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Five Islands Holiday Rentals

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Our top choices for Five Islands holiday rentals

Across the road from Pemaquid Beach — wooded king-bed cabin for couples

Across the road from Pemaquid Beach — wooded king-bed cabin for couples
Pemaquid Beach
10.0 out of 10, Exceptional, (21 reviews)
"I wish we had more time to spend here! The cabin was well stocked and the location was out of the way, but close enough to sites and eateries "
United States
Sarah D.
The price is AU$431
includes taxes & fees
11 June - 12 June
Across the road from Pemaquid Beach — wooded king-bed cabin for couples

Newly Renovated Cozy Cove Cabin at White Anchor Inn

Newly Renovated Cozy Cove Cabin at White Anchor Inn
Boothbay
8.4 out of 10, Very good, (6 reviews)
"As advertised, comfy bed cozy cabin. Would stay again "
United States
Joseph B.
The price is AU$328
includes taxes & fees
16 June - 17 June
Newly Renovated Cozy Cove Cabin at White Anchor Inn

Captain's Guest Room. The authenticity & value in one place. Walk to everything!

Captain's Guest Room. The authenticity & value in one place. Walk to everything!
Bath
8.2 out of 10, Very good, (21 reviews)
"Great location and a beautiful property. Great walking/driving distance from town and the waterfront, we had a great stay and would do it again! "
United States
Nina P.
The price is AU$195
includes taxes & fees
21 June - 22 June
Captain's Guest Room. The authenticity & value in one place. Walk to everything!

Across the road from Pemaquid Beach — quiet wooded king-bed cabin

Across the road from Pemaquid Beach — quiet wooded king-bed cabin
Pemaquid Beach
9.2 out of 10, Wonderful, (5 reviews)
"Loved our stay"
United States
Jeanne
The price is AU$431
includes taxes & fees
11 June - 12 June
Across the road from Pemaquid Beach — quiet wooded king-bed cabin

Across the road from Pemaquid Beach — 2-bedroom seasonal family cottage

Across the road from Pemaquid Beach — 2-bedroom seasonal family cottage
Pemaquid Beach
9.8 out of 10, Exceptional, (7 reviews)
"Great beach cottage !"
United States
Gwen M.
The price is AU$440
includes taxes & fees
1 July - 2 July
Across the road from Pemaquid Beach — 2-bedroom seasonal family cottage

Across the road from Pemaquid Beach — 4-bedroom 19th-century Maine home

Across the road from Pemaquid Beach — 4-bedroom 19th-century Maine home
Pemaquid Beach
10.0 out of 10, Exceptional, (8 reviews)
"Comfortable, clean and beautiful "
United States
Corina
The price is AU$975
includes taxes & fees
16 June - 17 June
Across the road from Pemaquid Beach — 4-bedroom 19th-century Maine home

Sweet comfy cottage on Small Point Road

Sweet comfy cottage on Small Point Road
Small Point
9.4 out of 10, Exceptional, (3 reviews)
"Lovely home with plenty of space and seating. Not the most comfortable of beds but we enjoyed the space. Perfect location and would love to stay again. "
United States
Liz J.
The price is AU$791
includes taxes & fees
11 June - 12 June
Sweet comfy cottage on Small Point Road

Captain's House 1BR Suite. Walk to everything. Large yard. Pets welcome!

Captain's House 1BR Suite. Walk to everything. Large yard. Pets welcome!
Bath
7.6 out of 10, Good, (14 reviews)
"We stayed for two nights. Good location."
United States
Maryanne E.
The price is AU$240
includes taxes & fees
11 June - 12 June
Captain's House 1BR Suite. Walk to everything. Large yard. Pets welcome!

Spacious 1 Bedroom Close to Everything 4

Spacious 1 Bedroom Close to Everything 4
Edgecomb
9.8 out of 10, Exceptional, (23 reviews)
"We will return next year! Love these little cottages. There is no better location for day tripping. Cottages are well equipped and very comfortable."
United States
Lee R.
The price is AU$371
includes taxes & fees
15 June - 16 June
Spacious 1 Bedroom Close to Everything 4

Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (58 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is AU$521
includes taxes & fees
12 June - 13 June
Camp Forever cottage

Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
Brunswick
10.0 out of 10, Exceptional, (152 reviews)
"Such a fabulous stay. The space was bright, clean, and comfortable, and the special touches made it feel even more welcoming. It was larger than expected, and we loved having a mini fridge and coffee machine, perfect for slow mornings or a little wine and cheese at the end of the day. We’d return in a heartbeat."
Canada
Coral
The price is AU$218
includes taxes & fees
15 June - 16 June
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor

Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor
East Boothbay
10.0 out of 10, Exceptional, (23 reviews)
"Beautiful place, had everything we needed!"
United States
Kathy H.
The price is AU$737
includes taxes & fees
11 June - 12 June
Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor

Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy

Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy
Boothbay
6.0 out of 10, (5 reviews)
"It had a very homey feel, was nice to stay at for the night and wasn’t far from town."
United States
Audreyana P.
The price is AU$349
includes taxes & fees
11 June - 12 June
Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy

Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.4 out of 10, Exceptional, (6 reviews)
"Second time we have stay in this cottage. The perfect location for a Maine vacation. "
United States
chuck c.
The price is AU$288
includes taxes & fees
11 June - 12 June
Mid Coast Getaway w/ water views

Tiny Cottage Near Everything 10

Tiny Cottage Near Everything 10
Edgecomb
9.0 out of 10, Wonderful, (2 reviews)
"We recently stayed at the Tiny Cottage in Edgecomb, Maine, and truly enjoyed our visit. Except for a small initial issue, which was promptly and professionally addressed, everything was wonderful. The location is perfect for exploring the area, and the cottage itself was spotless, comfortable, and well-maintained. A lovely and relaxing getaway spot!"
United States
Elaine
The price is AU$307
includes taxes & fees
11 June - 12 June
Tiny Cottage Near Everything 10

Fully Renovated "Saltbox" Home in Boothbay

Fully Renovated "Saltbox" Home in Boothbay
Boothbay
The price is AU$785
includes taxes & fees
13 June - 14 June
Fully Renovated "Saltbox" Home in Boothbay

Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (61 reviews)
"Great spot to relax and enjoy the beautiful outdoors. Very quiet and amazing views of the water. Everything needed for a comfortable and relaxing getaway. Highly recommend if coming to the area! "
United States
Erin
The price is AU$672
includes taxes & fees
11 June - 12 June
Centerview cottage

Pond Cabin: Private Sauna+Near Beach+FirePit+Pond

Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
Georgetown
The price is AU$757
includes taxes & fees
15 June - 16 June
Pond Cabin: Private Sauna+Near Beach+FirePit+Pond

1 Mi to Maine Street! Mcm-style Home in Brunswick

1 Mi to Maine Street! Mcm-style Home in Brunswick
3.0 star property
Brunswick
The price is AU$531
includes taxes & fees
2 July - 3 July
1 Mi to Maine Street! Mcm-style Home in Brunswick

Pemaquid Escape | Curated Comfort + Hot Tub

Pemaquid Escape | Curated Comfort + Hot Tub
Walpole
10.0 out of 10, Exceptional, (3 reviews)
"The place was beautiful, with charming and had perfect design choices. Check in was so convenient, and the hosts were quite responsive to any needs. We all felt so comfortable there. It felt private, yet was conveniently located to Damariscotta. I would absolutely rent here again."
United States
Tera P.
The price is AU$953
includes taxes & fees
11 June - 12 June
Pemaquid Escape | Curated Comfort + Hot Tub
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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Top Five Islands Hotel Reviews

Find out more about Five Islands

Everything you need to know about Five Islands holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Five Islands holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Five Islands holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Five Islands holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Five Islands. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Five Islands holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Five Islands holiday rentals we have selected for you start as low as AU$195 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Five Islands rentals

At Expedia, we put the best Five Islands holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Five Islands rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Five Islands holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Five Islands. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Five Islands?

Yes, there are holiday rentals close to the most popular sights in Five Islands, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Five Islands has to offer?

Smuggler's Retreat ExploreTrails, Botanic Gardens, Kayak and MORE: This holiday home rental outside of Five Islands is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals will I find in Five Islands?

With 5 Expedia holiday rentals, you're guaranteed to find just the right place for your Five Islands stay.

What’s there to see and do in Five Islands?

Explore the area and family-friendly sights such as Maine Maritime Museum, or get out into nature at a spot like Coastal Maine Botanical Gardens. In the wider area, you’ll find Reid State Park and Burnt Island Living Lighthouse.

What’s a holiday rental in Five Islands like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Five Islands. Holiday rentals feature extras such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a sanitised environment, holiday rentals can offer a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for families.