Holiday Rentals in Five Islands

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Our top choices for Five Islands holiday rentals

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, (146 reviews)
"Lovely space, comfortable bed, very convenient to downtown Brunswick."
United States
Kimberly G.
The price is €108
includes taxes & fees
22 Mar - 23 Mar
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (51 reviews)
"Super clean and lovely place to stay! Highly recommend!"
United States
Evan B.
The price is €318
includes taxes & fees
30 Mar - 31 Mar
Full sized home

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 €313
includes taxes & fees
13 Apr - 14 Apr
Camp Forever cottage

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, (46 reviews)
"Excellent, clean property. "
United States
Andy H.
The price is €399
includes taxes & fees
30 Mar - 31 Mar
Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor

Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath
Bath
10.0 out of 10, Exceptional, (8 reviews)
"Such a great location! We could easily walk all over the cute downtown."
United States
Keisha C.
The price is €194
includes taxes & fees
22 Mar - 23 Mar
Modern style in historic building in downtown Bath

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 €387
includes taxes & fees
25 Mar - 26 Mar
Newly Renovated Cozy Cove Cabin at White Anchor Inn

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, (7 reviews)
"This was perfect for our one night stay to visit the botanical gardens, it was only minutes away. Also very close to quite a few dinner and shopping options. "
United States
Nichole W.
The price is €176
includes taxes & fees
27 Mar - 28 Mar
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything

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 €234
includes taxes & fees
24 Mar - 25 Mar
1 Mi to Maine Street! Mcm-style Home in Brunswick

Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (59 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 €407
includes taxes & fees
12 Apr - 13 Apr
Centerview cottage

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, (22 reviews)
"The entire process was seamless. The home is adorable and was perfect for our weekend in Boothbay Harbour."
United States
Leslie B.
The price is €474
includes taxes & fees
1 Apr - 2 Apr
Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor

Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (8 reviews)
"Such a beautiful home and peaceful location. We loved our stay and the host was responsive and helpful with any questions we had!"
United States
Diana H.
The price is €378
includes taxes & fees
16 Apr - 17 Apr
Mere Point Sunrise Views at Eastern Shore!

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 €1,032
includes taxes & fees
18 Apr - 19 Apr
Charming Sheepscot Overlook Cottage

Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Private Home w/ Office Year Round in town Brunswick next to Bowdoin
Brunswick
9.0 out of 10, Wonderful, (25 reviews)
"We enjoyed our stay! Comfortable beds, fenced yard was great for dogs. Had everything we needed."
United States
Margaret R.
The price is €339
includes taxes & fees
1 Apr - 2 Apr
Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)

Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
Brunswick
9.6 out of 10, Exceptional, (30 reviews)
"This property is newly renovated and is in a great location--right across from the Brunswick Hotel and next to campus. Parking is easy (in the driveway) and the apartment is really spacious!"
United States
Jill C.
The price is €288
includes taxes & fees
22 Mar - 23 Mar
Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)

Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.8 out of 10, Exceptional, (16 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is €228
includes taxes & fees
24 Mar - 25 Mar
Fantastic Waterfront Views

Laughton House @ Pemaquid Beach

Laughton House @ Pemaquid Beach
Pemaquid Beach
10.0 out of 10, Exceptional, (8 reviews)
"This house is in a great location. We could walk to the beach, or to Fort Henry to let my grandsons run around. The house is lovely and had everything we needed. We have come to this area of Maine since 2017, and this had been our favorite place to stay! "
United States
Dawn W.
The price is €548
includes taxes & fees
20 Mar - 21 Mar
Laughton House @ Pemaquid Beach

Waterfront Private Apartment, minutes from LLBean!

Waterfront Private Apartment, minutes from LLBean!
Freeport
10.0 out of 10, Exceptional, (17 reviews)
"The room was clean and the area is great for walking with the dog."
United States
Anonymous traveller
The price is €293
includes taxes & fees
21 Mar - 22 Mar
Waterfront Private Apartment, minutes from LLBean!

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, (9 reviews)
"An exceptional property and guest. Would love to stay again next time Thank you Jared and Heather!"
United States
Ronald H.
The price is €558
includes taxes & fees
20 Mar - 21 Mar
Award Winning Luxury Carriage House a short stroll from town!

Vacation Creation Downtown Brunswick 2King Beds

Vacation Creation Downtown Brunswick 2King Beds
Brunswick
9.6 out of 10, Exceptional, (19 reviews)
"Stayed here while visiting Bowdoin. Great place!"
United States
Deborah B.
The price is €316
includes taxes & fees
23 Mar - 24 Mar
Vacation Creation Downtown Brunswick 2King Beds

2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
10.0 out of 10, Exceptional, (3 reviews)
"The host was welcoming. The home was clean, comfortable and the views were outstanding. "
United States
Rachel K.
The price is €189
includes taxes & fees
29 Mar - 30 Mar
2 bedroom w/ expansive water views
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 €228 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?

Peaceful Lake waterfront! Full Kitchen! Heat&AC! 5min to town, 8min to Garden!: This holiday home rental outside of Five Islands is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Kick off your shoes and enjoy yourself 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 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.