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Compare 261 Apartments in Bailey Island with updated reviews, rates, and availability.

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."
The price is AED 826
AED 1,670 total
includes taxes & fees
30 Apr - 1 May
Completely remodeled 2 bedroom apartment in Portland's West End

Charming West End Hideaway. Private Parking

10.0 out of 10, Exceptional, (28)
"i think it is important to remark that:parking is assigned. for me this is far better than just available.the property has a private entrance. the property description left me wondering if this was a shared property.it is every bit as wonderful as the other reviews declare. thank you, jennifer and caitlin."
The price is AED 503
AED 897 total
includes taxes & fees
14 Apr - 15 Apr
Charming West End Hideaway. Private Parking

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

9.8 out of 10, Exceptional, (59)
"We loved this apartment. Great location, beautifully decorated, loved the rooftop deck! Highly recommend! Will be back!"
The price is AED 1,466
AED 2,446 total
includes taxes & fees
1 May - 2 May
2 Bedroom Apartment on Top Floor in Portland's West End

Glorious getaway on Portland's Eastern Promenade.

10.0 out of 10, Exceptional, (148)
"Gorgeous, cozy VRBO stocked with everything we needed. Hosts were so kind and accommodating. One of the best rental home experiences I’ve had. Definitely recommend!"
The price is AED 562
AED 1,057 total
includes taxes & fees
15 Apr - 16 Apr
Glorious getaway on Portland's Eastern Promenade.

The perfect refinement of vintage seduction. May-June-July special!!!

9.8 out of 10, Exceptional, (40)
"Some girlfriends and I stayed here to celebrate a 40th birthday "
The perfect refinement of vintage seduction. May-June-July special!!!

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

Adorable Portland getaway on the Eastern Promenade

9.8 out of 10, Exceptional, (95)
"Cozy apartment. Was clean and comfortable Great view of Portland Harbor. Stairs are quite steep which makes trying to bring up luggage a bit of a challenge. Parking is on the street. "
The price is AED 422
AED 777 total
includes taxes & fees
14 Apr - 15 Apr
Adorable Portland getaway on the Eastern Promenade

Vintage Maine & Modern Convenience in Portlands Exclusive East End

9.8 out of 10, Exceptional, (42)
"Nikoline's home was a great home base for a fun weekend exploring downtown Portland. Super clean, well-furnished and in a great location just a short walk away from lots of cool restaurants and bars in Old Port.Nikoline was very friendly and responsive. Looking forward to going back and staying again for another Portland adventure."
Vintage Maine & Modern Convenience in Portlands Exclusive East End

Historic Home in the West End. Private Parking.

9.8 out of 10, Exceptional, (29)
"We absolutely loved this apartment. It was the perfect location for walking to the downtown area and up and down Commercial Street. The apartment itself was exactly as it was described and shown in the listing. Super clean and had sheets, towels, dishes, etc. to make for a very easy stay. We generally like to eat out when traveling so the mini fridge, microwave, and electric kettle were exactly what we needed. The added touch of chocolates and bread sticks was very thoughtful. We will definitely...
The price is AED 466
AED 925 total
includes taxes & fees
20 Apr - 21 Apr
Historic Home in the West End. Private Parking.

Fall In Love With Portland!

9.6 out of 10, Exceptional, (114)
"We loved our stay here, beds were comfortable, host was communicative and accommodating, and the location was great. Would definitely stay here again! "
Fall In Love With Portland!

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

10.0 out of 10, Exceptional, (124)
"We had such a lovely stay in Susan’s guest suite while bringing my daughter to tour Bowdoin. Incredibly clean with a very comfortable bed and lots of thoughtful touches (including an ice cold Diet Coke in the mini-fridge, which my teen really appreciated). Thank you! "
The price is AED 331
AED 440 total
includes taxes & fees
13 Apr - 14 Apr
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Cozy West End apartment minutes from the Old Port

9.8 out of 10, Exceptional, (9)
"We enjoyed ourselves in this space, the location was close to everything around us and everything was in 10 minute walking distance to our stay. "
The price is AED 466
AED 857 total
includes taxes & fees
15 Apr - 16 Apr
Cozy West End apartment minutes from the Old Port

Charming Downtown Penthouse - The Cabana

9.0 out of 10, Wonderful, (13)
"Spacious 3 bedroom apartment. Large living room, with good lighting. Clean and stocked with everything we needed. Corresponding with property manager was extremely easy and straightforward. "
The price is AED 623
AED 1,327 total
includes taxes & fees
13 Apr - 14 Apr
Charming Downtown Penthouse - The Cabana

Ocean Point OCEANFRONT with private rugged BEACH

10.0 out of 10, Exceptional, (83)
"Beautiful location, lovely accommodations, and great hosts! Oceanfront bliss for a peaceful sunrise and an evening by the fire pit. "
Ocean Point OCEANFRONT with private rugged BEACH

Bright & Sunny West End Apartment with Private Parking.

9.8 out of 10, Exceptional, (26)
"Our family of four enjoyed our stay at the apartment. The space is beautifully appointed with comfortable beds and sheets. Communication with our host was prompt and helpful. We would stay again if we were in the area!"
The price is AED 687
AED 1,213 total
includes taxes & fees
16 Apr - 17 Apr
Bright & Sunny West End Apartment with Private Parking.

Spacious 3 BR in Portland's Libbytown!

9.8 out of 10, Exceptional, (30)
"The apartment was just as described. Very comfortable and easy to get to. Very clean."
Spacious 3 BR in Portland's Libbytown!

Brand New 2 Bedroom Apartment in Heart of West End

9.8 out of 10, Exceptional, (27)
"Here for a short overnight stay in Portland on our way to Acadia. Space was nice - clean with comfortable beds and clean bath and kitchen. Easy walk to Old Port area. Thank you! "
Brand New 2 Bedroom Apartment in Heart of West End

West End Bright Spot with Parking.

10.0 out of 10, Exceptional, (3)
"We loved the apartment. It was in a great neighborhood and it was only about a 10 to 15 min walk to the downtown area "
The price is AED 536
AED 965 total
includes taxes & fees
16 Apr - 17 Apr
West End Bright Spot with Parking.

“Percival” Penthouse Suite: Breathtaking Views, Cupola, Parking!

10.0 out of 10, Exceptional, (224)
"Our whole family loved the views from the windows, porch and cupola! Great Portland location and having parking included was a huge bonus for us with a rental car. "
“Percival” Penthouse Suite: Breathtaking Views, Cupola, Parking!

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

9.8 out of 10, Exceptional, (105)
"It was great overall. I had a problem with the check in process . Don't know what happened exactly but did not receive the final information about check in code then could not reach the host at first . When I did reach him he immediately gave me the code and then came by in person to make sure all was fine "
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
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

Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage

9.4 out of 10, Exceptional, (16)
"Loved the location."
Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage

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

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

10.0 out of 10, Exceptional, (212)
"We had a peaceful time at this home. It served as a home base for exploring. When my daughter left her most priced possession, her stuffed otter, the lovely hosts found it and shipped it back to us. We're so grateful for the thoughtfulness. "
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
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: Completely remodeled 2 bedroom apartment in Portland’s West End: Located in Portland, 14.8 mi/23.9 km from the heart of Bailey Island. Includes free WiFi and Smart TVs. Access to a fitness center is available on site. 1 room luxury ocean front studio cottage: Located 3.1 mi/5 km away in Harpswell. Outdoor space and sofa beds are included. Studio Apartment In-town Walkable!: 14.5 mi/23.4 km away in Portland.
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.