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Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

Apartments in Bailey Island

Studio Unit Walkable Everywhere
1 bedroom, bed sheets

Studio Unit Walkable Everywhere

The price is AED 482
AED 754 total
includes taxes & fees
22 Jul - 23 Jul
Studio Unit Walkable Everywhere
East end. Walk to food, beer and downtown fun.
TV

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

9.8 out of 10, Exceptional, (24)
"Great spot in Portland. Close to dozens of food options, breweries, and sites. Clean, comfortable, and spacious."
The price is AED 745
AED 1,296 total
includes taxes & fees
6 Aug - 7 Aug
East end. Walk to food, beer and downtown fun.
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

9.8 out of 10, Exceptional, (25)
"The cabin was very clean and a nice quiet location. Had everything we needed for a comfortable stay."
Oceanfront escape with deck, views of Lobster Cove & firepit - walk to town
Charming Studio apartment with WiFi, AC in welcoming Portland
Interior

Charming Studio apartment with WiFi, AC in welcoming Portland

10.0 out of 10, Exceptional, (2)
"This was a great stay through and through. Excellent condition, very responsive before and during the stay, and a great location. 10/10 will recommend to anyone staying in Portland! "
The price is AED 459
AED 845 total
includes taxes & fees
18 Aug - 19 Aug
Charming Studio apartment with WiFi, AC in welcoming Portland
Beautiful Studio in downtown Boothbay Harbor
Smart TV

Beautiful Studio in downtown Boothbay Harbor

9.0 out of 10, Wonderful, (8)
"Very cozy comfortable and convenient. Every thing we needed. "
The price is AED 327
AED 729 total
includes taxes & fees
27 Jul - 28 Jul
Beautiful Studio in downtown Boothbay Harbor
Chic Studio Cabin in Boothbay Harbor: Ocean Views, Sprucewold Beach Access
Internet, bed sheets

Chic Studio Cabin in Boothbay Harbor: Ocean Views, Sprucewold Beach Access

8.8 out of 10, Excellent, (43)
"Loved the private setting, but still 5 minutes from main drag"
The price is AED 459
AED 1,476 total
includes taxes & fees
11 Aug - 12 Aug
Chic Studio Cabin in Boothbay Harbor: Ocean Views, Sprucewold Beach Access
The Portland Getaway
Fridge, microwave, oven, stovetop

The Portland Getaway

9.6 out of 10, Exceptional, (25)
"Loved this spot just outside the city. Very clean and comfortable and super cute! We did drive and uber into town, but would have walked if it wasn’t snowing! Would definitely come back! "
The Portland Getaway
In-town no frills 2 bedroom apt
TV

In-town no frills 2 bedroom apt

7.0 out of 10, Good, (4)
"The frills of the neighborhood carried into the apartment. Floors and bathrooms seemed clean. Dishes and Keurig filthy - broken window a/c on floor. Broken chairs. No tlc for the property. Neighborhood beyond the stated description- would not recommend . Best to say is that rental car made it out with all windows and tires. Very disappointed "
The price is AED 463
AED 747 total
includes taxes & fees
10 Aug - 11 Aug
In-town no frills 2 bedroom apt
Private Entrance Residential Portland
Fridge, microwave, oven, stovetop

Private Entrance Residential Portland

8.0 out of 10, Very Good, (1)
"Great location for seeing the Portland Head Lighthouse. Comfortable bed."
The price is AED 347
AED 611 total
includes taxes & fees
22 Jul - 23 Jul
Private Entrance Residential Portland
Spacious 3 BR in Portland's Libbytown!
Fridge, microwave, oven, stovetop

Spacious 3 BR in Portland's Libbytown!

