Bailey Island Holiday Rentals

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Holiday Rentals in Bailey Island

Holiday Home in Bailey Island

10.0 out of 10, Exceptional, (234)
"Tremendous stay, great property and host."
United States
Curtis G.
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Aparthotel in Downtown Portland

4.5 star property
9.8 out of 10, Exceptional, (88)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
The price is AU$449
includes taxes & fees
16 Dec - 17 Dec
The Weldon Hotel

Apartment in West Bayside

5.8 out of 10, (7)
"We didn't stay there at all. Canceled reservation "
United States
Dianne
The price is AU$215
includes taxes & fees
15 Dec - 16 Dec
Studio Unit Walkable Everywhere

Apartment in Deering Center

9.2 out of 10, Wonderful, (5)
"Great location for seeing the Portland Head Lighthouse. Comfortable bed."
United States
Michelle S.
Private Entrance Residential Portland

Holiday Home in Boothbay Harbor

10.0 out of 10, Exceptional, (20)
"We loved our stay in Boothbay. The cottage was clean and comfortable, location was ideal, easy walk into town and to the park. Everything was fantastic, would highly recommend. "
United States
Emma D.
Enjoy spectacular views of Lobster Cove. Large yard, EV charger & dog friendly.

Holiday Home in Georgetown

9.8 out of 10, Exceptional, (44)
"Amazing views and good location "
United States
Adriana R.
Oceanfront Cabin-Castle in Maine Woods

Cottage in Long Island

10.0 out of 10, Exceptional, (7)
"Great island house! Loved how stocked the kitchen was, we had comfortable beds and even beach chairs and cooler. We would definitely stay here again. "
United States
Serra C.
Updated Long Island Maine Cottage

Holiday Home in East Deering

10.0 out of 10, Exceptional, (66)
"Nice stay. Good amenities. "
United States
Laura H.
The price is AU$1,645
includes taxes & fees
7 Dec - 8 Dec
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Apartment in Harpswell

9.6 out of 10, Exceptional, (170)
"Very clean beautiful view we definitely enjoyed ourselves "
United States
Ilona F.
1 room luxury ocean front studio cottage

Holiday Home in Falmouth

8.8 out of 10, Excellent, (6)
"We had a wonderful stay. Nice comfortable camp. We enjoyed swimming in the lake. "
United States
Darcie B.
Charming 2-bedroom house with AC, WiFi in lovely Falmouth

Holiday Home in Munjoy Hill

9.8 out of 10, Exceptional, (6)
"Clean, comfortable. "
United States
Nick P.
The price is AU$1,282
includes taxes & fees
7 Dec - 8 Dec
Spacious 4-bedroom house located in the heart of Portland, ME.

Apartment in West Bayside

8.6 out of 10, Excellent, (16)
"Host was very accommodating. Apartment worked well for. Description accurate. Would stay again."
United Kingdom
Martha F.
The price is AU$239
includes taxes & fees
15 Dec - 16 Dec
In-town no frills 2 bedroom apt

Holiday Home in Harpswell

9.4 out of 10, Exceptional, (23)
"We loved our stay! Gorgeous view, lots of thoughtful little amenities. The home was extremely clean and the host was just lovely. "
United States
Catherine O.
Beautiful Oceanfront House- Stunning Water Views

Holiday Home in Munjoy Hill

10.0 out of 10, Exceptional, (93)
"Beautiful house in great area."
United States
Amber W.
The Globe House on Munjoy Hill - Walk to Breweries

Apartment in Parkside

8.8 out of 10, Excellent, (25)
"peaceful apartment. located near great restaurants. walk to town. "
United States
NATHAN F.
The price is AU$428
includes taxes & fees
8 Dec - 9 Dec
Knock on Wood | Airy Charm in Heart of Downtown

Condo in Munjoy Hill

9.8 out of 10, Exceptional, (52)
"Excellent stay and location"
United States
David M.
The price is AU$563
includes taxes & fees
1 Jan - 2 Jan 2026
Cozy, Elegant and Bright 2 bed in the East End

Holiday Home in Back Cove

9.2 out of 10, Wonderful, (19)
"Wonderful view, great park, spacious home, well-appointed... all the things you wish for in a Maine vacation!"
United States
Ben M.
Beautiful, single story ranch. Next to city park with ocean view!

Cottage in Phippsburg

9.8 out of 10, Exceptional, (69)
"It was everything we hoped for!"
United States
Kate L.
Popham Beach Direct Oceanfront Cottage Steps to the sand

Condo in Downtown Portland

9.6 out of 10, Exceptional, (21)
"We loved the walkable neighborhood & had a great, comfortable stay!"
United States
Erin R.
The price is AU$587
includes taxes & fees
9 Dec - 10 Dec
Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo

Holiday Home in Portland

9.8 out of 10, Exceptional, (22)
"Excellent home overall! Great equipment, great kitchen, great pool, nice patio! Easy access to the home and driveway! Probably the best house I’ve stayed in ! "
United States
Justin J.
Back yard paradise
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 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$215 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?

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.