Five Islands Holidays from £1,593

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Your Five Islands Holiday

Come and discover this wonderful city for yourself with a Five Islands holiday package. Consider spending some time in the neighbourhood 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 holiday to Five Islands to match your travel style, whatever that may be!

Top Five Islands Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Skowhegan By Kasa

The Skowhegan By Kasa

2 out of 5
Price was £1,672, price is now £1,593 per person
£1,593
per person
29 Sept - 2 Oct
found 1 day ago
Return flight included
London (LON) to Augusta (AUG)
8.8/10 Excellent! (105 reviews)
The place was beautiful, It could use an easy chair to sit in to read, in both the bedroom and the living room. I would stay there again if I was back that way. The bench in the shower was not near the shower.

Reviewed on 22 Jul 2026

Red Cedar Haven in Sidney

Red Cedar Haven in Sidney

2 out of 5
Price was £2,528, price is now £2,324 per person
£2,324
per person
29 Sept - 2 Oct
found 1 day ago
Return flight included
London (LON) to Augusta (AUG)
No reviews

Gables End Cottage in Belgrade

Gables End Cottage in Belgrade

2 out of 5
Price was £2,453, price is now £2,261 per person
£2,261
per person
29 Sept - 2 Oct
found 1 day ago
Return flight included
London (LON) to Augusta (AUG)
No reviews

Pressey House Lakeside Bed & Breakfast

Pressey House Lakeside Bed & Breakfast

3 out of 5
Price was £1,833, price is now £1,695 per person
£1,695
per person
29 Sept - 2 Oct
found 1 day ago
Return flight included
London (LON) 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 £2,136, price is now £2,014 per person
£2,014
per person
29 Sept - 2 Oct
found 1 day ago
Return flight included
London (LON) to Augusta (AUG)
10/10 Exceptional! (2 reviews)

Five Islands Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
-1.11ºC
Max Temp Summer
21ºC
Top Sights
Reid State Park, Half Mile Beach and Georgetown Historical Society

Top hotels in Five Islands

Flagship Inn and Suites

Flagship Inn and Suites

2.5 out of 5
200 Townsend Avenue Boothbay Harbor ME
The price is £92 per night from 4 Aug to 5 Aug
£92
4 Aug - 5 Aug
includes taxes & fees
Flagship Inn and Suites
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 £155 per night from 30 Aug to 31 Aug
£155
30 Aug - 31 Aug
includes taxes & fees
9.4/10 Exceptional! (1,003 reviews)
"Restaurant / bar is closed Mondays."

Reviewed on 1 Aug 2026

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 £88 per night from 25 Aug to 26 Aug
£88
25 Aug - 26 Aug
includes taxes & fees
Travelers Inn
See all 1,582 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Five Islands travel package cost?
Go from looking to booking with our Five Islands travel packages, which start from a low £1,593. Handpick the flights and hotels that match your travel plans. Then, add on one or two enriching experiences for an incredible escape.
If I'm not able to travel, can I cancel my Five Islands travel package?
It's difficult to predict what tomorrow might bring, so it's comforting to know that you can cancel or change your Five Islands travel package. If your booking was made in the last 24 hours, you may be entitled to a refund. If it's an older booking, your airline, hotel or car rental company may charge a fee. Check our Customer Service Portal for further details.
How do I get a cheap travel package to Five Islands?
You'll save a pile of money if you combine your flights, hotels and car rentals into a Five Islands holiday package. Sometimes cheap packages mean fewer options. But that's not the case with Expedia. We offer over 550 airlines and 1,000,000 properties globally, which means you'll always have plenty of variety to choose from. Eager to save even more? Add some popular activities to your package deal to unlock even bigger discounts! After all, travel is about more than simply getting to your destination.
Does Expedia offer Book Now, Pay Later Five Islands holidays?
Expedia has joined forces with online lender Klarna to make booking your next trip a bit easier on the wallet. Paying by instalment means you can spread the costs of your next big adventure, leaving you with more money to spend while you're travelling. Klarna has several payment plans to choose from, so you're sure to find something that fits into your budget. Check out these flexible payment options:

  • Pay monthly holidays: If paying bite-sized amounts each month sounds best for you, Klarna can help. Paying in easy monthly instalments will make that dream holiday possible.
  • Pay in instalments holidays: Into the idea of paying off your holiday in multiple transactions? Then check out this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the full total upfront) makes it easier to click that "book now" button, choose a low deposit holiday payment plan from Klarna.

Where should I stay in Five Islands?
You'll want to stay where the action is. Many people favor hotels within easy reach of top attractions, such as Reid State Park, Georgetown Historical Society and Josephine Newman Audubon Sanctuary.
What are the top hotels in Five Islands?
If it's your first time staying in Five Islands, secure a room at Enjoy The Stunning Views While Relaxing On The Deck At East Ledge Cottage or Grey Havens Inn. Both hotels offer friendly service and are favourites with many savvy travellers.
How far in advance should I book my Five Islands holiday?
While not all airlines advertise tickets early, you can usually compare international airfares on Expedia up to 12 months in advance. This is the time you'll bag some incredible bargains. If you've left everything to the last minute, you may still be in luck. Sometimes the lowest prices become available just weeks before departure.
What does an Expedia Five Islands travel package include?
That depends on what sort of getaway you have in mind. Five Islands travel deals can include flights, car rentals and hotels. You can mix and match to create the travel package that suits you. You can also add on activities and experiences after you've booked to score even bigger discounts.
What should I know before booking a Five Islands travel package?
You can look forward to saving with an Expedia travel package. Combine your airfares, rental cars and hotels and be rewarded with fabulous discounts. Hotels aren't your only choice, however. Book with us and take your pick of beachfront villas, cosy city apartments and even houseboats and castles!
Can I choose my airline with a Five Islands Expedia travel package?
You can, and with over 550 airlines to choose from all over the world, it's all about choice. Take a look at the available options and see which airline best fits your budget and needs.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.