Jamestown Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to Rp16.000.000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Jamestown

Timber Pointe Resort

Timber Pointe Resort

2 out of 5
2671 Kentucky 92 Jamestown KY
The price is Rp2.136.171 per night from 5 Aug to 6 Aug
Rp2.136.171
Rp2.354.957 total
5 Aug - 6 Aug
includes taxes & fees
9.4/10 Exceptional! (36 reviews)
"This was our second time staying here and we’ll be back. The rooms are clean and comfortable. The resort is very close to both Jamestown Marina and Lily Creek boat ramp, if you are there to hang out at Lake Cumberland."

Reviewed on 20 Jul 2026

Timber Pointe Resort
Dale Hollow Lake State Resort Park

Dale Hollow Lake State Resort Park

3.5 out of 5
5970 State Park Rd Burkesville KY
The price is Rp2.099.019 per night from 26 Jul to 27 Jul
Rp2.099.019
Rp2.314.036 total
26 Jul - 27 Jul
includes taxes & fees
9/10 Wonderful! (380 reviews)
"We stayed here last year came back this year, love the view and everyone was nice amd friendly. Great breakfast and clean rooms. Love the balcony"

Reviewed on 15 Jul 2026

Dale Hollow Lake State Resort Park
Best Western Lake Cumberland Inn

Best Western Lake Cumberland Inn

2.5 out of 5
2030 E Highway 90 Monticello KY
Fully refundableReserve now, pay when you stay
The price is Rp2.333.061 per night from 22 Jul to 23 Jul
Rp2.333.061
Rp2.571.948 total
22 Jul - 23 Jul
includes taxes & fees
Best Western Lake Cumberland Inn
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 US Relax at Lure Lodge after a day exploring scenic trails or enjoying the park's disc golf course.
See properties

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.