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.
Mountain View Inn Irvine Near Richmond KY

Mountain View Inn Irvine Near Richmond KY

2 out of 5
Price was CA $910, price is now CA $848 per person
CA $848
per person
Aug 7 - Aug 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Lexington (LEX)
6/10 (30 reviews)
Window curtains too sheer, too many bird feces on railing/stairs

Reviewed on Mar 28, 2026

21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
Price was CA $1,218, price is now CA $1,073 per person
CA $1,073
per person
Aug 7 - Aug 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Lexington (LEX)
8.8/10 Excellent! (1,004 reviews)
Gorgeous hotel in a fantastic part of downtown Louisville. The art museum was really special. And all kinds of wonderful restaurants within walking distance.

Reviewed on Jun 21, 2026

The Campbell House Lexington, Curio Collection by Hilton

The Campbell House Lexington, Curio Collection by Hilton

4 out of 5
Price was CA $1,174, price is now CA $1,086 per person
CA $1,086
per person
Aug 7 - Aug 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Lexington (LEX)
8.2/10 Very good! (1,013 reviews)
Stayed two nights for my son’s orientation at UK. Close location to campus and downtown Lexington. Nice property with clean and spacious rooms. Dined at on site restaurant our first night. The food was good and the staff friendly.

Reviewed on Jun 18, 2026

Origin Lexington a Wyndham Hotel

Origin Lexington a Wyndham Hotel

3.5 out of 5
Price was CA $1,182, price is now CA $1,100 per person
CA $1,100
per person
Aug 7 - Aug 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Lexington (LEX)
9.4/10 Exceptional! (1,022 reviews)
The bar and accommodations were excellent.

Reviewed on Jun 21, 2026

GuestHouse Lexington

GuestHouse Lexington

2.5 out of 5
Price was CA $975, price is now CA $914 per person
CA $914
per person
Aug 7 - Aug 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Lexington (LEX)
8.4/10 Very good! (1,610 reviews)
Room was worn down with large scuffs on most furniture. Blinds were missing the tilt wands, and one slat was broken. Lots of light came into the room at night. The shower door would roll open when closed. Two stories and no elevator on site. Not a big deal but difficult when carrying a child and luggage. It was clean and the bed was good. Breakfast was great and filling. Parking was easy.

Reviewed on Jun 22, 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 $107 per night from Jun 24 to Jun 25
CA $107
CA $118 total
Jun 24 - Jun 25
includes taxes & fees
7.2/10 Good! (813 reviews)
"Great people clean rooms and the pool works"

Reviewed on Jun 8, 2026

Baymont by Wyndham Winchester
Value Stay

Value Stay

2 out of 5
5100 Revilo Rd Winchester KY
Fully refundableReserve now, pay when you stay
The price is CA $92 per night from Jun 24 to Jun 25
CA $92
CA $101 total
Jun 24 - Jun 25
includes taxes & fees
7.6/10 Good! (158 reviews)
"While the room was clean and maintained, the only grip I had was its location and the road you had to travel to reach the hotels. A sign would have been nice so drivers won't get lost on their first time getting to the hotel."

Reviewed on Jun 14, 2026

Value Stay
Marriott Lexington Griffin Gate Golf Resort & Spa

Marriott Lexington Griffin Gate Golf Resort & Spa

4.5 out of 5
1800 Newtown Pike Lexington KY
Fully refundableReserve now, pay when you stay
The price is CA $146 per night from Jun 29 to Jun 30
CA $146
CA $198 total
Jun 29 - Jun 30
includes taxes & fees
8.4/10 Very good! (708 reviews)
"AC wouldn’t keep room cool. Front desk staff wasn’t always available or terribly helpful. Room fridge didn’t keep things cool & no microwave in room. Bathroom fixtures were in moderately poor repair. Great location & the room service food available was outstanding, however."

Reviewed on Jun 22, 2026

Marriott Lexington Griffin Gate Golf Resort & Spa
See all 1,204 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

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
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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
Fayette Mall

Fayette Mall

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

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 $82
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
100% of travellers recommend
Lexington: Downtown Walking Food & History Tour
Bites of the Bluegrass Cocktails & Bites Tour

Bites of the Bluegrass Cocktails & Bites Tour

CA $173
per adult
100% of travellers recommend
Bites of the Bluegrass Cocktails & Bites 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.