Bailey Island Holiday Rentals

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Holiday Rentals in Bailey Island

Sunset Hideaway on Bailey Island

Harpswell
8.0 out of 10, Very good, (4)
"Hubby and I enjoyed our stay. It was nice watching the lobster boats go in and out of the bay every day. I actually did see a dolphin on our second day there but none after that. Getting in and out of the drivers side of our vehicle was a bit rough; as we used our new pick up truck to take on vacation, and there isn't a lot of room between the yard and the railroad tie wall. I'd return though. "
United States
Shirley S.
The price is NZ$418
includes taxes & fees
24 Nov - 25 Nov
Sunset Hideaway on Bailey Island

Orchid Harbor, Bailey Island 3BR

Harpswell
9.8 out of 10, Exceptional, (7)
"We enjoyed our weekend tremendously, especially being right on the beach, with miles of private access to the rocky shores to search for treasures and sea glass! Thank you so much!"
United States
Jason M.
The price is NZ$730
includes taxes & fees
24 Nov - 25 Nov
Orchid Harbor, Bailey Island 3BR

Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome

Boothbay
9.2 out of 10, Wonderful, (69)
"The house was so charming, clean, and comfortable. We couldn’t have found a better place to stay during our visit to the Boothbay area. The Dome House is off the beaten track, right on a tidal river, which made every day and every hour a new private view. Be sure to schedule time to simply be. This is the perfect house for it!"
United States
Lawton S.
The price is NZ$545
includes taxes & fees
17 Nov - 18 Nov
Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome

Solitude @ The Offshore House

Boothbay
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 NZ$530
includes taxes & fees
17 Nov - 18 Nov
Solitude @ The Offshore House

Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Brunswick
10.0 out of 10, Exceptional, (144)
"Lovely space, comfortable bed, very convenient to downtown Brunswick."
United States
Kimberly G.
The price is NZ$211
includes taxes & fees
17 Nov - 18 Nov
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Sunny Spot with Private Parking.

2.0 star property
Knightville
9.8 out of 10, Exceptional, (24)
"Had a great stay here! The place was very clean and well-equipped. Convenient parking and a short drive to Portland center. Would stay here again!"
United States
Emre G.
The price is NZ$317
includes taxes & fees
17 Nov - 18 Nov
Sunny Spot with Private Parking.

Seabed @ The Offshore House

Boothbay
9.8 out of 10, Exceptional, (14)
"A very clean and well appointed property. The attention to detail for every aspect of our stay was impressive. We especially appreciated the guideline booklet that dealt with rules of the house to what to do in Boothbay Harbor. The location was perfect for our puffin cruise. We would totally book again. "
United States
Joan K.
The price is NZ$530
includes taxes & fees
17 Nov - 18 Nov
Seabed @ The Offshore House

Captain's 2BR Quarters. Walk to everything . No fees. Dogs Free'

Bath
8.6 out of 10, Excellent, (10)
"Great location and interesting layout in this historic house. It was the perfect respite for our stay before our puffin tour the next day and close to town for a concert on the common and restaurants. Note : to access one of the bedrooms you need to go through the bathroom, but it worked out fine. Dmitri was super communicative and was kind enough to let us know we left a pair of shoes there after we departed. Since we were still in the area, he left them on the porch for us to retrieve, which...
United States
Erika B.
The price is NZ$288
includes taxes & fees
19 Nov - 20 Nov
Captain's 2BR Quarters. Walk to everything . No fees. Dogs Free'

Modern, Luxurious Cabin in the Woods - 03

Freeport
10.0 out of 10, Exceptional, (6)
"This was a perfect little cabin. It was clean, well equipped with a nice kitchen and bathroom, quiet and wooded location, and comfy bed. "
United States
Chris B.
The price is NZ$412
includes taxes & fees
2 Dec - 3 Dec
Modern, Luxurious Cabin in the Woods - 03

Little Lincoln beautiful home

Brunswick
9.0 out of 10, Wonderful, (13)
"Nice little cottage, lots of sun, great layout, full kitchen which is so important to me, and less than a block to the commercial center! Plenty of parking, easy to unload and load my car, only a step up or two into the property which was perfect for my very small dog. "
United States
Linda B.
The price is NZ$416
includes taxes & fees
17 Nov - 18 Nov
Little Lincoln beautiful home

Stunning Ocean Views, newly renovated cottage-close to preserves, trails, and Harpswell Beaches

Harpswell
10.0 out of 10, Exceptional, (4)
"Beautiful location!! Very comfortable and clean home "
United States
Beth L.
The price is NZ$990
includes taxes & fees
17 Nov - 18 Nov
Stunning Ocean Views, newly renovated cottage-close to preserves, trails, and Harpswell Beaches

Brunswick Downtown Sugar Cube next to Bowdoin

Brunswick
8.4 out of 10, Very good, (7)
"Stayed for one night. Very convenient to campus"
United States
Lin-Lin R.
The price is NZ$466
includes taxes & fees
24 Nov - 25 Nov
Brunswick Downtown Sugar Cube next to Bowdoin

Studio Apartment in Freeport

2.0 star property
Freeport
The price is NZ$261
includes taxes & fees
16 Dec - 17 Dec
Studio Apartment in Freeport

Shipwright @ The Offshore House

Boothbay
9.4 out of 10, Exceptional, (13)
"Room was as advertised. Clean, good location, easy check in/out. The Shipwright room had a cute little kitchenette and sitting area. "
United States
Virginia G.
The price is NZ$530
includes taxes & fees
17 Nov - 18 Nov
Shipwright @ The Offshore House

Studio Apartment near downtown Walkable!

West Bayside
7.6 out of 10, Good, (5)
"The apartment was exactly as advertised: relatively spacious because of all the clear space, with everything needed for someone on a brief visit. The person who rents the apartment went out of his way to be helpful when I contacted him. "
United States
Helaine
The price is NZ$246
includes taxes & fees
17 Nov - 18 Nov
Studio Apartment near downtown Walkable!

Adorable Portland getaway on the Eastern Promenade

Munjoy Hill
9.6 out of 10, Exceptional, (125)
"Welcoming small apartment in a beautiful Portland neighborhood. Clean and stocked with everything we needed. Very helpful hosts. "
United States
Annalise M.
The price is NZ$332
includes taxes & fees
30 Nov - 1 Dec
Adorable Portland getaway on the Eastern Promenade

The Outlet Studio, Rustic Comfort w Fireplace

Freeport
10.0 out of 10, Exceptional, (11)
"Very comfortable and homey Great location to the outlets. "
United States
Patricia C.
The price is NZ$289
includes taxes & fees
17 Nov - 18 Nov
The Outlet Studio, Rustic Comfort w Fireplace

Modern style in historic building in downtown Bath

Bath
10.0 out of 10, Exceptional, (8)
"Urban loft in a great location in the coolest little city in Maine. Highly recommended!!"
United States
Christopher D.
The price is NZ$393
includes taxes & fees
17 Nov - 18 Nov
Modern style in historic building in downtown Bath

Mere Point Sunrise Views at Eastern Shore!

Brunswick
9.8 out of 10, Exceptional, (7)
"Such a beautiful home and peaceful location. We loved our stay and the host was responsive and helpful with any questions we had!"
United States
Diana H.
The price is NZ$730
includes taxes & fees
2 Dec - 3 Dec
Mere Point Sunrise Views at Eastern Shore!

King Size Sun Rise Midcoast Lovely Stay

Topsham
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 NZ$401
includes taxes & fees
23 Nov - 24 Nov
King Size Sun Rise Midcoast Lovely Stay
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 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 NZ$202 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 22 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.