Jamestown Vacations from $608
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The Latest Jamestown Vacation Packages
- River Terrace Resort & Convention Center
Oct 18 - Oct 22River Terrace Resort & Convention Center + Flight
Downtown Gatlinburg4 nights3.5 star property7.6/10 - Good (1,001 reviews)Roundtrip • Boston (BOS) - Knoxville (TYS)BOS - TYS • 1 stop TYS - BOS • 1 stop$862$608found 1 day agoper traveler - Westgate Smoky Mountain Resort & Water Park
Oct 8 - Oct 11Westgate Smoky Mountain Resort & Water Park + Flight
Gatlinburg3 nights4.0 star property8.4/10 - Very Good (1,281 reviews)"Grate"Reviewed August 1, 2026Roundtrip • Boston (BOS) - Knoxville (TYS)BOS - TYS • 1 stop TYS - BOS • 1 stop$1,312$879found 1 day agoper traveler - Laurel Point Resort
Oct 6 - Oct 11Laurel Point Resort + Flight
Chalet Village5 nights2.5 star property9.0/10 - Wonderful (336 reviews)"Very nice facility! Staff was nice and helpful! Room was excellent! Will stay again!"Reviewed July 27, 2026Roundtrip • Chicago (CHI) - Knoxville (TYS)ORD - TYS • Nonstop TYS - ORD • Nonstop - The Ramsey Hotel and Convention Center Pigeon Forge
Oct 12 - Oct 17The Ramsey Hotel and Convention Center Pigeon Forge + Flight
Downtown Pigeon Forge5 nights3.0 star property8.4/10 - Very Good (1,546 reviews)"Our room was clean and organized and the staff were amazing! However the breakfast wasn’t really a hit for us, and they lacked refilling the trays so there were very little options with how busy it also was."Reviewed August 1, 2026Roundtrip • Boston (BOS) - Knoxville (TYS)BOS - TYS • 1 stop TYS - BOS • 1 stop$1,287$934found 1 day agoper traveler - Hotel Indigo Gatlinburg Downtown by IHG
Oct 23 - Oct 27Hotel Indigo Gatlinburg Downtown by IHG + Flight
Downtown Gatlinburg4 nights3.5 star property9.6/10 - Exceptional (534 reviews)Roundtrip • Chicago (CHI) - Knoxville (TYS)ORD - TYS • Nonstop TYS - ORD • Nonstop
Discover the most popular places to visit in Jamestown
Jamestown Hotel Deals
Quality Inn & Suites Monterey I-40
Quality Inn & Suites Monterey I-40
Super 8 by Wyndham Crossville TN
Super 8 by Wyndham Crossville TN
Quality Inn Crossville Near Cumberland Mountain State Park
Quality Inn Crossville Near Cumberland Mountain State ParkFrequently Asked Questions
How much does a Jamestown vacation package cost?
You can pick up a vacation package to this popular destination from $608 on Expedia. But how much your vacation 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?
If you'd like to score a cheap Jamestown vacation package, consider visiting in September, October and December. You're likely to find better rates on flights and accommodations during these quieter months — ideal for budget-conscious travelers.
How many days is enough for Jamestown?
The ideal duration of your Jamestown vacation depends on what you'd like to do and see. Generally, a few days to a week will give you enough time to hit all the major sights and explore some hidden gems along the way.
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 vacation as a package?
An Expedia vacation 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 vacation package to Jamestown?
If you've got your Jamestown vacation 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.
Does Expedia offer Book Now, Pay Later Jamestown vacation packages?
Your Jamestown getaway should be a relaxing escape from your daily routine, not a reason for money worries. So to give you extra flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.
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Things to do in and around Jamestown
Jamestown, Tennessee, is a perfect destination for outdoor and adventure enthusiasts, offering scenic views and various activities. Visitors can explore the recreational areas, hike along beautiful trails, and enjoy campgrounds. Key experiences include historic tours, local events, and unforgettable outdoor adventures that showcase the area's natural beauty. Whether you're looking for a memorable getaway or a thrilling outdoor experience, Jamestown has something for everyone.
Shopping
In Jamestown, the Mountain Top Flea Market offers a vibrant public market experience with local vendors and unique finds. If you're up for a drive, head to nearby shopping malls for more diverse retail options and national brands.
Recreation
At Big South Fork National River and Recreation Area, immerse yourself in nature with hiking and peaceful picnics. Hidden Valley Golf and Country Club offers a great outdoor experience with pristine golf courses. Brimstone Recreation invites you to relax with various outdoor activities amidst beautiful scenery.
Adventure
Explore the rugged beauty of Angel Falls Trail, a 15-mile hike offering stunning scenery and adventure. Visit White Oak Overlook, located 14 miles away, for breathtaking views in a serene outdoor setting. For family fun, camp at Lillydale Recreation Area, 24 miles from Jamestown, surrounded by nature.
Nightlife
In Jamestown, Tennessee, enjoy cozy bars like The Cabin and local hotspots like The Back Porch, where you can unwind with friends. Experience live music at venues like the Jamestown Community Center, showcasing local talent and creating a lively atmosphere perfect for a fun night out.
Find the best attractions in Jamestown
Jamestown, Tennessee, is perfect for outdoor and adventure enthusiasts, offering stunning scenery and a rich cultural experience. Explore local attractions, including national and state parks, historic buildings, and museums. Don't miss the chance to learn about Jamestown's history through sites like Jamestown Rediscovery and Historic Jamestowne, ensuring a memorable visit filled with top attractions and engaging activities for every traveler.
- Jamestown Town Hall: Explore the historic Jamestown Town Hall, a centerpiece of local culture that reflects the town's rich heritage. This charming building offers a glimpse into the past and hosts community events, making it a great stop for those interested in local history.
- Old Jail Museum: Visit the Old Jail Museum, where you can step back in time and uncover the intriguing stories of law and order in the area. This quaint museum showcases artifacts and exhibits that highlight the unique history of Jamestown and its legal system.
- Whispering Wind Lake: Experience the serene beauty of Whispering Wind Lake, a perfect spot for relaxation and romance. Enjoy scenic views, outdoor activities, or a peaceful day by the beach, making it an ideal destination for nature lovers.
Best time to go to Jamestown
The best time to visit Jamestown can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Jamestown falls in July, when visitor numbers are moderately high and weather is mostly sunny with light rain. The coolest average temperature in Jamestown falls in January, visitor numbers are moderately low and weather is mostly cloudy with light rain.
Tips to save on your trip to Jamestown
- Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Jamestown.
- Consider traveling to Jamestown during the low season (January to February and November) for more affordable options.
- Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
- Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.