Five Islands Vacation Packages

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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.
Grand Summit Hotel

Grand Summit Hotel

3 out of 5
per person
Aug 25 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Augusta (AUG)
8.2/10 Very Good! (265 reviews)
Loved the gondola to the top of the mountain

Reviewed on Jul. 12, 2025

Hawthorn Extended Stay by Wyndham Ellsworth / Bar Harbor

Hawthorn Extended Stay by Wyndham Ellsworth / Bar Harbor

3 out of 5
per person
Aug 25 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Augusta (AUG)
8.2/10 Very Good! (1,008 reviews)
There is a grocery store just steps from the hotel. Also, sveral restaurants within walking distance.

Reviewed on Jul. 14, 2025

Newagen Seaside Inn

Newagen Seaside Inn

3.5 out of 5
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Augusta (AUG)
9.4/10 Exceptional! (298 reviews)
Abby and all the staff were all so helpful and welcoming! The Newagen Seaside Inn is so picturesque! We only spent one night there but wished we could have spent a week. The complimentary breakfast was delicious and the Tuesday evening lobster dinner was a great experience! Wished we lived closer! It was hands down the best place we stayed during our trip to New England!

Reviewed on Jul. 11, 2025

Mid-Town Motel

Mid-Town Motel

2 out of 5
per person
Aug 25 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Augusta (AUG)
9/10 Wonderful! (161 reviews)
Very comfortable great location. We walked to everything.

Reviewed on Jul. 11, 2025

Flagship Inn and Suites

Flagship Inn and Suites

2.5 out of 5
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Augusta (AUG)
8.2/10 Very Good! (1,007 reviews)
Room was clean. Beds are small for 2 ppl. Quiet and breakfast was not bad for self serve.

Reviewed on Jul. 13, 2025

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Five Islands Hotel Deals

Charming cottage near the beach with balcony, deck, grill, fireplace - dogs OK
Charming cottage near the beach with balcony, deck, grill, fireplace - dogs OK
Georgetown
Summer 2024
"This was a wonderful place to stay!"

Reviewed on Aug. 20, 2024

Get rates
Charming cottage near the beach with balcony, deck, grill, fireplace - dogs OK
Charming Oceanfront House with Deck, Cozy Loft, and Direct Beach Access
Charming Oceanfront House with Deck, Cozy Loft, and Direct Beach Access
Georgetown
4/10 (2 reviews)
"The amenities on Travelocity site does not match the amenities Vacasa sends to you after you book. No washer, no (working?) central heating (1 electric oil heater on wheels provided). Safety lists deadbolt lock but only 2 of 5 doors have a deadbolt, 2 doors have no locks or latches. Several windows ..."

Reviewed on Jun. 19, 2025

Get rates
Charming Oceanfront House with Deck, Cozy Loft, and Direct Beach Access
Flagship Inn and Suites
Flagship Inn and Suites
2.5 out of 5
200 Townsend Avenue, Boothbay Harbor, ME
The price is CA $141 per night from Jul 16 to Jul 17
CA $141
CA $186 total
Jul 16 - Jul 17
includes taxes & fees
8.2/10 Very Good! (1,010 reviews)
"Room was clean. Beds are small for 2 ppl. Quiet and breakfast was not bad for self serve."

Reviewed on Jul. 13, 2025

Flagship Inn and Suites
See all 1,420 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

Discover the most popular places to visit in Five Islands

Josephine Newman Audubon Sanctuary

Explore the lovely green spaces of Josephine Newman Audubon Sanctuary and also enjoy the boating in Georgetown. While you're in the area, stroll along the seaside.

Josephine Newman Audubon Sanctuary

Frequently asked questions

How much does a Five Islands vacation package cost?
Offering excellent value package deals from CA $803 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.