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Check prices for these dates

Next weekend
14 Feb - 16 Feb
In two weeks
21 Feb - 23 Feb
In one month
7 Mar - 9 Mar
In two months
4 Apr - 6 Apr

Compare 195 Apartments in Bailey Island with updated reviews, rates, and availability.

Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.

10.0 out of 10, Exceptional, (144)
"This rental is adorable with so many thoughtful touches from the host. From the personalized card and snacks to the labels explaining most everything you'd like to know about the space, everything has been considered. A great base from which to explore a fun town."
The price is AED 364
AED 805 total
includes taxes & fees
4 Feb - 5 Feb
Glorious getaway on Portland's Eastern Promenade.
Fall In Love With Portland!
Living area

Fall In Love With Portland!

9.6 out of 10, Exceptional, (110)
"We had a great time at Nick's apartment, it is spaceous and tastefully furnished. We were able to feel right at home and used the kitchen every day, the dining room had space for all of us which made for some great holiday meals together. The location is nearly unbeatable with just two blocks to the promenade by the water and a short walk to downtown. Congress Street, which is 50 yards from the front door, has a really cool vibe with bars, cafes and restaurants. Yet, you are clearly nestled in a...
The price is AED 731
AED 1,810 total
includes taxes & fees
4 Feb - 5 Feb
Fall In Love With Portland!
Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade

9.8 out of 10, Exceptional, (93)
"Perfect location. Wonderful accommodations"
The price is AED 320
AED 649 total
includes taxes & fees
4 Feb - 5 Feb
Adorable Portland getaway on the Eastern Promenade
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
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, (5)
"Fantastic hosts and a great place to stay!"
The price is AED 448
AED 821 total
includes taxes & fees
4 Feb - 5 Feb
Cozy West End apartment minutes from the Old Port
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, (102)
"This apartment on Munjoy Hill was very comfortable for 3 generations to spend the holidays together. It allowed for visits with friends since my mom is not very mobile these days. We got to spend some time enjoying our old neighborhood and all that it offers, including a growing number of restaurants and bars!"
The price is AED 731
AED 1,810 total
includes taxes & fees
4 Feb - 5 Feb
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Charming West End Hideaway. Private Parking
Room

Charming West End Hideaway. Private Parking

10.0 out of 10, Exceptional, (24)
"Communication with the owner was seamless and there were no details missed. The location was perfect for going out and also great if you're looking to shop. The apartment was clean and adorable with a little private balcony. Would definitely stay again!"
The price is AED 360
AED 713 total
includes taxes & fees
4 Feb - 5 Feb
Charming West End Hideaway. Private Parking
Completely remodeled 2 bedroom apartment in Portland's West End
Living area

Completely remodeled 2 bedroom apartment in Portland's West End

10.0 out of 10, Exceptional, (60)
"We had a very nice stay in this apartment. I would definitely recommend it to others. The owners were friendly and it was easy to get into the unit. The only drawback for anyone who's not quite so agile is the steep staircase to get to the bedrooms. It worked out fine for our family of four, so I just list this for anyone with mobility issues."
Completely remodeled 2 bedroom apartment in Portland's West End
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
The Portland Getaway
Private kitchen

The Portland Getaway

9.6 out of 10, Exceptional, (21)
"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
Bright & Sunny West End Apartment with Private Parking.
Dining

Bright & Sunny West End Apartment with Private Parking.

9.8 out of 10, Exceptional, (23)
"This third floor apartment was conveniently located to downtown Portland. There are lots of good restaurants within walking distance. It was spacious and well equipped. It only came with 1 parking space but my son was able to find a spot nearby on the street."
The price is AED 650
AED 1,157 total
includes taxes & fees
9 Feb - 10 Feb
Bright & Sunny West End Apartment with Private Parking.
Beautiful Old Port Apt-Downtown

Beautiful Old Port Apt-Downtown

9.6 out of 10, Exceptional, (14)
"It was all terrific. There was one issue with the apartment on the last night but they responded promptly and while it could not be fixed because of the holiday they were attentive and apologetic."
The price is AED 1,197
AED 2,315 total
includes taxes & fees
21 Feb - 22 Feb
Beautiful Old Port Apt-Downtown
Prime Downtown Location/Beautiful Brownstone Apt/Sleeps2

Prime Downtown Location/Beautiful Brownstone Apt/Sleeps2

9.8 out of 10, Exceptional, (16)
"Extremely clean, modern and great locattion"
Prime Downtown Location/Beautiful Brownstone Apt/Sleeps2
Historic Home in the West End. Private Parking.
Room

Historic Home in the West End. Private Parking.

