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Compare 200 Apartments in Bailey Island with updated reviews, rates, and availability.

Perfectly Located Portland Apartment!
Room
Perfectly Located Portland Apartment!
6.0 out of 10, (3)
"If you are wanting lots of amenities with your rental, this isn't it, but the location is great, and it's reasonably priced compared to hotels in the same area. You may have to message for the wifi password (I didn't, but it wasn't a big deal to use my data), and the mattresses are very basic, but not uncomfortable. The a/c worked great, and the water pressure is good."
Perfectly Located Portland Apartment!
Hip & Luxurious Garden Retreat for Families, Foodies & Adventurers
Hip & Luxurious Garden Retreat for Families, Foodies & Adventurers
10.0 out of 10, Exceptional, (36)
"(As above) Would stay again if it’s available next time we visit Portland. Wonderful location. We walked to the water 2-3 a day every day we stayed. Owner was EXCELLENT at communication. Internet, also cell reception, were a bit spotty but not a deal-breaker by any means. I love the plantings in the courtyard and mature landscaping out the windows. Beds were very comfortable with plenty of extra blankets and pillows. A/C (in every bedroom) worked perfectly!"
The price is SAR 2,060
SAR 3,279 total
includes taxes & fees
29 Sep - 30 Sep
Hip & Luxurious Garden Retreat for Families, Foodies & Adventurers
Beautiful NEW apt on top of Munjoy Hill with private deck and private parking.
Living room with flat screen TV and desk overlooking North Street.
Beautiful NEW apt on top of Munjoy Hill with private deck and private parking.
2.0 star property
10.0 out of 10, Exceptional, (5)
"5 star visit in the “real” part of Portland. Located in Munjoy Hill neighborhood on the east end of the pennisula - close to ocean and amazing restaurants and stores on Washington Ave. Will definitely stay here again. "
Beautiful NEW apt on top of Munjoy Hill with private deck and private parking.
1200 Sq Ft ♦ West End Gem ♦ Perfect Location
1200 Sq Ft ♦ West End Gem ♦ Perfect Location
9.4 out of 10, Exceptional, (88)
"This place is in a great location, close to many things in Portland. There is a cute little coffee shop just blocks away. Both beds were super comfy. There isn't much seating in the living for 4, just a couch and wooden bench. The shower doesn't give much water pressure and there isn't anywhere to put your toiletries as it's a single pedestal sink so that was a challenge with 3 girls. It could of used some additional cleaning also."
The price is SAR 842
SAR 1,539 total
includes taxes & fees
29 Sep - 30 Sep
1200 Sq Ft ♦ West End Gem ♦ Perfect Location
East end. Walk to food, beer and downtown fun.
East end. Walk to food, beer and downtown fun.
10.0 out of 10, Exceptional, (19)
"Apartment was perfectly clean and comfortable. Very close to the Old Port and just around the corner from the event we attended. Highly recommended "
The price is SAR 812
SAR 1,365 total
includes taxes & fees
1 Oct - 2 Oct
East end. Walk to food, beer and downtown fun.
The Beach House Bailey Island Maine
Aerial view
The Beach House Bailey Island Maine
10.0 out of 10, Exceptional, (31)
"We had a magical stay with Roxanne and Ron. Their property is spectacular. The sandy beach, the picturesque scenery, the well maintained landscape. It really has it all. We also saw many cute little creatures around, a ferret, chipmunk, many songbirds and a funny seagull family. Our son was very enchanted by the experience. It was hard to leave at the end of our stay! Roxanne and Ron were very warm and welcoming. The apartment is very charming with a good layout. The large window that...
