Jamestown Holidays

Photo by Penny E
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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Jamestown

Fiordland Discovery
Fiordland Discovery
4 out of 5
Berth 5, Milford Wharf, Milford Sound
9.6/10 Exceptional! (45 reviews)
"Loved our overnight cruise on Milford Sound! Shared a quad cabin room and though small & cozy, was a perfect place to sleep & so good to wake up to a great view!! Food on the cruise was excellent & all the staff very helpful & informative! One of our highlights on our holiday I would definetly recomend ..."

Reviewed on 23 Apr, 2025

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Fiordland Discovery
See all 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'll find cheap prices on Expedia for your Jamestown break. However, factors like the length of stay, the season and your choice of hotel will determine how much your holiday to Jamestown costs.
What are the cheapest months to go to Jamestown?
If you're looking to snag a cheap Jamestown holiday package, consider visiting in May, June and July. You'll generally find better rates on hotels and airfares during these quieter months --- perfect for a budget-friendly break.
How many days is enough for Jamestown?
The ideal duration for your Jamestown holiday depends on what you'd like to do and see. Typically, a few days to a week will give you time to hit all the major sights and discover some hidden treasures along the way.
How to find the best Jamestown package deals?
Use Expedia's filters to help you find some unbeatable 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're looking to save, plan your escape for midweek, or browse for Jamestown package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your holiday package as early as possible.
Is it cheaper to book a Jamestown holiday as a package?
An Expedia holiday package could score you significant savings when compared to booking flights and accommodation separately. Better still, you can tailor your Jamestown escape to fit your exact style. Pick 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 travel dates finalized, book early to score some fantastic deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for travelling on a whim.
How to plan a trip to Jamestown?

  1. Pick the best time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to visit Jamestown.
  2. Work out your budget: Ensure you have enough money to cover everything from food and transportation to airfares and activities. Your accommodation will probably be the biggest expense during your trip to Jamestown.
  3. Set the duration of your trip: Start by making a list of all the attractions and activities you want to get to in Jamestown. Then, estimate how long you'll need for each, along with any travel time.
  4. Combine your accommodation and airfare: After you've nailed down your dates and duration, lock in the right Jamestown holiday package for you.

* 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.