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

Sunset Hideaway on Bailey Island

Sunset Hideaway on Bailey Island
Harpswell
8.0 out of 10, Very good, (4 reviews)
"Wonderful views. Comfortable. "
United States
Susy K.
The price is AU$428
includes taxes & fees
10 Aug - 11 Aug
Sunset Hideaway on Bailey Island

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (54 reviews)
"Wonderful stay!"
United States
Erika T.
The price is AU$526
includes taxes & fees
21 July - 22 July
Full sized home

Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.6 out of 10, Exceptional, (7 reviews)
"Second time we have stay in this cottage. The perfect location for a Maine vacation. "
United States
chuck c.
The price is AU$442
includes taxes & fees
3 Aug - 4 Aug
Mid Coast Getaway w/ water views

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, (154 reviews)
"Susan and Jeff were amazing hosts! There were so kind, thoughtful and welcoming. The suite was extremely spacious, well decorated and very comfortable. We were very close to the Air Show which was the reason for our trip. They gave us great instructions for a short cut to the airfield and amazing dinner recommendations. We could not have chosen a better place to stay. We highly recommend this place!"
United States
Asha
The price is AU$225
includes taxes & fees
3 Aug - 4 Aug
Large suite/private bath/private entrance on quiet street near Thomas Bay

Captain's Guest Room. Authenticity. Value. Near everything. No fees.

Captain's Guest Room. Authenticity. Value. Near everything. No fees.
Bath
8.2 out of 10, Very good, (25 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$227
includes taxes & fees
21 July - 22 July
Captain's Guest Room. Authenticity. Value. Near everything. No fees.

Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath
Bath
9.8 out of 10, Exceptional, (10 reviews)
"Clean comfortable and right downtown"
United States
stephen e.
The price is AU$357
includes taxes & fees
22 July - 23 July
Modern style in historic building in downtown Bath

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$343
includes taxes & fees
21 July - 22 July
Fortland Island Campground

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 AU$242
includes taxes & fees
21 July - 22 July
Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.

Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
The price is AU$838
includes taxes & fees
22 July - 23 July
Fully Updated Airy Historic Home in South Freeport

Modern cabin w/ full bath & kitchenette - 03

Modern cabin w/ full bath & kitchenette - 03
Freeport
10.0 out of 10, Exceptional, (7 reviews)
"This was a perfect little cabin. It was clean, well equipped with a nice kitchen and bathroom, quiet and wooded location, and comfy bed. "
United States
Chris B.
The price is AU$509
includes taxes & fees
26 July - 27 July
Modern cabin w/ full bath & kitchenette - 03

King Size Sun Rise Midcoast Lovely Stay

King Size Sun Rise Midcoast Lovely Stay
Topsham
9.4 out of 10, Exceptional, (16 reviews)
"Great location surroundings a little unkept but tis the spring cleanup season. Excellent accommodation and located near town shopping but quiet neighborhood"
United States
Douglas H.
The price is AU$468
includes taxes & fees
26 July - 27 July
King Size Sun Rise Midcoast Lovely Stay

Studio Apartment in Freeport

Studio Apartment in Freeport
Freeport
10.0 out of 10, Exceptional, (3 reviews)
"Was pet friendly, as pictured. Very nice"
United States
Kelly L.
The price is AU$404
includes taxes & fees
18 Aug - 19 Aug
Studio Apartment in Freeport

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)
"We really enjoyed our visit with family and friends and the location was perfect for what we needed. "
United States
Eliza
The price is AU$461
includes taxes & fees
2 Aug - 3 Aug
Downtown Brunswick New Look Old Charm Next to Bowdoin

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 AU$794
includes taxes & fees
31 July - 1 Aug
Sweet comfy cottage on Small Point Road

Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (9 reviews)
"Lovely location "
United States
Michelle S.
The price is AU$804
includes taxes & fees
19 Aug - 20 Aug
Mere Point Sunrise Views at Eastern Shore!

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, (33 reviews)
"Wonderful location. It’s right next to Bowdoin. There is a great coffee shop a block away and a grocery store within easy walking distance. The place was spotless. "
United States
Mike S.
The price is AU$613
includes taxes & fees
21 July - 22 July
Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)

Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.2 out of 10, Very good, (10 reviews)
"A perfectly decent place to stay, plenty of restaurants and bars within reasonable walking distance. Neighborhood is a bit rough, as the listing mentioned, but no problems while I was there. Response time on questions to the host could be better."
Canada
Brian
The price is AU$271
includes taxes & fees
3 Aug - 4 Aug
Studio Apartment near downtown Walkable!

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$549
includes taxes & fees
28 July - 29 July
Glamping cabin w/ full bath + spa access - 21

Beautiful 3BR Home with Office in Town of Brunswick with King beds

Beautiful 3BR Home with Office in Town of Brunswick with King beds
Brunswick
9.0 out of 10, Wonderful, (6 reviews)
"Great place for our family to stay while visiting the Maine coast."
United States
Craig C.
The price is AU$648
includes taxes & fees
21 July - 22 July
Beautiful 3BR Home with Office in Town of Brunswick with King beds

Private Entrance Residential Portland

Private Entrance Residential Portland
Deering Center
8.4 out of 10, Very good, (7 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$192
includes taxes & fees
2 Aug - 3 Aug
Private Entrance Residential Portland
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$227 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. 

Explore a world of travel with Expedia

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. Our travellers also rate Johnson Homestead. One level living, ocean view with semi-private beach access. as a favourite home for rent in Bailey Island.

How many holiday rentals are there in Bailey Island?

With 31 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.