Bailey Island Holiday Rentals

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Check prices for these dates

In two weeks
13 Feb - 15 Feb
In two months
27 Mar - 29 Mar
In three months
24 Apr - 26 Apr
In four months
22 May - 24 May

Our top choices for Bailey Island holiday rentals

Egyptian cotton sheets, premium bedding, down duvets, bed sheets

Fortland Island Campground

Fortland Island Campground
1.0 star property
Portland
10.0 out of 10, Exceptional, (3 reviews)
"It was very quiet and liked the experience of staying in a camp like setting."
United States
leela srinivas
Fortland Island Campground
Interior

1 Mi to Maine Street! Mcm-style Home in Brunswick

1 Mi to Maine Street! Mcm-style Home in Brunswick
3.0 star property
Brunswick
The price is HK$569
HK$1,790 total
includes taxes & fees
5 Feb - 6 Feb
1 Mi to Maine Street! Mcm-style Home in Brunswick
Living area

Escape to Positive Outlook

Escape to Positive Outlook
West Point
10.0 out of 10, Exceptional, (3 reviews)
"The host was welcoming. The home was clean, comfortable and the views were outstanding. "
United States
Rachel K.
The price is HK$737
HK$1,575 total
includes taxes & fees
28 Jan - 29 Jan
Escape to Positive Outlook
TV

Brunswick Downtown Sugar Cube next to Bowdoin

Brunswick Downtown Sugar Cube next to Bowdoin
Brunswick
8.4 out of 10, Very good, (7 reviews)
"Stayed for one night. Very convenient to campus"
United States
Lin-Lin R.
The price is HK$663
HK$1,972 total
includes taxes & fees
28 Jan - 29 Jan
Brunswick Downtown Sugar Cube next to Bowdoin
Exterior

Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
Brunswick
10.0 out of 10, Exceptional, (145 reviews)
"Great location to access the area especially route 1 n and s. Room totally met our needs and Susan and Jeff were super nice. This place will make our trip most memorable!"
United States
Don E.
The price is HK$702
HK$935 total
includes taxes & fees
28 Jan - 29 Jan
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
Interior

Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath
Bath
10.0 out of 10, Exceptional, (8 reviews)
"Such a great location! We could easily walk all over the cute downtown."
United States
Keisha C.
The price is HK$780
HK$1,725 total
includes taxes & fees
28 Jan - 29 Jan
Modern style in historic building in downtown Bath
Outdoor dining

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, (7 reviews)
"This well- appointed apartment was perfect for our stay in the Portland area. Jennifer was always quick to answer any questions. We would definitely recommend this listing."
United States
Lynn E.
The price is HK$649
HK$1,524 total
includes taxes & fees
28 Jan - 29 Jan
Peaceful & minutes from the Old Port with private parking
Interior

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (25 reviews)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
The price is HK$643
HK$1,423 total
includes taxes & fees
28 Jan - 29 Jan
Sunny Spot with Private Parking.
Interior

2King Bed BR Private Apt Downtown Brunswick

2King Bed BR Private Apt Downtown Brunswick
Brunswick
8.4 out of 10, Very good, (10 reviews)
"Small place in a great location. Easily walk to several shops and restaurants. "
United States
Jillian B.
The price is HK$686
HK$1,802 total
includes taxes & fees
30 Jan - 31 Jan
2King Bed BR Private Apt Downtown Brunswick
3 bedrooms, WiFi

Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.6 out of 10, Exceptional, (15 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is HK$819
HK$1,902 total
includes taxes & fees
28 Jan - 29 Jan
Fantastic Waterfront Views
Outdoor dining

Modern, Luxurious, Cabin in the Woods - 17

Modern, Luxurious, Cabin in the Woods - 17
Freeport
10.0 out of 10, Exceptional, (3 reviews)
"Awesome camping in a great, quiet campground. The staff is very responsive and all the little details make this place special."
United States
Miranda K.
The price is HK$1,310
HK$2,218 total
includes taxes & fees
1 Feb - 2 Feb
Modern, Luxurious, Cabin in the Woods - 17
Interior

Little Lincoln beautiful home

Little Lincoln beautiful home
Brunswick
9.2 out of 10, Wonderful, (15 reviews)
"Simon was very easy to communicate with, the place was clean, the bed was quite comfortable, and we were right by Main Street in Brunswick which made for easy access to food and things to do. Wonderful place to stay!"
United States
Jessica B.
The price is HK$616
HK$1,912 total
includes taxes & fees
28 Jan - 29 Jan
Little Lincoln beautiful home
TV

