Jamestown Holidays

Photo by Roger Younce

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Top hotels in Jamestown

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 S$149 per night from 28 Aug to 29 Aug
S$149
28 Aug - 29 Aug
includes taxes & fees
8.8/10 Excellent! (591 reviews)
"As with most stays you get what you pay for and this was no exception. The beds were the best I had my whole two week vacation. There was plenty of hot water and the room was properly clean. What tickled my partner the most was the well thought out furnishings. Every time we went to look for something ..."

Reviewed on 12 Aug, 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 S$115 per night from 17 Aug to 18 Aug
S$115
17 Aug - 18 Aug
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
"It was clean, comfortable, quiet in a great location. A little dated but great price- would totally stay again!"

Reviewed on 12 Aug, 2025

Hawthorne Inn and Conference Center
Grandover Resort & Spa, a Wyndham Grand Hotel

Grandover Resort & Spa, a Wyndham Grand Hotel

4 out of 5
1000 Club Rd, Greensboro, NC
Fully refundableReserve now, pay when you stay
The price is S$268 per night from 17 Aug to 18 Aug
S$268
17 Aug - 18 Aug
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
"Great hotel on the golf course"

Reviewed on 14 Aug, 2025

Grandover Resort & Spa, a Wyndham Grand Hotel
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.

Popular places to visit

Celebration Station

You can take time to visit Celebration Station during your travels to Greensboro. Experience the acclaimed theatre scene or attend a sporting event in this family-friendly area.

Celebration Station

What to do in Jamestown

Greensboro Scavenger Hunt: Greensboro's Greatest!

Self-Guided Greensboro Scavenger Hunt: Greensboro's Greatest!

S$16
per adult
Self-Guided Greensboro Scavenger Hunt: Greensboro's Greatest!
Greensboro Ghost Tour

Carolina History & Haunts Greensboro Historical Ghost Tour

S$33
per adult
100% of travellers recommend
Carolina History & Haunts Greensboro Historical Ghost Tour
Lantern Light and Spooky Stories

Carolina History & Haunts Winston-Salem Historical Ghost Tour

S$33
per adult
100% of travellers recommend
Carolina History & Haunts Winston-Salem Historical Ghost Tour
See all activities in Jamestown

Frequently asked questions

How much does a Jamestown holiday package cost?
You can pick up a holiday package to this popular destination on Expedia. However, 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?
Plan your trip for the off-season and you're likely to get cheap Jamestown holiday packages. Bear in mind that school holiday 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 holiday to immerse yourself in everything that makes this place special. Explore key neighbourhoods, 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 holiday package to Jamestown?
Boasting a host of highlights starting with its excellent golfing, Jamestown is a good holiday 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 holiday.
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 holiday package as soon as possible.
Is it cheaper to book a Jamestown holiday as a package?
An Expedia holiday 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 holiday 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 personalised Jamestown holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.