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Compare 198 Apartments in Bailey Island with updated reviews, rates, and availability.

Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Living area

Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants

9.8 out of 10, Exceptional, (101)
"So happy that I did not pass this one up...the home was gorgeous, comfortable, close to the water, and exactly what was listed. Nick was very responsive, honest, and answered my many questions. Our family's first visit to Portland to celebrate with my daughter for her white coat ceremony at UNE was one to remember. From waking up early to get some Holy Donuts, cheering on the local hockey team, meeting a wonderful florist, walking next to the ocean, and having an owl in the tree right outside...
The price is AED 558
AED 1,610 total
includes taxes & fees
7 Jan - 8 January 2025
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Cozy West End apartment minutes from the Old Port
Private kitchen

Cozy West End apartment minutes from the Old Port

10.0 out of 10, Exceptional, (4)
"Enjoyed staying in the west end again. "
The price is AED 448
AED 813 total
includes taxes & fees
5 Jan - 6 January 2025
Cozy West End apartment minutes from the Old Port
Incredible Location! Heart of Old Port|Roomy Condo

Incredible Location! Heart of Old Port|Roomy Condo

10.0 out of 10, Exceptional, (24)
"We stayed here for a weekend in November and had a fabulous time. This place is located right in the heart of everything. The condo was immaculate and everything was perfect. Highly recommend staying here if you want to be right in the heart of the city!"
Incredible Location! Heart of Old Port|Roomy Condo
Bright & Sunny West End Apartment with Private Parking.
Dining

Bright & Sunny West End Apartment with Private Parking.

9.8 out of 10, Exceptional, (21)
"Our stay at the cozy West End apartment was fairly comfortable. It was very clean. The beds were very comfortable. This apartment is better suited to a family who lives together as one bedroom access is through the main bedroom. There is no kitchen. A Keurig and small refrigerator and dishes for takeout so plan on eating most meals out. "
The price is AED 650
AED 1,157 total
includes taxes & fees
5 Jan - 6 January 2025
Bright & Sunny West End Apartment with Private Parking.
2 Bedroom Downtown Portland
Screenshot 2024-06-18 at 8.51 (1)

2 Bedroom Downtown Portland

2.0 out of 10, (3)
"I felt like I paid to stay in a homeless urinal. The worst place ever."
The price is AED 343
AED 799 total
includes taxes & fees
2 Jan - 3 January 2025
2 Bedroom Downtown Portland
1 room luxury ocean front studio cottage
Terrace/patio

1 room luxury ocean front studio cottage

9.6 out of 10, Exceptional, (149)
"Very clean, amazinv views, perfect weekend!!!! "
1 room luxury ocean front studio cottage
Upscale large 3 bedroom unit within walking distance to everything!
Room

Upscale large 3 bedroom unit within walking distance to everything!

10.0 out of 10, Exceptional, (11)
"We came to Portland to visit our daughter and had a delightful stay. The apartment is exactly as pictured and was very clean and cute. The linens were luxurious and the beds were very comfortable. If you or someone in your group has mobility issues, the stairs going up to the unit were quite steep. We had two seniors in our group that required some help getting up and down. The location of this property is very convenient to the waterfront, and we were always able to find a close parking...
Upscale large 3 bedroom unit within walking distance to everything!
East end. Walk to food, beer and downtown fun.

East end. Walk to food, beer and downtown fun.

