Jamestown Vacations

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Find the Best Jamestown Vacation Packages

Jamestown Hotel Deals

Sunset RidgeĀ·Sleeps 16Ā·Panoramic Lake Cumberland ViewsĀ·3 DecksĀ·Jamestown Marina

Sunset RidgeĀ·Sleeps 16Ā·Panoramic Lake Cumberland ViewsĀ·3 DecksĀ·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 July 2026

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Sunset RidgeĀ·Sleeps 16Ā·Panoramic Lake Cumberland ViewsĀ·3 DecksĀ·Jamestown Marina
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 SARĀ 1,123 per night from Aug 16 to Aug 17
SARĀ 1,123
SARĀ 2,120 total
16 Aug - 17 Aug
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 July 2026

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

Timber Pointe Resort

2 out of 5
2671 Kentucky 92 Jamestown KY
The price is SARĀ 447 per night from Aug 5 to Aug 6
SARĀ 447
SARĀ 493 total
5 Aug - 6 Aug
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 July 2026

Timber Pointe Resort
See all 659 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?
Offering great value package deals 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 ā€” perfect for budget-conscious travelers.
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.