Bailey Island Holiday Rentals

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Check prices for these dates

In two weeks
27 Mar - 29 Mar
In two months
8 May - 10 May
In three months
5 Jun - 7 Jun
In four months
3 Jul - 5 Jul

Our top choices for Bailey Island holiday rentals

Desk, laptop workspace, free WiFi

HomeAwhile

HomeAwhile
4.0 star property
Scarborough
The price is HK$669
HK$729 total
includes taxes & fees
14 Mar - 15 Mar
HomeAwhile
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$1,448
HK$2,534 total
includes taxes & fees
15 Mar - 16 Mar
Large, luxurious geodesic dome - 04
Exterior detail

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
East Deering
10.0 out of 10, Exceptional, (68 reviews)
"Had a really nice stay. "
United States
John F.
The price is HK$5,458
HK$8,261 total
includes taxes & fees
18 Mar - 19 Mar
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
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$2,110 total
includes taxes & fees
24 Mar - 25 Mar
1 Mi to Maine Street! Mcm-style Home in Brunswick
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$704
HK$938 total
includes taxes & fees
23 Mar - 24 Mar
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
2 bedrooms, WiFi, bed sheets

Large, luxurious geodesic dome - 09

Large, luxurious geodesic dome - 09
Freeport
The price is HK$1,596
HK$2,712 total
includes taxes & fees
15 Mar - 16 Mar
Large, luxurious geodesic dome - 09
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$2,348
HK$4,239 total
includes taxes & fees
26 Mar - 27 Mar
Sweet comfy cottage on Small Point Road
Interior

Modern Getaway by the Sea

Modern Getaway by the Sea
South Portland
10.0 out of 10, Exceptional, (2 reviews)
"Had a nice stay! House was great."
United States
Karen T.
The price is HK$2,348
HK$3,959 total
includes taxes & fees
14 Mar - 15 Mar
Modern Getaway by the Sea
Fridge, microwave, oven, stovetop

Award Winning Luxury Carriage House a short stroll from town!

Award Winning Luxury Carriage House a short stroll from town!
Bath
10.0 out of 10, Exceptional, (9 reviews)
"An exceptional property and guest. Would love to stay again next time Thank you Jared and Heather!"
United States
Ronald H.
The price is HK$3,326
HK$5,084 total
includes taxes & fees
19 Mar - 20 Mar
Award Winning Luxury Carriage House a short stroll from town!
Property grounds

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

Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
Georgetown
The price is HK$1,530
HK$2,858 total
includes taxes & fees
17 Mar - 18 Mar
Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
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, (126 reviews)
"Perfect location and the host was immediately repsonsive and always friendly!"
United States
Jon L.
The price is HK$845
HK$2,005 total
includes taxes & fees
15 Mar - 16 Mar
City Amenities, Casco Bay Sunrises and Natural Beauty
TV, offices

Sleeps 16+ | W/D | Parking | 15 mins to Old Port

Sleeps 16+ | W/D | Parking | 15 mins to Old Port
Westbrook
The price is HK$3,334
HK$7,371 total
includes taxes & fees
15 Mar - 16 Mar
Sleeps 16+ | W/D | Parking | 15 mins to Old Port
TV, stereo, offices

Spectacular Views & Comforts of Home in Portland s Most Desirable Neighborhood

Spectacular Views & Comforts of Home in Portland s Most Desirable Neighborhood
Munjoy Hill
10.0 out of 10, Exceptional, (18 reviews)
"Great host and very clean, comfortable stay! We all wished we would have had more time here and loved every bit of our stay. Sunrise on the rooftop deck, city lights up there at night. It was wonderful! We hope to return someday! "
United States
JESSICA S.
The price is HK$2,349
HK$4,045 total
includes taxes & fees
15 Mar - 16 Mar
Spectacular Views & Comforts of Home in Portland s Most Desirable Neighborhood
Outdoor dining

Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (8 reviews)
"Such a beautiful home and peaceful location. We loved our stay and the host was responsive and helpful with any questions we had!"
United States
Diana H.
The price is HK$1,697
HK$3,749 total
includes taxes & fees
26 Mar - 27 Mar
Mere Point Sunrise Views at Eastern Shore!
Terrace/patio

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (51 reviews)
"Super clean and lovely place to stay! Highly recommend!"
United States
Evan B.
The price is HK$1,585
HK$2,862 total
includes taxes & fees
16 Mar - 17 Mar
Full sized home
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, (21 reviews)
"Great place, super convenient to downtown."
United States
Heather C.
The price is HK$1,057
HK$2,986 total
includes taxes & fees
15 Mar - 16 Mar
Beautiful Delightful 3BR Downtown Brunswick All King Beds
Fridge, microwave, oven, stovetop

Harborview - Curated East End Escape w/ Parking

Harborview - Curated East End Escape w/ Parking
Munjoy Hill
10.0 out of 10, Exceptional, (9 reviews)
"What a wonderful weekend in Portland Maine. The property was exceptional and in a great area. We felt comfortable and safe for our stay. We had a great time!"
United States
Kristyn E.
The price is HK$2,559
HK$4,453 total
includes taxes & fees
16 Mar - 17 Mar
Harborview - Curated East End Escape w/ Parking
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$783
HK$1,732 total
includes taxes & fees
25 Mar - 26 Mar
Modern style in historic building in downtown Bath
Terrace/patio

Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (58 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is HK$1,644
HK$2,764 total
includes taxes & fees
31 Mar - 1 Apr
Camp Forever cottage
Exterior

New 2-bedroom townhouse close to Town, ocean, recreational, and Bowdoin College

New 2-bedroom townhouse close to Town, ocean, recreational, and Bowdoin College
Brunswick
The price is HK$1,158
HK$1,885 total
includes taxes & fees
5 Apr - 6 Apr
New 2-bedroom townhouse close to Town, ocean, recreational, and Bowdoin College
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

Inn at St John Portland In-Town

Inn at St John Portland In-Town

10/10 Excellent
"Staff was very helpful and kind. Conveniently located to Maine Health. "
Kathleen 1-night trip
Posted 2 hours ago
Inn at St John Portland In-Town

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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  • 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 27 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.