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.
Baymont by Wyndham Louisville South I 65

Baymont by Wyndham Louisville South I 65

2.5 out of 5
Price was CA $1,389, price is now CA $1,209 per person
CA $1,209
per person
Sep 10 - Sep 13
found 8 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
6.4/10 (1,003 reviews)
Hole in the door, the shower was broke did not help to fix it. I told her about the door. She said we still couldn’t put me in a different room I had booked the Jacuzzi room. Did I receive a Jacuzzi room said I booked the wrong room not never staying here a again no elevators

Reviewed on Jun 27, 2026

Galt House Hotel Trademark Collection by Wyndham

Galt House Hotel Trademark Collection by Wyndham

4 out of 5
Downtown Louisville
Price was CA $1,739, price is now CA $1,526 per person
CA $1,526
per person
Sep 18 - Sep 21
found 19 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Louisville (SDF)
9/10 Wonderful! (4,141 reviews)
Checking in was a breeze, everyone was so helpful and so nice!! Rodger helped my husband put together a great tour of Churchill Downs!

Reviewed on Jul 1, 2026

21c Museum Hotel Louisville

21c Museum Hotel Louisville

4.5 out of 5
Downtown Louisville
Price was CA $2,071, price is now CA $1,826 per person
CA $1,826
per person
Sep 18 - Sep 21
found 19 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Louisville (SDF)
9.4/10 Exceptional! (1,000 reviews)
I’ve always wanted to stay in a 21C hotel and I am glad I made the decision to in Louisville. Not only was the art awe inspiring, but the hotel and its staff were amazing. They were very accommodating, everything was clean and cute, and they even give you a free nightcap shot of bourbon. The location was near a lot of the sites I wanted to visit. I would definitely stay here again.

Reviewed on Jun 30, 2026

Moxy Louisville Downtown

Moxy Louisville Downtown

3.5 out of 5
Downtown Louisville
Price was CA $1,498, price is now CA $1,335 per person
CA $1,335
per person
Sep 26 - Sep 28
found 11 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Louisville (SDF)
9.2/10 Wonderful! (783 reviews)
Great location, the staff was friendly and room was clean

Reviewed on Jun 29, 2026

Aloft by Marriott Louisville Downtown

Aloft by Marriott Louisville Downtown

3 out of 5
Downtown Louisville
Price was CA $1,669, price is now CA $1,508 per person
CA $1,508
per person
Sep 18 - Sep 21
found 19 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Louisville (SDF)
9/10 Wonderful! (1,004 reviews)
Nice clean place to stay within walking distance to restaurants and some shopping

Reviewed on Jul 1, 2026

Ready to book your vacation to Jamestown?

 

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Jamestown Hotel Deals

Timber Pointe Resort

Timber Pointe Resort

2 out of 5
2671 Kentucky 92 Jamestown KY
The price is CA $169 per night from Jul 5 to Jul 6
CA $169
CA $187 total
Jul 5 - Jul 6
includes taxes & fees
9.4/10 Exceptional! (32 reviews)
"The property was amazing, the staff was amazing and so was the food at the restaurant."

Reviewed on Jun 14, 2026

Timber Pointe Resort
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 KY
10/10 Exceptional! (57 reviews)
"Very good communication and excellent destination for a weekend at Lake Cumberland"

Reviewed on Jun 14, 2026

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NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!

Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!

Jamestown KY
The price is CA $424 per night from Jul 29 to Jul 30
CA $424
CA $803 total
Jul 29 - Jul 30
includes taxes & fees
9.8/10 Exceptional! (27 reviews)
"Great location. Host was nice and very attentive."

Reviewed on Jun 9, 2026

Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
See all 647 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
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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.
See properties

Frequently asked questions

How much does a Jamestown vacation package cost?
Offering great value package deals from CA $1,209 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.

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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.