Jamestown Island Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Jamestown Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Wingate by Wyndham Richmond Short Pump

Wingate by Wyndham Richmond Short Pump

3 out of 5
Short Pump
Price was CA $1,330, price is now CA $1,058 per person
CA $1,058
per person
Dec 17 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.4/10 Very good! (1,715 reviews)

Hyatt Select Richmond/Chester

Hyatt Select Richmond/Chester

3 out of 5
Price was CA $1,371, price is now CA $1,212 per person
CA $1,212
per person
Dec 17 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.4/10 Very good! (1,010 reviews)
Conveniently located , excellent breakfast included, and friendly staff

Reviewed on Nov 8, 2026

Kingsmill Resort

Kingsmill Resort

4 out of 5
Kingsmill
Price was CA $1,836, price is now CA $1,656 per person
CA $1,656
per person
Dec 23 - Dec 27
found 16 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Richmond (RIC)
8.6/10 Excellent! (1,006 reviews)
We stayed for 4 nights and never received any room service to clean the room even after calling twice. Best we got was a maintenance man who came to the room with a garbage bag full of towels. Their excuse was that they were too busy with 300 check ins. It appeared like those that used Expedia to book a room was on the bottom of the priority list.

Reviewed on Nov 6, 2026

Hyatt House Richmond / Short Pump

Hyatt House Richmond / Short Pump

3 out of 5
Short Pump
Price was CA $1,412, price is now CA $1,276 per person
CA $1,276
per person
Dec 17 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9/10 Wonderful! (1,000 reviews)

Hyatt Place Richmond/Arboretum

Hyatt Place Richmond/Arboretum

3 out of 5
North Chesterfield
Price was CA $1,311, price is now CA $1,194 per person
CA $1,194
per person
Dec 17 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8/10 Very good! (1,005 reviews)
This is my 2nd time staying at this location and overall is my 4th time in the pass2 years. I love staying at the Hyatt in North Chesterfield. The staff is wonderful. Mrs Tomasa, she was so wonderful. She gave me a warm welcome to the hotel at check-in. Also Mrs Tomasa was very friendly as well as the other staff members. I look forward to seen y'all again in the spring of 2027. Keep up the wonderful work y'all do for us travelers.

Reviewed on Nov 9, 2026

Ready to book your vacation to Jamestown Island?

 

Choose your dates

Jamestown Island Hotel Deals

Hilton Vacation Club The Historic Powhatan Williamsburg

Hilton Vacation Club The Historic Powhatan Williamsburg

3.5 out of 5
3601 Ironbound Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $95 per night from Nov 15 to Nov 16
CA $95
CA $149 total
Nov 15 - Nov 16
includes taxes & fees
9.2/10 Wonderful! (4,016 reviews)
"Everything was great I just wish that the interior was up to date."

Reviewed on Nov 9, 2026

Hilton Vacation Club The Historic Powhatan Williamsburg
Vacation Village At Williamsburg

Vacation Village At Williamsburg

3 out of 5
4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $118 per night from Nov 30 to Dec 1
CA $118
CA $150 total
Nov 30 - Dec 1
includes taxes & fees
8.8/10 Excellent! (3,061 reviews)
"The property is clean and roomy. Furniture and decor are typical hotel room variety. Beds were very comfortable. Maintenance staff was very responsive, we lost an earring down the tub drain and they were very helpful retrieving it."

Reviewed on Nov 8, 2026

Vacation Village At Williamsburg
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

3 out of 5
105 Visitors Center Dr Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $123 per night from Nov 10 to Nov 11
CA $123
CA $174 total
Nov 10 - Nov 11
includes taxes & fees
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
See all 1,818 properties in Jamestown Island
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Jamestown Island attractions

Historic Jamestowne

9.2/10 (1,334 reviews)
The site of America’s oldest colony, this historical park offers an intriguing perspective into the lives of the country’s first settlers.
See properties

What to do in Jamestown Island

Colonial Williamsburg Admission

Colonial Williamsburg Admission

CA $55
per adult
84% of travellers recommend
Colonial Williamsburg Admission
Jamestown Settlement American Revolution Museum 7-Day Ticket

Jamestown Settlement American Revolution Museum 7-Day Ticket

CA $41
per adult
100% of travellers recommend
Jamestown Settlement American Revolution Museum 7-Day Ticket
Virginia: speakeasy-themed murder mystery dinner at King ́s C

Virginia: speakeasy-themed murder mystery dinner at King ́s C

CA $85
per adult
Virginia: speakeasy-themed murder mystery dinner at King ́s C
See all activities in Jamestown Island

Frequently asked questions

How much does a Jamestown Island vacation package cost?
Explore the best of Jamestown Island from as little as CA $1,058. Choose from a wonderful selection of flights, hotels and rental cars to suit every budget. You can pick up even better deals when you add some sightseeing activities to your package.
How do I get a cheap travel package to Jamestown Island?
Combine your hotel and flight bookings, add on extras such as tours, and save with a Jamestown Island vacation package. You won't just land exciting discounts on your adventure — you'll have a world of choice at your fingertips too. When you book with Expedia, you can choose from more than 550 air carriers and 1,000,000 properties all over the world. Your affordable vacation starts right here, right now!
Where should I stay in Jamestown Island?
Most who travel to Jamestown Island include both Busch Gardens Williamsburg and Water Country USA on their must-see lists. Why not select a hotel that's close to these top attractions?
How far in advance should I book my Jamestown Island vacation?
Reserving your spot early with Expedia means one less thing to have to worry about. Most carriers advertise prices up to 12 months prior to take off. Typically, this is the cheapest time to book. If circumstances have left you booking late, discount flights to Jamestown Island occasionally appear a few weeks before departure.
What does an Expedia Jamestown Island travel package include?
Rental cars, flights and hotels, or any combination of them — it's up to you! Whether you're headed to Jamestown Island with the whole family or adventuring solo, there's a package to match every style and budget. Once you've made your booking, why not add on a few tours or activities?
What should I know before booking a Jamestown Island travel package?
So many places to wander around, so many things to do. With a travel package, you'll be able to cross more of them off your list. Combine your hotels, rental cars and flights and land big savings.
Can I choose my airline with a Jamestown Island Expedia vacation package?
Expedia has access to more than 550 airline partners globally, so you sure can! Simply select your favorite carrier and craft the perfect Jamestown Island escape.
If I'm not able to travel, can I cancel my Jamestown Island vacation package?
Plans can change in a flash, so yes, you can. You may be able to change or cancel your Jamestown Island vacation package at no cost within 24 hours of booking. For older bookings, you can still make the necessary changes, but your car rental company, hotel or airline may impose a fee. Want more information? Look up our Customer Service Portal. We'll help make sure your getaway goes off without a hitch.

Explore a world of travel with Expedia

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