Bailey Island Holiday Rentals

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Holiday Rentals in Bailey Island

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Property grounds
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
10.0 out of 10, Exceptional, (94)
"We celebrated our Mom’s 70th birthday in this beautiful space. It exceeded our expectations and the property manager David is the best!"
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Fridge, microwave, oven, stovetop
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces
TV, fireplace
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces
8.8 out of 10, Excellent, (33)
"Great views. House pretty clean & supplies were fine except only 3 coffee cups for 6 adults. VACasa said they would get more cups. They failed, never received. Some lights didn't work & lots of dead bugs in light fixtures."
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces
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Quaint one-bedroom suite
1 bedroom, WiFi
Quaint one-bedroom suite
9.8 out of 10, Exceptional, (39)
"Super convenient in a quiet riverfront neighbor. Easy to connect with owner, check in and out. Private. Good for quiet couple enjoying a restful evening!"
The price is HK$1,172
per night
19 Jun - 20 Jun
Quaint one-bedroom suite
Full sized home
Fridge, microwave, oven, stovetop
Full sized home
9.6 out of 10, Exceptional, (4)
"Great place to stay. Host was helpful and responsive."
The price is HK$1,953
per night
19 Jun - 20 Jun
Full sized home
Unique oceanfront home with a deck, tons of natural light, & amazing views
Interior
Unique oceanfront home with a deck, tons of natural light, & amazing views
8.8 out of 10, Excellent, (43)
"We needed a quiet place to visit with elderly aunt and uncle. This was a great place with all the living space on the same floor with spacious area to visit."
Unique oceanfront home with a deck, tons of natural light, & amazing views
Walk Everywhere! Entire Downtown Apt - "La Maison"
Property grounds
Walk Everywhere! Entire Downtown Apt - "La Maison"
10.0 out of 10, Exceptional, (7)
"Good location for walking to Portland destinatons. Parking was a bit challenging. Nice apartment for 4 people. Clean, comfortable beds."
The price is HK$1,603
per night
18 Jun - 19 Jun
Walk Everywhere! Entire Downtown Apt - "La Maison"
Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.
Smart TV, books
Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.
9.8 out of 10, Exceptional, (27)
"We spent our 19th wedding anniversary here. It was the perfect romantic getaway. The views are stunning and the location is tranquil. Just a short drive to the general store for necessities, and Uber Eats delivers. We didn’t want to leave. Would 100% stay here again."
Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.
Popham Beach Direct Oceanfront Cottage Steps to the sand
View from property
Popham Beach Direct Oceanfront Cottage Steps to the sand
10.0 out of 10, Exceptional, (47)
"Beautiful place. Everything just as listed. Thank you."
Popham Beach Direct Oceanfront Cottage Steps to the sand
Elegant condo - walk to Portland's best restaurants & Old Port
Private kitchen
Elegant condo - walk to Portland's best restaurants & Old Port
9.4 out of 10, Exceptional, (47)
"My two sisters and I loved everything about the place especially the kitchen and the temperature control via AC or heat. The only concern about the place is that it took 1-3 tries each time we had to unlock the front door by code. There was supposed to be music to help but couldn't really hear anything. May need some attention but have to admit we never alerted anyone at the time thinking it was related to our ineptitude! I tried to do this review on the Vacasa site but the page never came up...
The price is HK$1,648
per night
18 Jun - 19 Jun
Elegant condo - walk to Portland's best restaurants & Old Port
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
Property grounds
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
10.0 out of 10, Exceptional, (20)
"This apartment is fantastic! Great location, perfectly appointed, and Dena was awesome with her communications. The roof deck is a great bonus."
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
Vintage, Log Cabin in the Woods with Beach Club Access About One Mile Away
Property grounds
Vintage, Log Cabin in the Woods with Beach Club Access About One Mile Away
8.0 out of 10, Very good, (32)
"We really enjoyed our stay at this cabin. Authentic vintage experience! Off course, if your are looking for a neet and sophisticate lodding, it might not be the place for you… but it was perfect for us! Very well located, near a private beach with 2 kayaks and chairs for our convinience. Also very near to the action of Boothbay Harbor that was a nice discorery! The cabin is very confortable, with everything we needed to prepare a nice meal and relax at anytime of the day. The only thing that...
Vintage, Log Cabin in the Woods with Beach Club Access About One Mile Away
Ocean view Victorian
Aerial view
Ocean view Victorian
9.8 out of 10, Exceptional, (73)
"It was the best view of Casco Bay and such a unique home. Beautiful accommodations that are both historic yet updated for comfort and convenience. Our host was phenomenal! So friendly…we thought he was one of our neighbors from Louisiana (not just because of his homemade hot sauce that he sent home with us, but more importantly because of his hospitality!)"
Ocean view Victorian
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
Fridge, microwave, oven, stovetop
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
8.8 out of 10, Excellent, (20)
"Clean and easy to access, nice property for a short stay. Easy communication."
The price is HK$1,437
per night
1 Jul - 2 Jul
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Private kitchen
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
9.8 out of 10, Exceptional, (89)
"Six of us stayed for our daughter's graduation. Nicely appointed property! We were able to walk to dinner, and it was a short drive to our other activities. Highly recommend!"
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Cozy, Elegant and Bright 2 bed in the East End
Fridge, microwave, oven, stovetop
Cozy, Elegant and Bright 2 bed in the East End
10.0 out of 10, Exceptional, (27)
"I had an unexpected death in the family. Unfortunately could not make the trip.. John was a great communicator.. hopefully we can try again another time.. I would try with John again.."
Cozy, Elegant and Bright 2 bed in the East End
Luxe Bayfront Cabin w/ Stunning Views & Shared Dock- Ideal for Hunting & Fishing
Fridge, microwave, oven, stovetop
Luxe Bayfront Cabin w/ Stunning Views & Shared Dock- Ideal for Hunting & Fishing
9.4 out of 10, Exceptional, (74)
"A simple yet comfortable cabin with beautiful view of tidal river."
Luxe Bayfront Cabin w/ Stunning Views & Shared Dock- Ideal for Hunting & Fishing
Completely remodeled 2 bedroom apartment in Portland's West End
Exterior
Completely remodeled 2 bedroom apartment in Portland's West End
10.0 out of 10, Exceptional, (36)
"This home is at such a great location. It was so easy to walk to great restaurants, shops, and other points of interest. The building is a charming townhouse on a pretty street and the interior is well- appointed, neat and clean. All the essentials plus some extras were supplied, from coffee to personal care items. Having dedicated parking was key. We very much appreciated how responsive the hosts were. They promptly answered questions and made sure we had everything we needed for a great stay."
The price is HK$2,961
per night
3 Jul - 4 Jul
Completely remodeled 2 bedroom apartment in Portland's West End
Oceanfront escape with deck, views of Lobster Cove & firepit - walk to town
Fridge, microwave, oven, stovetop
Oceanfront escape with deck, views of Lobster Cove & firepit - walk to town
10.0 out of 10, Exceptional, (13)
"My husband and I stayed two nights, arriving late in the afternoon. We had no difficulty finding or getting into the property. The place was clean and the bed was comfortable. We were out doing things in the area most of the time, but did enjoy a slow, quiet morning and loved being able to walk to the nearby park and enjoy the view. We were also in the apartment early one evening because of light rain, just reading and checking emails, etc., and missed the basics for preparing our own food....
Oceanfront escape with deck, views of Lobster Cove & firepit - walk to town
Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe
TV, fireplace, books, stereo
Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe
9.4 out of 10, Exceptional, (24)
"What a great stay. Our first time in Maine, and New England and so glad we had this location. Booth bay is the “just right” costal town to stay in. 5 minutes from the harbor, so much to do locally, and the home was great. The property stole the show, though. The water, deck, dock, fire pit, grill, the trees! All so great. The house is large and well equipped, but could use some updating, better humidity control, and AC. Highly recommend."
Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe
Don't see what you're looking for?
See all available properties in Bailey Island
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.

