Five Islands Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 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 hotels in Five Islands

Flagship Inn and Suites

Flagship Inn and Suites

2.5 out of 5
200 Townsend Avenue Boothbay Harbor ME
The price is €142 per night from 23 Aug to 24 Aug
€142
23 Aug - 24 Aug
includes taxes & fees
Flagship Inn and Suites
The Brunswick Hotel

The Brunswick Hotel

3 out of 5
4 Noble St Brunswick ME
Fully refundableReserve now, pay when you stay
The price is €181 per night from 30 Aug to 31 Aug
€181
30 Aug - 31 Aug
includes taxes & fees
9.4/10 Exceptional! (1,002 reviews)
"Restaurant / bar is closed Mondays."

Reviewed on 1 Aug 2026

The Brunswick Hotel
Travelers Inn

Travelers Inn

2 out of 5
130 Pleasant St Brunswick ME
Fully refundableReserve now, pay when you stay
The price is €103 per night from 25 Aug to 26 Aug
€103
25 Aug - 26 Aug
includes taxes & fees
Travelers Inn
See all 1,582 properties in Five Islands
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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.