Jamestown Vacations from $572
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Your Jamestown Vacation
When a fun city break is calling, answer it with a Jamestown vacation package. The neighborhood of Downtown Greensboro, which is good for shopping, history and dining, makes an excellent base for your adventures. Fill your free time with visits to High Point University, Wet n Wild Emerald Pointe Water Park and Celebration Station, some of the attractions you really should see during a trip to Jamestown. Check out Expedia's wide range of travel options and book your dream vacation to Jamestown now.
The Latest Jamestown vacation packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Winston Salem Sw Clemmons by IHG
$782
per person
Nov 25 - Dec 2
found 1 day ago
Roundtrip flight included
New York (LGA) to Greensboro (GSO)
9.4/10 Exceptional! (553 reviews)
Spacious room that was really comfortable and spotless. Yummy breakfast selections and amazing staff. Angel, Jessica, & Sharron were all delightful, &;Kelly jo made breakfast lovely. Would certainly stay here again
Reviewed on Sep 1, 2026
O.Henry Hotel
$1,304
per person
Nov 24 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
9.8/10 Exceptional! (851 reviews)
It's our third time staying, & the staff remains exemplary. They are the standout and the reason that we will always stay at the o henry. It was wonderful seeing Sherone again. Hannah, Lakiya,& other front desk goddesses are delightful. The tea & jazz staff are fantastic. Kate & Courtney improved our mornings dramatically, & Ashleigh was lovely for our dinner.
Tyler and the other porters are fantastic at their jobs, though it hurt my heart to see them dressed like it was 50 degrees out amidst the brutal heat & humidity. It would be lovely if they could lose the sweater vest and long sleeves and have more suitable summer attire.
The only downside was I had to use my cell as a Hotspot to access wifi for my tablet, my dad's laptop, and our Amazon fire.
Reviewed on Aug 31, 2026
Stay near popular Jamestown attractions
Castle McCulloch
8.2/10 (10 reviews)
This 1832 gold refinery turned event venue captivates with medieval architecture and a working drawbridge. Cross into grand halls with wrought-iron chandeliers or enjoy the Victorian Crystal Garden.
World's Largest Highboy Dresser
This 85-foot-tall replica of an 18th-century chest marks the entrance to the world's largest furniture store. Snap a photo of this quirky roadside attraction before exploring Furnitureland South.
Mendenhall Homeplace
This 1811 Quaker homestead showcases a rare false-bottom wagon used in the Underground Railroad. Explore the preserved farmhouse and outbuildings while guides reveal the compelling stories of local abolitionists.
What to do in Jamestown
Carolina History & Haunts Winston-Salem Historical Ghost Tour
$26
per adult
100% of travellers recommend
Carolina History & Haunts Greensboro Historical Ghost Tour
$26
per adult
100% of travellers recommend
Jamestown Hotel Deals
Hawthorne Inn and Conference Center
420 High St Winston-Salem NC
Fully refundableReserve now, pay when you stay
$78 nightly
$89 total
Sep 15 - Sep 16
Total with taxes and fees
Sheraton Greensboro at Four Seasons
3121 West Gate City Boulevard Greensboro NC
Fully refundableReserve now, pay when you stay
$110 nightly
$124 total
Sep 7 - Sep 8
Total with taxes and fees
Four Points by Sheraton Greensboro Airport
7619 Thorndike Rd Greensboro NC
Fully refundableReserve now, pay when you stay
$104 nightly
$117 total
Sep 7 - Sep 8
Total with taxes and fees
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.
Find the Best Jamestown Vacation Packages
Jamestown Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Piedmont Triad Intl. Airport (GSO) |
Population | 3,700 |
Max Temp Winter | 50ºF |
Max Temp Summer | 90ºF |
Top Sights | Wet n Wild Emerald Pointe Water Park, Steven Tanger Center for the Performing Arts and Greensboro Science Center |
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Frequently asked questions
How much does a Jamestown vacation package cost?
You can pick up a vacation package to this popular destination from $572 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?
If you're looking to score a cheap Jamestown vacation package, consider traveling in November, December and January. You'll generally find lower rates on hotels and airfares during these months — ideal for a budget-friendly getaway.
How many days is enough for Jamestown?
Usually, a few days is ideal for a Jamestown vacation. With a well-organized schedule, you can visit all the leading attractions including Mendenhall Homeplace, as well as discover some hidden treasures along the way.
Is it worth booking a vacation package to Jamestown?
Boasting a host of highlights starting with its amazing golfing, Jamestown is a good vacation destination. Whether you'd like to visit attractions such as Castle McCulloch and High Point City Lake Park or take the path less traveled, you'll find plenty 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.
Does Expedia offer Book Now, Pay Later Jamestown vacation packages?
Your Jamestown trip is meant to be a relaxing escape from your busy life, not a source of 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. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
