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.
Hilton Garden Inn Louisville Airport

Hilton Garden Inn Louisville Airport

3 out of 5
Fairgrounds
Price was CA $1,763, price is now CA $1,091 per person
CA $1,091
per person
Oct 16 - Oct 22
found 24 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Louisville (SDF)
9/10 Wonderful! (1,001 reviews)
Nice spacious rooms with comfy beds. Not a lot of food options for breakfast

Reviewed on Aug. 10, 2025

Embassy Suites Louisville Downtown

Embassy Suites Louisville Downtown

4 out of 5
Downtown Louisville
Price was CA $2,363, price is now CA $1,671 per person
CA $1,671
per person
Oct 16 - Oct 22
found 24 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Louisville (SDF)
9/10 Wonderful! (1,007 reviews)
Staff was very nice but the carpet in the room was very stained up. Would stay closer to the river next time in a little better location.

Reviewed on Aug. 28, 2025

Hyatt Regency Louisville

Hyatt Regency Louisville

4 out of 5
Downtown Louisville
Price was CA $2,101, price is now CA $1,608 per person
CA $1,608
per person
Oct 16 - Oct 22
found 24 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Louisville (SDF)
8.8/10 Excellent! (1,006 reviews)
Great location and courteous staff

Reviewed on Aug. 28, 2025

Crowne Plaza Louisville Airport Expo Ctr by IHG

Crowne Plaza Louisville Airport Expo Ctr by IHG

3.5 out of 5
Fairgrounds
Price was CA $1,677, price is now CA $1,297 per person
CA $1,297
per person
Oct 16 - Oct 22
found 24 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Louisville (SDF)
8.8/10 Excellent! (771 reviews)
Rooms were very clean and comfortable

Reviewed on Aug. 29, 2025

Embassy Suites Louisville East

Embassy Suites Louisville East

3.5 out of 5
Price was CA $1,717, price is now CA $1,332 per person
CA $1,332
per person
Oct 16 - Oct 22
found 24 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Louisville (SDF)
9/10 Wonderful! (1,001 reviews)
It was extremely clean. It was in a very quiet area. I have always enjoyed my stays at embassy suites hotels

Reviewed on Jul. 27, 2025

Ready to book your vacation to Jamestown?

 

Choose your dates

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 $130 per night from Sep 8 to Sep 9
CA $130
CA $143 total
Sep 8 - Sep 9
includes taxes & fees
Lake Cumberland State Resort Park
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.

LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.

Jamestown
The price is CA $413 per night from Sep 18 to Sep 19
CA $413
CA $925 total
Sep 18 - Sep 19
includes taxes & fees
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.
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
Get rates
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking
See all 560 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
Family Vacations

Frequently asked questions

How much does a Jamestown vacation package cost?
Offering great value package deals from CA $1,091 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.