9.8 out of 10, Exceptional, (23)
"Our host was an excellent, prompt communicator. He even offered information about things to do in the area. He was very clear about expectations about our stay which at first was a little off-putting. Cooking no greasy food seemed a little much and had us wondering what was allowed. The property was well stocked and as described including the slanted floor. We weren’t aware at booking that parking was only on the street. That would have been nice to know. It’s a 20 minute walk to downtown which...
East end. Walk to food, beer and downtown fun.
Charming West End Hideaway. Private Parking
Room

Charming West End Hideaway. Private Parking

10.0 out of 10, Exceptional, (23)
"Jens place had everything we needed for a great weekend getaway. Very Comfortable and location location location!"
The price is AED 503
AED 893 total
includes taxes & fees
8 Jan - 9 January 2025
Charming West End Hideaway. Private Parking
The Portland Getaway
Private kitchen

The Portland Getaway

9.6 out of 10, Exceptional, (20)
"This property is well maintained and very clean . Host was easy to communicate with and it was well stocked with basic needs. "
The Portland Getaway
WestEnd Large Penthouse walk to Old Port w/Parking
Master bedroom with queen bed with sitting area and desk.

WestEnd Large Penthouse walk to Old Port w/Parking

10.0 out of 10, Exceptional, (10)
"What a perfect location and cozy home for our family to stay while we were in town for our niece’s baby shower! There was plenty of room for all of us and it was so much better than having to stay in a hotel. "
WestEnd Large Penthouse walk to Old Port w/Parking
Beautiful Studio in downtown Boothbay Harbor
Living area

Beautiful Studio in downtown Boothbay Harbor

9.4 out of 10, Exceptional, (6)
"Very cozy comfortable and convenient. Every thing we needed. "
Beautiful Studio in downtown Boothbay Harbor
Harborview - Curated East End Escape w/ Parking
Dining

Harborview - Curated East End Escape w/ Parking

10.0 out of 10, Exceptional, (1)
"We had such a good time! The apartment was beautifully decorated. The beds were comfortable. The view was fantastic and we easily walked everywhere. We had all the amenities needed. We will definitely recommend it to friends. Thank you again."
The price is AED 1,275
AED 2,166 total
includes taxes & fees
1 Jan - 2 January 2025
Harborview - Curated East End Escape w/ Parking
Oceanfront escape with deck, views of Lobster Cove & firepit - walk to town

Oceanfront escape with deck, views of Lobster Cove & firepit - walk to town

9.8 out of 10, Exceptional, (24)
"It was just as advertised. Nice ,clean and very comfortable! I would love to stay here again !"
Oceanfront escape with deck, views of Lobster Cove & firepit - walk to town
Historic Boothbay Harbor cottage with antique decor, washer/dryer & deck

Historic Boothbay Harbor cottage with antique decor, washer/dryer & deck

9.2 out of 10, Wonderful, (86)
"Great place, quiet despite being close to two businesses. Could not ask for a better location for Boothbay Harbor exploration. Well appointed, cozy and clean. Bathroom and kitchen could use an upgrade. Nothing technically wrong, very clean, just old."
Historic Boothbay Harbor cottage with antique decor, washer/dryer & deck
2 Bedroom Apartment on Top Floor in Portland's West End
Living area

2 Bedroom Apartment on Top Floor in Portland's West End

9.8 out of 10, Exceptional, (58)
"We had a seamless check in process, even arriving a bit early. There was a gorgeous welcome basket waiting for us with a full binder of recommendations and things to do during our stay. The apartment is even bigger in person than what is shown in the photos. The deck is gorgeous and spacious. I will definitely stay here again when visiting Portland! "
2 Bedroom Apartment on Top Floor in Portland's West End
King Size Sun Rise Midcoast Lovely Stay
Dining

King Size Sun Rise Midcoast Lovely Stay

9.8 out of 10, Exceptional, (10)
"Clean and neat"
The price is AED 312
AED 671 total
includes taxes & fees
8 Jan - 9 January 2025
King Size Sun Rise Midcoast Lovely Stay
Inviting apartment with full kitchen, porch, convenient location, & fast WiFi

Inviting apartment with full kitchen, porch, convenient location, & fast WiFi

6.8 out of 10, (5)
"Total mess in the entryway, stair was extremely tight. "
Inviting apartment with full kitchen, porch, convenient location, & fast WiFi
Beautiful 1st Floor Apartment & Amazing Shower
Living area

