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Five Islands Vacation Rentals

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Five Islands vacation rentals

Exterior

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.
$1,099 nightly
The price is $1,169
Jul 12 - Jul 13
Total with taxes and fees
Charming Sheepscot Overlook Cottage
Exterior

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.
$143 nightly
The price is $155
Jul 29 - Jul 30
Total with taxes and fees
Large suite/private bath/private entrance on quiet street near Thomas Bay
Interior

Vacation Creation Downtown Brunswick 2King Beds

Vacation Creation Downtown Brunswick 2King Beds
Brunswick
9.6 out of 10, Exceptional, (19 reviews)
$606 nightly
The price is $661
Jul 13 - Jul 14
Total with taxes and fees
Vacation Creation Downtown Brunswick 2King Beds
House (2 Bedrooms) | Interior

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
$269 nightly
The price is $293
Jul 16 - Jul 17
Total with taxes and fees
1 Mi to Maine Street! Mcm-style Home in Brunswick
Smart TV

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
$681 nightly
The price is $742
Jul 12 - Jul 13
Total with taxes and fees
Across the road from Pemaquid Beach — 4-bedroom 19th-century Maine home
Beach nearby

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
$312 nightly
The price is $340
Jul 12 - Jul 13
Total with taxes and fees
Across the road from Pemaquid Beach — wooded king-bed cabin for couples
Beach

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.
$704 nightly
The price is $767
Jul 13 - Jul 14
Total with taxes and fees
Pemaquid Escape | Curated Comfort + Hot Tub
Fridge, microwave, oven, stovetop

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, (49 reviews)
"Excellent, clean property. "
United States
Andy H.
$553 nightly
The price is $602
Jul 18 - Jul 19
Total with taxes and fees
Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor
TV

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.
$369 nightly
The price is $402
Jul 12 - Jul 13
Total with taxes and fees
Brunswick Downtown Sugar Cube next to Bowdoin
Exterior detail

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.
$418 nightly
The price is $455
Jul 12 - Jul 13
Total with taxes and fees
Tiny A-Frame Romantic Getaway
Pool

Little Spruce Cottage | Wood Stove + Porch

Little Spruce Cottage | Wood Stove + Porch
Boothbay Harbor
$1,033 nightly
The price is $1,126
Jul 23 - Jul 24
Total with taxes and fees
Little Spruce Cottage | Wood Stove + Porch
Interior

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)
$364 nightly
The price is $397
Jul 12 - Jul 13
Total with taxes and fees
Downtown Brunswick New Look Old Charm Next to Bowdoin
Property grounds

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

Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
Georgetown
$633 nightly
The price is $679
Jul 20 - Jul 21
Total with taxes and fees
Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
Beach nearby

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.
$334 nightly
The price is $364
Jul 12 - Jul 13
Total with taxes and fees
Across the road from Pemaquid Beach — 2-bedroom seasonal family cottage
Interior

Three bedroom in United States of America, Freeport

Three bedroom in United States of America, Freeport
Freeport
$862 nightly
The price is $940
Jul 13 - Jul 14
Total with taxes and fees
Three bedroom in United States of America, Freeport
Interior

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.
$280 nightly
The price is $297
Jul 12 - Jul 13
Total with taxes and fees
Spacious 1 Bedroom Close to Everything 4
2 bedrooms, iron/ironing board, bed sheets

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.
$262 nightly
The price is $277
Jul 22 - Jul 23
Total with taxes and fees
Cheerful Cottage with Loft 9
Interior

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.
$511 nightly
The price is $557
Jul 31 - Aug 1
Total with taxes and fees
Sweet comfy cottage on Small Point Road
Exterior

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.
$302 nightly
The price is $321
Jul 15 - Jul 16
Total with taxes and fees
Spacious 1 Bedroom Cottage Close to Everything 3
Property grounds

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
$437 nightly
The price is $476
Jul 19 - Jul 20
Total with taxes and fees
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

Ocean Gate Inn

Ocean Gate Inn

10/10 Excellent
"So nice ✅ I would definitely come back. The staff was great and very accommodating. The kids loved it and it’s always safe next time I come I’m gonna bring a fishing rod and a bike."
Maddy 1-night trip
Posted 1 hour ago
Ocean Gate Inn

Find out more about Five Islands

Everything you need to know about Five Islands vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Five Islands vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Five Islands vacation 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 low season months. For more hustle and bustle, you may prefer to visit Five Islands in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $155 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Five Islands rentals

At Expedia, we put the best Five Islands vacation 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 vacation.

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 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 Boothbay Railway Village, or get out into nature at a spot like Coastal Maine Botanical Gardens. In the larger area, you’ll find Reid State Park and Hodgdon Island.

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.