The Beach House Bailey Island Maine
Historic Boothbay Harbor cottage with antique decor, washer/dryer & deck
Historic Boothbay Harbor cottage with antique decor, washer/dryer & deck
9.4 out of 10, Exceptional, (83)
"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
Charming 2-bedroom steps from the Eastern Promenade
Ocean views just a few doors away
Charming 2-bedroom steps from the Eastern Promenade
9.8 out of 10, Exceptional, (70)
"This property is in a great location just a short walk from the Eastern Promenade and lots of tasty restaurants. "
Charming 2-bedroom steps from the Eastern Promenade
Stunning apartment in beautiful Freeport
Private kitchen
Stunning apartment in beautiful Freeport
2.0 star property
10.0 out of 10, Exceptional, (7)
"The stay was perfect! A very modern, spacious and clean place, with a nice big TV and plenty of couch space. The kitchen is big, the bedrooms and beds are everything you'd need. Melissa and Scott were great. I highly recommend!"
Stunning apartment in beautiful Freeport
Elegant home with veranda & water view, walk to downtown Boothbay Harbor
Elegant home with veranda & water view, walk to downtown Boothbay Harbor
2.0 star property
10.0 out of 10, Exceptional, (2)
"I can’t say enough nice things about this rental. Perfect location. Very tidy. All the amenities you want and then some. We just had the best stay."
Elegant home with veranda & water view, walk to downtown Boothbay Harbor
Inviting apartment with full kitchen, porch, convenient location, & fast WiFi
Inviting apartment with full kitchen, porch, convenient location, & fast WiFi
7.6 out of 10, Good, (17)
"After a bit of confusion getting into the house, we found a nice, very well lit, spacious home with lots of windows. The beds were pretty comfy. The location was great, easy walk to the state theater, easy to walk to lots of cool bars and restaurants. The harbor and that touristy area were about 20 to 25 minute walk away, which was lovely in the nice weather. Overall, it Served well, for four people wanting to explore Portland. "
Inviting apartment with full kitchen, porch, convenient location, & fast WiFi
Glorious getaway on Portland's Eastern Promenade.
Glorious getaway on Portland's Eastern Promenade.
10.0 out of 10, Exceptional, (133)
"We spent 1 night here before heading to Bar Harbor. It was easy to find, good instructions for getting inside and the amenities were nice. It has an older home charm and we felt very comfortable. The location was close to stores, restaurants and downtown. I would stay there again.downtown.restaurantsand"
The price is SAR 1,039
SAR 1,665 total
includes taxes & fees
25 Sep - 26 Sep
Glorious getaway on Portland's Eastern Promenade.
Walk Everywhere! Entire Downtown Apt - "La Maison"
Walk Everywhere! Entire Downtown Apt - "La Maison"
9.8 out of 10, Exceptional, (12)
"Nice place. A lot of stairs..place was clean with a lot of room .. communication was great. Neat little places to walk to for food. Need more kitchen supplies..more dishes , silverware and cooking items. No spat! Parking was terrible and unit shouldn’t list that it has parking. Plenty of laundry supplies and towels. Owner replies immediately to needs."
Walk Everywhere! Entire Downtown Apt - "La Maison"
Brand New 1 Bedroom Apartment in Portland
Living area
Brand New 1 Bedroom Apartment in Portland
10.0 out of 10, Exceptional, (31)
"Loved Portland and the location was great! Walking distance or short Uber to everything. Stain on carpet and air conditioner "
The price is SAR 709
SAR 1,534 total
includes taxes & fees
25 Sep - 26 Sep
Brand New 1 Bedroom Apartment in Portland
2 Bedroom Apartment on Top Floor in Portland's West End
Dining
2 Bedroom Apartment on Top Floor in Portland's West End
10.0 out of 10, Exceptional, (53)
"My wide daughter and I were vacationing in Portland and wanted to explore the city. The space was very nice and the location was perfect. It was a 10-minute walk to harbor and very quiet in the evenings. WE parked are rental when we arrived and never moved it until we left. There is a fantastic restaurant, Chaval, only 2 blocks away "
The price is SAR 1,047
SAR 1,947 total
includes taxes & fees
6 Oct - 7 Oct
2 Bedroom Apartment on Top Floor in Portland's West End
Beautiful Oceanfront Apartment, scenic views and water access
Queen bed and built in dressers
Beautiful Oceanfront Apartment, scenic views and water access
9.8 out of 10, Exceptional, (76)
"The Anchor Loft is the perfect size for the solo traveler or a duo and has everything you need to live comfortably for your getaway. Very clean, up to date, well maintained, and in a quiet, peaceful, and absolutely gorgeous setting. Far superior to a hotel for the same or a lesser price. If you need anything while at the property, Paul is very responsive, personable, and kind. Very easy to make trips into town or nearby Portland and Freeport. A great place to come back to after a longer day trip...
