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Five Islands Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Five Islands vacation rentals

A treehouse with a wooden staircase and a small building with a colorful mural.

1. Perfect stopover, getaway, base to explore the area, or to simply stay in town.

Perfect stopover, getaway, base to explore the area, or to simply stay in town.
Bath
8.0 out of 10, Very good, (31 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
$162 nightly
The price is $176
Oct 17 - Oct 18
Total with taxes and fees
Perfect stopover, getaway, base to explore the area, or to simply stay in town.
A large industrial facility with multiple cranes and a prominent American flag.

2. Top floor loft apartment in downtown Bath

Top floor loft apartment in downtown Bath
Bath
9.4 out of 10, Exceptional, (8 reviews)
"Great location!"
United States
James E.
$213 nightly
The price is $232
Nov 9 - Nov 10
Total with taxes and fees
Top floor loft apartment in downtown Bath
A garden with hydrangea flowers, a wooden chair, and a "NO PARKING" sign.

3. Boothbay Harbor, 2-Story Cottage, downtown

Boothbay Harbor, 2-Story Cottage, downtown
Boothbay Harbor
9.4 out of 10, Exceptional, (31 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.
$337 nightly
The price is $367
Oct 19 - Oct 20
Total with taxes and fees
Boothbay Harbor, 2-Story Cottage, downtown
A two-story house with a covered porch, a garage, and a front yard with potted plants.

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, (175 reviews)
"Jeff and Susan are excellent hosts. They are very thoughtful and the little extras they provide really set their place a part from others."
United States
Miranda
$115 nightly
The price is $125
Nov 3 - Nov 4
Total with taxes and fees
Large suite/private bath/private entrance on quiet street near Thomas Bay
A coastal area with a beach, forested land, and a few buildings.

5. 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
Oct 17 - Oct 18
Total with taxes and fees
Across the road from Pemaquid Beach — wooded king-bed cabin for couples
A wooden staircase with a wooden railing, surrounded by green foliage.

6. 1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!

1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!
Bath
8.2 out of 10, Very good, (21 reviews)
"Cute but aging small space, Near attractions"
United States
michael
$164 nightly
The price is $179
Oct 18 - Oct 19
Total with taxes and fees
1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!
A lakeside deck with four blue Adirondack chairs, a canoe, and a paddleboard.

7. Peaceful Lake waterfront! Full Kitchen! Ht&AC! Is Private entry waterside in-law

Peaceful Lake waterfront! Full Kitchen! Ht&AC! Is Private entry waterside in-law
Boothbay Harbor
10.0 out of 10, Exceptional, (126 reviews)
"A delightful, restful place to come home to after our daytime adventures. Wendy was great to work with"
United States
jennifer r.
$315 nightly
The price is $343
Nov 1 - Nov 2
Total with taxes and fees
Peaceful Lake waterfront! Full Kitchen! Ht&AC! Is Private entry waterside in-law
A white two-story house with a symmetrical facade, a central entrance, and a small porch.

8. Historic Bath's, Home Away from Home

Historic Bath's, Home Away from Home
Bath
9.0 out of 10, Wonderful, (4 reviews)
"My husband and I stayed at this property with our adult daughter and found it to be a quiet and comfortable place. It was very convenient to the downtown area and waterfront; within walking distance for those who do not have any disabilities, but adequate parking for anyone needing to use a car also."
United States
Roberta M.
$313 nightly
The price is $342
Oct 28 - Oct 29
Total with taxes and fees
Historic Bath's, Home Away from Home
A bedroom with a bed, a small table with a yellow mug, and a window with a view of a forest.

9. 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.
$373 nightly
The price is $395
Nov 1 - Nov 2
Total with taxes and fees
Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
A wooden deck with a glass door leading to a room.

10. Tiny Cottage Near Everything 10

Tiny Cottage Near Everything 10
Edgecomb
9.0 out of 10, Wonderful, (6 reviews)
"Great location awesome place to take it easy for a few"
United States
Gene
$209 nightly
The price is $211
Oct 19 - Oct 20
Total with taxes and fees
Tiny Cottage Near Everything 10
A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

11. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (12 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
$203 nightly
The price is $215
Nov 1 - Nov 2
Total with taxes and fees
Mid Coast Getaway w/ water views
A coastal landscape with a beach, forested area, and a small cluster of buildings.

