Winchester Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Nawa Aseen

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.
Home2 Suites by Hilton Lexington University / Medical Center

Home2 Suites by Hilton Lexington University / Medical Center

3 out of 5
Zandale
Price was CA $835, price is now CA $687 per person
CA $687
per person
Oct 30 - Nov 2
found 14 hours ago
Roundtrip non-stop flight included
Syracuse (SYR) to Lexington (LEX)
8.8/10 Excellent! (990 reviews)
Angel was very helpful and friendly.

Reviewed on Aug. 31, 2025

21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
Price was CA $1,045, price is now CA $789 per person
CA $789
per person
Oct 30 - Nov 2
found 14 hours ago
Roundtrip non-stop flight included
Syracuse (SYR) to Lexington (LEX)
8.8/10 Excellent! (1,003 reviews)
Amazing staff and beautiful hotel

Reviewed on Aug. 29, 2025

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 $1,154, price is now CA $968 per person
CA $968
per person
Oct 30 - Nov 2
found 14 hours ago
Roundtrip non-stop flight included
Syracuse (SYR) to Lexington (LEX)
9.4/10 Exceptional! (820 reviews)
Like: The neighborhood and close dining. Breakfast was nice. Staff were awesome! Thank you. A little bit let down by the "spa shower".

Reviewed on Jul. 29, 2025

Hotel LEX, Trademark Collection by Wyndham

Hotel LEX, Trademark Collection by Wyndham

3 out of 5
Price was CA $1,240, price is now CA $1,043 per person
CA $1,043
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Lexington (LEX)
8.4/10 Very Good! (481 reviews)
Perfect place to stay

Reviewed on Aug. 31, 2025

The Campbell House Lexington, Curio Collection by Hilton

The Campbell House Lexington, Curio Collection by Hilton

4 out of 5
Price was CA $843, price is now CA $711 per person
CA $711
per person
Oct 30 - Nov 2
found 14 hours ago
Roundtrip non-stop flight included
Syracuse (SYR) to Lexington (LEX)
8/10 Very Good! (1,008 reviews)
The staff was inconsistent in knowledge and helpfulness. The hotel its self is pretty confusing to get around. Some rooms had a mini fridge in an odd spot and dome rooms had no fridge at all. Inconsistency was the theme during our stay.

Reviewed on Aug. 23, 2025

Ready to book your vacation to Winchester?

 

Choose your dates

Winchester Hotel Deals

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 $157 per night from Sep 14 to Sep 15
CA $157
CA $182 total
Sep 14 - Sep 15
includes taxes & fees
DoubleTree Suites by Hilton Hotel Lexington
GuestHouse Lexington

GuestHouse Lexington

2.5 out of 5
2261 Elkhorn Road, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is CA $87 per night from Sep 14 to Sep 15
CA $87
CA $101 total
Sep 14 - Sep 15
includes taxes & fees
GuestHouse Lexington
Hilton Lexington/Downtown

Hilton Lexington/Downtown

3.5 out of 5
369 West Vine Street, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is CA $224 per night from Sep 7 to Sep 8
CA $224
CA $260 total
Sep 7 - Sep 8
includes taxes & fees
Hilton Lexington/Downtown
See all 1,137 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
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Winchester

University of Kentucky

University of Kentucky

4.5/5(7 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
The Kentucky Castle

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 $67
per adult
88% 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 $136
per adult
Lexington: Downtown Walking Food & History Tour
Distillery District Food & History Tour in Lexington

Distillery District Food & History Tour in Lexington

CA $136
per adult
Distillery District Food & History Tour in Lexington
See all activities in Winchester
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.