Jamestown Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Top hotels in Jamestown

Three Bear Lodge

Three Bear Lodge

2 out of 5
3636 Pickett Park Hwy, Jamestown, TN
Fully refundableReserve now, pay when you stay
The price is S$144 per night from 27 Aug to 28 Aug
S$144
27 Aug - 28 Aug
includes taxes & fees
7.8/10 Good! (22 reviews)
"Lovely little property. Easy to check in, quiet and convenient!"

Reviewed on 19 Jul, 2025

Three Bear Lodge
Big South Fork Lodge

Big South Fork Lodge

2.5 out of 5
3605 Leatherwood Ford Road, Jamestown, TN
Fully refundableReserve now, pay when you stay
9.8/10 Exceptional! (209 reviews)
Will stay again!
"Wonderful southern hospitality, beautiful nature surrounding. Family friendly. Safe & comfortable. Beautiful interior."

Reviewed on 13 Aug, 2025

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Big South Fork Lodge
Quality Inn Crossville Near Cumberland Mountain State Park

Quality Inn Crossville Near Cumberland Mountain State Park

2.5 out of 5
4035 Highway 127 N, Crossville, TN
Fully refundableReserve now, pay when you stay
The price is S$97 per night from 2 Sept to 3 Sept
S$97
2 Sept - 3 Sept
includes taxes & fees
8.2/10 Very Good! (737 reviews)
"Our room was nice & the bathroom was clean. Bed was comfy, all bedding was clean. Internet service was good. Quiet. Breakfast was offered."

Reviewed on 12 Aug, 2025

Quality Inn Crossville Near Cumberland Mountain State Park
See all 657 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.

Frequently asked questions

How much does a Jamestown holiday package cost?
You can pick up a holiday package to this popular destination on Expedia. But 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?
February, March and December are the best times to search for cheap Jamestown holiday packages. Travelling in less busy periods means you'll typically find lower prices on flights and accommodation.
How many days is enough for Jamestown?
With a well-planned itinerary, you can easily tick off the most popular Jamestown attractions in a handful of days. But if you prefer to discover lesser-known spots or go on day tours, think about booking your Jamestown holiday for longer.
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 holiday as a package?
An Expedia holiday 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 holiday package to Jamestown?
If you've got your Jamestown holiday 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.
How to plan a trip to Jamestown?

  1. Pick your travel dates: What you'd like to do in Jamestown and your preferred season can help you decide when to go.
  2. Set your budget: Factor in expenses such as flights, food and transportation when working out how much to set aside for your trip to Jamestown. Then, pick a property that suits your budget, whether that's a wallet-friendly stay or a swankier getaway.
  3. Decide how long to go away for: Now that you're up to speed on Jamestown, you can work out the ideal length of your break. Create a draft itinerary and give yourself enough time to cover everything you want to see.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to choose a Jamestown holiday package that brings all your bookings together.

* 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.