Five Islands Vacations from $393
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Your Five Islands Vacation
Come and discover this wonderful city for yourself with a Five Islands vacation package. Consider spending some time in the neighborhood of Harpswell, which is great for nature and culture, and your time here is sure to be unforgettable. If a sightseeing tour is on the cards during your trip to Five Islands, look around well-known attractions like Reid State Park, Georgetown Pottery and Georgetown Historical Society. Expedia can help you escape your daily routine. Tailor your vacation to Five Islands to match your travel style, whatever that may be!
The Latest Five Islands vacation packages
Price found within the past 48 hours. Click for updated prices.
Evergreen Valley Inn by Coolvacay
$433
per person
Sep 24 - Sep 27
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Augusta (AUG)
8.2/10 Very Good! (188 reviews)
Friendly folks.Pet friendly and covenient to the lovell/Stoneham area.
Cons: Murphy beds no good for two especially older folks.
Tania and owner were very accomodating for night two, and upgraded us to larger bed.Our bones greatly appreciated it!!
Reviewed on Aug 11, 2026
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Flagship Inn and Suites
200 Townsend Avenue Boothbay Harbor ME
$162 nightly
$176 total
Sep 9 - Sep 10
Total with taxes and fees
8/10 Very Good! (1,028 reviews)
"It was not what it appeared online when I booked it. But it was clean & safe"
Reviewed on Aug 15, 2026
Travelers Inn
130 Pleasant St Brunswick ME
Fully refundableReserve now, pay when you stay
$109 nightly
$119 total
Aug 24 - Aug 25
Total with taxes and fees
9/10 Wonderful! (1,033 reviews)
"This place is a hidden gem!! Reminiscent of the motor courts of old, the charm starts as soon as you pull in. And then the rooms... WOW! Much more spacious than you would think from the outside and absolutely spotless. There is a walk-in closet with iron and ironing board perfect for stowing luggage ..."
Reviewed on Aug 15, 2026
The Brunswick Hotel
4 Noble St Brunswick ME
Fully refundableReserve now, pay when you stay
$183 nightly
$200 total
Sep 8 - Sep 9
Total with taxes and 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.
Find the Best Five Islands Vacation Packages
Five Islands Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Top Sights | Reid State Park, Georgetown Historical Society and Half Mile Beach |
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Frequently asked questions
How much does a Five Islands vacation package cost?
You can grab a vacation package to this destination from $393 on Expedia. However, how much your vacation 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?
If you're looking to score a cheap Five Islands vacation package, consider visiting in November, December and January. You're likely to find lower prices on airfares and hotels during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Five Islands?
Usually, a handful of days is enough to check out the major attractions during your Five Islands vacation. But if you prefer to have time to kick back or take day tours, consider 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 vacation package as early as possible.
Is it cheaper to book a Five Islands vacation as a package?
An Expedia vacation 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 vacation 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.
Does Expedia offer Book Now, Pay Later Five Islands vacation packages?
If you're like us, you love traveling but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Five Islands break over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