9.8 out of 10, Exceptional, (28)
"We had a lovely stay in this historic home. The decor is charming and original, beds are comfy and everything is clean. The neighborhood is attractive and quiet. The information from the host was helpful. It was great to have a dedicated parking space. As described, the kitchenette has no sink but otherwise is very well equipped for simple food/beverage preparation. We look forward to staying in the future."
The price is AED 437
AED 873 total
includes taxes & fees
4 Feb - 5 Feb
Historic Home in the West End. Private Parking.
Studio Apartment with views of Boothbay Harbor
Deck that overlooks the head of the head of the harbor.

Studio Apartment with views of Boothbay Harbor

10.0 out of 10, Exceptional, (9)
"Property is in a great location and very clean. Bed was very comfortable. The owners were great!"
Studio Apartment with views of Boothbay Harbor
Chic One Bedroom Apartment In Portland's Arts District
Welcome to our Chic One Bedroom at Portland on Avon!

Chic One Bedroom Apartment In Portland's Arts District

10.0 out of 10, Exceptional, (203)
"Sue and Barry were so accommodating, we have never been treated so well staying at a VRBO. They showed us local spots, told us great places for food and drinks, extremely kind and knowledgeable of the area. Couldn’t recommend them enough! "
Chic One Bedroom Apartment In Portland's Arts District
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, (2)
"We enjoyed our stay at Jennifer’s place very much .The location was excellent. Walkable distance to the city center and to all the best restaurants.The view was breathtaking and the apartment was amazing!We highly recommend this place. We hope to return soon!"
The price is AED 1,274
AED 2,162 total
includes taxes & fees
4 Feb - 5 Feb
Harborview - Curated East End Escape w/ Parking
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.
Superb Location!! Heart of Old Port/Spacious Condo

Superb Location!! Heart of Old Port/Spacious Condo

9.8 out of 10, Exceptional, (19)
"This was our second stay at Dena’s property. Perfect size, 3bedrooms and 3 baths. This unit is impeccable, very clean, spacious, and well stocked. Dena checked in with us to be sure we were able to check in easily and was very responsive to anything we needed. We were located in the center of everything. Easily walkable area. We loved our stay and would love to return! "
Superb Location!! Heart of Old Port/Spacious Condo
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
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
Dining Room Seating for ten, extra dining also available

Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

9.8 out of 10, Exceptional, (68)
"Great house very comfortable and well appointed. Very roomy for our entire family. Nice to have en suite bathrooms with all the bedrooms. The host was very good with communication. Located on a busy road and the driveway is on a curve which made it a little challenging entering and exiting the property. "
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
The Weldon Hotel
Front of property

The Weldon Hotel

4.0 star property
9.4 out of 10, Exceptional, (35)
"The full kitchen and appliances were perfect for my stay so that I did not have to eat out while I was there and save money "
The price is AED 562
AED 613 total
includes taxes & fees
23 Feb - 24 Feb
The Weldon 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.

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: Glorious getaway on Portland’s Eastern Promenade.: Situated in Portland, 13.5 mi/21.7 km from the heart of Bailey Island. Includes free WiFi, separate dining areas, and Smart TVs. 1 room luxury ocean front studio cottage: Located 3.1 mi/5 km away in Harpswell. Outdoor space and sofa beds are included. Fall In Love With Portland!: It’s situated in Portland, 13.4 mi/21.6 km away. Includes free WiFi, private patios, and separate dining areas. Adorable Portland getaway on the Eastern Promenade: 13.5 mi/21.8 km away in Portland. Free WiFi, private patios, and Smart TVs are included. Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants: It’s located in Portland, 13.4 mi/21.6 km from Bailey Island. Includes private patios.
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.