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

Bailey Island Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Bailey Island vacation rentals

A grassy area with a picnic table and chairs, a body of water, and two trees in the background.

1. Sunset Hideaway on Bailey Island

Sunset Hideaway on Bailey Island
Harpswell
9.0 out of 10, Wonderful, (8 reviews)
"Wonderful views. Comfortable. "
United States
Susy K.
The price is ￥11,004
￥29,974 total
includes taxes & fees
Nov 10 - Nov 11
Sunset Hideaway on Bailey Island
A grassy area with a picnic table and chairs, a body of water, and two trees in the background.

2. Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR
Harpswell
10.0 out of 10, Exceptional, (13 reviews)
"Lovely property, close to what we needed and wanted, host communicated promptly. Would definitely stay there again."
United States
Jane D.
The price is ￥27,279
￥67,143 total
includes taxes & fees
Nov 16 - Nov 17
Orchid Harbor, Bailey Island 3BR
A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

3. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (12 reviews)
"The location and views from the cottage are quintessential coastal Maine. Small community with lobster pound and Maine Oyster Company across the street. John is a welcoming host and eager to make sure you enjoy your stay. The cottage is great for 2 people, equipped with the basics and has a great deck to enjoy the views. Planning to return next year. Great spot!"
United States
Rebecca
The price is ￥13,271
￥30,103 total
includes taxes & fees
Nov 1 - Nov 2
Mid Coast Getaway w/ water views
A modern interior with a dining area, a living room, and a kitchen.

4. Studio Apartment in Freeport

Studio Apartment in Freeport
Freeport
10.0 out of 10, Exceptional, (4 reviews)
"The bed was the most comfortable I have ever slept on! Lovely large warm open room. I appreciated the coffee/tea options, and the condiments in the fridge. There was a white noise machine in the room though we did not use it."
United States
Susan S.
The price is ￥12,323
￥26,356 total
includes taxes & fees
Nov 1 - Nov 2
Studio Apartment in Freeport
A deck with white railings overlooking a body of water, boats, and a forested shoreline.

5. Captains Watch: A Coastal Escape

Captains Watch: A Coastal Escape
West Point
10.0 out of 10, Exceptional, (2 reviews)
"Such a beautiful stay!! My whole group wished we could have stayed longer. We plan to come back"
United States
Holly G.
The price is ￥26,032
￥29,643 total
includes taxes & fees
Nov 11 - Nov 12
Captains Watch: A Coastal Escape
A spacious room with a wooden floor, a dining area with chairs and a table, a sofa, a TV, and a balcony with a view of the sea.

6. 2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
9.8 out of 10, Exceptional, (7 reviews)
"Place was clean, beautiful and the photos do not do it justice. The perfect get away vacation from the rat race."
United States
Gregory M.
The price is ￥20,707
￥37,842 total
includes taxes & fees
Nov 11 - Nov 12
2 bedroom w/ expansive water views
A spacious bedroom with a large bed, a rocking chair, and a view of a balcony with a white railing.

7. Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.4 out of 10, Exceptional, (22 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is ￥24,849
￥28,288 total
includes taxes & fees
Nov 11 - Nov 12
Fantastic Waterfront Views
A covered porch with a view of a lake and trees.

8. Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (10 reviews)
"Lovely location "
United States
Michelle S.
The price is ￥22,472
￥61,647 total
includes taxes & fees
Nov 17 - Nov 18
Mere Point Sunrise Views at Eastern Shore!
A wooden deck with outdoor seating and string lights.

9. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (80 reviews)
"Wonderful stay!"
United States
Erika T.
The price is ￥31,948
￥58,212 total
includes taxes & fees
Nov 2 - Nov 3
Full sized home
A lakeside property with a deck, picnic table, and barbecue grill.

10. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (73 reviews)
"We had a really nice day in communication and check-in were very easy. Overall, it was a lovely day and we would definitely consider returning."
United States
Len B.
The price is ￥33,132
￥57,266 total
includes taxes & fees
Nov 1 - Nov 2
Camp Forever cottage
A two-story house with a covered porch, a garage, and a front yard with potted plants.

11. 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, (176 reviews)
"This is a really lovely place to stay. Clean and very comfortable with lovely hosts."
United Kingdom
Lucinda
The price is ￥14,988
￥19,776 total
includes taxes & fees
Nov 24 - Nov 25
Large suite/private bath/private entrance on quiet street near Thomas Bay
A treehouse with a wooden staircase and a small building with a colorful mural.

12. Guest Room + Bath + Private Emtrance. Walk to everything, Large yard,

Guest Room + Bath + Private Emtrance. Walk to everything, Large yard,
Bath
8.0 out of 10, Very good, (31 reviews)
"A charming, quiet, and clean room with separate bathroom close to everything downtown. Felt a bit like staying at my grandparent’s house in a good way - it’s very homey. Dmitri is very nice and communication was thorough and easy!"
United States
Esther
The price is ￥19,074
￥29,561 total
includes taxes & fees
Nov 2 - Nov 3
Guest Room + Bath + Private Emtrance. Walk to everything, Large yard,
A modern kitchen with white cabinets, a wooden dining table, and a vase with green leaves.

