Jamestown Vacations

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Find the Best Jamestown Vacation Packages

Jamestown Hotel Deals

Timber Pointe Resort

Timber Pointe Resort

2 out of 5
2671 Kentucky 92 Jamestown KY
The price is ￥19,324 per night from Aug 5 to Aug 6
￥19,324
￥21,303 total
Aug 5 - Aug 6
includes taxes & fees
9.4/10 Exceptional! (33 reviews)
"We thoroughly enjoyed our stay and did not want to leave. The staff was very friendly and helpful. The lodge was perfect and clean. We will definitely be back."

Reviewed on Jul 9, 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 ￥48,546 per night from Jul 13 to Jul 14
￥48,546
￥91,820 total
Jul 13 - Jul 14
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 Jul 9, 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 Jul 6, 2026

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Sunset Ridge-Sleeps 16-Panoramic Lake Cumberland Views-3 Decks-Jamestown Marina
See all 657 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 U.S. 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 vacation package cost?
You can pick up a vacation package to this popular destination on Expedia. But how much your vacation 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 vacation 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 vacation 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 vacation package well in advance.
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 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 vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation 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 vacation 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 accommodations 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 accommodations and airfare: Once you've settled on your trip dates and duration, book the right Jamestown vacation 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.