Jamestown Trips (flight + hotel)

Photo by Teresa Durrant Pierce

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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! (469 reviews)
"We live the lake."

Reviewed on Jul 31, 2025

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Lake Cumberland State Resort Park
Timber Pointe Resort

Timber Pointe Resort

2 out of 5
2671 Kentucky 92, Jamestown, KY
Fully refundableReserve now, pay when you stay
The price is P8,160 per night from Aug 6 to Aug 7
P8,160
P8,996 total
Aug 6 - Aug 7
includes taxes & fees
10/10 Exceptional! (5 reviews)
"A very pleasant stay"

Reviewed on Mar 29, 2025

Timber Pointe Resort
Anchor Inn & Suites

Anchor Inn & Suites

2 out of 5
1633 Highway 92 South, Jamestown, KY
The price is P8,725 per night from Aug 5 to Aug 6
P8,725
P9,618 total
Aug 5 - Aug 6
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 Jul 27, 2025

Anchor Inn & Suites
See all 552 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.

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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.