Five Islands Vacations from $415

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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.
210 Main St

210 Main St

3 out of 5
Price was $500, price is now $415 per person
$415
per person
Sep 18 - Sep 20
found 8 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Augusta (AUG)
9.2/10 Wonderful! (11 reviews)
Such a cool place to stay. Love the history of the building yet had modern amenities. Good location.

Reviewed on Oct 17, 2025

Topside Inn

Topside Inn

3 out of 5
Save 100% on your flight
Price was $1,493, price is now $1,150 per person
$1,150
per person
Aug 26 - Aug 30
found 17 hours ago
Roundtrip flight included
Chicago (CHI) to Augusta (AUG)
9.8/10 Exceptional! (108 reviews)
Amazing view! Room was spacious, clean and well decorated. Breakfast was excellent! Greg, the property manager, was courteous and very personable. Definitely recommend!

Reviewed on Jul 1, 2026

The Brunswick Hotel

The Brunswick Hotel

3 out of 5
Save 100% on your flight
Price was $1,504, price is now $1,192 per person
$1,192
per person
Aug 26 - Aug 30
found 17 hours ago
Roundtrip flight included
Chicago (CHI) to Augusta (AUG)
9.4/10 Exceptional! (965 reviews)
The mattress and bedding were extremely comfortable. Everything was top notch! The front desk was very welcoming and helpful.

Reviewed on Jun 27, 2026

Pressey House Lakeside Bed & Breakfast

Pressey House Lakeside Bed & Breakfast

3 out of 5
Price was $1,441, price is now $1,195 per person
$1,195
per person
Aug 2 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Augusta (AUG)
No reviews

Best Western Plus Brunswick Bath

Best Western Plus Brunswick Bath

2.5 out of 5
Price was $782, price is now $652 per person
$652
per person
Aug 26 - Aug 30
found 17 hours ago
Roundtrip flight included
Chicago (CHI) to Augusta (AUG)
8.2/10 Very Good! (1,003 reviews)
The 6:99 am breakfast works great with my work schedule

Reviewed on Jun 28, 2026

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Five Islands Hotel Deals

Flagship Inn and Suites

Flagship Inn and Suites

2.5 out of 5
200 Townsend Avenue Boothbay Harbor ME
Fully refundableReserve now, pay when you stay
$193 nightly
The price is $211 total per night from Jul 14 to Jul 15
$211 total
Jul 14 - Jul 15
Total with taxes and fees
8/10 Very Good! (1,002 reviews)
"We stayed overnight and found the staff to be very helpful, the room clean and spacious, and the complementary breakfast buffet was very good."

Reviewed on Jun 29, 2026

Flagship Inn and Suites
Ocean Gate Inn

Ocean Gate Inn

3 out of 5
70 Ocean Gate Rd Southport ME
$267 nightly
The price is $291 total per night from Jul 2 to Jul 3
$291 total
Jul 2 - Jul 3
Total with taxes and fees
8.6/10 Excellent! (1,005 reviews)
"Ok"

Reviewed on Jun 30, 2026

Ocean Gate Inn
Travelers Inn

Travelers Inn

2 out of 5
130 Pleasant St Brunswick ME
$89 nightly
The price is $97 total per night from Jul 2 to Jul 3
$97 total
Jul 2 - Jul 3
Total with taxes and fees
9/10 Wonderful! (1,013 reviews)
"Very clean. Microwave and refrigerator were helpful. Room was quite spacious. For a quick 1 night stay passing through town it was great"

Reviewed on Jun 30, 2026

Travelers Inn
See all 1,436 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.

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 $415 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.