A rocky shoreline with a boat, a house, and a forest in the background.

Search Apartment Rentals in Bailey Island

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Bailey Island apartments

Property grounds

1. Sunset Hideaway on Bailey Island

Sunset Hideaway on Bailey Island
Harpswell
8.4 out of 10, Very good, (5 reviews)
"Wonderful views. Comfortable. "
United States
Susy K.
The price is CA $124
CA $293 total
includes taxes & fees
Sep 23 - Sep 24
Sunset Hideaway on Bailey Island
Private kitchen

2. Bird Watching Paradise @ Waterfront Harpswell with Private Deck

Bird Watching Paradise @ Waterfront Harpswell with Private Deck
Harpswell
10.0 out of 10, Exceptional, (3 reviews)
"Super location, very private, responsive host, lovely, clean. Very lucky to have been able to stay here!"
United States
Kate K.
The price is CA $245
CA $509 total
includes taxes & fees
Oct 4 - Oct 5
Bird Watching Paradise @ Waterfront Harpswell with Private Deck
Property grounds

3. Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean

Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean
Freeport
10.0 out of 10, Exceptional, (17 reviews)
"Hosts were very responsive with messages. The stay was clean and comfortable."
United States
Hana L.
The price is CA $245
CA $420 total
includes taxes & fees
Sep 20 - Sep 21
Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean
Interior

4. Studio Apartment in Freeport

Studio Apartment in Freeport
Freeport
10.0 out of 10, Exceptional, (3 reviews)
"Was pet friendly, as pictured. Very nice"
United States
Kelly L.
The price is CA $169
CA $302 total
includes taxes & fees
Oct 6 - Oct 7
Studio Apartment in Freeport
Exterior

5. Large suite/private bath/private entrance on quiet street near Thomas Bay

Large suite/private bath/private entrance on quiet street near Thomas Bay
Brunswick
10.0 out of 10, Exceptional, (170 reviews)
"What a beautiful place to stay. Jeff and Susan made your stay a very special experience."
United States
DENESE
The price is CA $185
CA $232 total
includes taxes & fees
Sep 27 - Sep 28
Large suite/private bath/private entrance on quiet street near Thomas Bay
Dining

6. King Size Sun Rise Midcoast Lovely Stay

King Size Sun Rise Midcoast Lovely Stay
Topsham
9.6 out of 10, Exceptional, (18 reviews)
"Perfect for a my husband and I. Close to everything!"
United States
Tabcline S.
The price is CA $175
CA $363 total
includes taxes & fees
Sep 29 - Sep 30
King Size Sun Rise Midcoast Lovely Stay
Interior

7. Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath
Bath
10.0 out of 10, Exceptional, (11 reviews)
"Great location! We spent very little time in the room, but it was a great place to come back and crash! "
United States
Kristina M.
The price is CA $140
CA $308 total
includes taxes & fees
Sep 29 - Sep 30
Modern style in historic building in downtown Bath
Interior

8. King size Bed Big Smile Big Sunshine 1st FL Washer&Dryer

King size Bed Big Smile Big Sunshine 1st FL Washer&Dryer
Topsham
9.4 out of 10, Exceptional, (6 reviews)
"Perfect place and location for visiting Bowdoin."
United States
Kristen S.
The price is CA $210
CA $437 total
includes taxes & fees
Sep 21 - Sep 22
King size Bed Big Smile Big Sunshine 1st FL Washer&Dryer
Living area

9. 1st FL Downtown Grand Brunswick

1st FL Downtown Grand Brunswick
Brunswick
The price is CA $203
CA $457 total
includes taxes & fees
Oct 5 - Oct 6
1st FL Downtown Grand Brunswick
TV

10. Portland 1-bedroom with enclosed porch & parking

Portland 1-bedroom with enclosed porch & parking
Deering Center
8.4 out of 10, Very good, (12 reviews)
"Place was fine, good amount of space, host was very nice"
United States
Jillian F.
The price is CA $117
CA $148 total
includes taxes & fees
Sep 28 - Sep 29
Portland 1-bedroom with enclosed porch & parking
Interior

11. 2King Bed BR Private Apt Downtown Brunswick

2King Bed BR Private Apt Downtown Brunswick
Brunswick
8.6 out of 10, Excellent, (14 reviews)
"Clean convenient location and quiet with comfortable beds. Just what we needed. "
United States
caralyn g.
The price is CA $203
CA $401 total
includes taxes & fees
Oct 12 - Oct 13
2King Bed BR Private Apt Downtown Brunswick
1 bedroom, WiFi, bed sheets

12. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.4 out of 10, Very good, (19 reviews)
"I will admit the location and surrounding areas are a bit sketchy, but, once inside, we felt super secure. There are multiple doors and gates with locks to ensure safety. Place was clean and had everything we needed for a quick stay."
United States
Krysta
The price is CA $125
CA $225 total
includes taxes & fees
Oct 6 - Oct 7
Studio Apartment near downtown Walkable!
Fridge, microwave, oven, stovetop

13. Great suburban location close to town!

Great suburban location close to town!
Deering Center
The price is CA $119
CA $149 total
includes taxes & fees
Sep 27 - Sep 28
Great suburban location close to town!
Coffee/tea maker, fridge, microwave, oven

14. Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)

Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
Brunswick
9.6 out of 10, Exceptional, (34 reviews)
"Perfect for what we needed for the week. All that was missing was some oven mitts and maybe a pair of scissors but we made it work!! Great little spot - thank you!! "
United States
Britta M.
The price is CA $273
CA $596 total
includes taxes & fees
Oct 5 - Oct 6
Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
Interior

15. Willard Beach–Apartment Near Portland & Parks

Willard Beach–Apartment Near Portland & Parks
Willard Beach
10.0 out of 10, Exceptional, (7 reviews)
"Excellent in every way."
United States
Robert B.
The price is CA $254
CA $518 total
includes taxes & fees
Sep 29 - Sep 30
Willard Beach–Apartment Near Portland & Parks
Interior

16. Charming Studio apartment with WiFi, AC in welcoming Portland

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.6 out of 10, Exceptional, (28 reviews)
"Great place! We would definitely return if we were in the area."
United States
Preston
The price is CA $186
CA $316 total
includes taxes & fees
Oct 20 - Oct 21
Charming Studio apartment with WiFi, AC in welcoming Portland
Interior

17. Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
10.0 out of 10, Exceptional, (33 reviews)
"This is a perfect location. 6 minutes from downtown Portland. Secure, Clean and Jen was a Perfect and attentive host. It is a hidden Gem!"
United States
Irish D.
The price is CA $276
CA $457 total
includes taxes & fees
Sep 22 - Sep 23
Sunny Spot with Private Parking.
Interior

18. Walkable near downtown 1 Bedroom

Walkable near downtown 1 Bedroom
West Bayside
4.8 out of 10, (6 reviews)
"Stay was ok! Not worth the listing price. Does the trick if you need a quick place to stay. Other than two mugs, very few supplies. "
United States
Thomas H.
The price is CA $117
CA $218 total
includes taxes & fees
Sep 21 - Sep 22
Walkable near downtown 1 Bedroom
Smart TV

19. Beautiful Delightful 3BR Downtown Brunswick All King Beds

Beautiful Delightful 3BR Downtown Brunswick All King Beds
Brunswick
10.0 out of 10, Exceptional, (25 reviews)
"This was just what we needed and close to everything we were doing!"
United States
Darryl T.
The price is CA $280
CA $828 total
includes taxes & fees
Oct 8 - Oct 9
Beautiful Delightful 3BR Downtown Brunswick All King Beds
Outdoor dining

20. Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.8 out of 10, Exceptional, (13 reviews)
"Cute, convenient spot!"
United States
Kelly S.
The price is CA $345
CA $556 total
includes taxes & fees
Sep 23 - Sep 24
Peaceful & minutes from the Old Port with private parking
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Bailey Island Hotel Reviews

Clarion Pointe South Portland

Clarion Pointe South Portland

10/10 Excellent
"Room very clean and well appointed, except no hangers available. Hairdryer. Beds comfortable. Coffee maker and pods. Staff friendly. Would stay again."
Theresa 1-night trip
Posted 1 hour ago
Clarion Pointe South Portland

Find out more about Bailey Island

Bailey Island Apartments information

Number of reviews
354
Accommodation
290 Apartments
Lowest Price
CA $148
Highest Price
CA $828

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?
Here is a top apartment in the area to consider: Oceanfront Studio w/ Private Dock in Harpswell!: It's situated in Harpswell, 5 mi/8.1 km away. 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?
Mackerel Cove and Ragged Island 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.

Explore a world of travel with Expedia