Jamestown Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Jamestown Vacation
When you choose a Jamestown vacation package, you can kick back and enjoy your adventure to the fullest. Delve into the best parts of this fascinating city knowing that all the travel planning has been taken care of before you go. Hoping to do a little sightseeing? Spend some time enjoying well-known attractions like Lake Cumberland State Resort Park during your trip to Jamestown. A few clicks is all it takes to create the ideal Jamestown vacation on Expedia.
Top Jamestown Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Louisville Airport South by IHG
Price was CA $1,056, price is now CA $877 per person
CA $877
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
8.8/10 Excellent! (882 reviews)
The room was clean and the staff was wonderful
Reviewed on May 11, 2026
Cottonwood Airport & Expo Hotel Louisville
Shively
Price was CA $1,570, price is now CA $1,208 per person
CA $1,208
per person
Jul 10 - Jul 13
found 18 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Louisville (SDF)
8.6/10 Excellent! (1,011 reviews)
yes everything was great the lady that worked in afternoon was excellent
Reviewed on May 15, 2026
Crowne Plaza Louisville Airport Expo Ctr by IHG
Fairgrounds
Price was CA $1,338, price is now CA $1,048 per person
CA $1,048
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
8.8/10 Excellent! (1,366 reviews)
Delicious fresh breakfast, very friendly staff, beautiful facility overall. Will definitely stay at Crown Plaza again!
Reviewed on May 17, 2026
Hilton Garden Inn Louisville Downtown
Downtown Louisville
Price was CA $1,917, price is now CA $1,553 per person
CA $1,553
per person
Jul 9 - Jul 13
found 16 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Louisville (SDF)
8.4/10 Very Good! (1,001 reviews)
Parking was good. Bed was terrible, air conditioner was super loud, our internet didn't work so we couldnt watch TV and they had no one to fix it.
Reviewed on May 16, 2026
Hyatt Regency Louisville
Downtown Louisville
Price was CA $1,136, price is now CA $927 per person
CA $927
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
8.8/10 Excellent! (1,009 reviews)
They Nickle and dime you for everything. They should at least provide you fresh brewed coffee in the lobby. A cookie, apple, or orange.
Come on. 2 free bottles of purified water in your room! Really? You'd expect more for a high-end hotel with a $350 per night room (excluding taxes and fees).
I know you are a business. But this model of squeezing your customer for every penny is horrible.
At this price, you can do better.
Reviewed on May 14, 2026
Jamestown Hotel Deals
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.
Jamestown KY
The price is CA $371 per night from May 18 to May 19
CA $371
CA $884 total
May 18 - May 19
includes taxes & fees
10/10 Exceptional! (171 reviews)
House was perfect for our large family. Kitchen had everything you would need for cooking. The house was very clean the large decks off the back over looking the lake is where we spent most of our time. we will definitely stay here again
Reviewed on May 17, 2026
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
Jamestown KY
The price is CA $411 per night from May 20 to May 21
CA $411
CA $778 total
May 20 - May 21
includes taxes & fees
9.8/10 Exceptional! (26 reviews)
We had a wonderful stay here! There are two single bed rooms, and one room with two full (queen possibly?) bunk beds. So 6 big beds all together and the couch pulls out as well. Check in and check out instructions were clear. There were corn hole boards and bags available. The hot tub was great, ...
Reviewed on Oct 30, 2025
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking
Jamestown KY
10/10 Exceptional! (55 reviews)
Perfect stay, once again! We love this place. Beautiful views, everything included and wonderful/responsive host!
Reviewed on Apr 7, 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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
