Search Apartments in Bailey Island

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Compare 192 Apartments in Bailey Island with updated reviews, rates, and availability.

Convenient Downtown Location w/Harbor View
Living area
Convenient Downtown Location w/Harbor View
10.0 out of 10, Exceptional, (35)
"This place met all our needs. Boothbay Harbor is a beautiful place to visit!! Parking is a little tight at times. Thank you again for everything and we also met the owner who was a very very kind man!! Tim T Deltona Florida"
Convenient Downtown Location w/Harbor View
Prime Downtown Location/Beautiful Brownstone Apt/Sleeps2
Prime Downtown Location/Beautiful Brownstone Apt/Sleeps2
9.8 out of 10, Exceptional, (14)
"Nice location with PMA across the street and several good restaurants a few minute walk from the apartment. The apartment was comfortable. Dena was very responsive. Great experience!"
Prime Downtown Location/Beautiful Brownstone Apt/Sleeps2
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, (75)
"Charming home in quiet neighborhood. For us the location was perfect - two blocks from the ocean on the Eastern Prom. Enjoyed outdoor activity (jogging/walking the surrounding trails) and the beautiful sunrises and autumn foliage while also within walking distance to the bustling Old Port restaurants, shopping and tours. Highly recommend."
Charming 2-bedroom steps from the Eastern Promenade
Stunning South Portland Apartment w/Pool
Stunning South Portland Apartment w/Pool
2.0 star property
8.0 out of 10, Very Good, (1)
"Very clean and thoughtful touches. The manager was very accommodating."
Stunning South Portland Apartment w/Pool
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
Very comfortable king size bed
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
10.0 out of 10, Exceptional, (118)
"Our stay was fantastic! The house was very comfortable, had everything we needed and was located in a great location. Would stay again!"
The price is AED 331
AED 440 total
includes taxes & fees
17 Nov - 18 Nov
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
Cozy Newly Renovated 1st Floor Apt
Interior
Cozy Newly Renovated 1st Floor Apt
10.0 out of 10, Exceptional, (22)
"We really enjoyed our stay in this spacious and lovely 1st floor apt! Location was great for us, comfortable tv/living room area, having 2bathrooms was a bonus, and the beds were super comfy! Would highly recommend. "
The price is AED 1,245
AED 1,770 total
includes taxes & fees
1 Dec - 2 Dec
Cozy Newly Renovated 1st Floor Apt
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
10.0 out of 10, Exceptional, (35)
"What a great place! Located in the arts district, this refurbished brownstone has every modern convenience within walking distance of restaurants and museums. Windows on both sides of the apartment provide street views, one active and bustling, one quiet with a view of Casco Bay and sunrises. And the rooftop patio is a dream - we loved being part of Portland history with an up close view of the florist's ad mural!"
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
Beautiful Old Port Apt-Downtown
Beautiful Old Port Apt-Downtown
9.8 out of 10, Exceptional, (12)
"A beautiful place to stay, close to restaurants and amenities "
The price is AED 901
AED 1,948 total
includes taxes & fees
16 Nov - 17 Nov
Beautiful Old Port Apt-Downtown
1 room luxury ocean front studio cottage
Terrace/patio
1 room luxury ocean front studio cottage
9.6 out of 10, Exceptional, (148)
"What a perfect place to unwind and watch the sunrise. "
1 room luxury ocean front studio cottage
Large beautiful ocean front studio with private dock
Exterior
Large beautiful ocean front studio with private dock
9.8 out of 10, Exceptional, (24)
"This unique property features three walls of windows for enjoying the beauty of the water, sky, trees around you. Relax inside or out while watching the birds and boaters. Everything you need is inside, including a fully furnished kitchen and a bathroom with generous samples of anything you might have forgotten. Our time here was very relaxing and the view was hard to leave."
Large beautiful ocean front studio with private dock
Eclectic & Unique 3 Bedroom Apt on Munjoy Hill
Private kitchen
Eclectic & Unique 3 Bedroom Apt on Munjoy Hill
Eclectic & Unique 3 Bedroom Apt on Munjoy Hill
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, (13)
"Perfect location, extremely clean and very comfortable apartment. Brian was very responsive and helpful. "
Beautiful NEW apt on top of Munjoy Hill with private deck and private parking.
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, (4)
"B"
Elegant home with veranda & water view, walk to downtown Boothbay Harbor
Glorious getaway on Portland's Eastern Promenade.
Glorious getaway on Portland's Eastern Promenade.
10.0 out of 10, Exceptional, (139)
"Nice and spacious 2 bedroom unit steps from the promenade. Jennifer was very helpful and accommodating. Easy check in and plenty of parking. Amazing central location. "
The price is AED 613
AED 1,125 total
includes taxes & fees
18 Nov - 19 Nov
Glorious getaway on Portland's Eastern Promenade.
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, (98)
"The apartment is just as pictured. Very clean, cute neighborhood, easy access to shops and restaurants. Definitely consider the paid parking because there are so many street parkers even in off season. The kitchen is well set up with pots and pans, silverware, glasses etc. Beds are comfortable and there are plenty of towels. Very easy to get in touch with landlord with questions. Great idea lace!"
The price is AED 826
AED 1,942 total
includes taxes & fees
17 Nov - 18 Nov
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
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
Superb Location!! Heart of Old Port/Spacious Condo
Superb Location!! Heart of Old Port/Spacious Condo
9.8 out of 10, Exceptional, (18)
"Place was great and an awesome location!!"
Superb Location!! Heart of Old Port/Spacious Condo
Pet Friendly-Steps from All-Harbor View Apt Heart of Boothbay Harbor's Downtown.
Nice and Bright
Pet Friendly-Steps from All-Harbor View Apt Heart of Boothbay Harbor's Downtown.
9.8 out of 10, Exceptional, (46)
"Prime location! Patty thoughtfully sent us dining and activities recommendations. The apartment was exactly as pictured. Would love to stay again. "
Pet Friendly-Steps from All-Harbor View Apt Heart of Boothbay Harbor's Downtown.
The Nest ~ Quiet location close to shops, dining and Downtown Freeport.
The Nest ~ Quiet location close to shops, dining and Downtown Freeport.
10.0 out of 10, Exceptional, (59)
"Charming and cozy. Nice beds. Perfect for 2 or 3"
The Nest ~ Quiet location close to shops, dining and Downtown Freeport.
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
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
Adorable Portland getaway on the Eastern Promenade
Adorable Portland getaway on the Eastern Promenade
9.8 out of 10, Exceptional, (90)
"We really enjoyed our stay. This little third floor walk up was a perfect place for my husband and I to explore Portland. It is homey and comfortable and spotless. If you have any issues with mobility you should look elsewhere, but that is disclosed in the listing. The last set of stairs are very steep, but we found it charming. I highly recommend this rental. Well done! "
The price is AED 408
AED 761 total
includes taxes & fees
17 Nov - 18 Nov
Adorable Portland getaway on the Eastern Promenade
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.