Bailey Island Holiday Rentals

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Holiday Rentals in Bailey Island

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

10.0 out of 10, Exceptional, (226)
"We had a wonderful stay at this cottage. Great location to explore the surrounding areas."
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (76)
"Absolutely beautiful place to stay. "
The price is AU$623
includes taxes & fees
23 Sept - 24 Sept
The Weldon Hotel

Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

2.0 star property
10.0 out of 10, Exceptional, (2)
"The property was as described, clean, and in a quiet neighborhood. Conveniently located to many local attractions. Check in and check out process was smooth. Overall enjoyed my stay very much. "
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!

8.0 out of 10, Very good, (15)
"Clean, well maintained, slighly funky in an historical way . Very convenient to great breakfast spots and downtown Bath. Would stay there again."
The price is AU$254
includes taxes & fees
30 Sept - 1 Oct
Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!

Studio Unit Walkable Everywhere

8.0 out of 10, Very good, (2)
"Great, comfortable place to stay. The location is super walkable. There are several bars/restaurants very close, and other areas are close enlighten to walk to as well (I.e. Congress Street). Commercial is a bit of a walk, but if you’re like us and love to walk a new area. It’s not that far. The bed is comfortable and the place was very clean. Communication was great. We would stay here again!"
The price is AU$277
includes taxes & fees
8 Sept - 9 Sept
Studio Unit Walkable Everywhere

Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room

10.0 out of 10, Exceptional, (52)
"Cozy spot on a beautiful beach - hard to beat!"
Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room

Captain's Quarters 2BR Apartment. Walk to Everything!

8.6 out of 10, Excellent, (7)
The price is AU$403
includes taxes & fees
24 Sept - 25 Sept
Captain's Quarters 2BR Apartment. Walk to Everything!

Oceanfront Cabin-Castle in Maine Woods

9.8 out of 10, Exceptional, (32)
"Place was amazing with an incredible view and fun layout. "
Oceanfront Cabin-Castle in Maine Woods

Full sized home

9.8 out of 10, Exceptional, (37)
"The house was lovely. Very comfortable place. Within 15- 20 mins to a store or restaurants."
The price is AU$572
includes taxes & fees
15 Sept - 16 Sept
Full sized home

Your own private island! Rustic and close to Nature.

9.4 out of 10, Exceptional, (33)
"wonderful place, glamping, wildlife all around, you can't but enjoy the beauty of Mid Coast Maine. Thanks for sharing your island with all of us !"
Your own private island! Rustic and close to Nature.

In-town no frills 2 bedroom apt

8.0 out of 10, Very good, (8)
"The frills of the neighborhood carried into the apartment. Floors and bathrooms seemed clean. Dishes and Keurig filthy - broken window a/c on floor. Broken chairs. No tlc for the property. Neighborhood beyond the stated description- would not recommend . Best to say is that rental car made it out with all windows and tires. Very disappointed "
The price is AU$280
includes taxes & fees
15 Sept - 16 Sept
In-town no frills 2 bedroom apt

Private Entrance Residential Portland

9.0 out of 10, Wonderful, (4)
"Check in was simple. Quaint place. "
The price is AU$257
includes taxes & fees
6 Sept - 7 Sept
Private Entrance Residential Portland

Camp Forever cottage

9.6 out of 10, Exceptional, (52)
"Great stay. My husband and I were there for 4 days. Peaceful and quiet. Lovely views. Just perfect for the two of us. Short drive to area sites, businesses and restaurants."
The price is AU$434
includes taxes & fees
1 Oct - 2 Oct
Camp Forever cottage

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

10.0 out of 10, Exceptional, (61)
"Very clean, lots of room for gathering. Perfect location on a quiet street with great views of the lake. Plenty of towels, bedding, water, etc. Would come back!"
The price is AU$1,704
includes taxes & fees
8 Sept - 9 Sept
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C

10.0 out of 10, Exceptional, (103)
"Adorable place, roomy, quiet, upscale yet felt just like home. Will definitely stay again! "
Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C

Spacious Historic Home | 7BR West End for Groups

10.0 out of 10, Exceptional, (5)
"Seven of us stayed at this beautiful home in a perfect location by the Western Promenade. Everyone had a comfortable bed, bathrooms and showers were plentiful, and the kitchen was perfectly appointed. Both cars we had fit into the garage (an added luxury). The beds were very comfortable and had soft sheets and fluffy towels. We loved every minute of our stay and made great use of the family room. Can't thank our hosts enough...very easy to work with and I would certainly rent from them again...
The price is AU$2,469
includes taxes & fees
7 Sept - 8 Sept
Spacious Historic Home | 7BR West End for Groups

Updated Long Island Maine Cottage

10.0 out of 10, Exceptional, (6)
"Great location. Comfortable living room. Well stocked kitchen. Great communication with owner."
Updated Long Island Maine Cottage

Century-old oceanfront home with wraparound porch - walk downtown, dogs OK

8.8 out of 10, Excellent, (38)
"This was our second stay here. We love the comfort of this home and the location is perfect."
Century-old oceanfront home with wraparound porch - walk downtown, dogs OK

Large, light filled 4 bedroom house - walk to ocean and ferry

10.0 out of 10, Exceptional, (34)
"I stayed here for a weekend with a group of friends and it was a dream! So lovely!"
Large, light filled 4 bedroom house - walk to ocean and ferry

Walkable near downtown 1 Bedroom

6.0 out of 10, (1)
The price is AU$278
includes taxes & fees
10 Sept - 11 Sept
Walkable near downtown 1 Bedroom
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

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$254 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 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?

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.