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Our top choices for Five Islands holiday rentals

1. Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC

Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
Georgetown
10.0 out of 10, Exceptional, (2 reviews)
"Really lovely cabin with all the amenities within a stone’s throw to amazing trails and beaches. Would love to come back!"
United States
Palmer M.
The price is £313
includes taxes & fees
18 Oct - 19 Oct
Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC

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

Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
Georgetown
The price is £408
includes taxes & fees
18 Oct - 19 Oct
Pond Cabin: Private Sauna+Near Beach+FirePit+Pond

3. 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, (62 reviews)
"Cute place with lots of ambiance. Close to Bay and Coastal Botanical Gardens. Very quiet and clean."
United States
Elaine G.
The price is £413
includes taxes & fees
22 Sept - 23 Sept
Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor

4. 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, (170 reviews)
"What a beautiful place to stay. Jeff and Susan made your stay a very special experience."
United States
DENESE
The price is £127
includes taxes & fees
24 Sept - 25 Sept
Large suite/private bath/private entrance on quiet street near Thomas Bay

5. Harold Room 8 | 2 Queens + Gable Windows

Harold Room 8 | 2 Queens + Gable Windows
Boothbay Harbor
The price is £228
includes taxes & fees
28 Sept - 29 Sept
Harold Room 8 | 2 Queens + Gable Windows

6. Boothbay Harbor, 2-Story Cottage, downtown

Boothbay Harbor, 2-Story Cottage, downtown
Boothbay Harbor
9.4 out of 10, Exceptional, (30 reviews)
"Location, location, location! We stayed for 4 days and didn't have to drive ONCE. David was easy to communicate with and very helpful. House was clean and comfortable. Would definitely stay again!"
United States
Justin T.
The price is £280
includes taxes & fees
2 Oct - 3 Oct
Boothbay Harbor, 2-Story Cottage, downtown

7. Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything

Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Boothbay
8.0 out of 10, Very good, (13 reviews)
"Great stay! Pet friendly, super responsive host and excellent location!"
United States
Cassie M.
The price is £152
includes taxes & fees
24 Sept - 25 Sept
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything

8. Boothbay Harbor, The Francis Greene House, downtown

Boothbay Harbor, The Francis Greene House, downtown
Boothbay Harbor
9.4 out of 10, Exceptional, (51 reviews)
"Host communication was excellent. Location was ideal, walkable to the Boothbay Harbor attractions. Nice new wooden floors upstairs with the bedrooms. No AC which was fine for our stay. We must have stayed the first of the season, as the negatives were related to this. The toilets were disgusting with a foul odor and green mold on toilet seats, presumably from 9 months of zero use and the maids not cleaning prior to our arrival. Either way they should be replaced. All else with home was fine."
United States
Timothy M.
The price is £552
includes taxes & fees
23 Sept - 24 Sept
Boothbay Harbor, The Francis Greene House, downtown

9. 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 £154
includes taxes & fees
19 Sept - 20 Sept
Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy

10. Spacious 1 Bedroom Cottage Close to Everything 3

Spacious 1 Bedroom Cottage Close to Everything 3
Edgecomb
9.6 out of 10, Exceptional, (18 reviews)
"Great central location"
United States
Bruce O.
The price is £230
includes taxes & fees
19 Oct - 20 Oct
Spacious 1 Bedroom Cottage Close to Everything 3

11. 1920s Riverfront Cottage – Historic Maine Charm

1920s Riverfront Cottage – Historic Maine Charm
Edgecomb
9.6 out of 10, Exceptional, (4 reviews)
"Beautiful spot. Make sure to use the hot tub!"
United States
Sam D.
The price is £315
includes taxes & fees
28 Sept - 29 Sept
1920s Riverfront Cottage – Historic Maine Charm

12. Tide Haven Cottage on Bay Point

Tide Haven Cottage on Bay Point
Georgetown
Tide Haven Cottage on Bay Point

13. Captain's House. The fall in Maine! Enjoy the colors, weather & quality air!

Captain's House. The fall in Maine! Enjoy the colors, weather & quality air!
Bath
8.0 out of 10, Very good, (19 reviews)
"Cute but aging small space, Near attractions"
United States
michael
The price is £146
includes taxes & fees
28 Sept - 29 Sept
Captain's House. The fall in Maine! Enjoy the colors, weather & quality air!

14. Sweet comfy cottage on Small Point Road

Sweet comfy cottage on Small Point Road
Small Point
9.6 out of 10, Exceptional, (4 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 £415
includes taxes & fees
23 Sept - 24 Sept
Sweet comfy cottage on Small Point Road

15. Spacious 1 Bedroom Cottage Close to Everything 5

Spacious 1 Bedroom Cottage Close to Everything 5
Edgecomb
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful, clean, small cottage close to the coast, shopping and dining."
United States
Theresa
The price is £192
includes taxes & fees
22 Sept - 23 Sept
Spacious 1 Bedroom Cottage Close to Everything 5

16. Award Winning Luxury Carriage House a short stroll from town!

Award Winning Luxury Carriage House a short stroll from town!
Bath
10.0 out of 10, Exceptional, (13 reviews)
"The house matches exactly what was described online. It's clean and cozy in a quite neighborhood. I'd rate it a five star and highly recommend!"
United States
Shisheng
The price is £590
includes taxes & fees
19 Sept - 20 Sept
Award Winning Luxury Carriage House a short stroll from town!

17. Pelican Cottage | 2 BR + Waterfront Porch

Pelican Cottage | 2 BR + Waterfront Porch
Boothbay Harbor
The price is £518
includes taxes & fees
27 Sept - 28 Sept
Pelican Cottage | 2 BR + Waterfront Porch

18. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.4 out of 10, Exceptional, (9 reviews)
"The location and views from the cottage are quintessential coastal Maine. Small community with lobster pound and Maine Oyster Company across the street. John is a welcoming host and eager to make sure you enjoy your stay. The cottage is great for 2 people, equipped with the basics and has a great deck to enjoy the views. Planning to return next year. Great spot!"
United States
Rebecca
The price is £166
includes taxes & fees
30 Sept - 1 Oct
Mid Coast Getaway w/ water views

19. 2BR Apt. Authenticity, value, walk to everything. big yard, treehouse. No fees.

2BR Apt. Authenticity, value, walk to everything. big yard, treehouse. No fees.
Bath
9.0 out of 10, Wonderful, (25 reviews)
"Clean, walkable to town, nice backyard to sit and talk."
United States
Kathleen
The price is £199
includes taxes & fees
21 Sept - 22 Sept
2BR Apt. Authenticity, value, walk to everything. big yard, treehouse. No fees.

20. Apartment over shops in Bath Historic District

Apartment over shops in Bath Historic District
Bath
8.8 out of 10, Excellent, (6 reviews)
"Great breakfast spot right across the street!!"
United States
Jessica K.
The price is £196
includes taxes & fees
22 Sept - 23 Sept
Apartment over shops in Bath Historic District
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, apart-hotels, 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 £142 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?

Beautiful house on the Harpswell Peninsula over looking Casco Bay: This holiday home rental outside of Five Islands is located by the ocean, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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.