Five Islands Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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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!

Top Five Islands Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Evergreen Valley Inn by Coolvacay

Evergreen Valley Inn by Coolvacay

3 out of 5
Price was CA $715, price is now CA $570 per person
CA $570
per person
Sep 4 - Sep 7
found 1 hour ago
Roundtrip flight included
Montreal (YMQ) to Augusta (AUG)
8.2/10 Very good! (188 reviews)
Great spot to relax and use as a jump off point for local hiking.

Reviewed on Jul 21, 2026

Grand Summit Hotel

Grand Summit Hotel

3 out of 5
Price was CA $722, price is now CA $620 per person
CA $620
per person
Sep 24 - Sep 27
found 3 hours ago
Roundtrip flight included
Montreal (YMQ) to Augusta (AUG)
8.4/10 Very good! (388 reviews)
Couldn’t have asked for a better place for a summer weekend getaway. Our kitchenette room was excellent; so much space for our kids, and very convenient to have utensils, coffee maker, dishwasher, etc. Staff was welcoming and helped with all questions. Gym and pool (perfect temp) area was also a treat, providing complimentary headphones and sunscreen at the desk. Lastly, which was a big hit with the kids, marshmallow toasting was available in the evenings outside around the fireplace. Would absolutely stay here again.

Reviewed on Aug 2, 2026

Jordan Hotel

Jordan Hotel

3 out of 5
Price was CA $717, price is now CA $624 per person
CA $624
per person
Sep 24 - Sep 27
found 3 hours ago
Roundtrip flight included
Montreal (YMQ) to Augusta (AUG)
8.8/10 Excellent! (547 reviews)
Clean room, staff were excellent, outdoor pool great and hot tub. Breakfast was a bust. 3 Overnight oats and a small coffee ran me $40! Disappointed in the breakfast selection and price!

Reviewed on Aug 1, 2026

Pressey House Lakeside Bed & Breakfast

Pressey House Lakeside Bed & Breakfast

3 out of 5
Price was CA $2,031, price is now CA $1,819 per person
CA $1,819
per person
Oct 22 - Oct 28
found 12 hours ago
Roundtrip flight included
Toronto (YYZ) to Augusta (AUG)
No reviews

Flagship Inn and Suites

Flagship Inn and Suites

2.5 out of 5
Price was CA $801, price is now CA $718 per person
CA $718
per person
Sep 4 - Sep 7
found 1 hour ago
Roundtrip flight included
Montreal (YMQ) to Augusta (AUG)
8/10 Very good! (1,007 reviews)

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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
The price is CA $154 per night from Aug 24 to Aug 25
CA $154
CA $222 total
Aug 24 - Aug 25
includes taxes & fees
Flagship Inn and Suites
The Brunswick Hotel

The Brunswick Hotel

3 out of 5
4 Noble St Brunswick ME
The price is CA $269 per night from Aug 30 to Aug 31
CA $269
CA $293 total
Aug 30 - Aug 31
includes taxes & fees
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 CA $153 per night from Aug 25 to Aug 26
CA $153
CA $167 total
Aug 25 - Aug 26
includes taxes & fees
9/10 Wonderful! (1,008 reviews)
"Room was very clean and it was in a very quiet area of town. Lots of free parking."

Reviewed on Aug 3, 2026

Travelers Inn
See all 1,584 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.
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Frequently asked questions

How much does a Five Islands vacation package cost?
Offering excellent value package deals from CA $570 on Expedia, you'll be pleasantly surprised at how much a vacation to Five Islands costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Five Islands?
The off-season is the best time to head to Five Islands if you're hoping to keep costs down. Another tip for getting cheap Five Islands vacation packages? Try to avoid visiting during public holidays and any major festivals or events.
How many days is enough for Five Islands?
The ideal duration of your Five Islands vacation depends on what you'd like to do. Typically, a few days to a week will give you time to visit all the leading sights and explore some hidden gems along the way.
How to find the best Five Islands package deals?
Use Expedia's handy filters to find some terrific Five Islands package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or browse for Five Islands package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a Five Islands vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging accommodations and flights individually. Better still, you can tailor your Five Islands escape to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Five Islands?
If you're considering a spontaneous Five Islands getaway, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can land incredible deals on your hotels and flights by booking well in advance.
How to plan a trip to Five Islands?

  1. Choose the right time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to visit Five Islands.
  2. Set a budget: Consider costs such as flights, meals and transportation when working out how much to put aside for your trip to Five Islands. Then, select a hotel that works with your budget, whether that's a low-cost option or a deluxe getaway.
  3. Work out your trip length: Consider how much time you want to spend discovering Five Islands. Plan your days so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a personalized Five Islands vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.