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.
Comfort Suites Georgetown

Comfort Suites Georgetown

2.5 out of 5
Price was CA $1,012, price is now CA $919 per person
CA $919
per person
Jun 5 - Jun 7
just found
Roundtrip non-stop flight included
Calgary (YYC) to Lexington (LEX)
8.6/10 Excellent! (1,003 reviews)
The hotel was clean and staff was very nice. The location is excellent if you are attending an event at the KY Horse Park. The breakfast was fair. It can be a little noisy since it is by a main road.

Reviewed on Apr 27, 2026

GuestHouse Lexington

GuestHouse Lexington

2.5 out of 5
Price was CA $1,076, price is now CA $947 per person
CA $947
per person
Jun 5 - Jun 7
just found
Roundtrip non-stop flight included
Calgary (YYC) to Lexington (LEX)
8.4/10 Very Good! (1,577 reviews)
Quiet high pleasant ceilings on first floor

Reviewed on Apr 29, 2026

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

3 out of 5
Price was CA $1,141, price is now CA $1,023 per person
CA $1,023
per person
Jun 5 - Jun 7
just found
Roundtrip non-stop flight included
Calgary (YYC) to Lexington (LEX)
8.8/10 Excellent! (1,146 reviews)
Room was clean. Daily housekeeping. Breakfast variety was great, including hot foods. Pool was nice with comfortable temperature. Overall great stay.

Reviewed on Apr 29, 2026

Comfort Suites Richmond

Comfort Suites Richmond

2.5 out of 5
Price was CA $1,191, price is now CA $1,070 per person
CA $1,070
per person
Jun 5 - Jun 7
just found
Roundtrip non-stop flight included
Calgary (YYC) to Lexington (LEX)
7.4/10 Good! (740 reviews)
We wanted just a place to get away from the Northern weather and see our youngest do some rock climbing. Richmond was a great place for us. But we had car trouble and had to extend our stay. The motel staff was so supportive, it blew our minds and in fact made us want to go back to Richmond.

Reviewed on Apr 18, 2026

Comfort Inn & Suites Lexington - Hamburg I-75

Comfort Inn & Suites Lexington - Hamburg I-75

2.5 out of 5
Price was CA $1,068, price is now CA $975 per person
CA $975
per person
Jun 5 - Jun 7
just found
Roundtrip non-stop flight included
Calgary (YYC) to Lexington (LEX)
8/10 Very Good! (1,004 reviews)
Room was spacious and quiet even with the location being right beside the interstate... Breakfast was hot ... Only problem was I asked for extra pillows when booking and at check in and they said they didn't have any.. had to go buy some to use.

Reviewed on Apr 26, 2026

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Winchester Hotel Deals

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

2.5 out of 5
960 Interstate Dr Winchester KY
Fully refundableReserve now, pay when you stay
The price is CA $114 per night from May 18 to May 19
CA $114
CA $126 total
May 18 - May 19
includes taxes & fees
7.2/10 Good! (795 reviews)
The staff was very friendly and helpful. However, the place wasn’t the cleanest. And I wish the breakfast had more variety

Reviewed on Apr 28, 2026

Baymont by Wyndham Winchester
Spark by Hilton Lexington Hamburg

Spark by Hilton Lexington Hamburg

2.5 out of 5
2381 Buena Vista Rd Lexington KY
Fully refundableReserve now, pay when you stay
The price is CA $100 per night from May 12 to May 13
CA $100
CA $116 total
May 12 - May 13
includes taxes & fees
8.8/10 Excellent! (455 reviews)
Staff was great. Breakfast was good.

Reviewed on Apr 29, 2026

Spark by Hilton Lexington Hamburg
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 17 to May 18
CA $162
CA $188 total
May 17 - May 18
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
Great customer service. Clean. Quit. Very comfortable room. Will stay again for sure.

Reviewed on Apr 28, 2026

DoubleTree Suites by Hilton Hotel Lexington
See all 1,208 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.
All Inclusive Vacations
All Inclusive Vacations
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Beach Vacations
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Family Vacations

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.