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

Holiday Rentals in Bailey Island

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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 €221
includes taxes & fees
27 Sept - 28 Sept
Sunset Hideaway on Bailey Island

2. Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR
Harpswell
10.0 out of 10, Exceptional, (12 reviews)
"Lovely property, close to what we needed and wanted, host communicated promptly. Would definitely stay there again."
United States
Jane D.
The price is €391
includes taxes & fees
16 Sept - 17 Sept
Orchid Harbor, Bailey Island 3BR

3. 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 €247
includes taxes & fees
1 Sept - 2 Sept
Mid Coast Getaway w/ water views

4. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (67 reviews)
"The house was lovely and well kept and in a great location."
United States
Angela M.
The price is €375
includes taxes & fees
20 Sept - 21 Sept
Full sized home

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 €318
includes taxes & fees
22 Sept - 23 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
Brunswick
9.6 out of 10, Exceptional, (11 reviews)
"Quiet, clean, well appointed house close to Maine St Brunswick and convenient to both Portland and points north. "
United States
Kendra G.
The price is €238
includes taxes & fees
23 Sept - 24 Sept
1 Mi to Maine Street! MCM-Style Home in Brunswick

7. 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, (164 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 €143
includes taxes & fees
2 Sept - 3 Sept
Large suite/private bath/private entrance on quiet street near Thomas Bay

8. Apartment over shops in Bath Historic District

Apartment over shops in Bath Historic District
Bath
8.8 out of 10, Excellent, (5 reviews)
"Great breakfast spot right across the street!!"
United States
Jessica K.
The price is €196
includes taxes & fees
15 Sept - 16 Sept
Apartment over shops in Bath Historic District

9. 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 €233
includes taxes & fees
23 Sept - 24 Sept
1 Mi to Maine Street! Mcm-style Home in Brunswick

10. Captain's Guest Room. Authenticity. Great Value. Large yard. Walk to everything.

Captain's Guest Room. Authenticity. Great 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 €166
includes taxes & fees
30 Aug - 31 Aug
Captain's Guest Room. Authenticity. Great Value. Large yard. Walk to everything.

11. Private Entrance Residential Portland

Private Entrance Residential Portland
Deering Center
8.6 out of 10, Excellent, (10 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 €146
includes taxes & fees
7 Sept - 8 Sept
Private Entrance Residential Portland

12. Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.8 out of 10, Exceptional, (17 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is €359
includes taxes & fees
30 Aug - 31 Aug
Fantastic Waterfront Views

13. King Size Sun Rise Midcoast Lovely Stay

King Size Sun Rise Midcoast Lovely Stay
Topsham
9.6 out of 10, Exceptional, (18 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 €248
includes taxes & fees
7 Sept - 8 Sept
King Size Sun Rise Midcoast Lovely Stay

14. Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (68 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
The price is €405
includes taxes & fees
2 Sept - 3 Sept
Centerview cottage

15. Great suburban location close to town!

Great suburban location close to town!
Deering Center
The price is €177
includes taxes & fees
25 Sept - 26 Sept
Great suburban location close to town!

16. Captain's 1BR Suite. Authenticity. Value. Near everything. Large yard. No fees.

Captain's 1BR Suite. Authenticity. Value. Near everything. Large yard. No fees.
Bath
8.0 out of 10, Very good, (18 reviews)
"Cute but aging small space, Near attractions"
United States
michael
The price is €149
includes taxes & fees
30 Aug - 31 Aug
Captain's 1BR Suite. Authenticity. Value. Near everything. Large yard. No fees.

17. Walk to Town 4BR, 200yr old home! #1

Walk to Town 4BR, 200yr old home! #1
Brunswick
Walk to Town 4BR, 200yr old home! #1

18. 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 €400
includes taxes & fees
7 Sept - 8 Sept
Fortland Island Campground

19. 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 €197
includes taxes & fees
1 Sept - 2 Sept
Modern style in historic building in downtown Bath

20. 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 €285
includes taxes & fees
8 Sept - 9 Sept
Modern cabin w/ full bath & kitchenette - 03
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, apart-hotels, 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 favorite 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 depends 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 €146 per night. Entering your travel dates in the search wizard you might find 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. 

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.