Search Condos in Bailey Island

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 12 - Sep 14
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23
In four months
Dec 19 - Dec 21

Condo Rentals in Bailey Island

City Amenities, Casco Bay Sunrises and Natural Beauty
Interior

City Amenities, Casco Bay Sunrises and Natural Beauty

9.8 out of 10, Exceptional, (112)
"While minutes away from the Old Port, our stay on Casco Bay allowed us to relax and unwind."
The price is ￥37,821
￥65,173 total
includes taxes & fees
Sep 10 - Sep 11
City Amenities, Casco Bay Sunrises and Natural Beauty
Elegant condo - walk to Portland's best restaurants & Old Port
Fridge, microwave, oven, stovetop

Elegant condo - walk to Portland's best restaurants & Old Port

9.4 out of 10, Exceptional, (66)
"Right off a Main Street with tons of food and drink options. Loved the area, felt safe and fun. Close to walking trails as well. Inside decor was nice. "
The price is ￥23,637
￥62,036 total
includes taxes & fees
Sep 2 - Sep 3
Elegant condo - walk to Portland's best restaurants & Old Port
Charming 3-bedroom 3-bath condo with WiFi, in quaint Yarmouth
Property grounds

Charming 3-bedroom 3-bath condo with WiFi, in quaint Yarmouth

10.0 out of 10, Exceptional, (3)
"Beautiful place to stay. We are planning on doing this again next year. "
Charming 3-bedroom 3-bath condo with WiFi, in quaint Yarmouth
Shipwright @ The Offshore House
Smart TV

Shipwright @ The Offshore House

9.4 out of 10, Exceptional, (11)
"Luv the area and the room location was great A few steps from Bets fish and chips short drive into town "
The price is ￥30,810
￥53,604 total
includes taxes & fees
Sep 1 - Sep 2
Shipwright @ The Offshore House
Spacious 4 bedroom luxury Condo
Exterior

Spacious 4 bedroom luxury Condo

10.0 out of 10, Exceptional, (33)
"A great place to stay minutes from downtown Freeport and a short ride to Portland. Had a great time visiting family and the house was perfect for our getaway! Very close to all the Freeport attractions but quiet enough to rest and relax!"
Spacious 4 bedroom luxury Condo
Walking Distance To Shops, Restaurants And Footbridge
Fridge, microwave, oven, stovetop

Walking Distance To Shops, Restaurants And Footbridge

10.0 out of 10, Exceptional, (42)
"This is a great place right downtown which makes for easy walking access. Would definitely stay again!"
Walking Distance To Shops, Restaurants And Footbridge
Elegant Oceanfront Condo with Stunning Harbor Views & Spectacular Sunsets
Fridge, microwave, oven, stovetop

Elegant Oceanfront Condo with Stunning Harbor Views & Spectacular Sunsets

2.0 star property
9.6 out of 10, Exceptional, (5)
"This was a great condo. We really enjoyed watching the action on the harbor from the covered deck. The furnishings and appliances were brand new. There was plenty of room for a group with the layout of the bedrooms. It was very convenient to have the restaurant in the same building and it was a short drive to downtown. Our only suggestions would be to add a coffeemaker and directions for the dishwasher and garbage removal.Also it would be helpful to explain the parking situation and that the...
Elegant Oceanfront Condo with Stunning Harbor Views & Spectacular Sunsets
Oceanfront, dog-friendly condo with Boothbay Harbor views & prime location
Outdoor dining

Oceanfront, dog-friendly condo with Boothbay Harbor views & prime location

9.4 out of 10, Exceptional, (17)
"Loved the location, lots of activity but also very private and relaxing. Great place, everyone was really nice and friendly"
Oceanfront, dog-friendly condo with Boothbay Harbor views & prime location
Cozy, Elegant and Bright 2 bed in the East End
Smart TV

Cozy, Elegant and Bright 2 bed in the East End

9.8 out of 10, Exceptional, (42)
"Excellent stay and location"
The price is ￥28,016
￥52,395 total
includes taxes & fees
Sep 16 - Sep 17
Cozy, Elegant and Bright 2 bed in the East End
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
Fridge, microwave, oven, stovetop

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

8.8 out of 10, Excellent, (33)
"Was a very comfortable stay!! Walking distance to pier restaurants etc!"
The price is ￥19,648
￥56,945 total
includes taxes & fees
Sep 2 - Sep 3
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
Waterfront Condo in Boothbay Harbor
Property grounds

Waterfront Condo in Boothbay Harbor

10.0 out of 10, Exceptional, (2)
"Location was perfect! And the host even better! Highly recommend!!"
Waterfront Condo in Boothbay Harbor
The perfect seaside retreat overlooking scenic Mackerel Cove on Bailey Island
Outdoor dining

