Bailey Island Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Bailey Island

Solitude @ The Offshore House
9.8 out of 10, Exceptional, (6)
"Awesome place will stay again… Owners were a pleasure to deal with."
United States
Philip M.
The price is AU$513
includes taxes & fees
20 Oct - 21 Oct
Solitude @ The Offshore House
Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome
9.0 out of 10, Wonderful, (66)
"Everything was perfect. It’s an amazing home and the area is peaceful. The house was clean and it has everything you need. I will definitely be back. Thanks for a wonderful stay."
United States
Luis Correa
The price is AU$514
includes taxes & fees
21 Oct - 22 Oct
Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome
Seabed @ The Offshore House
9.8 out of 10, Exceptional, (14)
"This was a great place to stay that let me explore the area I wanted to."
United States
Lori A.
The price is AU$513
includes taxes & fees
20 Oct - 21 Oct
Seabed @ The Offshore House
Captain's Guest Room w/private bath & house entrance. Walk to everything.
8.0 out of 10, Very good, (19)
"Dmitri is accommodating and check-in easy. Property details are accurate "
United States
Lori Z.
The price is AU$231
includes taxes & fees
2 Nov - 3 Nov
Captain's Guest Room w/private bath & house entrance. Walk to everything.
Modern style in historic building in downtown Bath
10.0 out of 10, Exceptional, (8)
"Property was nice little apartment with what I needed"
United States
stephen e.
The price is AU$348
includes taxes & fees
20 Oct - 21 Oct
Modern style in historic building in downtown Bath
Shipwright @ The Offshore House
9.4 out of 10, Exceptional, (13)
"Luv the area and the room location was great A few steps from Bets fish and chips short drive into town "
Canada
Judy M.
The price is AU$516
includes taxes & fees
20 Oct - 21 Oct
Shipwright @ The Offshore House
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
10.0 out of 10, Exceptional, (142)
"Wonderful hosts, truly made guests feel welcomed and valued. "
United States
Emiley
The price is AU$188
includes taxes & fees
2 Nov - 3 Nov
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
King Size Sun Rise Midcoast Lovely Stay
10.0 out of 10, Exceptional, (14)
"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$361
includes taxes & fees
3 Nov - 4 Nov
King Size Sun Rise Midcoast Lovely Stay
Sunny Spot with Private Parking.
2.0 star property
9.8 out of 10, Exceptional, (24)
"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 AU$312
includes taxes & fees
2 Nov - 3 Nov
Sunny Spot with Private Parking.
Adorable Portland getaway on the Eastern Promenade
9.8 out of 10, Exceptional, (123)
"So clean! Loved all the little notes, very helpful. Such a great location close to the water and would definitely recommend this place in the future."
United States
Lorena
The price is AU$322
includes taxes & fees
3 Nov - 4 Nov
Adorable Portland getaway on the Eastern Promenade
Modern, luxurious cabin in the woods - 21
10.0 out of 10, Exceptional, (1)
The price is AU$455
includes taxes & fees
27 Oct - 28 Oct
Modern, luxurious cabin in the woods - 21
Private Entrance Residential Portland
9.2 out of 10, Wonderful, (5)
"Great location for seeing the Portland Head Lighthouse. Comfortable bed."
United States
Michelle S.
The price is AU$243
includes taxes & fees
21 Oct - 22 Oct
Private Entrance Residential Portland
Little Lincoln beautiful home
9.2 out of 10, Wonderful, (12)
"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 AU$416
includes taxes & fees
22 Oct - 23 Oct
Little Lincoln beautiful home
Camp Forever cottage
9.6 out of 10, Exceptional, (56)
"Most enjoyed vacation this year.Location was beautiful. "
United States
Debra S.
The price is AU$422
includes taxes & fees
22 Oct - 23 Oct
Camp Forever cottage
Mid Coast Getaway w/ water views
8.8 out of 10, Excellent, (3)
"You couldn’t ask for a better view, it was everything we had hoped and more."
United States
Andrew S.
The price is AU$334
includes taxes & fees
2 Nov - 3 Nov
Mid Coast Getaway w/ water views
Classic New England 1st Floor 3 BR Downtown Brunswick
9.6 out of 10, Exceptional, (9)
"Nothing beats this location! All parts of town and campus are within walking distance. Host was very communicative and space was super comfortable."
United States
Jeanne P.
The price is AU$582
includes taxes & fees
21 Oct - 22 Oct
Classic New England 1st Floor 3 BR Downtown Brunswick
Escape to Positive Outlook
10.0 out of 10, Exceptional, (1)
"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 AU$374
includes taxes & fees
26 Oct - 27 Oct
Escape to Positive Outlook
Peaceful & minutes from the Old Port with private parking
9.8 out of 10, Exceptional, (7)
"Great little place in south Portland! Close to many parks, lighthouses, and driving distance to downtown. Parking downtown and in the old port area can be tricky and expensive though. "
United States
Christopher R.
The price is AU$385
includes taxes & fees
2 Nov - 3 Nov
Peaceful & minutes from the Old Port with private parking
Beautiful 1st Floor Apartment & Amazing Shower
9.0 out of 10, Wonderful, (24)
"My brother in law and I stayed here while my husband was hospitalized at the Maine Med and it was a lovely property. Everything was clean and organized, check in was easy and the hosts were responsive and kind. I would stay here again!"
United States
Lillian L.
The price is AU$276
includes taxes & fees
10 Nov - 11 Nov
Beautiful 1st Floor Apartment & Amazing Shower
Kayaker's and Land Lubber’s Dream Delight
The price is AU$652
includes taxes & fees
20 Oct - 21 Oct
Kayaker's and Land Lubber’s Dream Delight
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.
Save an average of 15% on thousands of hotels when you're signed in

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$231 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. 

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 23 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?

Ragged Island and Mackerel Cove 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.