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Five Islands Holiday Rentals

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Our top choices for Five Islands holiday rentals

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

Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Boothbay
7.8 out of 10, Good, (10 reviews)
"Great stay! Pet friendly, super responsive host and excellent location!"
United States
Cassie M.
The price is AU$234
includes taxes & fees
11 Aug - 12 Aug
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything

2. Captain's Guest Room. Authenticity. Great Value. Walk to everything.

Captain's Guest Room. Authenticity. Great Value. Walk to everything.
Bath
8.4 out of 10, Very good, (27 reviews)
"A charming, quiet, and clean room with separate bathroom close to everything downtown. Felt a bit like staying at my grandparent’s house in a good way - it’s very homey. Dmitri is very nice and communication was thorough and easy!"
United States
Esther
The price is AU$265
includes taxes & fees
30 Aug - 31 Aug
Captain's Guest Room. Authenticity. Great Value. Walk to everything.

3. Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath
Bath
9.8 out of 10, Exceptional, (10 reviews)
"Clean comfortable and right downtown"
United States
stephen e.
The price is AU$334
includes taxes & fees
8 Sept - 9 Sept
Modern style in historic building in downtown Bath

4. 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 AU$662
includes taxes & fees
31 Aug - 1 Sept
Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC

5. Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.

Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.
Bath
8.0 out of 10, Very good, (16 reviews)
"We stayed for two nights. Good location."
United States
Maryanne E.
The price is AU$253
includes taxes & fees
11 Aug - 12 Aug
Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.

6. 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, (159 reviews)
"Susan and Jeff were amazing hosts! There were so kind, thoughtful and welcoming. The suite was extremely spacious, well decorated and very comfortable. We were very close to the Air Show which was the reason for our trip. They gave us great instructions for a short cut to the airfield and amazing dinner recommendations. We could not have chosen a better place to stay. We highly recommend this place!"
United States
Asha
The price is AU$248
includes taxes & fees
11 Aug - 12 Aug
Large suite/private bath/private entrance on quiet street near Thomas Bay

7. 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$292
includes taxes & fees
1 Sept - 2 Sept
Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy

8. Spacious 1 Bedroom Cottage Close to Everything 5

Spacious 1 Bedroom Cottage Close to Everything 5
Edgecomb
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful, clean, small cottage close to the coast, shopping and dining."
United States
Theresa
The price is AU$394
includes taxes & fees
18 Aug - 19 Aug
Spacious 1 Bedroom Cottage Close to Everything 5

9. Happy Cottage Near Everything 11

Happy Cottage Near Everything 11
Edgecomb
6.8 out of 10, (3 reviews)
"Great quit little place, great accommodations with even better help and information about the local area."
United States
George
The price is AU$332
includes taxes & fees
17 Aug - 18 Aug
Happy Cottage Near Everything 11

10. Newly Renovated Cozy Cove Cabin at White Anchor Inn

Newly Renovated Cozy Cove Cabin at White Anchor Inn
Boothbay
8.6 out of 10, Excellent, (7 reviews)
"As advertised, comfy bed cozy cabin. Would stay again "
United States
Joseph B.
The price is AU$320
includes taxes & fees
17 Aug - 18 Aug
Newly Renovated Cozy Cove Cabin at White Anchor Inn

11. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.6 out of 10, Exceptional, (7 reviews)
"Second time we have stay in this cottage. The perfect location for a Maine vacation. "
United States
chuck c.
The price is AU$432
includes taxes & fees
28 Aug - 29 Aug
Mid Coast Getaway w/ water views

12. Boothbay Harbor, 2-Story Cottage, downtown

Boothbay Harbor, 2-Story Cottage, downtown
Boothbay Harbor
9.4 out of 10, Exceptional, (29 reviews)
"Enjoyed the place, great location. "
United States
Erik P.
The price is AU$587
includes taxes & fees
17 Aug - 18 Aug
Boothbay Harbor, 2-Story Cottage, downtown

13. Renovated The Driftwood Cabin at White Anchor Inn

Renovated The Driftwood Cabin at White Anchor Inn
Boothbay
8.8 out of 10, Excellent, (3 reviews)
"Communication with Property Owner was excellent. This cute little cottage has been renovated and has a nice feel indoors. There is a beautiful porch on the back with a lovely view. The unit includes a mini fridge and mini microwave along with a little table and two chairs. If you have long hair, water pressure could be a concern. My shower worked great but the sink water pressure was not strong. The bed was comfortable and the decor was nice. The air conditioning works fine."
United States
Abra H.
The price is AU$346
includes taxes & fees
17 Aug - 18 Aug
Renovated The Driftwood Cabin at White Anchor Inn

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

Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
Georgetown
The price is AU$807
includes taxes & fees
9 Sept - 10 Sept
Pond Cabin: Private Sauna+Near Beach+FirePit+Pond

15. 1 Mi to Maine Street! MCM-Style Home in Brunswick

1 Mi to Maine Street! MCM-Style Home in Brunswick
Brunswick
9.6 out of 10, Exceptional, (11 reviews)
"Quiet, clean, well appointed house close to Maine St Brunswick and convenient to both Portland and points north. "
United States
Kendra G.
The price is AU$417
includes taxes & fees
25 Aug - 26 Aug
1 Mi to Maine Street! MCM-Style Home in Brunswick

16. 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, (32 reviews)
"Close enough to BoothBay Harbour and Botanical Gardens but private and quiet get away. Very comfortable! Spacious, good appliances and bedding. I would guess very new. Loved it!"
United States
Judith
The price is AU$817
includes taxes & fees
5 Sept - 6 Sept
Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor

17. Modern Cape -3 Bedroom- Boothbay Harbor - Near Ocean -Golf-Botanical Gardens

Modern Cape -3 Bedroom- Boothbay Harbor - Near Ocean -Golf-Botanical Gardens
Boothbay Harbor
10.0 out of 10, Exceptional, (4 reviews)
"The house was very charming, very clean & perfectly located to trails, botanical gardens, train museum & harbor! The house had everything that you could possibly need & we especially enjoyed the fire pit multiple nights!"
United States
Sharon H.
The price is AU$863
includes taxes & fees
1 Sept - 2 Sept
Modern Cape -3 Bedroom- Boothbay Harbor - Near Ocean -Golf-Botanical Gardens

18. Historic Bath's, Home Away from Home

Historic Bath's, Home Away from Home
Bath
10.0 out of 10, Exceptional, (1 review)
"My family and I really enjoyed our stay here! Very clean and comfortable. We were able to walk to downtown Bath which is absolutely adorable, many great places to eat, shop, and enjoy the coastline. Also a close drive to many other attractions in the area."
United States
Christine C.
The price is AU$707
includes taxes & fees
19 Aug - 20 Aug
Historic Bath's, Home Away from Home

19. Cheerful Cottage with Loft 9

Cheerful Cottage with Loft 9
Edgecomb
10.0 out of 10, Exceptional, (4 reviews)
"Immaculate, very cute - “tiny cottage”We loved it!"
United States
Daniel B.
The price is AU$381
includes taxes & fees
7 Sept - 8 Sept
Cheerful Cottage with Loft 9
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$234 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?

Spacious Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach: This holiday home rental outside of Five Islands is located on the beach, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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 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.