Beautiful Oceanfront Apartment, scenic views and water access
West End Portland Apartment
Kitchen into TV Room
West End Portland Apartment
9.4 out of 10, Exceptional, (61)
"We were happily surprised to discover that this apartment was more spacious than we expected. The decor was eclectic and attractive. We loved the location because we could easily walk anywhere downtown and to the Western Promenade. The stairs are very narrow and steep if that might be an issue for someone. We would definitely rent this apartment again when we’re in Portland."
West End Portland Apartment
Beautiful Harbor Views Heart of Boothbay Harbor Downtown Village near all Piers
Kitchen! New~
Beautiful Harbor Views Heart of Boothbay Harbor Downtown Village near all Piers
9.6 out of 10, Exceptional, (71)
"Fantastic location, owners were nearby and easy to communicate with for any questions. Perfect views and cozy apartment for our family of 3. Would definitely stay here again!"
Beautiful Harbor Views Heart of Boothbay Harbor Downtown Village near all Piers
Charming West End Hideaway. Private Parking
Room
Charming West End Hideaway. Private Parking
10.0 out of 10, Exceptional, (17)
"We loved this beautiful room and roof garden! "
The price is SAR 702
SAR 1,153 total
includes taxes & fees
21 Oct - 22 Oct
Charming West End Hideaway. Private Parking
Bright & Spacious Apartment with Amazing Shower
Private kitchen
Bright & Spacious Apartment with Amazing Shower
8.4 out of 10, Very Good, (8)
"Very cute apartment that was just a few minutes walk from downtown north Portland. The property owner was very communicative and helpful throughout the whole process."
The price is SAR 500
SAR 881 total
includes taxes & fees
25 Sep - 26 Sep
Bright & Spacious Apartment with Amazing Shower
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.
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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, (98)
"All was good except the bedroom with the waterbed-like frame. It was uncomfortable. Also not air conditioned. We could have used a dishwasher. The setting was great. Overall, it was a good experience."
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
9.8 out of 10, Exceptional, (6)
"Overall this location is a great spot for those that dont need many amenities. There is no tv and no ac but the view and the breeze from the water make up for that! The space was clean and there was a grill plus Cooks Lobster house was a quick walk down the street! "
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Unique oceanfront home with a deck, tons of natural light, & amazing views
Unique oceanfront home with a deck, tons of natural light, & amazing views
8.6 out of 10, Excellent, (49)
"Beautiful property. Saw seals from living room catching fish. Front door did not lock but it’s a safe neighborhood but a bit isolated. Kitchen is well equipped for cooking. Laundry facilities were a great help! Gorgeous views of the water and excellent service and communication."
Unique oceanfront home with a deck, tons of natural light, & amazing 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.

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: Adorable Portland getaway on the Eastern Promenade: Situated in Portland, 13.5 mi/21.8 km from the heart of Bailey Island. Includes free WiFi, private patios, and Smart TVs. Completely remodeled 2 bedroom apartment in Portland’s West End: Located 14.8 mi/23.9 km away in Portland. Free WiFi and Smart TVs are included. Access to a fitness center is available on site. Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist: It’s situated in Portland, 14.2 mi/22.8 km away. Includes private balconies and sofa beds. Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants: 13.4 mi/21.6 km away in Portland. Amenities include private patios. Ocean view Victorian: It’s located in Portland, 13.3 mi/21.4 km from Bailey Island. Includes free WiFi.
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, April, March, and February, with each month seeing an average of 9 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.