The perfect seaside retreat overlooking scenic Mackerel Cove on Bailey Island

9.8 out of 10, Exceptional, (21)
"We thoroughly enjoyed a long weekend on Bailey Island. The condo was clean and new, very nicely furnished. It was a quiet easy to access property, very good experience."
The perfect seaside retreat overlooking scenic Mackerel Cove on Bailey Island
Brand New Listing! 3 Bedrooms, all En Suite- Yellow Door Guesthouse
Fridge, microwave, oven, stovetop

Brand New Listing! 3 Bedrooms, all En Suite- Yellow Door Guesthouse

10.0 out of 10, Exceptional, (3)
"Great place to stay in the cutest town of Freeport! 10/10 would recommend! "
Brand New Listing! 3 Bedrooms, all En Suite- Yellow Door Guesthouse
Historic Brick Apartment | Parking + Prime Location
Property grounds

Historic Brick Apartment | Parking + Prime Location

10.0 out of 10, Exceptional, (9)
"Visited my adult children and new baby granddaughter. Beautiful home, very convenient spot, and equipped with all the amenities needed- including a decorative Christmas tree. Thank you, Steve and Kristen!"
The price is ￥63,819
￥114,777 total
includes taxes & fees
Sep 1 - Sep 2
Historic Brick Apartment | Parking + Prime Location
Renovated condo with prime West End location, 2 en suite bathrooms, & HGTV style
Fridge, microwave, oven, stovetop

Renovated condo with prime West End location, 2 en suite bathrooms, & HGTV style

9.8 out of 10, Exceptional, (43)
"Perfect two bedroom for us to stay in during our work event."
Renovated condo with prime West End location, 2 en suite bathrooms, & HGTV style
Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo
Exterior

Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo

10.0 out of 10, Exceptional, (17)
"We had a lovely weekend staying at this condo! It was clean, cozy, and the coffee bar was amazing! "
The price is ￥53,138
￥97,210 total
includes taxes & fees
Aug 28 - Aug 29
Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo
Waterfront Two Master Suite Penthouse with Rooftop
Exterior

Waterfront Two Master Suite Penthouse with Rooftop

10.0 out of 10, Exceptional, (183)
"We very much enjoyed our stay in Portland. The apartment has a great location and of course nice water views. "
The price is ￥142,525
￥211,521 total
includes taxes & fees
Sep 8 - Sep 9
Waterfront Two Master Suite Penthouse with Rooftop
Seabed @ The Offshore House
Outdoor dining

Seabed @ The Offshore House

9.8 out of 10, Exceptional, (13)
"This was a great place to stay that let me explore the area I wanted to."
Seabed @ The Offshore House
Walk to Old Port ♦ West End Condo ♦ Parking
Microwave, oven, coffee/tea maker, cookware/dishes/utensils

Walk to Old Port ♦ West End Condo ♦ Parking

9.6 out of 10, Exceptional, (77)
"Cute place, close to old port! We brought our pup and she was happy as well. We would definitely stay there again! "
Walk to Old Port ♦ West End Condo ♦ Parking
Back Cove Views
2 bedrooms, iron/ironing board, free WiFi, bed sheets

Back Cove Views

10.0 out of 10, Exceptional, (8)
"Easy to get to, conveniently located close to restaurants, bars, shops, and downtown. There are stairs to climb, which didn't bother us, but be mindful as it is on the 3rd floor. Parking is only available on the street, and it was hard to find a spot close by the condo. But, we eventually did park close, so it worked out. We would definitely book this place again and again!"
Back Cove 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.
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

Casco Bay Hotel Portland Airport - Maine Mall, Ascend Hotel Collection

Casco Bay Hotel Portland Airport - Maine Mall, Ascend Hotel Collection

10/10 Excellent
"The staff was amazing. My family experienced a loss and we were comforted by Kadyia who was on staff. She made a real difference for us in a difficult time. The breakfast was hot and delicious and convenient as was the location. "
Shoshana 2-night trip
Posted 1 day ago
Casco Bay Hotel Portland Airport - Maine Mall, Ascend Hotel Collection

Find out more about Bailey Island

Find out more about Bailey Island

Bailey Island Condo Rentals information

Number of reviews
565
Accommodation
65 Condo Rentals
Lowest Price
￥19,648
Highest Price
￥142,525

Frequently asked questions

Why book your condo in Bailey Island with Expedia?
We think that getaways should be a piece of cake, so if you're chasing condos at the perfect price, Expedia has your back. Keep costs down and stay in something small and affordable, or book a 5-star condo and spoil the ones you love most. Our search filters make it a breeze to find a stay in Bailey Island that suits your needs.
How can I find cheap condos in Bailey Island?
The simplest way to uncover cheap condos in Bailey Island is with Expedia's nifty filter tool. Refine your search by star rating, budget and amenities to nab excellent rates with only a few clicks.