12. 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, (7 reviews)
"Perfect location! Family friendly and a comfortable 3 night stay for the first part of our Mid-Coast Maine adventure! Love this area. Such a gem."
United States
Janelle H.
Across the road from Pemaquid Beach — 2-bedroom seasonal family cottage
A cozy living room with a wooden ceiling, a white sofa, a coffee table, and a dark armchair.

13. A Spacious Vacation Cottage in Sheepscot Harbour

A Spacious Vacation Cottage in Sheepscot Harbour
Edgecomb
10.0 out of 10, Exceptional, (71 reviews)
"Great place and great restaurants."
United States
Julie D.
$268 nightly
The price is $292
Oct 25 - Oct 26
Total with taxes and fees
A Spacious Vacation Cottage in Sheepscot Harbour
A deck with white railings overlooking a body of water, boats, and a forested shoreline.

14. Captains Watch: A Coastal Escape

Captains Watch: A Coastal Escape
West Point
$213 nightly
The price is $214
Oct 19 - Oct 20
Total with taxes and fees
Captains Watch: A Coastal Escape
A spacious room with a wooden floor, a dining area with chairs and a table, a sofa, a TV, and a balcony with a view of the sea.

15. 2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
9.8 out of 10, Exceptional, (6 reviews)
"Place was clean, beautiful and the photos do not do it justice. The perfect get away vacation from the rat race."
United States
Gregory M.
$227 nightly
The price is $241
Nov 1 - Nov 2
Total with taxes and fees
2 bedroom w/ expansive water views
A cozy living room with a sofa, a small table, and a view of a backyard through large windows.

16. Spacious 1 Bedroom Cottage Close to Everything 2

Spacious 1 Bedroom Cottage Close to Everything 2
Edgecomb
9.4 out of 10, Exceptional, (22 reviews)
"We enjoyed our stay. The cottage had everything that we needed. The cottage was clean and well stocked with the essentials for our visit. Thank you for a nice stay."
United States
Terrence F.
$236 nightly
The price is $249
Nov 9 - Nov 10
Total with taxes and fees
Spacious 1 Bedroom Cottage Close to Everything 2
A rocking chair and a small table with a decorative plate, both placed on a wooden deck in front of a red building with a white door.

17. 2BR Apt. Authenticic value, Walk to everything, Large yard, Treehouse. No fees.

2BR Apt. Authenticic value, Walk to everything, Large yard, Treehouse. No fees.
Bath
9.0 out of 10, Wonderful, (28 reviews)
"Clean, walkable to town, nice backyard to sit and talk."
United States
Kathleen
$224 nightly
The price is $244
Oct 18 - Oct 19
Total with taxes and fees
2BR Apt. Authenticic value, Walk to everything, Large yard, Treehouse. No fees.
A compact kitchen with a dining table, two chairs, a sofa, a lamp, and a refrigerator.

18. 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
$312 nightly
The price is $340
Oct 17 - Oct 18
Total with taxes and fees
Across the road from Pemaquid Beach — quiet wooded king-bed cabin
A narrow hallway with a window on the right, leading to a room with a visible door.

19. Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath
Bath
9.8 out of 10, Exceptional, (13 reviews)
"Great location! We spent very little time in the room, but it was a great place to come back and crash! "
United States
Kristina M.
$203 nightly
The price is $221
Oct 18 - Oct 19
Total with taxes and fees
Modern style in historic building in downtown Bath
A modern kitchen with a central island, bar stools, and a dining area with a view of trees.

20. 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, (63 reviews)
"Tucked away in a wooded lot, quick drive to Boothbay Harbor. Side by side units are great for friends or families traveling together."
United States
Carly C.
$505 nightly
The price is $551
Oct 17 - Oct 18
Total with taxes and fees
Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor
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

Tugboat Inn

Tugboat Inn

10/10 Excellent
"Super location, great scenery."
Mike 1-night trip
Posted 2 hours ago
Tugboat 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 $125 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?

Spacious Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach: You might want to consider this vacation home rental near Five Islands, which is located on the beach and has a patio, a garden, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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.