13. King Size Sun Rise Midcoast Lovely Stay

King Size Sun Rise Midcoast Lovely Stay
Topsham
9.6 out of 10, Exceptional, (19 reviews)
"Perfect for a my husband and I. Close to everything!"
United States
Tabcline S.
The price is ￥14,988
￥35,375 total
includes taxes & fees
Nov 2 - Nov 3
King Size Sun Rise Midcoast Lovely Stay
A spacious living room with a large window overlooking a lake, a flat-screen TV mounted on the wall, and a round wooden coffee table.

14. Casco Bay Oceanfront Retreat by Everrow

Casco Bay Oceanfront Retreat by Everrow
Freeport
10.0 out of 10, Exceptional, (13 reviews)
"What can I say about my stay; peaceful, beautiful views, and relaxing! Home was clean with modern finishes but super comfortable for my four guests. The downstairs area is very private from the main floor. The yard was a great space where we had our outdoor fire looking up at the stars at night. The deck was perfect for our family lunch and dinners. We took chairs down to the beach area to sit closer to the water which was perfect. It's super close to town, Wolfe's Neck and other amenities....
United States
Lisa E.
The price is ￥57,232
￥140,221 total
includes taxes & fees
Nov 1 - Nov 2
Casco Bay Oceanfront Retreat by Everrow
A spacious living room with large windows, a sofa, a chair, and a small table.

15. 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 ￥23,666
￥51,041 total
includes taxes & fees
Nov 1 - Nov 2
1 Mi to Maine Street! Mcm-style Home in Brunswick
A spacious kitchen with a large island, bar stools, and a dining area with a sofa.

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

King size Bed Big Smile Big Sunshine 1st FL Washer&Dryer
Topsham
9.6 out of 10, Exceptional, (8 reviews)
"Perfect place and location for visiting Bowdoin."
United States
Kristen S.
The price is ￥15,777
￥39,837 total
includes taxes & fees
Nov 2 - Nov 3
King size Bed Big Smile Big Sunshine 1st FL Washer&Dryer
A wooden staircase with a wooden railing, surrounded by green foliage.

17. 1BR Apt. Authenticity. Value. Walk to everything, Sundeck. Big yard. Treehouse.

1BR Apt. Authenticity. Value. Walk to everything, Sundeck. Big yard. Treehouse.
Bath
8.2 out of 10, Very good, (21 reviews)
"Cute but aging small space, Near attractions"
United States
michael
The price is ￥19,485
￥30,010 total
includes taxes & fees
Nov 2 - Nov 3
1BR Apt. Authenticity. Value. Walk to everything, Sundeck. Big yard. Treehouse.
A cabin with two chairs facing a fire pit, surrounded by trees.

18. Cabin w/ bath + kitchenette | Hot tub add-on - 03

Cabin w/ bath + kitchenette | Hot tub add-on - 03
Freeport
9.8 out of 10, Exceptional, (10 reviews)
"Easy check in process. More than clean, it looked brand new. Overall a great stay. Kitchen was well stocked with plates, utensils, and cookware. "
United States
Michael H.
The price is ￥35,548
￥57,863 total
includes taxes & fees
Nov 1 - Nov 2
Cabin w/ bath + kitchenette | Hot tub add-on - 03
A spacious living room with a wooden staircase, a dining area with chairs, and a cozy seating area with a plaid sofa.

19. Sweet comfy cottage on Small Point Road

Sweet comfy cottage on Small Point Road
Small Point
9.6 out of 10, Exceptional, (4 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 ￥47,331
￥87,360 total
includes taxes & fees
Nov 29 - Nov 30
Sweet comfy cottage on Small Point Road
A sign for Leon Gorman Park with a wooden fence and lush greenery.

20. The Bow Street Abode / Charming 2 BR Retreat

The Bow Street Abode / Charming 2 BR Retreat
Freeport
10.0 out of 10, Exceptional, (28 reviews)
"Great location and super clean apartment!"
United States
Jo B.
The price is ￥39,443
￥67,928 total
includes taxes & fees
Nov 9 - Nov 10
The Bow Street Abode / Charming 2 BR Retreat
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
"Beautiful hotel and a convenient location!"
Terri 1-night trip
Posted 3 hours 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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  • 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 vacation rental in Bailey Island?

Yes, we give you a choice of vacation rentals in Bailey Island near Land's End Gift Shop, or you can choose a secluded option if you're looking for extra privacy while you relax. 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 vacation rentals that Bailey Island has to offer?

Spacious Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach: This highly rated vacation home rental in Bailey Island is located on the beach and has a patio, a garden, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Bailey Island?

With 34 Expedia vacation rentals, you're sure 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 vacation rentals like in Bailey Island?

Vacation rentals are private properties you can reserve for several days or longer in Bailey Island. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for a small group gathering.