Other types of properties in Bailey Island you may be interested in

Casco Bay Hotel, Ascend Hotel Collection
Lobby
Casco Bay Hotel, Ascend Hotel Collection
3.5 star property
8.6 out of 10, Excellent, (1618)
"A great place to stay. Clean and comfortable rooms, great breakfast included. "
The price is HK$907
per night
23 Jun - 24 Jun
Casco Bay Hotel, Ascend Hotel Collection
The Westin Portland Harborview
Water view
The Westin Portland Harborview
4.0 star property
8.6 out of 10, Excellent, (1051)
"All staff we encountered were incredibly kind and helpful. Beautiful, clean and well-located hotel."
The price is HK$2,054
per night
23 Jun - 24 Jun
The Westin Portland Harborview
Portland Harbor Hotel
Premium bedding, desk, blackout curtains, iron/ironing board
Portland Harbor Hotel
4.0 star property
9.0 out of 10, Wonderful, (1205)
"Gorgeous garden. Good food."
The price is HK$2,272
per night
1 Jul - 2 Jul
Portland Harbor Hotel
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.

Search for holiday rentals in Bailey Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Bailey Island using one of the methods below:

  • View our selection of featured holiday rentals in Bailey Island
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  • Enter your travel dates to view the best deals on holiday rentals in Bailey Island while they last

Look no further and take a look at our great range of rental properties in Bailey Island!

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?

Stunning oceanfront cottage w/ private deck and Atlantic views: This holiday home rental outside of 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 29 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?

Family-friendly attractions include Land's End Gift Shop, whereas Ragged Island is a spot to enjoy the outdoors. 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.

Recent reviews of Bailey Island properties
Expedia verified reviews

La Quinta Inn & Suites by Wyndham Portland

La Quinta Inn & Suites by Wyndham Portland

5/5 Excellent
"It was very nice and convenient for us. "
A verified traveller stayed at La Quinta Inn & Suites by Wyndham Portland
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Portland