Five Islands Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

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.
Pressey House Lakeside Bed & Breakfast

Pressey House Lakeside Bed & Breakfast

3 out of 5
Price was CA $1,752, price is now CA $1,608 per person
CA $1,608
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Augusta (AUG)
10/10 Exceptional! (1 review)
Very charming place with great breakfast and beautiful lake

Reviewed on Oct 4, 2026

Red Cedar Haven in Sidney

Red Cedar Haven in Sidney

2 out of 5
Price was CA $3,329, price is now CA $3,065 per person
CA $3,065
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Augusta (AUG)
No reviews

Cozy Keyes Cottage-family-friendly Amazing Views

Cozy Keyes Cottage-family-friendly Amazing Views

3.5 out of 5
Price was CA $2,601, price is now CA $2,425 per person
CA $2,425
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Augusta (AUG)
No reviews

Sunset Chalet-amazing Views Private hot tub

Sunset Chalet-amazing Views Private hot tub

3 out of 5
Price was CA $2,184, price is now CA $2,040 per person
CA $2,040
per person
Jan 1 - Jan 4
found 4 hours ago
Roundtrip flight included
Toronto (YYZ) to Augusta (AUG)
10/10 Exceptional! (2 reviews)

Tree-lined Home With Screened Porch & Perfect Midcoast Location

Tree-lined Home With Screened Porch & Perfect Midcoast Location

2 out of 5
Price was CA $3,469, price is now CA $3,249 per person
CA $3,249
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Augusta (AUG)
No reviews

Ready to book your vacation to Five Islands?

 

Choose your dates

Five Islands Hotel Deals

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 CA $168 per night from Nov 15 to Nov 16
CA $168
CA $183 total
Nov 15 - Nov 16
includes taxes & fees
The Brunswick Hotel
Moonlight Inn

Moonlight Inn

2 out of 5
215 Pleasant St Brunswick ME
Fully refundableReserve now, pay when you stay
The price is CA $124 per night from Nov 2 to Nov 3
CA $124
CA $136 total
Nov 2 - Nov 3
includes taxes & fees
Moonlight Inn
Spark by Hilton Brunswick

Spark by Hilton Brunswick

2.5 out of 5
199 Pleasant St Brunswick ME
Fully refundableReserve now, pay when you stay
The price is CA $115 per night from Nov 8 to Nov 9
CA $115
CA $125 total
Nov 8 - Nov 9
includes taxes & fees
Spark by Hilton Brunswick
See all 1,499 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Five Islands vacation package cost?
Offering excellent value package deals from CA $1,608 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.