Jamestown Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Teresa Durrant Pierce

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Jamestown Holiday

Our pick of the best 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
8.6/10 Excellent! (465 reviews)
"Lovely"

Reviewed on 19 May 2025

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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! (45 reviews)
Cowgirls!
"We absoluetly enjoyed our stay! The beds were comfortable, stocked kitchen, beautiful furniture, but the best was the deck and the view!We are eight old ladies that have been coming down to Lake Cumberland for the last 40 years. We have stayed lots and lots of places and this rates at the stop."

Reviewed on 11 Jul. 2025

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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 NZ$743 per night from 28 July to 29 July
NZ$743
28 July - 29 July
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 23 Jun. 2025

Charming 5-bedroom/3-bath home with easy access to Lake Cumberland
See all 556 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.

Frequently asked questions

How much does a Jamestown holiday package cost?
You can pick up a holiday package to this popular destination on Expedia. But how much your holiday to Jamestown costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Jamestown?
December, January and February are the best times to look for cheap Jamestown holiday packages. Opting to travel in quieter months means you can usually find better prices on hotels and flights.
How many days is enough for Jamestown?
The ideal duration of your Jamestown holiday depends on what you'd like to do. Typically, a handful of days to a week will give you time to go to all the leading attractions and explore some hidden spots along the way.
How to find the best Jamestown package deals?
Use Expedia's filters to help you find some great Jamestown package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or browse for Jamestown package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your holiday package well in advance.
Is it cheaper to book a Jamestown holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll usually land a better deal than booking each component separately. And you'll still have the freedom to create a tailored Jamestown holiday by choosing your preferred type of stay, airline and car class.
When to book a holiday package to Jamestown?
Enjoy incredible bargains by booking your flights in advance with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Jamestown escape.
How to plan a trip to Jamestown?

  1. Choose when to go: Check your schedule and pack your bags. Your preferred season and the activities on offer will also help you decide when to holiday in Jamestown.
  2. Calculate your budget: Make sure you have enough money to cover everything from transportation and dining out to airfares and activities. Your accommodation will probably be the largest expense during your trip to Jamestown.
  3. Work out your trip length: Consider how much time you want to spend exploring Jamestown. Plan your days so you can get to all the activities and attractions you're interested in without rushing.
  4. Combine your accommodation and airfare: Once you've settled on your trip dates and duration, book the right Jamestown holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.