Jamestown Vacation Packages
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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.
Top Jamestown Vacation Deals
Price found within the past 48 hours. Click for updated prices.
O.Henry Hotel
CA $1,445
per person
Nov 12 - Nov 15
found 12 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Greensboro (GSO)
9.8/10 Exceptional! (854 reviews)
Beautifully appointed hotel in keeping with the fine tradition of Southern hospitality. Every staff member we encountered was gracious, friendly and helpful. Our king room was spacious and inviting. Even the bathroom was sublime. The hotel bar was buzzing with good cheer on a Friday night. Our evening dinner and service at the on-site Green Valley Grill were excellent. Thanks goes to those who resurrected this newer O.Henry in the spirit and style of the original 1919 downtown landmark. Highly recommend.
Reviewed on Sep 22, 2026
Ready to book your vacation to Jamestown?
Jamestown Hotel Deals
Hawthorne Inn and Conference Center
420 High St Winston-Salem NC
Fully refundableReserve now, pay when you stay
CA $95
CA $108 total
Oct 5 - Oct 6
includes taxes & fees
DoubleTree by Hilton Greensboro Airport
6426 Burnt Poplar Road Greensboro NC
Fully refundableReserve now, pay when you stay
CA $126
CA $142 total
Oct 5 - Oct 6
includes taxes & fees
Sheraton Greensboro at Four Seasons
3121 West Gate City Boulevard Greensboro NC
Fully refundableReserve now, pay when you stay
CA $179
CA $202 total
Oct 5 - Oct 6
includes taxes & fees
9/10 Wonderful! (1,534 reviews)
"The Skyline Cafe hours were open when the evening events were over."
Reviewed on Sep 24, 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
Castle McCulloch
8.2/10 (10 reviews)
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.
World's Largest Highboy Dresser
Learn about the local history of Jamestown when you spend time at World's Largest Highboy Dresser. Experience the great live music or attend a sporting event in this family-friendly area.
Mendenhall Homeplace
You can spend time browsing the exhibits at Mendenhall Homeplace during your trip to Jamestown. Experience the great live music or attend a sporting event in this family-friendly area.
What to do in Jamestown
Carolina History & Haunts Greensboro Historical Ghost Tour
CA $36
per adult
100% of travellers recommend
Frequently asked questions
How much does a Jamestown vacation package cost?
Offering excellent value package deals from CA $942 on Expedia, you'll be pleasantly surprised at how much a vacation to Jamestown costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Jamestown?
The off-season is the best time to travel to Jamestown if you're on a budget. Another tip for scoring cheap Jamestown vacation packages? Avoid visiting during public holidays and any major events or festivals.
How many days is enough for Jamestown?
Jamestown vacations come in various shapes and sizes, but to get a true feel for this destination, we reckon 3 days is a good ballpark. With this timeframe, you can fit in major attractions like International Home Furnishings Centre and Castle McCulloch and track down some hidden gems. Don't forget to explore cool areas such as Sedgefield and Holden Farms either. If you're smart with your time, you can even schedule a day trip outside of Jamestown too.
Is it worth booking a vacation package to Jamestown?
Well known for its golfing and home to popular attractions like Castle McCulloch, a Jamestown vacation is sure to leave an impression. Another top sight to visit? Don't miss High Point City Lake Park.
How to find the best Jamestown package deals?
Use Expedia's handy filters to help you find some fabulous Jamestown package deals. When you start your search, just 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 look for Jamestown package deals in the off-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 vacation package well in advance.
Is it cheaper to book a Jamestown vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component individually. And you'll still enjoy the freedom to create a personalized Jamestown vacation by choosing your favourite type of stay, airline and car class.
When to book a vacation package to Jamestown?
If you have your Jamestown vacation dates locked in, book early to bag some awesome deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Jamestown?
- Pick the best time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to travel to Jamestown.
- Figure out your budget: Ensure you have enough money to pay for everything from dining out and transportation to activities and airfares. Your hotel will likely be the largest expense during your trip to Jamestown.
- Decide how long to go for: Now that you're more familiar with Jamestown, you can work out the right length of your vacation. Pull together a draft itinerary and allocate enough time to cover everything you want to see.
- Bundle your accommodations and airfare: Once you've nailed down your dates and duration, lock in the ideal Jamestown vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
