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Five Islands Vacation Rentals

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Our top choices for Five Islands vacation rentals

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, (8 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 CA $183
CA $280 total
includes taxes & fees
Jun 23 - Jun 24
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything

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 CA $246
CA $447 total
includes taxes & fees
Jun 21 - Jun 22
Across the road from Pemaquid Beach — wooded king-bed cabin for couples

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 CA $208
CA $432 total
includes taxes & fees
Jul 1 - Jul 2
Across the road from Pemaquid Beach — 2-bedroom seasonal family 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 CA $158
CA $203 total
includes taxes & fees
Jun 22 - Jun 23
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

3 Bedroom Happy Cottage 15

3 Bedroom Happy Cottage 15
Edgecomb
10.0 out of 10, Exceptional, (6 reviews)
"Great property with central location in mid coast Maine. Beautifully decorated with very comfortable beds! Jeff was great with communication throughout to ensure we had everything we needed! Would stay again! "
United States
Decourcey D.
The price is CA $402
CA $703 total
includes taxes & fees
Jun 22 - Jun 23
3 Bedroom Happy Cottage 15

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 CA $246
CA $447 total
includes taxes & fees
Jun 21 - Jun 22
Across the road from Pemaquid Beach — quiet wooded king-bed cabin

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 CA $423
CA $963 total
includes taxes & fees
Jun 21 - Jun 22
Across the road from Pemaquid Beach — 4-bedroom 19th-century Maine home

•Tranquil 2BR Summer Home•Steps to Private Beach•

•Tranquil 2BR Summer Home•Steps to Private Beach•
Harpswell
The price is CA $271
CA $774 total
includes taxes & fees
Jul 8 - Jul 9
•Tranquil 2BR Summer Home•Steps to Private Beach•

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 CA $188
CA $386 total
includes taxes & fees
Jun 18 - Jun 19
Spacious 1 Bedroom Close to Everything 4

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 CA $420
CA $784 total
includes taxes & fees
Jul 5 - Jul 6
Sweet comfy cottage on Small Point Road

Fully Renovated "Saltbox" Home in Boothbay

Fully Renovated "Saltbox" Home in Boothbay
Boothbay
The price is CA $281
CA $792 total
includes taxes & fees
Jun 18 - Jun 19
Fully Renovated "Saltbox" Home in Boothbay

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

Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
Georgetown
The price is CA $476
CA $771 total
includes taxes & fees
Jun 21 - Jun 22
Pond Cabin: Private Sauna+Near Beach+FirePit+Pond

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 CA $232
CA $339 total
includes taxes & fees
Jun 18 - Jun 19
Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy

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 CA $161
CA $338 total
includes taxes & fees
Jun 21 - Jun 22
Tiny Cottage Near Everything 10

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 CA $200
CA $484 total
includes taxes & fees
Jul 16 - Jul 17
1 Mi to Maine Street! Mcm-style Home in Brunswick

Spacious 1 Bedroom Cottage Close to Everything 3

Spacious 1 Bedroom Cottage Close to Everything 3
Edgecomb
9.6 out of 10, Exceptional, (15 reviews)
"Great central location"
United States
Bruce O.
The price is CA $176
CA $372 total
includes taxes & fees
Jun 18 - Jun 19
Spacious 1 Bedroom Cottage Close to Everything 3

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 CA $482
CA $1,036 total
includes taxes & fees
Jun 18 - Jun 19
Pemaquid Escape | Curated Comfort + Hot Tub

Tide Haven Cottage on Bay Point

Tide Haven Cottage on Bay Point
Georgetown
The price is CA $317
CA $831 total
includes taxes & fees
Jul 1 - Jul 2
Tide Haven Cottage on Bay Point

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 CA $294
CA $512 total
includes taxes & fees
Jun 18 - Jun 19
Camp Forever cottage

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

Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.
Bath
7.6 out of 10, Good, (14 reviews)
"We stayed for two nights. Good location."
United States
Maryanne E.
The price is CA $182
CA $229 total
includes taxes & fees
Jun 24 - Jun 25
Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Five Islands. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Five Islands?

Yes, you can find vacation rentals near well known attractions in Five Islands, or you can go with a more secluded option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals in Five Islands?

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

How many vacation rentals will I find in Five Islands?

With 5 Expedia vacation rentals, you're sure 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 larger area, you’ll find Reid State Park and Burnt Island Living Lighthouse.

What’s a vacation rental in Five Islands like?

A vacation rental is a private property where you can stay for short or long periods in Five Islands. Vacation rentals feature extras like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from public hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for a family trip.