Jamestown Holidays
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Top hotels in Jamestown
Big South Fork Lodge
3605 Leatherwood Ford Road Jamestown TN
Fully refundableReserve now, pay when you stay
Rp2.077.335
Rp2.378.548 total
13 Aug - 14 Aug
includes taxes & fees
9.8/10 Exceptional! (242 reviews)
"This lodge is exactly what we were looking for - a great place to spend the night. Room was very updated and clean. Wi-fi worked great!"
Reviewed on 11 Aug 2026
Quality Inn Crossville Near Cumberland Mountain State Park
4035 Highway 127 N Crossville TN
Fully refundable
Rp1.358.258
Rp1.619.722 total
1 Sept - 2 Sept
includes taxes & fees
8.4/10 Very good! (955 reviews)
"Nice pool. Decent breakfast … better than most, but not the best."
Reviewed on 11 Aug 2026
Dale Hollow Lake State Resort Park
5970 State Park Rd Burkesville KY
Rp2.076.447
Rp2.289.152 total
16 Aug - 17 Aug
includes taxes & fees
9/10 Wonderful! (384 reviews)
"The staff is great. The room was nice. It was very quiet. Very nice pool."
Reviewed on 8 Aug 2026
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
Jamestown Town Hall
Jamestown Town Hall functions as the administrative centre for local government and public services. Visitors can witness municipal governance by attending city council meetings during weekday hours.
Highland Manor Winery
Tennessee's oldest winery offers complimentary tastings and guided tours showcasing traditional winemaking. Bring a picnic to enjoy with local cheeses in the charming wine cellar or on the picturesque grounds.
Whispering Wind Lake
This tranquil Tennessee reservoir offers a peaceful escape with scenic lake views and abundant fishing opportunities. Bring a picnic and enjoy the natural beauty while watching wildlife along the shoreline.
Jamestown City Lake
This serene reservoir offers peaceful waters for fishing and boating amid Tennessee's picturesque landscapes. Arrive early morning to experience the tranquil atmosphere and glimpse local wildlife.
Mountain Top Flea Market
This beloved local marketplace showcases an eclectic mix of antiques, crafts, and regional goods. Arrive in the morning to experience the vibrant community atmosphere and discover unique treasures from area vendors.
Fentress County Public Library
The Fentress County Public Library offers a welcoming space with diverse resources for the Jamestown community. Explore the updated children's room with special computers and an extensive collection of books and media.
Old Jail Museum
Step back in time at Fentress County's second jail, where original cells from 1900-1979 remain intact. Explore local history through exhibits depicting rural Tennessee's past in this sandstone structure.
Old Jail
This 1898 sandstone jail now showcases Fentress County history with original cells still intact. Explore local artefacts spanning centuries while learning about the building's storied past as a working jail until 1979.
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 your hotel choice, season and length of stay.
What are the cheapest months to go to Jamestown?
February, March and December are the best times to search for cheap Jamestown holiday packages. Travelling in less busy periods means you'll typically find lower prices on flights and accommodation.
How many days is enough for Jamestown?
With a well-planned itinerary, you can easily tick off the most popular Jamestown attractions in a handful of days. But if you prefer to discover lesser-known spots or go on day tours, think about booking your Jamestown holiday for longer.
How to find the best Jamestown package deals?
Begin your search for a Jamestown package deal by entering your destination and travel dates under our "Packages" tab. Then add a few filters, like "Property type" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Jamestown package deal right away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Jamestown escape underway.
Is it cheaper to book a Jamestown holiday as a package?
An Expedia holiday package could land you considerable savings when compared to arranging hotels and flights individually. Better still, you can tailor your Jamestown escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a holiday package to Jamestown?
If you've got your Jamestown holiday dates finalized, book early to snap up some incredible deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Jamestown?
- Pick your travel dates: What you'd like to do in Jamestown and your preferred season can help you decide when to go.
- Set your budget: Factor in expenses such as flights, food and transportation when working out how much to set aside for your trip to Jamestown. Then, pick a property that suits your budget, whether that's a wallet-friendly stay or a swankier getaway.
- Decide how long to go away for: Now that you're up to speed on Jamestown, you can work out the ideal length of your break. Create a draft itinerary and give yourself enough time to cover everything you want to see.
- Combine your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to choose a Jamestown holiday package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
