Jamestown Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 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

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! (180 reviews)
"We had the best weekend! Perfect place for a fun family getaway!"

Reviewed on 2 Aug 2026

Get rates
Sunset Ridge·Sleeps 16·Panoramic Lake Cumberland Views·3 Decks·Jamestown Marina
Timber Pointe Resort

Timber Pointe Resort

2671 Kentucky 92 Jamestown KY
€119
31 Aug - 1 Sept
includes taxes & fees
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
€478
27 Aug - 28 Aug
includes taxes & fees
9.8/10 Exceptional! (29 reviews)
"Great place!"

Reviewed on 19 Jul 2026

Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
See all 648 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

Jamestown Marina

Explore the waterfront in Jamestown with a trip to Jamestown Marina. Stroll along the area's lakeside or simply enjoy its restaurants.
See properties

Jamestown City Hall

Jamestown City Hall anchors historic Monument Square, serving as the town's administrative heart. Visitors can access municipal services while exploring the quaint surroundings of this Kentucky landmark.
See properties

Lowgap Island

This serene island in Lake Cumberland offers four sheltered coves ideal for tent camping along its southern shore. Boaters appreciate the relatively flat banks for overnight stays. Bring all supplies.
See properties

Judicial Center Fountain Park

This small urban park features a fountain adjacent to Louisville's judicial buildings. A peaceful spot to take a break while exploring downtown's legal district.
See properties

The Park at Jamestown Square

The Park at Jamestown Square offers a peaceful green space for locals seeking outdoor relaxation. Enjoy the well-maintained grounds and community atmosphere away from typical tourist crowds.
See properties

The Links Resort Golf Course

This championship golf course once featured 80 sand bunkers and four waterfalls across its challenging layout. The signature par-3 6th hole required a dramatic tee shot over a cascading waterfall to a two-tiered green.
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.

Explore a world of travel with Expedia

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