Five Islands Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Five Islands
Flagship Inn and Suites
200 Townsend Avenue Boothbay Harbor ME
S$230
27 Aug - 28 Aug
includes taxes & fees
8/10 Very good! (1,040 reviews)
"The continental breakfast was excellent. The pool and surrounding area was clean. A nice little park next-door was a little ice cream shack which we could walk to at night. There was also a little farmers market next-door to the ice cream shack which was nice to bring homemade goodies from Maine ..."
Reviewed on 24 Aug, 2026
Travelers Inn
130 Pleasant St Brunswick ME
Fully refundableReserve now, pay when you stay
S$151
31 Aug - 1 Sept
includes taxes & fees
9/10 Wonderful! (1,047 reviews)
"Breakfast. It will be good if there’s an egg variety"
Reviewed on 24 Aug, 2026
The Brunswick Hotel
4 Noble St Brunswick ME
S$218
8 Sept - 9 Sept
includes taxes & fees
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 Five Islands holiday package cost?
You can grab a holiday package to this destination on Expedia. However, how much your holiday to Five Islands costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Five Islands?
The off-season is the best time to visit Five Islands if you're hoping to keep costs down. Another tip for finding cheap Five Islands holiday packages? Try to avoid visiting during public holidays and any major festivals or events.
How many days is enough for Five Islands?
Typically, a handful of days is enough to explore the major sights during your Five Islands holiday. But if you prefer to have some time to relax or take day tours, think about extending your trip.
How to find the best Five Islands package deals?
Use Expedia's filters to find some terrific Five Islands package deals. When you begin 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 break for midweek, or browse for Five Islands package deals in the off-peak season. Play around with your travel dates and you may land even better 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 Five Islands holiday as a package?
An Expedia holiday package could land you significant savings when compared to arranging flights and hotels separately. Better still, you can tailor your Five Islands getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Five Islands?
Score fantastic discounts by reserving your flights in advance with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for a spur-of-the-moment Five Islands break.
How to plan a trip to Five Islands?
- Choose when to get away: Check your calendar and get packing. Your favourite time of year and the activities on offer will also help you decide when to escape to Five Islands.
- Figure out your budget: Ensure you have enough money to pay for everything from food and transportation to activities and flights. Your accommodation will probably be the biggest expense during your trip to Five Islands.
- Work out your trip length: Think about how much time you'd like to spend exploring Five Islands. Plan your days so you can get to all the attractions and experiences you're interested in without rushing.
- Bundle your airfare and accommodation: After you've nailed down your travel dates and duration, lock in the ideal Five Islands 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.
