Bailey Island Holiday Rentals

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Our top choices for Bailey Island holiday rentals

Sunset Hideaway on Bailey Island

Sunset Hideaway on Bailey Island
Harpswell
8.0 out of 10, Very good, (4 reviews)
"Wonderful views. Comfortable. "
United States
Susy K.
The price is AU$424
includes taxes & fees
10 June - 11 June
Sunset Hideaway on Bailey Island

Boothbay Harbor, 2-Story Cottage, downtown

Boothbay Harbor, 2-Story Cottage, downtown
Boothbay Harbor
9.4 out of 10, Exceptional, (28 reviews)
"I absolutely LOVED staying here and wished we had booked a longer stay! The cottage was so sweet and nice. It was exceptionally clean. The couch was wonderful and the TV was great. Parking was easy and the cottage was easy to find. It also had a great location. Kitchen was also nice. I loved the upstairs bedroom. The bed and pillows were so comfy! (I actually purchased the same pillows when I got back home). I haven't had a nice rest in a long time. Since we didn't overspend on our lodging, we...
United States
Christine
The price is AU$430
includes taxes & fees
15 June - 16 June
Boothbay Harbor, 2-Story Cottage, downtown

Boothbay Harbor, The Francis Greene House, downtown

Boothbay Harbor, The Francis Greene House, downtown
Boothbay Harbor
9.4 out of 10, Exceptional, (44 reviews)
"We spent three nights at this location, which is just a short walk from the commercial area of Boothbay Harbor. In addition to restaurants in town it is only minutes away from Robinson's Wharf, which had some of the best food we experienced in 14 days of travel - definitely the best lobster. The house was as advertised and suited our needs well."
United States
Terry F.
Boothbay Harbor, The Francis Greene House, downtown

Pond Cabin: Private Sauna+Near Beach+FirePit+Pond

Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
Georgetown
Pond Cabin: Private Sauna+Near Beach+FirePit+Pond

Sweet comfy cottage on Small Point Road

Sweet comfy cottage on Small Point Road
Small Point
9.4 out of 10, Exceptional, (3 reviews)
"Lovely home with plenty of space and seating. Not the most comfortable of beds but we enjoyed the space. Perfect location and would love to stay again. "
United States
Liz J.
The price is AU$783
includes taxes & fees
4 June - 5 June
Sweet comfy cottage on Small Point Road

2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
10.0 out of 10, Exceptional, (3 reviews)
"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$397
includes taxes & fees
7 June - 8 June
2 bedroom w/ expansive water views

Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.4 out of 10, Exceptional, (6 reviews)
"Second time we have stay in this cottage. The perfect location for a Maine vacation. "
United States
chuck c.
The price is AU$341
includes taxes & fees
4 June - 5 June
Mid Coast Getaway w/ water views

Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.8 out of 10, Exceptional, (16 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
Fantastic Waterfront Views

Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath
Bath
9.8 out of 10, Exceptional, (9 reviews)
"Clean comfortable and right downtown"
United States
stephen e.
The price is AU$311
includes taxes & fees
8 June - 9 June
Modern style in historic building in downtown Bath

Award Winning Luxury Carriage House a short stroll from town!

Award Winning Luxury Carriage House a short stroll from town!
Bath
10.0 out of 10, Exceptional, (9 reviews)
"An exceptional property and guest. Would love to stay again next time Thank you Jared and Heather!"
United States
Ronald H.
The price is AU$1,026
includes taxes & fees
9 June - 10 June
Award Winning Luxury Carriage House a short stroll from town!

Captain's Guest Room. The authenticity & value in one place. Walk to everything!

Captain's Guest Room. The authenticity & value in one place. Walk to everything!
Bath
8.2 out of 10, Very good, (21 reviews)
"Great location and a beautiful property. Great walking/driving distance from town and the waterfront, we had a great stay and would do it again! "
United States
Nina P.
The price is AU$200
includes taxes & fees
10 June - 11 June
Captain's Guest Room. The authenticity & value in one place. Walk to everything!

Top floor loft apartment in downtown Bath

Top floor loft apartment in downtown Bath
Bath
9.6 out of 10, Exceptional, (7 reviews)
"Great location!"
United States
James E.
The price is AU$388
includes taxes & fees
9 June - 10 June
Top floor loft apartment in downtown Bath

Captain's House 2BR Apt. Great value, walk to everything, large yard, treehouse.

Captain's House 2BR Apt. Great value, walk to everything, large yard, treehouse.
Bath
8.8 out of 10, Excellent, (11 reviews)
"Clean rooms. Quiet location walkable to much of downtown Bath "
United States
randy k.
The price is AU$324
includes taxes & fees
4 June - 5 June
Captain's House 2BR Apt. Great value, walk to everything, large yard, treehouse.

Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (58 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is AU$511
includes taxes & fees
4 June - 5 June
Camp Forever cottage

Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (60 reviews)
"Great spot to relax and enjoy the beautiful outdoors. Very quiet and amazing views of the water. Everything needed for a comfortable and relaxing getaway. Highly recommend if coming to the area! "
United States
Erin
The price is AU$659
includes taxes & fees
4 June - 5 June
Centerview cottage

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, (151 reviews)
"Such a fabulous stay. The space was bright, clean, and comfortable, and the special touches made it feel even more welcoming. It was larger than expected, and we loved having a mini fridge and coffee machine, perfect for slow mornings or a little wine and cheese at the end of the day. We’d return in a heartbeat."
Canada
Coral
The price is AU$214
includes taxes & fees
17 June - 18 June
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Walk to town, 200yr-old 4BR house adjacent to Bowdoin campus! #2

Walk to town, 200yr-old 4BR house adjacent to Bowdoin campus! #2
Brunswick
The price is AU$658
includes taxes & fees
4 June - 5 June
Walk to town, 200yr-old 4BR house adjacent to Bowdoin campus! #2

Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)

Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
Brunswick
9.6 out of 10, Exceptional, (33 reviews)
" Very spacious, clean and beautiful."
United States
robert p.
The price is AU$598
includes taxes & fees
17 June - 18 June
Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (52 reviews)
"Wonderful stay!"
United States
Erika T.
The price is AU$506
includes taxes & fees
15 June - 16 June
Full sized home

Downtown Brunswick New Look Old Charm Next to Bowdoin

Downtown Brunswick New Look Old Charm Next to Bowdoin
Brunswick
9.8 out of 10, Exceptional, (20 reviews)
"We really enjoyed our visit with family and friends and the location was perfect for what we needed. "
United States
Eliza
The price is AU$435
includes taxes & fees
24 June - 25 June
Downtown Brunswick New Look Old Charm Next to Bowdoin
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$200 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?

Spacious 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 30 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.