Jamestown Holidays

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Top hotels in Jamestown

Timber Pointe Resort

Timber Pointe Resort

2 out of 5
2671 Kentucky 92 Jamestown KY
The price is €115 per night from 16 Jul to 17 Jul
€115
16 Jul - 17 Jul
includes taxes & fees
9.4/10 Exceptional! (34 reviews)
"The property is located near the Jamestown ramp where we put our boat in making it a convenient place to stay. The rooms were clean. The bathrooms could be updated to match the room but other than that everything else was nice."

Reviewed on 11 Jul 2026

Timber Pointe Resort
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 €498 per night from 14 Jul to 15 Jul
€498
14 Jul - 15 Jul
includes taxes & fees
9.8/10 Exceptional! (28 reviews)
"There were bolts and screws in the driveway. We popped a tire and had to drive back home on the spare. The floors were not vacuumed and the bathroom was not cleaned. I had to clean before bringing in our luggage. The space in the house was nice and the hot tub and outdoor space was great."

Reviewed on 9 Jul 2026

Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
Sunset Ridge-Sleeps 16-Panoramic Lake Cumberland Views-3 Decks-Jamestown Marina

Sunset Ridge-Sleeps 16-Panoramic Lake Cumberland Views-3 Decks-Jamestown Marina

Jamestown KY
10/10 Exceptional! (176 reviews)
"We enjoyed our family retreat at this amazing property. The space was ample and very comfortable for our family of 12. The spacious rooms were neat, clean and welcoming. Family gathering areas on the main floor, and lower levels including dining area, kitchen and balconies were spacious and very ..."

Reviewed on 6 Jul 2026

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Sunset Ridge-Sleeps 16-Panoramic Lake Cumberland Views-3 Decks-Jamestown Marina
See all 658 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.

Stay near popular Jamestown attractions

Lake Cumberland State Resort Park

9.2/10 (195 reviews)
Nestled along a 52,000-acre lake, this park offers premier fishing and boating in the Eastern US Relax at Lure Lodge after a day exploring scenic trails or enjoying the park's disc golf course.
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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.

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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.