Jamestown Vacation Packages
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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.
Louisville Marriott Downtown
Downtown Louisville
CA $1,122
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Louisville (SDF)
9/10 Wonderful! (1,000 reviews)
Property was nice! Room was as expected! Valet/service was much to be desired! Room service snd bar service was some of the worst I’ve ever encountered! Was told by room service they had water; but if I wanted then I had to come get them myself! She wasn’t delivering them! Bartender in the hotel lounge was so bad it was laughable!! Told us she was doing us a favor by waiting on us! Lost her mind when I ask for 3 small bowls to put nuts in so our party of eight didn’t have to pass around the same cardboard cup she put them in!
Reviewed on Aug 16, 2026
Wingate by Wyndham Louisville Fair and Expo
Hayfield Dundee
CA $2,141
per person
Sep 23 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
8.4/10 Very good! (1,248 reviews)
Definitely not the most quiet stay. Right off the interstate and if your room is on that side you will hear all of the traffic through the night. Bring a sound machine with you. I had to put white noise on just to get to sleep because of all the traffic noise.
Reviewed on Aug 13, 2026
The Duke Hotel
Downtown Louisville
CA $2,030
per person
Sep 23 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
8.6/10 Excellent! (20 reviews)
The room was in a great spot in the hidden gem of Louisville Kentucky, maybe not so hidden, but I had no clue. So glad I chose this option over your standard hotel. Lots of restaurants, bars and shops right outside your door and parking was easy as well. I decided to grab some food from Traders Joe’s and the kitchen was stocked will all the essentials to cook a meal, plenty of space for 2 adults or more. Will definitely be my first choice and would recommend to those that like trendy areas or want to live like a local as they advertise.
Reviewed on Jul 19, 2026
Baymont by Wyndham Louisville Southwest
CA $1,528
per person
Sep 23 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
6.4/10 (430 reviews)
I had a wonderful one-night stay at Baymont by Wyndham Louisville Southwest, and overall, it was a great experience!
The property looked very new, clean, and well-maintained, everything was literally shining. The room was very spacious, comfortable, and neatly arranged, with all the amenities needed for a convenient stay, including a refrigerator, microwave, iron and ironing table, hair dryer, shampoo, conditioner, moisturizer, and body wash.
The cleanliness was definitely one of the highlights. The only small downside was that there seemed to be a little too much cleaning solution/soap used on the floor, which made it slightly sticky to walk on.
The coffee was amazing! ☕ The breakfast, however, could have been a little better. There were bananas, apples, and muffins, but having a few additional options like bread and butter would have made it more complete.
Overall, a wonderful place to stay in the area, clean, spacious, comfortable, and definitely worth the money. I would happily stay here again
Reviewed on Aug 18, 2026
Ready to book your vacation to Jamestown?
Jamestown Hotel Deals
Sunset Ridge·Sleeps 16·Panoramic Lake Cumberland Views·3 Decks·Jamestown Marina
Jamestown KY
10/10 Exceptional! (180 reviews)
"We had the best weekend! Perfect place for a fun family getaway!"
Reviewed on Aug 2, 2026
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
Jamestown KY
CA $415
CA $782 total
Aug 20 - Aug 21
includes taxes & fees
9.8/10 Exceptional! (29 reviews)
"Great place!"
Reviewed on Jul 19, 2026
Timber Pointe Resort
2671 Kentucky 92 Jamestown KY
CA $165
CA $182 total
Sep 17 - Sep 18
includes taxes & fees
9.2/10 Wonderful! (42 reviews)
"Gross. The management there can not be trusted."
Reviewed on Aug 13, 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.
Stay near popular Jamestown attractions
Wolf Creek National Fish Hatchery
9.0/10 (40 reviews)
Commune with nature and explore the great outdoors at Wolf Creek National Fish Hatchery during your travels in Jamestown. Stroll along this family-friendly area's lakeside, or simply enjoy its restaurants.
Jamestown Marina
Explore the waterfront in Jamestown with a trip to Jamestown Marina. Stroll along the area's lakeside or simply enjoy its restaurants.
Lowgap Island
Commune with nature and explore the great outdoors at Lowgap Island during your travels in Jamestown. Stroll along the area's lakeside or simply enjoy its restaurants.
Jamestown City Hall
Jamestown City Hall is just one of the places to see in Jamestown, so why not enjoy the other things to explore during your travels? Stroll along the area's lakeside or simply enjoy its restaurants.
The Park at Jamestown Square
After visiting The Park at Jamestown Square, make a plan to see the other sights and activities in Jamestown. Stroll along the area's lakeside or simply enjoy its restaurants.
The Links Resort Golf Course
Enjoy a round of golf in Jamestown at The Links Resort Golf Course. Stroll along the area's lakeside or simply enjoy its restaurants.
Judicial Center Fountain Park
Judicial Center Fountain Park is just one of the places to see in Jamestown, so why not enjoy the other things to explore during your travels? Stroll along the area's lakeside or simply enjoy its restaurants.
Frequently asked questions
How much does a Jamestown vacation package cost?
Offering great value package deals from CA $1,122 on Expedia, you'll be pleasantly surprised at how much a vacation to Jamestown costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Jamestown?
If you're looking to book a cheap Jamestown vacation package, consider planning a trip in December, January and February. You'll typically find lower prices on flights and hotels during these quieter months — perfect for budget-conscious travellers.
How many days is enough for Jamestown?
Generally, a handful of days is enough to explore the main sights during your Jamestown vacation. However, if you prefer to have some time to rest or go on day trips, consider extending your itinerary.
How to find the best Jamestown package deals?
Begin your search for a Jamestown package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select some filters, like "Property type" and "Popular locations," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Jamestown package deal straight away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Jamestown getaway off to a flying start.
Is it cheaper to book a Jamestown vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll typically get a better deal than booking each component individually. And you'll still get the freedom to create a customized Jamestown vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Jamestown?
If you're considering a spontaneous Jamestown trip, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can score incredible deals on your flights and hotels by booking ahead.
How to plan a trip to Jamestown?
- Choose when to go: Check your calendar and get packing. Your preferred time of year and the activities available will also help you decide when to vacation in Jamestown.
- Calculate your budget: Make sure you have enough money to pay for everything from transportation and meals to experiences and flights. Your hotel will likely be the biggest expense during your trip to Jamestown.
- Decide your trip length: Think about how long you want to spend discovering Jamestown. Plan your itinerary so you can get to all the attractions and activities you're interested in without rushing.
- Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to pick a Jamestown vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