Classic New England 1st Floor 3 BR Downtown Brunswick

Classic New England 1st Floor 3 BR Downtown Brunswick
Brunswick
9.6 out of 10, Exceptional, (9 reviews)
"We had a good time in Brunswick.... great location and jumping off point to explore."
United States
Karin S.
The price is HK$936
HK$2,592 total
includes taxes & fees
28 Jan - 29 Jan
Classic New England 1st Floor 3 BR Downtown Brunswick
Outdoor dining

Port City Nest: Beautiful 2bd w/ Balcony & Parking

Port City Nest: Beautiful 2bd w/ Balcony & Parking
Parkside
10.0 out of 10, Exceptional, (1 review)
"Loved staying at your Nest! All was great but maybe a couple of cozy blanks in living room for lounging? Thanks again-Ruth"
United States
Ruth R.
The price is HK$624
HK$1,683 total
includes taxes & fees
28 Jan - 29 Jan
Port City Nest: Beautiful 2bd w/ Balcony & Parking
Interior

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, (11 reviews)
"A great location and a comfortable place to stay!"
United States
Andrew K.
The price is HK$877
HK$1,653 total
includes taxes & fees
28 Jan - 29 Jan
Charming Studio apartment with WiFi, AC in welcoming Portland
Interior

Vacation Creation Downtown Brunswick 2King Beds

Vacation Creation Downtown Brunswick 2King Beds
Brunswick
9.6 out of 10, Exceptional, (18 reviews)
"Stayed here while visiting Bowdoin. Great place!"
United States
Deborah B.
The price is HK$897
HK$2,303 total
includes taxes & fees
28 Jan - 29 Jan
Vacation Creation Downtown Brunswick 2King Beds
Private kitchen

The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (91 reviews)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
The price is HK$1,266
HK$1,965 total
includes taxes & fees
3 Feb - 4 Feb
The Weldon Hotel
Smart TV

Lovely 2-bedroom apartment with AC in charming Topsham. Close to everything!

Lovely 2-bedroom apartment with AC in charming Topsham. Close to everything!
Topsham
10.0 out of 10, Exceptional, (2 reviews)
"Pet friendly place and good spot! Would stay again "
United States
Shiloh F.
The price is HK$1,046
HK$1,956 total
includes taxes & fees
28 Jan - 29 Jan
Lovely 2-bedroom apartment with AC in charming Topsham. Close to everything!
Smart TV

Beautiful 3BR Home with Office in Town of Brunswick with King beds

Beautiful 3BR Home with Office in Town of Brunswick with King beds
Brunswick
9.2 out of 10, Wonderful, (5 reviews)
"Great place for our family to stay while visiting the Maine coast."
United States
Craig C.
The price is HK$975
HK$2,635 total
includes taxes & fees
28 Jan - 29 Jan
Beautiful 3BR Home with Office in Town of Brunswick with King beds
3 bedrooms, premium bedding, iron/ironing board, travel cot

Cozy 3BR | Pet Friendly | Near Portland | Parking

Cozy 3BR | Pet Friendly | Near Portland | Parking
Westbrook
10.0 out of 10, Exceptional, (12 reviews)
"We had a great stay here. It was very clean and conveniently located."
United States
Angela B.
The price is HK$904
HK$2,830 total
includes taxes & fees
28 Jan - 29 Jan
Cozy 3BR | Pet Friendly | Near Portland | 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.
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Top Bailey Island Hotel Reviews

Portland Harbor Hotel

Portland Harbor Hotel

10/10 Excellent
"Nice outside fire place in winter"
AMANDA JANE CHENG YEE 1-night trip
Posted 1 day ago
Portland Harbor Hotel

Find out more about Bailey Island

Search for holiday rentals in Bailey Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Bailey Island using one of the methods below:

  • View our selection of featured holiday rentals in Bailey Island
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Look no further and take a look at our great range of rental properties in Bailey Island!

Frequently asked questions

Can I find a holiday rental in Bailey Island?

Yes, there are holiday rentals in Bailey Island close to Land's End Gift Shop, or you can select a more secluded option if you're looking for a relaxing stay. Bailey Island is known for its shopping and seafood restaurants. Make sure you have time to check out the local tours and monuments during your trip.

What are some of the best holiday rentals that Bailey Island has to offer?

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port: This holiday home rental outside of Bailey Island is located on a river, and has a fireplace, a furnished patio and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a private garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Bailey Island?

With 26 Expedia holiday rentals, you're guaranteed to find just the right place for your Bailey Island stay.

What can I see and do 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. Cobwork Bridge and Bailey Island Bridge are other places to visit while you're in town.

What are holiday rentals like in Bailey Island?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Bailey Island. Holiday rentals feature amenities like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a great option for family trips or small group gatherings.