A rocky shoreline with a boat, a house, and a forest in the background.

Bailey Island Holiday Rentals

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Our top choices for Bailey Island holiday rentals

1. Sunset Hideaway on Bailey Island

Sunset Hideaway on Bailey Island
Harpswell
8.4 out of 10, Very good, (5 reviews)
"Wonderful views. Comfortable. "
United States
Susy K.
The price is AU$319
includes taxes & fees
23 Sept - 24 Sept
Sunset Hideaway on Bailey Island

2. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (68 reviews)
"The house was lovely and well kept and in a great location."
United States
Angela M.
The price is AU$541
includes taxes & fees
5 Oct - 6 Oct
Full sized home

3. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.6 out of 10, Exceptional, (8 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
The price is AU$391
includes taxes & fees
14 Sept - 15 Sept
Mid Coast Getaway w/ water views

4. 2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
10.0 out of 10, Exceptional, (5 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.
The price is AU$402
includes taxes & fees
7 Sept - 8 Sept
2 bedroom w/ expansive water views

5. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (65 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is AU$506
includes taxes & fees
7 Sept - 8 Sept
Camp Forever cottage

6. 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 AU$377
includes taxes & fees
23 Sept - 24 Sept
1 Mi to Maine Street! Mcm-style Home in Brunswick

7. Captain's 1BR Suite. Authenticity. Value. Walk to everything. Large yard.

Captain's 1BR Suite. Authenticity. Value. Walk to everything. Large yard.
Bath
8.0 out of 10, Very good, (19 reviews)
"Cute but aging small space, Near attractions"
United States
michael
The price is AU$228
includes taxes & fees
7 Sept - 8 Sept
Captain's 1BR Suite. Authenticity. Value. Walk to everything. Large yard.

8. Guest room + bath in Bath!. Authenticity. Value. Large yard. Walk to everything.

Guest room + bath in Bath!. Authenticity. Value. Large yard. Walk to everything.
Bath
8.2 out of 10, Very good, (29 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$222
includes taxes & fees
7 Sept - 8 Sept
Guest room + bath in Bath!. Authenticity. Value. Large yard. Walk to everything.

9. Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.8 out of 10, Exceptional, (18 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is AU$588
includes taxes & fees
9 Sept - 10 Sept
Fantastic Waterfront Views

10. Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath
Bath
10.0 out of 10, Exceptional, (11 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.
The price is AU$334
includes taxes & fees
9 Sept - 10 Sept
Modern style in historic building in downtown Bath

11. 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, (166 reviews)
"What a beautiful place to stay. Jeff and Susan made your stay a very special experience."
United States
DENESE
The price is AU$244
includes taxes & fees
15 Sept - 16 Sept
Large suite/private bath/private entrance on quiet street near Thomas Bay

12. Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (69 reviews)
"Incredible home in a beautiful location!"
United States
Catherine G.
The price is AU$652
includes taxes & fees
7 Sept - 8 Sept
Centerview cottage

13. Modern cabin w/ full bath & kitchenette - 03

Modern cabin w/ full bath & kitchenette - 03
Freeport
10.0 out of 10, Exceptional, (8 reviews)
"Easy check in process. More than clean, it looked brand new. Overall a great stay. Kitchen was well stocked with plates, utensils, and cookware. "
United States
Michael H.
The price is AU$401
includes taxes & fees
8 Sept - 9 Sept
Modern cabin w/ full bath & kitchenette - 03

14. King Size Sun Rise Midcoast Lovely Stay

King Size Sun Rise Midcoast Lovely Stay
Topsham
9.6 out of 10, Exceptional, (18 reviews)
"Perfect for a my husband and I. Close to everything!"
United States
Tabcline S.
The price is AU$365
includes taxes & fees
28 Sept - 29 Sept
King Size Sun Rise Midcoast Lovely Stay

15. Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean

Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean
Freeport
10.0 out of 10, Exceptional, (17 reviews)
"Hosts were very responsive with messages. The stay was clean and comfortable."
United States
Hana L.
The price is AU$506
includes taxes & fees
20 Sept - 21 Sept
Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean

16. Glamping cabin w/ full bath + spa access - 21

Glamping cabin w/ full bath + spa access - 21
Freeport
10.0 out of 10, Exceptional, (1 review)
The price is AU$401
includes taxes & fees
8 Sept - 9 Sept
Glamping cabin w/ full bath + spa access - 21

17. Fortland Island Campground

Fortland Island Campground
1.0 star property
Portland
10.0 out of 10, Exceptional, (3 reviews)
"It was very quiet and liked the experience of staying in a camp like setting."
United States
leela srinivas
The price is AU$518
includes taxes & fees
24 Sept - 25 Sept
Fortland Island Campground

18. Private Entrance Residential Portland

Private Entrance Residential Portland
Deering Center
8.8 out of 10, Excellent, (11 reviews)
"This was a great place to stay. Easy to get to all of our destinations. Place was clean and comfortable. Would stay here again. "
United States
Ameleah B.
The price is AU$234
includes taxes & fees
7 Sept - 8 Sept
Private Entrance Residential Portland

19. 'Osprey Cottage' South Freeport Home on Casco Bay!

'Osprey Cottage' South Freeport Home on Casco Bay!
Freeport
8.8 out of 10, Excellent, (22 reviews)
"This was an adorable cottage in a picturesque location. The cottage was clean and comfortable, right on the water. Additional friends stayed in the adjacent Heron cottage, and we joined them on the patio for a fire one evening as summer faded to autumn."
United States
John J.
The price is AU$872
includes taxes & fees
30 Sept - 1 Oct
'Osprey Cottage' South Freeport Home on Casco Bay!

20. Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport

Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport
Freeport
10.0 out of 10, Exceptional, (11 reviews)
"Our whole family was impressed by this house!"
United States
Gary B.
The price is AU$952
includes taxes & fees
7 Sept - 8 Sept
Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport
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 Bailey Island Hotel Reviews

Find out more about Bailey Island

Everything you need to know about Bailey Island 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 Bailey Island 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 Bailey Island holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Bailey Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Bailey Island. 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 Bailey Island 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 Bailey Island 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 Bailey Island rentals

At Expedia, we put the best Bailey Island 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 Bailey Island 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 Bailey Island 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 Bailey Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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Frequently asked questions

Can I find a holiday rental in Bailey Island?

Yes, there are holiday rentals in Bailey Island close to Land's End Gift Shop, or you can select a more secluded option if you're looking for a relaxing stay. Bailey Island is known for its shopping and seafood restaurants. Make sure you have time to check out the local tours and monuments during your trip.

What are some of the best holiday rentals that Bailey Island has to offer?

Spacious Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach: This highly rated holiday home rental in Bailey Island 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 are there in Bailey Island?

With 32 Expedia holiday rentals, you're guaranteed to find just the right place for your Bailey Island stay.

What can I see and do in Bailey Island?

Mackerel Cove and Ragged Island are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Land's End Gift Shop. Bailey Island Bridge and Cobwork Bridge are other places to visit while you're in town.

What are holiday rentals like in Bailey Island?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Bailey Island. Holiday rentals feature amenities like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a great option for family trips or small group gatherings.