Jamestown Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Teresa Durrant Pierce

Top hotels in Jamestown

Lake Cumberland State Resort Park

Lake Cumberland State Resort Park

3 out of 5
5465 State Park Rd, Jamestown, KY
8.6/10 Excellent! (476 reviews)
"Good hotel! I just didn't like the cleanliness of my room."

Reviewed on 8 Aug 2025

Get rates
Lake Cumberland State Resort Park
Timber Pointe Resort

Timber Pointe Resort

2 out of 5
2671 Kentucky 92, Jamestown, KY
The price is 3.479.883 ₫ per night from 24 Aug to 25 Aug
3.479.883 ₫
3.836.223 ₫ total
24 Aug - 25 Aug
includes taxes & fees
9.6/10 Exceptional! (6 reviews)
"Overall, we liked the room. Two things would have brought a higher rating; 1) one more chair, maybe with a desk for easy use of tablets/laptops, and 2) knowing that the room was up a flight of steps; we have some mobility issues."

Reviewed on 15 Aug 2025

Timber Pointe Resort
Anchor Inn & Suites

Anchor Inn & Suites

2 out of 5
1633 Highway 92 South, Jamestown, KY
The price is 3.946.950 ₫ per night from 27 Aug to 28 Aug
3.946.950 ₫
4.351.118 ₫ total
27 Aug - 28 Aug
includes taxes & fees
9/10 Wonderful! (44 reviews)
Wonderful motel
"My family and I have stayed at this motel multiple times over the past several years. It's a great experience and very clean, comfortable quiet rooms. Newly renovated and everything is nicely updated."

Reviewed on 27 Jul 2025

Anchor Inn & Suites
See all 557 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.

Popular places to visit

Lake Cumberland State Resort Park

Lake Cumberland State Resort Park

Explore the great outdoors at Lake Cumberland State Resort Park, a lovely green space in Jamestown. Stroll along the lakeside or seek out the fishing spots.

Lake Cumberland State Resort Park

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.