Jamestown Vacations

Book a Hotel + Flight or Car together to unlock savings

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Find the Best Jamestown Vacation Packages

Jamestown Hotel Deals

DoubleTree by Hilton Greensboro Airport

DoubleTree by Hilton Greensboro Airport

4 out of 5
6426 Burnt Poplar Road, Greensboro, NC
Fully refundableReserve now, pay when you stay
The price is ₩143,242 per night from Aug 25 to Aug 26
₩143,242
₩161,505 total
Aug 25 - Aug 26
includes taxes & fees
8.8/10 Excellent! (598 reviews)
"The rooms were very clean and nice and cold. I stayed in the summer. The staff is very friendly and helpful. The bed was so comfortable."

Reviewed on Aug 16, 2025

DoubleTree by Hilton Greensboro Airport
Hawthorne Inn and Conference Center

Hawthorne Inn and Conference Center

3 out of 5
420 High St, Winston-Salem, NC
Fully refundableReserve now, pay when you stay
The price is ₩109,930 per night from Aug 20 to Aug 21
₩109,930
₩124,213 total
Aug 20 - Aug 21
includes taxes & fees
8.2/10 Very Good! (1,016 reviews)
"Very nice and affordable. The only issue I had was the power kept going in and out"

Reviewed on Aug 18, 2025

Hawthorne Inn and Conference Center
Sheraton Greensboro at Four Seasons

Sheraton Greensboro at Four Seasons

3.5 out of 5
3121 West Gate City Boulevard, Greensboro, NC
Fully refundableReserve now, pay when you stay
The price is ₩152,680 per night from Aug 24 to Aug 25
₩152,680
₩172,147 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (1,062 reviews)
"Convenient of the restaurant, the only thing I really hate was the sheet wasn't hydroallergic friendly."

Reviewed on Aug 16, 2025

Sheraton Greensboro at Four Seasons
See all 1,115 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.

Discover the most popular places to visit in Jamestown

Greensboro College

Explore the campus of Greensboro College, during your travels in Greensboro. Experience the great live music or attend a sporting event in this family-friendly area.

Greensboro College

Castle McCulloch

You can learn about the history of Jamestown with a visit to Castle McCulloch. Experience the great live music or attend a sporting event in this family-friendly area.

Castle McCulloch

Frequently asked questions

How much does a Jamestown vacation package cost?
You can pick up a vacation package to this popular destination on Expedia. However, 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?
Plan your trip for the off-season and you're likely to get cheap Jamestown vacation packages. Bear in mind that school vacation periods and major festivals and events can have an impact on prices, so do a little research before booking.
How many days is enough for Jamestown?
Allow around 3 days for your Jamestown vacation to immerse yourself in everything that makes this place special. Explore key neighborhoods, including Sedgefield and Holden Farms. Then tick off top sights such as Mendenhall Homeplace and Mendenhall Homeplace. With a good itinerary, you can keep busy with room for some rest time too. Want to venture outside of Jamestown? Consider squeezing in a day trip or two.
Is it worth booking a vacation package to Jamestown?
Boasting a host of highlights starting with its excellent golfing, Jamestown is a good vacation destination. Whether you want to check out attractions such as Castle McCulloch and High Point City Lake Park or take the path less traveled, you'll find loads to see and do on your Jamestown vacation.
How to find the best Jamestown package deals?
Use Expedia's handy filters to help you find some tempting 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 escape for midweek, or look for Jamestown package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Jamestown vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and stays individually. Better still, you can tailor your Jamestown escape to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Jamestown?
Secure fantastic discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for an impromptu Jamestown escape.
How to plan a trip to Jamestown?

  1. Choose when to travel: Check your diary and get your bags packed. Your preferred time of year and the activities available will also help you decide when to escape to Jamestown.
  2. Budget wisely: In addition to the price of your hotel, you'll need to factor in other expenses. These include flights, food and transportation. Also, set aside some extra funds for unexpected costs that may come up during your trip to Jamestown.
  3. Set the duration of your trip: Start by compiling a list of the attractions you'd like to experience in Jamestown. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a personalized Jamestown vacation package.

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