Beautiful 1st Floor Apartment & Amazing Shower

8.8 out of 10, Excellent, (17)
"The location was perfect. Easy to walk anywhere! My partner and I rented bikes from the city supplied bike service—they were 800ft away! Also ate at several places within a 10 minute walk. Our host was VERY kind and hospitable. Book this place."
The price is AED 280
AED 605 total
includes taxes & fees
7 Jan - 8 January 2025
Beautiful 1st Floor Apartment & Amazing Shower
Brand new guest apartment with furnished deck, fast WiFi, dock, & water views

Brand new guest apartment with furnished deck, fast WiFi, dock, & water views

10.0 out of 10, Exceptional, (26)
"This was a nice place to stay while exploring the area. I would suggest some kind of window treatment. The road runs at the same level of the windows fairly close. Even Shutters on the bottoms of the side. The place was equipped except for a cutting board and coasters. The owners are very close by and to access the water you have to walk in front of their house. a little awkward. "
Brand new guest apartment with furnished deck, fast WiFi, dock, & water views
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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Other property types in Bailey Island

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
THE GILLS GROUP has two additional cottages available for larger groups

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

10.0 out of 10, Exceptional, (99)
"This property is stunning, and the view is spectacular. If this were my house, I’d never leave! We had a fabulous time. "
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Outdoor spa tub

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

9.2 out of 10, Wonderful, (30)
"We had a great time. Nate made check in/check out very easy and the location is great. Would recommend staying here!"
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces

Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces

8.4 out of 10, Very Good, (41)
"GORGEOUS house and view! Very spacious and accommodating. Things you should know before booking is that it is about an hour away from anything and everything. House could use some more TV's if you're going with children, pinball machines did not work and neither did "workout equipment" which was an elliptical and treadmill. One of the showers did not work and some of the fans that were provided did not either. I think its a tad over priced for its distance to do things but the views from...
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces
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.

Frequently asked questions

What's it like to stay at an apartment in Bailey Island?
You can choose from 5 apartments in Bailey Island for your stay.
How do you know if an apartment is a good option for you?
An apartment comes equipped with a kitchen, so you can cook some of your meals, and usually is more spacious than a traditional hotel room. Apartments are a good option for couples looking to stay away from the tourist areas, but also for families wanting the conveniences of home.
What's a favorite apartment for my stay in Bailey Island?
Below are some of the top apartments in the area: Incredible Location! Heart of Old Port|Roomy Condo: Situated in Portland, 14.1 mi/22.7 km from the heart of Bailey Island. Includes free WiFi and Smart TVs. Glorious getaway on Portland’s Eastern Promenade.: Located 13.5 mi/21.7 km away in Portland. Free WiFi, separate dining areas, and Smart TVs are included. 1 room luxury ocean front studio cottage: 3.1 mi/5 km away in Harpswell. Outdoor space and sofa beds are included. Inviting apartment with full kitchen, porch, convenient location, & fast WiFi: Located in Portland, 14.7 mi/23.7 km from Bailey Island. Includes sofa beds. Access to a water park is available on site.
How many apartments should I expect to find in Bailey Island?
Expedia has 5 apartments to book in Bailey Island.
What will the weather be like when I travel to Bailey Island?
Weather is only one factor, but it can really affect your travel plans, especially if you’re planning an extended stay in Bailey Island. The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Bailey Island are January, March, February, and December, with each month seeing an average of 7 inches of snowfall.
What are the must-see places to visit 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's the best way to get to and around Bailey Island?
Knowing a bit about the transportation options can you save you a headache when you get to your destination. Fly into Portland Intl. Jetport Airport (PWM), which is located 17 mi (27.3 km) from the city center. Otherwise, you can search for flights to Wiscasset, ME (ISS), which is 21.1 mi (33.9 km) away. If you’d like to venture out around the area, you may want to rent a car for your trip.