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.
The Brown Hotel
Downtown Louisville
CA $923
per person
Dec 5 - Dec 7
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Louisville (SDF)
9.4/10 Exceptional! (1,333 reviews)
It’s an old historic hotel which I like but it is not maintained to the standard I would have liked. Historic is great but it shouldn’t look old and in need of “help”. Paint peeling, dirty carpets, trim cracking, etc.
Reviewed on Oct 4, 2026
Hyatt Regency Louisville
Downtown Louisville
CA $1,039
per person
Dec 5 - Dec 7
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Louisville (SDF)
8.8/10 Excellent! (1,004 reviews)
Gorgeous atrium style hotel just steps away from convention center. Lots to do and see near hotel.
Reviewed on Oct 1, 2026
Hotel Distil, Autograph Collection
Downtown Louisville
CA $1,098
per person
Dec 5 - Dec 7
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Louisville (SDF)
9.6/10 Exceptional! (507 reviews)
Everything was great during our visit. The only tarnish was breakfast service was slow. But great location and wonderful hotel.
Reviewed on Oct 4, 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! (183 reviews)
"House was spacious and had plenty of room for everyone. Unfortunately, the weather was too hot to enjoy the balcony and it had just stormed so the chairs were a little dirty, but the view was excellent. Great communication with the host. Easy to find and it was close to several restaurants and stores ..."
Reviewed on Sep 20, 2026
Timber Pointe Resort
2671 Kentucky 92 Jamestown KY
CA $141
CA $156 total
Oct 13 - Oct 14
includes taxes & fees
9.2/10 Wonderful! (50 reviews)
"We only stayed here overnight for a new place to stay so we came in the evening and left in the morning. We didn't get to experience the amenities like swimming but the place was very pretty. One thing I didn't like was check inside the pub so when I got there it was pretty loud and hard to hear. ..."
Reviewed on Sep 20, 2026
Lake Cumberland Hideaway Cabin-2 miles above Jtown Marina-Boat Parking+Fire Pit!
Jamestown KY
10/10 Exceptional! (82 reviews)
"We absolutely LOVED this cabin! Everything about it was excellent. We will return."
Reviewed on Sep 24, 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.
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.
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.
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.
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.
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.
Frequently asked questions
How much does a Jamestown vacation package cost?
Offering great value package deals from CA $923 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.
