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Five Islands Holiday Rentals

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Our top choices for Five Islands holiday rentals

Charming Sheepscot Overlook Cottage

Charming Sheepscot Overlook Cottage
Edgecomb
10.0 out of 10, Exceptional, (10 reviews)
"Great location, great view, great house, great time"
United States
Carol P.
The price is NZ$2,041
includes taxes & fees
12 July - 13 July
Charming Sheepscot Overlook Cottage

Large suite/private bath/private entrance on quiet street near Thomas Bay

Large suite/private bath/private entrance on quiet street near Thomas Bay
Brunswick
10.0 out of 10, Exceptional, (153 reviews)
"The place was lovely, communications with the host were helpful and friendly. Dinner restaurant recommendations were great as well. "
United States
Jane T.
The price is NZ$282
includes taxes & fees
15 July - 16 July
Large suite/private bath/private entrance on quiet street near Thomas Bay

Vacation Creation Downtown Brunswick 2King Beds

Vacation Creation Downtown Brunswick 2King Beds
Brunswick
9.6 out of 10, Exceptional, (19 reviews)
"Easy to rent."
United States
Alan B.
The price is NZ$1,134
includes taxes & fees
13 July - 14 July
Vacation Creation Downtown Brunswick 2King Beds

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 NZ$509
includes taxes & fees
16 July - 17 July
1 Mi to Maine Street! Mcm-style Home in Brunswick

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, (9 reviews)
"Comfortable, clean and beautiful "
United States
Corina
The price is NZ$1,263
includes taxes & fees
12 July - 13 July
Across the road from Pemaquid Beach — 4-bedroom 19th-century Maine home

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, (22 reviews)
"The cabin was perfect; the location even better, and the hosts were everything you could wish for."
United States
Mia
The price is NZ$571
includes taxes & fees
12 July - 13 July
Across the road from Pemaquid Beach — wooded king-bed cabin for couples

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 NZ$1,254
includes taxes & fees
13 July - 14 July
Pemaquid Escape | Curated Comfort + Hot Tub

Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor

Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor
East Boothbay
10.0 out of 10, Exceptional, (50 reviews)
"Excellent, clean property. "
United States
Andy H.
The price is NZ$1,019
includes taxes & fees
18 July - 19 July
Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor

Brunswick Downtown Sugar Cube next to Bowdoin

Brunswick Downtown Sugar Cube next to Bowdoin
Brunswick
8.6 out of 10, Excellent, (9 reviews)
"We ahd a great stay in Maine over the 4th visiting family, eating good food and walking around in great weather. Great stay in Brunswick, easy in and easy out and all sorts of things Maine accessible. Would recommend for anyone looking for a hassle-free weekend in coastal Maine. "
United States
Tjorvi P.
The price is NZ$695
includes taxes & fees
12 July - 13 July
Brunswick Downtown Sugar Cube next to Bowdoin

Tiny A-Frame Romantic Getaway

Tiny A-Frame Romantic Getaway
Wiscasset
9.8 out of 10, Exceptional, (6 reviews)
"Very nice and very quiet "
United States
justin s.
The price is NZ$812
includes taxes & fees
12 July - 13 July
Tiny A-Frame Romantic Getaway

Little Spruce Cottage | Wood Stove + Porch

Little Spruce Cottage | Wood Stove + Porch
Boothbay Harbor
The price is NZ$1,957
includes taxes & fees
23 July - 24 July
Little Spruce Cottage | Wood Stove + Porch

Downtown Brunswick New Look Old Charm Next to Bowdoin

Downtown Brunswick New Look Old Charm Next to Bowdoin
Brunswick
9.8 out of 10, Exceptional, (21 reviews)
"We really enjoyed our visit with family and friends and the location was perfect for what we needed. "
United States
Eliza
The price is NZ$685
includes taxes & fees
12 July - 13 July
Downtown Brunswick New Look Old Charm Next to Bowdoin

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

Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
Georgetown
The price is NZ$1,206
includes taxes & fees
22 July - 23 July
Pond Cabin: Private Sauna+Near Beach+FirePit+Pond

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, (6 reviews)
"Great beach cottage !"
United States
Gwen M.
The price is NZ$610
includes taxes & fees
12 July - 13 July
Across the road from Pemaquid Beach — 2-bedroom seasonal family cottage

Three bedroom in United States of America, Freeport

Three bedroom in United States of America, Freeport
Freeport
The price is NZ$1,596
includes taxes & fees
13 July - 14 July
Three bedroom in United States of America, Freeport

Spacious 1 Bedroom Close to Everything 4

Spacious 1 Bedroom Close to Everything 4
Edgecomb
9.8 out of 10, Exceptional, (24 reviews)
"This was a lovely little cabin. Everything was as described and my husband and I really enjoyed our stay."
Canada
Christine M.
The price is NZ$509
includes taxes & fees
12 July - 13 July
Spacious 1 Bedroom Close to Everything 4

Cheerful Cottage with Loft 9

Cheerful Cottage with Loft 9
Edgecomb
10.0 out of 10, Exceptional, (3 reviews)
"Immaculate, very cute - “tiny cottage”We loved it!"
United States
Daniel B.
The price is NZ$477
includes taxes & fees
22 July - 23 July
Cheerful Cottage with Loft 9

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 NZ$941
includes taxes & fees
31 July - 1 Aug
Sweet comfy cottage on Small Point Road

Spacious 1 Bedroom Cottage Close to Everything 3

Spacious 1 Bedroom Cottage Close to Everything 3
Edgecomb
9.8 out of 10, Exceptional, (17 reviews)
"Great central location"
United States
Bruce O.
The price is NZ$545
includes taxes & fees
15 July - 16 July
Spacious 1 Bedroom Cottage Close to Everything 3

Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (63 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 NZ$827
includes taxes & fees
2 Aug - 3 Aug
Centerview cottage
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 favorite 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 depends 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 NZ$282 per night. Entering your travel dates in the search wizard you might find 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 Boothbay Railway Village, or get out into nature at a spot like Coastal Maine Botanical Gardens. In the wider area, you’ll find Reid State Park and Hodgdon Island.

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.