Holiday Rentals in Bailey Island

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Our top choices for Bailey Island holiday rentals

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 €231
includes taxes & fees
24 Mar - 25 Mar
1 Mi to Maine Street! Mcm-style Home in Brunswick

2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
10.0 out of 10, Exceptional, (3 reviews)
"The host was welcoming. The home was clean, comfortable and the views were outstanding. "
United States
Rachel K.
The price is €173
includes taxes & fees
12 Mar - 13 Mar
2 bedroom w/ expansive water views

Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath
Bath
10.0 out of 10, Exceptional, (8 reviews)
"Such a great location! We could easily walk all over the cute downtown."
United States
Keisha C.
The price is €190
includes taxes & fees
7 Mar - 8 Mar
Modern style in historic building in downtown Bath

Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.6 out of 10, Exceptional, (15 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is €203
includes taxes & fees
28 Feb - 1 Mar
Fantastic Waterfront Views

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, (146 reviews)
"Lovely space, comfortable bed, very convenient to downtown Brunswick."
United States
Kimberly G.
The price is €105
includes taxes & fees
5 Mar - 6 Mar
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

1 Mi to Maine Street! MCM-Style Home in Brunswick

1 Mi to Maine Street! MCM-Style Home in Brunswick
Brunswick
9.4 out of 10, Exceptional, (3 reviews)
"Good communication with host. Beautifully decorated. Well appointed kitchen and bath. Great wooded views. Quiet but close to restaurants and shopping."
United States
Lecia M.
The price is €233
includes taxes & fees
24 Mar - 25 Mar
1 Mi to Maine Street! MCM-Style Home in Brunswick

Brunswick Downtown Sugar Cube next to Bowdoin

Brunswick Downtown Sugar Cube next to Bowdoin
Brunswick
8.4 out of 10, Very good, (7 reviews)
"We ahd a great stay in Maine over the 4th visiting family, eating good food and walking around in great weather. Great stay in Brunswick, easy in and easy out and all sorts of things Maine accessible. Would recommend for anyone looking for a hassle-free weekend in coastal Maine. "
United States
Tjorvi P.
The price is €216
includes taxes & fees
1 Mar - 2 Mar
Brunswick Downtown Sugar Cube next to Bowdoin

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (51 reviews)
"Super clean and lovely place to stay! Highly recommend!"
United States
Evan B.
The price is €343
includes taxes & fees
1 Mar - 2 Mar
Full sized home

City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (125 reviews)
"Perfect location and the host was immediately repsonsive and always friendly!"
United States
Jon L.
The price is €215
includes taxes & fees
1 Mar - 2 Mar
City Amenities, Casco Bay Sunrises and Natural Beauty

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (25 reviews)
"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 €172
includes taxes & fees
1 Mar - 2 Mar
Sunny Spot with Private Parking.

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 reviews)
"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 €182
includes taxes & fees
3 Mar - 4 Mar
Peaceful & minutes from the Old Port with private parking

Modern, luxurious cabin in the woods - 19

Modern, luxurious cabin in the woods - 19
Freeport
10.0 out of 10, Exceptional, (3 reviews)
"Great location to Freeport shopping. Very clean and responsive staff and management. Fun for families with children. We would have liked more room inbetween cabins, but otherwise would highly recommend."
United States
Kathleen K.
The price is €283
includes taxes & fees
8 Mar - 9 Mar
Modern, luxurious cabin in the woods - 19

Private Entrance Residential Portland

Private Entrance Residential Portland
Deering Center
8.8 out of 10, Excellent, (6 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 €109
includes taxes & fees
2 Mar - 3 Mar
Private Entrance Residential Portland

Spruce Studio: Near Beach+FirePit+Pond+Heat/AC+Fast WiFi

Spruce Studio: Near Beach+FirePit+Pond+Heat/AC+Fast WiFi
Georgetown
10.0 out of 10, Exceptional, (1 review)
"This cabin is so cozy! The hosts are awesome, leaving a welcoming note, snacks, park passes, catalogs for nearby towns & activities, water, etc! I love the outdoor patio and rainfall shower. Overall I would definitely stay again and recommend to friends! Thank you!"
United States
Julia M.
The price is €266
includes taxes & fees
3 Mar - 4 Mar
Spruce Studio: Near Beach+FirePit+Pond+Heat/AC+Fast WiFi

Little Lincoln beautiful home

Little Lincoln beautiful home
Brunswick
9.2 out of 10, Wonderful, (15 reviews)
"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 €209
includes taxes & fees
11 Mar - 12 Mar
Little Lincoln beautiful home

Skyline 138: Charming West End Mansard Penthouse

Skyline 138: Charming West End Mansard Penthouse
Parkside
9.4 out of 10, Exceptional, (26 reviews)
"Nice easy process, clean place, cute decor, easy to walk and uber to hot spots we wanted to see"
United States
Faith E.
The price is €263
includes taxes & fees
2 Mar - 3 Mar
Skyline 138: Charming West End Mansard Penthouse

Charming Studio apartment with WiFi, AC in welcoming Portland

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.6 out of 10, Exceptional, (11 reviews)
"A great location and a comfortable place to stay!"
United States
Andrew K.
The price is €183
includes taxes & fees
28 Feb - 1 Mar
Charming Studio apartment with WiFi, AC in welcoming Portland

Captain's House 2BR Guest Suite. Discover the authenticity & best value in Bath!

Captain's House 2BR Guest Suite. Discover the authenticity & best value in Bath!
Bath
8.6 out of 10, Excellent, (10 reviews)
"Clean rooms. Quiet location walkable to much of downtown Bath "
United States
randy k.
Captain's House 2BR Guest Suite. Discover the authenticity & best value in Bath!

Cozy 3BR | Pet Friendly | Near Portland | Parking

Cozy 3BR | Pet Friendly | Near Portland | Parking
Westbrook
10.0 out of 10, Exceptional, (12 reviews)
"We had a great stay here. It was very clean and conveniently located."
United States
Angela B.
The price is €329
includes taxes & fees
2 Mar - 3 Mar
Cozy 3BR | Pet Friendly | Near Portland | Parking

2King Bed BR Private Apt Downtown Brunswick

2King Bed BR Private Apt Downtown Brunswick
Brunswick
8.4 out of 10, Very good, (11 reviews)
"Small place in a great location. Easily walk to several shops and restaurants. "
United States
Jillian B.
The price is €200
includes taxes & fees
18 Mar - 19 Mar
2King Bed BR Private Apt Downtown Brunswick
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 €99 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.