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.
Motel 6 Georgetown, KY - Lexington North

Motel 6 Georgetown, KY - Lexington North

2 out of 5
Price was CA $803, price is now CA $800 per person
CA $800
per person
Aug 17 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Lexington (LEX)
6.4/10 (997 reviews)
The staff was very friendly and the room was very clean. Easy parking gas station next door plus a Waffle house next door and Wendy’s across the street . Easy on and off the highway!! I’ll definitely stay there again !!

Reviewed on Jul 3, 2026

Sleep Inn

Sleep Inn

2.5 out of 5
Price was CA $875, price is now CA $845 per person
CA $845
per person
Aug 17 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Lexington (LEX)
8.2/10 Very good! (684 reviews)
Several high marks for a nice stay. Room had an odor, but bathroom and areas were clean. Some noise transfer from room above and hallways was not pleasant. Staff was informative and appropriate with all interactions and I would stay there again.

Reviewed on Jun 30, 2026

Country Inn & Suites by Radisson, Georgetown, KY

Country Inn & Suites by Radisson, Georgetown, KY

3 out of 5
Price was CA $896, price is now CA $880 per person
CA $880
per person
Aug 17 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Lexington (LEX)
8.8/10 Excellent! (1,008 reviews)
The room and motel in general were dated but very clean. We found the pool to be nice and refreshing. The staff was very friendly.

Reviewed on Jul 4, 2026

Studio 6 Georgetown, KY – Lexington North

Studio 6 Georgetown, KY – Lexington North

2 out of 5
Price was CA $834, price is now CA $831 per person
CA $831
per person
Aug 17 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Lexington (LEX)
6.6/10 (220 reviews)
Room was nice and clean staff was very helpful in parking was nearly at the door

Reviewed on Jun 6, 2026

Ready to book your vacation to Winchester?

 

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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 Jul 28 to Jul 29
CA $107
CA $118 total
Jul 28 - Jul 29
includes taxes & fees
7.2/10 Good! (818 reviews)
"Everything was good"

Reviewed on Jul 2, 2026

Baymont by Wyndham Winchester
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 $147 per night from Jul 6 to Jul 7
CA $147
CA $198 total
Jul 6 - Jul 7
includes taxes & fees
8.4/10 Very good! (730 reviews)
"The kids enjoyed the smore kits to use at the fire pits. The inside jacuzzi was lacking much need repairs and left our skin very irritated but the outdoor pool and jacuzzi was . Overall the property was nice and staff was very polite."

Reviewed on Jul 3, 2026

Marriott Lexington Griffin Gate Golf Resort & Spa
The Manchester

The Manchester

4 out of 5
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
The price is CA $267 per night from Jul 26 to Jul 27
CA $267
CA $335 total
Jul 26 - Jul 27
includes taxes & fees
9.6/10 Exceptional! (1,340 reviews)
"Great stay! The room was clean and had everything needed. All the bars and restaurants were great. The staff is very nice and responsive. I would not hesitate to stay again."

Reviewed on Jul 1, 2026

The Manchester
See all 1,202 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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Stay near popular Winchester attractions

Bluegrass Heritage Museum

7.4/10 (13 reviews)
You can spend time browsing the exhibits at Bluegrass Heritage Museum during your trip to Winchester. While you're here, you can savor the top-notch restaurants.
See properties

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's Art Walk Tour

Lexington's Art Walk Tour

CA $55
per adult
Lexington's Art Walk Tour
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
See all activities in Winchester

Frequently asked questions

How much does a Winchester vacation package cost?
You can grab a vacation package to this top destination from CA $800 on Expedia. However, how much your vacation to Winchester costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Winchester?
December, January and February are the best times to look for cheap Winchester vacation packages. Travelling in quieter months means you can usually find lower prices on flights and accommodations.
How many days is enough for Winchester?
Generally, a handful of days is enough to see the main sights during your Winchester vacation. But if you prefer to have more time to kick back or go on day trips, think about extending your itinerary.
Is it worth booking a vacation package to Winchester?
During your Winchester vacation, you can count on experiencing some top-notch dining and nature. Leave enough time in your itinerary to check out leading sights like Bluegrass Heritage Museum and Lykins Park.
How to find the best Winchester package deals?
Start your search for a Winchester package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Winchester package deal right away, just change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Winchester getaway off to a flying start.
Is it cheaper to book a Winchester vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component individually. And you'll still have the freedom to create a customized Winchester vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Winchester?
Enjoy incredible bargains by booking your flights ahead of time with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Winchester adventure.
How to plan a trip to Winchester?

  1. Choose when to get away: Check your schedule and get your bags packed. Your preferred time of year and the activities available will also help you decide when to visit Winchester.
  2. Calculate your budget: Make sure you have enough money to cover everything from dining out and transportation to activities and flights. Your hotel will probably be the largest expense during your trip to Winchester.
  3. Set the duration of your trip: Start by compiling a list of the sights and activities you want to experience in Winchester. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a customized Winchester vacation package.

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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.