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

Bailey Island Vacation Rentals

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  • Upfront pricing

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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, (7 reviews)
"Wonderful views. Comfortable. "
United States
Susy K.
$221 nightly
The price is $224
Oct 8 - Oct 9
Total with taxes and fees
Sunset Hideaway on Bailey Island
A wooden deck with outdoor seating and string lights.

2. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (71 reviews)
"The house was lovely and well kept and in a great location."
United States
Angela M.
$339 nightly
The price is $369
Oct 14 - Oct 15
Total with taxes and fees
Full sized home
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
$203 nightly
The price is $215
Nov 1 - Nov 2
Total with taxes and fees
Mid Coast Getaway w/ water views
A deck with white railings overlooking a body of water, boats, and a forested shoreline.

4. Captains Watch: A Coastal Escape

Captains Watch: A Coastal Escape
West Point
$213 nightly
The price is $214
Oct 19 - Oct 20
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.

5. Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.6 out of 10, Exceptional, (20 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
$210 nightly
The price is $212
Oct 28 - Oct 29
Total with taxes and fees
Fantastic Waterfront Views
A wooden house with a deck and a stone pathway leading to a grassy area.

6. Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean

Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean
Freeport
10.0 out of 10, Exceptional, (18 reviews)
"Hosts were very responsive with messages. The stay was clean and comfortable."
United States
Hana L.
$260 nightly
The price is $276
Oct 20 - Oct 21
Total with taxes and fees
Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean
A lakeside property with a deck, picnic table, and barbecue grill.

7. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (70 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
$335 nightly
The price is $365
Oct 13 - Oct 14
Total with taxes and fees
Camp Forever cottage
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.
$404 nightly
The price is $408
Oct 13 - Oct 14
Total with taxes and fees
Mere Point Sunrise Views at Eastern Shore!
A two-story house with a covered porch, a garage, and a front yard with potted plants.

9. 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, (173 reviews)
"What a beautiful place to stay. Jeff and Susan made your stay a very special experience."
United States
DENESE
$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 wooden deck with a view of a lake, surrounded by trees and shrubs.

10. Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (73 reviews)
"Incredible home in a beautiful location!"
United States
Catherine G.
$434 nightly
The price is $473
Oct 9 - Oct 10
Total with taxes and fees
Centerview cottage
A spacious living room with large windows, a sofa, a chair, and a small table.

11. 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, (12 reviews)
"Quiet, clean, well appointed house close to Maine St Brunswick and convenient to both Portland and points north. "
United States
Kendra G.
$301 nightly
The price is $328
Oct 20 - Oct 21
Total with taxes and fees
1 Mi to Maine Street! MCM-Style Home in Brunswick
A room with a sliding glass door leading to an outdoor deck with Adirondack chairs and a table.

12. Three bedroom in United States of America, Freeport

Three bedroom in United States of America, Freeport
Freeport
10.0 out of 10, Exceptional, (12 reviews)
$937 nightly
The price is $1,021
Nov 4 - Nov 5
Total with taxes and fees
Three bedroom in United States of America, Freeport
A spacious living room with large windows, a sofa, a chair, and a small table.

13. 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
Oct 20 - Oct 21
Total with taxes and fees
1 Mi to Maine Street! Mcm-style Home in Brunswick
A modern kitchen with white cabinets, a wooden dining table, and a vase with green leaves.

14. 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.
$267 nightly
The price is $270
Nov 2 - Nov 3
Total with taxes and fees
King Size Sun Rise Midcoast Lovely Stay
A cabin with a fire pit and outdoor seating.

15. Glamping cabin w/ full bath + spa access - 21

Glamping cabin w/ full bath + spa access - 21
Freeport
10.0 out of 10, Exceptional, (1 review)
$390 nightly
The price is $425
Oct 28 - Oct 29
Total with taxes and fees
Glamping cabin w/ full bath + spa access - 21
A cabin with two chairs facing a fire pit, surrounded by trees.

16. Modern cabin w/ full bath & kitchenette - 03

Modern cabin w/ full bath & kitchenette - 03
Freeport
10.0 out of 10, Exceptional, (9 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.
$303 nightly
The price is $330
Oct 8 - Oct 9
Total with taxes and fees
Modern cabin w/ full bath & kitchenette - 03
A treehouse with a wooden staircase and a small building with a colorful mural.

17. Perfect stopover, getaway, base to explore the area, or to simply stay in town.

Perfect stopover, getaway, base to explore the area, or to simply stay in town.
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
$172 nightly
The price is $187
Oct 18 - Oct 19
Total with taxes and fees
Perfect stopover, getaway, base to explore the area, or to simply stay in town.
A spacious kitchen with a large island, bar stools, and a dining area with a sofa.

18. 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, (7 reviews)
"Perfect place and location for visiting Bowdoin."
United States
Kristen S.
$305 nightly
The price is $308
Oct 28 - Oct 29
Total with taxes and fees
King size Bed Big Smile Big Sunshine 1st FL Washer&Dryer
A wooden staircase with a wooden railing, surrounded by green foliage.

19. 1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!

1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!
Bath
8.2 out of 10, Very good, (21 reviews)
"Cute but aging small space, Near attractions"
United States
michael
$164 nightly
The price is $179
Oct 12 - Oct 13
Total with taxes and fees
1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!
A modern kitchen with white cabinetry, a central island with stools, a refrigerator, and a microwave.

20. 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.
$375 nightly
The price is $409
Nov 2 - Nov 3
Total with taxes and fees
Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
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

Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

8/10 Good
"Staff members absolutely amazing even prior to checking in. There was a problem with the system generating keys, The staff made sure we could get in our room and rest. Hats off to the weekend staff!"
Paula 2-night trip
Posted 22 hours ago
Tru by Hilton Portland Airport Area

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 $147 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.