Bailey Island Holiday Rentals

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Our top choices for Bailey Island holiday rentals

Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR
Harpswell
9.8 out of 10, Exceptional, (9)
"Orchid Harbor was perfect for my 3 week escape from life. Bailey Island is quiet and the house is comfortable and accommodating for family and friends.The outdoor seating along the ocean was our favorite place to be."
United States
Karen T.
The price is NZ$808
includes taxes & fees
4 Jan - 5 Jan 2026
Orchid Harbor, Bailey Island 3BR

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
2.0 star property
Knightville
9.8 out of 10, Exceptional, (25)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
The price is NZ$347
includes taxes & fees
6 Jan - 7 Jan 2026
Sunny Spot with Private Parking.

Escape to Positive Outlook

Escape to Positive Outlook
West Point
10.0 out of 10, Exceptional, (3)
"The host was welcoming. The home was clean, comfortable and the views were outstanding. "
United States
Rachel K.
The price is NZ$326
includes taxes & fees
4 Jan - 5 Jan 2026
Escape to Positive Outlook

Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath
Bath
10.0 out of 10, Exceptional, (8)
"Such a great location! We could easily walk all over the cute downtown."
United States
Keisha C.
The price is NZ$381
includes taxes & fees
4 Jan - 5 Jan 2026
Modern style in historic building in downtown Bath

Modern, Luxurious, Cabin in the Woods - 17

Modern, Luxurious, Cabin in the Woods - 17
Freeport
10.0 out of 10, Exceptional, (3)
"Awesome camping in a great, quiet campground. The staff is very responsive and all the little details make this place special."
United States
Miranda K.
The price is NZ$511
includes taxes & fees
4 Jan - 5 Jan 2026
Modern, Luxurious, Cabin in the Woods - 17

Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
Brunswick
10.0 out of 10, Exceptional, (145)
"Great location to access the area especially route 1 n and s. Room totally met our needs and Susan and Jeff were super nice. This place will make our trip most memorable!"
United States
Don E.
The price is NZ$207
includes taxes & fees
18 Jan - 19 Jan 2026
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Brunswick Downtown Sugar Cube next to Bowdoin

Brunswick Downtown Sugar Cube next to Bowdoin
Brunswick
8.4 out of 10, Very good, (7)
"Stayed for one night. Very convenient to campus"
United States
Lin-Lin R.
The price is NZ$454
includes taxes & fees
1 Jan - 2 Jan 2026
Brunswick Downtown Sugar Cube next to Bowdoin

Solitude @ The Offshore House

Solitude @ The Offshore House
Boothbay
9.8 out of 10, Exceptional, (7)
"Managers were very responsive and helpful. Condo was very clean and comfortable and close to the town of Boothbay Harbor and Ocean Point and the Botanic Gardens. "
United States
Linda O.
The price is NZ$518
includes taxes & fees
3 Jan - 4 Jan 2026
Solitude @ The Offshore House

Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.6 out of 10, Exceptional, (14)
"The views are amazing! A very relaxing place to be, and the house was clean and comfortable. "
United States
Monika G.
The price is NZ$510
includes taxes & fees
9 Jan - 10 Jan 2026
Fantastic Waterfront Views

2King Bed BR Private Apt Downtown Brunswick

2King Bed BR Private Apt Downtown Brunswick
Brunswick
8.4 out of 10, Very good, (10)
"Small place in a great location. Easily walk to several shops and restaurants. "
United States
Jillian B.
The price is NZ$422
includes taxes & fees
4 Jan - 5 Jan 2026
2King Bed BR Private Apt Downtown Brunswick

Shipwright @ The Offshore House

Shipwright @ The Offshore House
Boothbay
9.6 out of 10, Exceptional, (14)
"Great location. Easy location to town and Dunkin Donuts accros street. "
United States
Steven
The price is NZ$518
includes taxes & fees
1 Jan - 2 Jan 2026
Shipwright @ The Offshore House

Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.8 out of 10, Exceptional, (7)
"This well- appointed apartment was perfect for our stay in the Portland area. Jennifer was always quick to answer any questions. We would definitely recommend this listing."
United States
Lynn E.
The price is NZ$366
includes taxes & fees
4 Jan - 5 Jan 2026
Peaceful & minutes from the Old Port with private parking

Seabed @ The Offshore House

Seabed @ The Offshore House
Boothbay
9.8 out of 10, Exceptional, (14)
"My husband and I stayed at Seabed because we were in town for a friend’s wedding. It was beautiful and clean! Check in was easy and the hosts are super responsive! Amazing location. "
United States
Hailey K.
The price is NZ$518
includes taxes & fees
1 Jan - 2 Jan 2026
Seabed @ The Offshore House

Little Lincoln beautiful home

Little Lincoln beautiful home
Brunswick
9.2 out of 10, Wonderful, (15)
"Simon was very easy to communicate with, the place was clean, the bed was quite comfortable, and we were right by Main Street in Brunswick which made for easy access to food and things to do. Wonderful place to stay!"
United States
Jessica B.
The price is NZ$444
includes taxes & fees
25 Jan - 26 Jan 2026
Little Lincoln beautiful home

Cozy, Elegant and Bright 2 bed in the East End

Cozy, Elegant and Bright 2 bed in the East End
Munjoy Hill
9.8 out of 10, Exceptional, (52)
"Great location and cozy."
United States
Heather G.
The price is NZ$397
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy, Elegant and Bright 2 bed in the East End

Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (128)
"The place was perfect. It was right in the middle of everything and a perfe spot for a getaway"
United States
Jon S.
The price is NZ$340
includes taxes & fees
2 Jan - 3 Jan 2026
Adorable Portland getaway on the Eastern Promenade

Cozy 3BR | Pet Friendly | Near Portland | Parking

Cozy 3BR | Pet Friendly | Near Portland | Parking
Westbrook
10.0 out of 10, Exceptional, (12)
"We had a great stay here. It was very clean and conveniently located."
United States
Angela B.
The price is NZ$655
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy 3BR | Pet Friendly | Near Portland | Parking

Port City Nest: Beautiful 2bd w/ Balcony & Parking

Port City Nest: Beautiful 2bd w/ Balcony & Parking
Parkside
10.0 out of 10, Exceptional, (1)
"Loved staying at your Nest! All was great but maybe a couple of cozy blanks in living room for lounging? Thanks again-Ruth"
United States
Ruth R.
The price is NZ$403
includes taxes & fees
4 Jan - 5 Jan 2026
Port City Nest: Beautiful 2bd w/ Balcony & Parking

Near Reid State Park Beach+FirePit+Pond+Heat/AC+Fast WiFi+S'mores

Near Reid State Park Beach+FirePit+Pond+Heat/AC+Fast WiFi+S'mores
2.0 star property
Georgetown
The price is NZ$552
includes taxes & fees
4 Jan - 5 Jan 2026
Near Reid State Park Beach+FirePit+Pond+Heat/AC+Fast WiFi+S'mores

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (50)
"It was a very nice house to stay at. "
United States
Anonymous traveller
The price is NZ$627
includes taxes & fees
26 Jan - 27 Jan 2026
Full sized home
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$232 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?

New 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 25 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.