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

Bailey Island Vacation Rentals

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.
$188 nightly
The price is $190
Nov 10 - Nov 11
Total with taxes and fees
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.
$421 nightly
The price is $425
Nov 16 - Nov 17
Total with taxes and fees
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
$181 nightly
The price is $191
Nov 1 - Nov 2
Total with taxes and fees
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.
$150 nightly
The price is $158
Nov 2 - Nov 3
Total with taxes and fees
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.
$186 nightly
The price is $188
Oct 31 - Nov 1
Total with taxes and fees
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.
$229 nightly
The price is $243
Nov 1 - Nov 2
Total with taxes and fees
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.
$178 nightly
The price is $179
Oct 30 - Oct 31
Total with taxes and fees
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.
$386 nightly
The price is $390
Nov 17 - Nov 18
Total with taxes and fees
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.
$339 nightly
The price is $369
Nov 2 - Nov 3
Total with taxes and fees
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.
$333 nightly
The price is $363
Nov 1 - Nov 2
Total with taxes and fees
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
$115 nightly
The price is $125
Nov 3 - Nov 4
Total with taxes and fees
Large suite/private bath/private entrance on quiet street near Thomas Bay
A backyard with a red Adirondack chair, a barbecue grill, and a wooden treehouse.

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
$173 nightly
The price is $188
Oct 30 - Oct 31
Total with taxes and fees
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.
$222 nightly
The price is $224
Nov 2 - Nov 3
Total with taxes and fees
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.
$794 nightly
The price is $865
Nov 1 - Nov 2
Total with taxes and fees
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
$297 nightly
The price is $324
Nov 1 - Nov 2
Total with taxes and fees
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.
$250 nightly
The price is $253
Nov 2 - Nov 3
Total with taxes and fees
King size Bed Big Smile Big Sunshine 1st FL Washer&Dryer
A silver convertible car parked in front of a red house with a garden.

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
$174 nightly
The price is $189
Oct 30 - Oct 31
Total with taxes and fees
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.
$336 nightly
The price is $366
Nov 1 - Nov 2
Total with taxes and fees
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.
$508 nightly
The price is $554
Nov 22 - Nov 23
Total with taxes and fees
Sweet comfy cottage on Small Point Road
A modern kitchen with white cabinets, wooden countertops, a stainless steel oven, and a microwave. There are hanging pendant lights and a window providing natural light.

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.
$395 nightly
The price is $431
Oct 30 - Oct 31
Total with taxes and fees
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.
View all properties
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, an Ascend Collection Hotel

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

10/10 Excellent
"This is a great option for crashing after a late flight into PWM. The shuttle came right away after I got it and called, super clean and spacious room and nice breakfast bar in the morning. Would definitely go back!"
Amanda 1-night trip
Posted 1 hour ago
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Find out more about Bailey Island

Everything you need to know about Bailey Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Bailey Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Bailey Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Bailey Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Bailey Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Bailey Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $87 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Bailey Island rentals

At Expedia, we put the best Bailey Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Bailey Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Bailey Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Bailey Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.