Williamsburg Vacation Packages
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Your Williamsburg Vacation
With a Williamsburg vacation package, say goodbye to endless planning and hello to stress-free adventure. Every detail of your escape has been taken care of before you depart, so you can get on with discovering this interesting city. When it's time to go out and explore, be sure to include University of the Cumberlands and Kentucky Splash Water Park on the itinerary for your trip to Williamsburg. Your ultimate Williamsburg vacation is only clicks away. Search flights, accommodations and more on Expedia for a getaway that's tailored to suit your travel style.
Top Williamsburg Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Capital Plaza Hotel
Price was CA $1,030, price is now CA $932 per person
CA $932
per person
Jun 5 - Jun 7
found 4 hours ago
Roundtrip flight included
Winnipeg (YWG) to Lexington (LEX)
8.2/10 Very Good! (1,063 reviews)
The room was clean & beds comfortable, but very dated/worn; lighting thought needs replacing; outlet in bathroom was broken (did advise front desk; only stayed for one night which was fine) The lounge/bar was not open; hotel was in the mist of remodeling. Has potential of being grand but…
Reviewed on Mar 31, 2026
Holiday Inn Lexington - Hamburg by IHG
Price was CA $1,270, price is now CA $1,166 per person
CA $1,166
per person
Jun 5 - Jun 7
found 4 hours ago
Roundtrip flight included
Winnipeg (YWG) to Lexington (LEX)
9/10 Wonderful! (1,012 reviews)
Excellent stay! I would certainly stay agaib
Reviewed on Mar 31, 2026
The Sire Hotel Lexington, Tapestry Collection by Hilton
Downtown Lexington
Price was CA $2,140, price is now CA $1,977 per person
CA $1,977
per person
Jun 5 - Jun 7
found 4 hours ago
Roundtrip flight included
Winnipeg (YWG) to Lexington (LEX)
9.4/10 Exceptional! (864 reviews)
Everything and everyone was beyond excellent!!!
WONDERFUL!!!!
Reviewed on Mar 24, 2026
Sleep Inn
Price was CA $1,026, price is now CA $953 per person
CA $953
per person
Jun 5 - Jun 7
found 4 hours ago
Roundtrip flight included
Winnipeg (YWG) to Lexington (LEX)
8.2/10 Very Good! (635 reviews)
Breakfast was fresh, make everyday, the room was somewhat clean, staff was very friendly' Air Conditioning and bed were good.
Reviewed on Mar 29, 2026
Holiday Inn Express Lexington Horse Park Area by IHG
Price was CA $1,565, price is now CA $1,455 per person
CA $1,455
per person
Jun 5 - Jun 7
found 4 hours ago
Roundtrip flight included
Winnipeg (YWG) to Lexington (LEX)
9.4/10 Exceptional! (2,211 reviews)
Clean room. Easy check in and checkout. Parking safe and easy. Breakfast was good enough.
Reviewed on Apr 4, 2026
Williamsburg Hotel Deals
Cumberland Falls State Resort Park
7351 Hwy. 90 Williamsburg KY
Fully refundableReserve now, pay when you stay
The price is CA $157 per night from Apr 6 to Apr 7
CA $157
CA $173 total
Apr 6 - Apr 7
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
Yes
Reviewed on Apr 3, 2026
Super 8 by Wyndham Williamsburg
30 W Highway 92 Williamsburg KY
The price is CA $95 per night from Apr 21 to Apr 22
CA $95
CA $106 total
Apr 21 - Apr 22
includes taxes & fees
5.6/10 (810 reviews)
Sketchy parking lot. Very dirty breezeways. Very dirty bathroom. Used towel in bathroom. Only a 1/4 roll of toilet paper. Was scared to sleep under covers. No frig. Do better. Lady at the counter was super nice.
Reviewed on Mar 30, 2026
Holiday Inn Express Williamsburg by IHG
56 West Highway 92 Williamsburg KY
Fully refundable
The price is CA $169 per night from Apr 20 to Apr 21
CA $169
CA $191 total
Apr 20 - Apr 21
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
Clean and well maintained. Breakfast with Egg White Omelets and Turkey Sausage was very good.
Reviewed on Apr 3, 2026
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
