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 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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. 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.
$386 nightly
The price is $390
Oct 27 - Oct 28
Total with taxes and fees
Orchid Harbor, Bailey Island 3BR
A grassy area with a picnic table and chairs, a body of water, and two trees in the background.

2. 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.
$192 nightly
The price is $194
Nov 10 - Nov 11
Total with taxes and fees
Sunset Hideaway on Bailey Island
A wooden deck with outdoor seating and string lights.

3. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (78 reviews)
"Wonderful stay!"
United States
Erika T.
$339 nightly
The price is $369
Oct 27 - Oct 28
Total with taxes and fees
Full sized home
A room with a sliding glass door leading to an outdoor deck with Adirondack chairs and a table.

4. 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.
$828 nightly
The price is $902
Nov 8 - Nov 9
Total with taxes and fees
Casco Bay Oceanfront Retreat by Everrow
A lakeside property with a deck, picnic table, and barbecue grill.

5. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (72 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.
$336 nightly
The price is $366
Nov 1 - Nov 2
Total with taxes and fees
Camp Forever cottage
A deck with white railings overlooking a body of water, boats, and a forested shoreline.

6. Captains Watch: A Coastal Escape

Captains Watch: A Coastal Escape
West Point
$185 nightly
The price is $187
Oct 25 - Oct 26
Total with taxes and fees
Captains Watch: A Coastal Escape
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
9.6 out of 10, Exceptional, (21 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
$178 nightly
The price is $179
Nov 1 - Nov 2
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.
$390 nightly
The price is $394
Nov 17 - Nov 18
Total with taxes and fees
Mere Point Sunrise Views at Eastern Shore!
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.

9. 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.
$227 nightly
The price is $241
Nov 1 - Nov 2
Total with taxes and fees
2 bedroom w/ expansive water views
A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

10. 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
$203 nightly
The price is $215
Nov 1 - Nov 2
Total with taxes and fees
Mid Coast Getaway w/ water views
A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

11. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (127 reviews)
"Really nice room and location"
United States
Victoria
$278 nightly
The price is $296
Nov 16 - Nov 17
Total with taxes and fees
The Weldon Hotel
A bedroom with a large window, a bed, a nightstand, and a wooden dresser.

12. Modern dome w/ full bath | Hot tub add-on - 04

Modern dome w/ full bath | Hot tub add-on - 04
Freeport
10.0 out of 10, Exceptional, (5 reviews)
"Pet friendly and the experience is just amazing. Thank you for having us! "
United States
Rene B.
$307 nightly
The price is $335
Oct 25 - Oct 26
Total with taxes and fees
Modern dome w/ full bath | Hot tub add-on - 04
A cabin with two chairs facing a fire pit, surrounded by trees.

13. 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.
$331 nightly
The price is $361
Oct 28 - Oct 29
Total with taxes and fees
Cabin w/ bath + kitchenette | Hot tub add-on - 03
A multi-story building with a stone facade, large windows, and a corner entrance.

14. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (16 reviews)
"This is a very nice hotel in a great location. It’s new and wonderfully appointed. Everything about it is first class."
United States
Rick
$421 nightly
The price is $459
Nov 10 - Nov 11
Total with taxes and fees
Evalina Hotel
A two-story house with a covered porch, a garage, and a front yard with potted plants.

15. 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 spacious living room with large windows, a sofa, a chair, and a small table.

16. 1 Mi to Maine Street! MCM-Style Home in Brunswick

1 Mi to Maine Street! MCM-Style Home in Brunswick
Brunswick
9.6 out of 10, Exceptional, (13 reviews)
"Quiet, clean, well appointed house close to Maine St Brunswick and convenient to both Portland and points north. "
United States
Kendra G.
$303 nightly
The price is $330
Nov 1 - Nov 2
Total with taxes and fees
1 Mi to Maine Street! MCM-Style Home in Brunswick
A modern kitchen with white cabinetry, a central island with stools, a refrigerator, and a microwave.

17. Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)

Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
Brunswick
9.6 out of 10, Exceptional, (34 reviews)
"Perfect for what we needed for the week. All that was missing was some oven mitts and maybe a pair of scissors but we made it work!! Great little spot - thank you!! "
United States
Britta M.
$358 nightly
The price is $390
Nov 1 - Nov 2
Total with taxes and fees
Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
A spacious living room with a blue sofa, a white chair, a tufted ottoman, and a wooden coffee table.

18. Beautiful Delightful 3BR Downtown Brunswick All King Beds

Beautiful Delightful 3BR Downtown Brunswick All King Beds
Brunswick
10.0 out of 10, Exceptional, (26 reviews)
"This was just what we needed and close to everything we were doing!"
United States
Darryl T.
$496 nightly
The price is $541
Oct 25 - Oct 26
Total with taxes and fees
Beautiful Delightful 3BR Downtown Brunswick All King Beds
A spacious living room with large windows, a sofa, a chair, and a small table.

19. 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 cozy room with wooden flooring, wicker furniture, and a white brick wall.

20. Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard

Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
Brunswick
10.0 out of 10, Exceptional, (5 reviews)
"Great location and super clean house"
United States
Gary R.
$680 nightly
The price is $741
Nov 8 - Nov 9
Total with taxes and fees
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
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

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
"Kind staff, checked out about 30 minutes late but they were very accommodating."
Juliana 1-night trip
Posted 9 hours 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 $97 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.