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. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (62 reviews)
"Wonderful stay!"
United States
Erika T.
The price is NZ$609
includes taxes & fees
24 Aug - 25 Aug
Full sized home

2. 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 NZ$503
includes taxes & fees
28 Aug - 29 Aug
Mid Coast Getaway w/ water views

3. •Tranquil 2BR Summer Home•Steps to Private Beach•

•Tranquil 2BR Summer Home•Steps to Private Beach•
Harpswell
The price is NZ$949
includes taxes & fees
1 Sept - 2 Sept
•Tranquil 2BR Summer Home•Steps to Private Beach•

4. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (62 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is NZ$605
includes taxes & fees
25 Aug - 26 Aug
Camp Forever cottage

5. 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 NZ$461
includes taxes & fees
25 Aug - 26 Aug
1 Mi to Maine Street! MCM-Style Home in Brunswick

6. 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, (162 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 NZ$281
includes taxes & fees
14 Sept - 15 Sept
Large suite/private bath/private entrance on quiet street near Thomas Bay

7. 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 NZ$460
includes taxes & fees
25 Aug - 26 Aug
1 Mi to Maine Street! Mcm-style Home in Brunswick

8. 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 NZ$383
includes taxes & fees
15 Sept - 16 Sept
Modern style in historic building in downtown Bath

9. Captain's Guest Room. Authenticity. Great Value. Walk to everything.

Captain's Guest Room. Authenticity. Great Value. Walk to everything.
Bath
8.4 out of 10, Very good, (27 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 NZ$303
includes taxes & fees
14 Sept - 15 Sept
Captain's Guest Room. Authenticity. Great Value. Walk to everything.

10. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.2 out of 10, Very good, (14 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 NZ$302
includes taxes & fees
18 Aug - 19 Aug
Studio Apartment near downtown Walkable!

11. Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.

Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.
Bath
8.0 out of 10, Very good, (16 reviews)
"We stayed for two nights. Good location."
United States
Maryanne E.
The price is NZ$295
includes taxes & fees
14 Sept - 15 Sept
Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.

12. 2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
10.0 out of 10, Exceptional, (4 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 NZ$691
includes taxes & fees
9 Sept - 10 Sept
2 bedroom w/ expansive water views

13. King Size Sun Rise Midcoast Lovely Stay

King Size Sun Rise Midcoast Lovely Stay
Topsham
9.6 out of 10, Exceptional, (17 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 NZ$544
includes taxes & fees
18 Aug - 19 Aug
King Size Sun Rise Midcoast Lovely Stay

14. Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (66 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 NZ$803
includes taxes & fees
29 Aug - 30 Aug
Centerview cottage

15. Cozy and charming coastal retreat

Cozy and charming coastal retreat
West Point
9.8 out of 10, Exceptional, (33 reviews)
"My family and I had an amazing time at the schoolhouse. It is much bigger than the pictures show! Great beds, the couches will force you to nap, and we had so much fun exploring the area. They had everything you need for fun at the beach, and lots of options for kids to keep busy. Highly recommend!"
United Kingdom
Byrony S.
The price is NZ$1,008
includes taxes & fees
23 Aug - 24 Aug
Cozy and charming coastal retreat

16. 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 NZ$782
includes taxes & fees
9 Sept - 10 Sept
Fantastic Waterfront Views

17. Private Entrance Residential Portland

Private Entrance Residential Portland
Deering Center
8.6 out of 10, Excellent, (8 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 NZ$226
includes taxes & fees
2 Sept - 3 Sept
Private Entrance Residential Portland

18. 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 NZ$910
includes taxes & fees
11 Sept - 12 Sept
Sweet comfy cottage on Small Point Road

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

Modern cabin w/ full bath & kitchenette - 03
Freeport
10.0 out of 10, Exceptional, (7 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 NZ$829
includes taxes & fees
2 Sept - 3 Sept
Modern cabin w/ full bath & kitchenette - 03

20. Brunswick Downtown Sugar Cube next to Bowdoin

Brunswick Downtown Sugar Cube next to Bowdoin
Brunswick
8.6 out of 10, Excellent, (9 reviews)
"Had a great overnight here with my mother as a Mother’s Day trip. Size was perfect for the two of us. Easy walk to town. Had a lovely stay!"
United States
Andrea L.
The price is NZ$585
includes taxes & fees
30 Aug - 31 Aug
Brunswick Downtown Sugar Cube next to Bowdoin
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 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 NZ$302 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. 

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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. 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 30 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.