Bailey Island Holiday Rentals

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Check prices for these dates

In two weeks
27 Feb - 1 Mar
In two months
10 Apr - 12 Apr
In three months
8 May - 10 May
In four months
5 Jun - 7 Jun

Our top choices for Bailey Island holiday rentals

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$782
HK$1,730 total
includes taxes & fees
16 Feb - 17 Feb
Modern style in historic building in downtown Bath
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$571
HK$1,795 total
includes taxes & fees
24 Feb - 25 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$821
HK$1,677 total
includes taxes & fees
23 Feb - 24 Feb
Escape to Positive Outlook
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, (146 reviews)
"Lovely space, comfortable bed, very convenient to downtown Brunswick."
United States
Kimberly G.
The price is HK$703
HK$937 total
includes taxes & fees
18 Feb - 19 Feb
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
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)
"We ahd a great stay in Maine over the 4th visiting family, eating good food and walking around in great weather. Great stay in Brunswick, easy in and easy out and all sorts of things Maine accessible. Would recommend for anyone looking for a hassle-free weekend in coastal Maine. "
United States
Tjorvi P.
The price is HK$664
HK$1,977 total
includes taxes & fees
16 Feb - 17 Feb
Brunswick Downtown Sugar Cube next to Bowdoin
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$1,026
HK$2,087 total
includes taxes & fees
11 Mar - 12 Mar
Fantastic Waterfront Views
Interior

The Outlet Studio, Rustic Comfort w Fireplace

The Outlet Studio, Rustic Comfort w Fireplace
Freeport
10.0 out of 10, Exceptional, (11 reviews)
"Very comfortable, clean, with a spacious bathroom and within walking distance of downtown Freeport and Bow Street Market"
United States
Deanna S.
The price is HK$528
HK$1,129 total
includes taxes & fees
17 Feb - 18 Feb
The Outlet Studio, Rustic Comfort w Fireplace
Property grounds

Spruce Studio: Near Beach+FirePit+Pond+Heat/AC+Fast WiFi

Spruce Studio: Near Beach+FirePit+Pond+Heat/AC+Fast WiFi
Georgetown
The price is HK$1,266
HK$2,620 total
includes taxes & fees
17 Feb - 18 Feb
Spruce Studio: Near Beach+FirePit+Pond+Heat/AC+Fast WiFi
Terrace/patio

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (50 reviews)
"Super clean and lovely place to stay! Highly recommend!"
United States
Evan B.
The price is HK$1,407
HK$2,641 total
includes taxes & fees
16 Feb - 17 Feb
Full sized home
Property grounds

Pond Cabin: Private Sauna+Near Beach+FirePit+Pond

Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
Georgetown
The price is HK$1,731
HK$3,092 total
includes taxes & fees
22 Feb - 23 Feb
Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
2 bedrooms, WiFi, bed sheets

Large, luxurious geodesic dome - 04

Large, luxurious geodesic dome - 04
Freeport
10.0 out of 10, Exceptional, (2 reviews)
"We didn’t get enough time to evaluate but from the short visit, we can say that this is the small paradise within the Main area. Best camp ground facilities we have ever seen or experienced. Looking forward to visit with friends and extended families as well. "
United States
Hrishi K.
The price is HK$1,892
HK$2,956 total
includes taxes & fees
18 Feb - 19 Feb
Large, luxurious geodesic dome - 04
Interior

Sweet comfy cottage on Small Point Road

Sweet comfy cottage on Small Point Road
Small Point
9.4 out of 10, Exceptional, (3 reviews)
"Lovely home with plenty of space and seating. Not the most comfortable of beds but we enjoyed the space. Perfect location and would love to stay again. "
United States
Liz J.
The price is HK$2,345
HK$4,354 total
includes taxes & fees
16 Feb - 17 Feb
Sweet comfy cottage on Small Point Road
Exterior

Charming Historic home steps away from downtown

Charming Historic home steps away from downtown
Bath
The price is HK$1,664
HK$5,963 total
includes taxes & fees
17 Feb - 18 Feb
Charming Historic home steps away from downtown
Beach

City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (124 reviews)
"Great location for an our trip; laundry in basement "
United States
maria h.
The price is HK$985
HK$2,190 total
includes taxes & fees
16 Feb - 17 Feb
City Amenities, Casco Bay Sunrises and Natural Beauty
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$703
HK$1,806 total
includes taxes & fees
23 Feb - 24 Feb
2King Bed BR Private Apt Downtown Brunswick
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$651
HK$1,536 total
includes taxes & fees
16 Feb - 17 Feb
Peaceful & minutes from the Old Port with private parking
Smart TV

Beautiful Delightful 3BR Downtown Brunswick All King Beds

Beautiful Delightful 3BR Downtown Brunswick All King Beds
Brunswick
10.0 out of 10, Exceptional, (19 reviews)
"Great place, super convenient to downtown."
United States
Heather C.
The price is HK$977
HK$2,369 total
includes taxes & fees
16 Feb - 17 Feb
Beautiful Delightful 3BR Downtown Brunswick All King Beds
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$618
HK$1,917 total
includes taxes & fees
11 Mar - 12 Mar
Little Lincoln beautiful home
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$758
HK$1,568 total
includes taxes & fees
19 Feb - 20 Feb
Sunny Spot with Private Parking.
TV, fireplace, books

1 Mi to Maine Street! MCM-Style Home in Brunswick

1 Mi to Maine Street! MCM-Style Home in Brunswick
Brunswick
10.0 out of 10, Exceptional, (2 reviews)
"Good communication with host. Beautifully decorated. Well appointed kitchen and bath. Great wooded views. Quiet but close to restaurants and shopping."
United States
Lecia M.
The price is HK$516
HK$1,814 total
includes taxes & fees
24 Feb - 25 Feb
1 Mi to Maine Street! MCM-Style Home in Brunswick
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

Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

10/10 Excellent
"We have stayed here many times. Great location, staff is amazing, always extremely clean. "
Nicole 1-night trip
Posted 2 days ago
Canopy by Hilton Portland Waterfront

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
  • Use the map to find apartments and other holiday homes in the Bailey Island neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Bailey Island while they last

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?

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach: This highly rated holiday home rental in Bailey Island is located on the beach, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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. Bailey Island Bridge and Cobwork 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.