Jamestown Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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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.
Caesars Southern Indiana

Caesars Southern Indiana

3.5 out of 5
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip flight included
Saskatoon (YXE) to Louisville (SDF)
8.2/10 Very Good! (1,002 reviews)
Bed was comfortable.. room was clean !

Reviewed on Aug. 2, 2025

Baymont by Wyndham Louisville East

Baymont by Wyndham Louisville East

2.5 out of 5
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip flight included
Saskatoon (YXE) to Louisville (SDF)
6/10 (1,001 reviews)
I was glad I was on the 3rd floor so I had an indoor entrance.

Reviewed on Jun. 8, 2025

Baymont by Wyndham Louisville Airport South

Baymont by Wyndham Louisville Airport South

2.5 out of 5
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip flight included
Saskatoon (YXE) to Louisville (SDF)
6.4/10 (1,000 reviews)
Location is good, 10 minutes driving to Kentucky Exposition Center. The facility is old, the breakfast is quite simple (no eggs), and no shampoo in the bathroom.

Reviewed on Jul. 14, 2025

The Brown Hotel

The Brown Hotel

4.5 out of 5
Downtown Louisville
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip flight included
Saskatoon (YXE) to Louisville (SDF)
9.4/10 Exceptional! (1,018 reviews)
Nice historic hotel. Clean but it is an old hotel

Reviewed on Aug. 2, 2025

Tempo By Hilton Louisville Downtown Nulu

Tempo By Hilton Louisville Downtown Nulu

3.5 out of 5
Downtown Louisville
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip flight included
Saskatoon (YXE) to Louisville (SDF)
9.4/10 Exceptional! (635 reviews)
The hotel itself was new. The interior was nice and modern. The bathroom was nicely appointed. The roof top bar was a lot of fun as well. The staff were very attentive. I’d stay there again.

Reviewed on Aug. 1, 2025

Ready to book your vacation to Jamestown?

 

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Jamestown Hotel Deals

Lake Cumberland State Resort Park

Lake Cumberland State Resort Park

3 out of 5
5465 State Park Rd, Jamestown, KY
Fully refundableReserve now, pay when you stay
The price is CA $186 per night from Aug 4 to Aug 5
CA $186
CA $205 total
Aug 4 - Aug 5
includes taxes & fees
8.6/10 Excellent! (470 reviews)
"We live the lake."

Reviewed on Jul. 31, 2025

Lake Cumberland State Resort Park
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking

NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking

Jamestown
10/10 Exceptional! (46 reviews)
New Overlook at Jamestown
"The house was great and the view of Jamestown Marina was really nice. Our host Jared was great and very helpful. We will stay again in the future. Thank you so much Jared"

Reviewed on Jul. 20, 2025

Get rates
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking
Charming 5-bedroom/3-bath home with easy access to Lake Cumberland

Charming 5-bedroom/3-bath home with easy access to Lake Cumberland

Jamestown
The price is CA $323 per night from Aug 11 to Aug 12
CA $323
CA $667 total
Aug 11 - Aug 12
includes taxes & fees
Perfect family stay
"Jenn was super responsive and gave us plenty of info on fishing/boating access in the area. The house was a great size with a cute unique layout. Huge deck for plenty of outside hang time and close to a boat ramp to easily drop my canoe in. Just a few minutes from the State Park too!"

Reviewed on Jun. 23, 2025

Charming 5-bedroom/3-bath home with easy access to Lake Cumberland
See all 559 properties in Jamestown
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
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Frequently asked questions

How much does a Jamestown vacation package cost?
Offering great value package deals from CA $1,438 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.