9.6 out of 10, Exceptional, (34)
"We really enjoyed the location,convenient to everything. Hosts were terrific as well"
The price is AED 1,157
AED 1,898 total
includes taxes & fees
30 Jul - 31 Jul
Spacious 3 BR in Portland's Libbytown!
Chic One Bedroom Apartment In Portland's Arts District
Fridge, microwave, oven, stovetop

Chic One Bedroom Apartment In Portland's Arts District

10.0 out of 10, Exceptional, (207)
"Great place to stay, friendly host. Great location, would stay there again if ever back in town."
Chic One Bedroom Apartment In Portland's Arts District
Vintage Maine & Modern Convenience in Portlands Exclusive East End
Beach

Vintage Maine & Modern Convenience in Portlands Exclusive East End

9.8 out of 10, Exceptional, (44)
"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
West End Apartment next to Longfellow Boutique Hotel
Fridge, microwave, oven, stovetop

West End Apartment next to Longfellow Boutique Hotel

9.4 out of 10, Exceptional, (65)
"Unique and beautiful spot, easy to walk around and communicate with the owner!"
West End Apartment next to Longfellow Boutique Hotel
Adorable Portland getaway on the Eastern Promenade
Interior

Adorable Portland getaway on the Eastern Promenade

9.8 out of 10, Exceptional, (104)
"Lovely place in the top floor of a multi property house. Everything you need in a cozy space. It is a walk up so pack up light. Clean, charming and comfy. Highly recommend. "
The price is AED 907
AED 1,381 total
includes taxes & fees
4 Aug - 5 Aug
Adorable Portland getaway on the Eastern Promenade
Luxury on Back Cove - Three Gables
Fridge, microwave, oven, stovetop

Luxury on Back Cove - Three Gables

10.0 out of 10, Exceptional, (2)
"GoodLocation, very clean. Would stay again "
The price is AED 1,230
AED 2,333 total
includes taxes & fees
4 Aug - 5 Aug
Luxury on Back Cove - Three Gables
Skyline 138: Charming West End Mansard Penthouse
Outdoor dining

Skyline 138: Charming West End Mansard Penthouse

9.2 out of 10, Wonderful, (17)
"Myself and a few friends stayed one night and the apartment was clean and comfortable and just what we needed."
The price is AED 1,071
AED 2,008 total
includes taxes & fees
21 Jul - 22 Jul
Skyline 138: Charming West End Mansard Penthouse
Large beautiful ocean front studio with private dock
Dining

Large beautiful ocean front studio with private dock

9.8 out of 10, Exceptional, (29)
"Great stay at a well-maintained property with a wonderful view and private dock! Fantastic communication with the owner, thank you!"
Large beautiful ocean front studio with private dock
Charming Brownstone Downtown Free St|Perfect Getaway for 2
Smart TV

Charming Brownstone Downtown Free St|Perfect Getaway for 2

10.0 out of 10, Exceptional, (25)
"Great location, in the property manager was a huge help in excellent communicator"
Charming Brownstone Downtown Free St|Perfect Getaway for 2
Private Rooftop Deck!/Artsy Apt/Old Port Arts Dist
Interior

Private Rooftop Deck!/Artsy Apt/Old Port Arts Dist

10.0 out of 10, Exceptional, (45)
"This was a great property and even better host. We had a great time staying in downtown Portland. The apartment has great finishes. I will definitely plan to stay here again."
Private Rooftop Deck!/Artsy Apt/Old Port Arts Dist
Old Port Penthouse Suite - Amazing Harbor Views
Outdoor dining

Old Port Penthouse Suite - Amazing Harbor Views

10.0 out of 10, Exceptional, (231)
"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. "
The price is AED 3,287
AED 4,780 total
includes taxes & fees
14 Aug - 15 Aug
Old Port Penthouse Suite - Amazing Harbor 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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Top Bailey Island Hotel Reviews

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

10/10 Excellent
"Always a nice stay here. We had a hard travel day and the staff made every effort to make us feel more comfortable. Great location and easy valet parking. Friendly staff. "
RACHEL 2-night trip
Posted 5 hours ago
Portland Regency Hotel & Spa

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: Studio Unit Walkable Everywhere: Situated in Portland, 14.5 mi/23.4 km from the heart of Bailey Island. Oceanfront escape with deck, views of Lobster Cove & firepit - walk to town: Located 20.4 mi/32.8 km away in Boothbay Harbor. Private patios and sofa beds are included. In-town no frills 2 bedroom apt: It's located in Portland, 14.5 mi/23.4 km away. 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. Private Entrance Residential Portland: Located in Portland, 15.3 mi/24.7 km from Bailey Island. Includes private balconies. Access to onsite laundry facilities 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?
Ragged Island and Mackerel Cove are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Land's End Gift Shop. 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.