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, (38)
"Quiet peaceful great accommodations and wonderful host"
The price is NZ$229
per night
5 Jun - 6 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 NZ$555
per night
5 Jun - 6 Jun
Full sized home
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, (45)
"The kitchen was very well equipped. Living room was so cozy with the fire. Bed was super comfortable. The unit has really tall ceilings and is cozy. Only issue was the dog upstairs. They kept barking and whining."
The price is NZ$766
per night
16 Jun - 17 Jun
Elegant condo - walk to Portland's best restaurants & Old Port
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 NZ$611
per night
10 Jun - 11 Jun
Walk Everywhere! Entire Downtown Apt - "La Maison"
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
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, (44)
"We had a great stay. Check in and communication was easy. Due to storm damage, our original booked cottage was not available and Deb offered us a different (much larger) home without added cost. We greatly appreciated it so we didn't have to cancel our vacation. The home was very clean and had everything we needed and then some. The area is beautiful and the beach was very clean. You cannot beat the views from the home. We look forward to staying here again!"
Popham Beach Direct Oceanfront Cottage Steps to the sand
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
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
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)
"Just got back to NYC after spending 3 nights at the house with my dog. I already miss it. It's practically on top of the water, and sits in a very private, quiet and secluded location on a heavily wooded lot. It's a bit off the beaten path, but still a relatively short drive (10-30 mins, depending) to anywhere within the Harpswell/Brunswick area. Comfortable bed and furniture. The outdoor furniture seemed brand new (Adirondack chairs). It's a very cozy house that's perfect - even spacious - for...
Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.
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, (23)
"Beautiful home that is a great proximity to Boothbay Harbor downtown. The pond is very nice but the water level was very low during our stay in March and there were no boats available as described in the listing. It is unclear whether this is something to note for all offseason travelers"
Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe
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, (19)
"Everything about our stay was wonderful ~ Host was amazing, condo was so nice & location was perfect."
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
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 NZ$706
per night
11 Jun - 12 Jun
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
Cozy, Elegant and Bright 2 bed in the East End
Smart TV
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.."
The price is NZ$593
per night
10 Jun - 11 Jun
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, (73)
"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)
"We very much enjoyed our stay at this location. The stairs were a bit scary, but with the light on, you'll be fine. :) Cozy spot for the three of us, well appointed and in a fantastic area. Very walkable, even down to the wharf. We are from a very non-walkable area, so it was amazing to see all the activity and places we could go just walking a bit. We enjoyed our first time in Maine, and can't wait to get back for a longer trip. Thanks to the hosts!"
The price is NZ$1,044
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
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, (1549)
"No complaints. Reception was nice and check in was fast and easy. The room was clean and bed were comfortable. "
The price is NZ$174
per night
9 Jun - 10 Jun
Casco Bay Hotel, Ascend Hotel Collection
Portland Harbor Hotel
Honeymoon Suite, 1 King Bed
Portland Harbor Hotel
4.0 star property
9.0 out of 10, Wonderful, (1190)
"Second time staying here… and both times were delightful. "
The price is NZ$462
per night
9 Jun - 10 Jun
Portland Harbor Hotel
Canopy by Hilton Portland Waterfront
Bar (on property)
Canopy by Hilton Portland Waterfront
4.0 star property
9.4 out of 10, Exceptional, (659)
"Stayed a couple of days. Valet was actually excellent, quick, and efficient. The guys doing valet were auper on it and friendly. Check in was very easy. Roman and Alicia at the front desk were great, providing us with amazing service. I will say, the room was not the cleanest. Dog hair was all over, and there was a lot of dust on the very cute wooden walls. Baseboards in our room really needed help. So, yeah, like a 3 on cleanliness, because my allergies were off the wall! But the rooms are...
The price is NZ$609
per night
9 Jun - 10 Jun
Canopy by Hilton Portland Waterfront
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Bailey Island holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Bailey Island. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Bailey Island. Seeing all the best attractions is bound to make you fall in love with Bailey Island. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Bailey Island short-term rentals, that won’t be hard to do.

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

Inn at St John Portland In-Town

Inn at St John Portland In-Town

5/5 Excellent
"Nice place "
A verified traveller from Leicester stayed at Inn at St John Portland In-Town
Posted 2 days ago
Inn at St John Portland In-Town