking Food & History Tour
See all activities in Winchester

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.