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
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Bailey Island vacation rentals

Property grounds

1. Sunset Hideaway on Bailey Island

Sunset Hideaway on Bailey Island
Harpswell
8.4 out of 10, Very Good, (5 reviews)
"Wonderful views. Comfortable. "
United States
Susy K.
$217 nightly
The price is $219
Sep 23 - Sep 24
Total with taxes and fees
Sunset Hideaway on Bailey Island
Terrace/patio

2. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (68 reviews)
"The house was lovely and well kept and in a great location."
United States
Angela M.
$339 nightly
The price is $369
Sep 22 - Sep 23
Total with taxes and fees
Full sized home
TV

3. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.4 out of 10, Exceptional, (9 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
$235 nightly
The price is $250
Sep 20 - Sep 21
Total with taxes and fees
Mid Coast Getaway w/ water views
Property grounds

4. Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (70 reviews)
"Incredible home in a beautiful location!"
United States
Catherine G.
$421 nightly
The price is $459
Sep 20 - Sep 21
Total with taxes and fees
Centerview cottage
Terrace/patio

5. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (67 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
$333 nightly
The price is $363
Sep 13 - Sep 14
Total with taxes and fees
Camp Forever cottage
Cottage (2 Bedrooms) | Interior

6. 'osprey Cottage' South Freeport Home on Casco Bay!

'osprey Cottage' South Freeport Home on Casco Bay!
3.0 star property
Freeport
$579 nightly
The price is $614
Sep 30 - Oct 1
Total with taxes and fees
'osprey Cottage' South Freeport Home on Casco Bay!
TV

7. 2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
10.0 out of 10, Exceptional, (5 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.
$265 nightly
The price is $282
Sep 16 - Sep 17
Total with taxes and fees
2 bedroom w/ expansive water views
Interior

8. Three bedroom in United States of America, Freeport

Three bedroom in United States of America, Freeport
Freeport
10.0 out of 10, Exceptional, (8 reviews)
$873 nightly
The price is $951
Oct 12 - Oct 13
Total with taxes and fees
Three bedroom in United States of America, Freeport
3 bedrooms, WiFi, bed sheets

9. Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.8 out of 10, Exceptional, (18 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
$347 nightly
The price is $350
Oct 11 - Oct 12
Total with taxes and fees
Fantastic Waterfront Views
Outdoor dining

10. 'Osprey Cottage' South Freeport Home on Casco Bay!

'Osprey Cottage' South Freeport Home on Casco Bay!
Freeport
8.8 out of 10, Excellent, (23 reviews)
"This was an adorable cottage in a picturesque location. The cottage was clean and comfortable, right on the water. Additional friends stayed in the adjacent Heron cottage, and we joined them on the patio for a fire one evening as summer faded to autumn."
United States
John J.
$570 nightly
The price is $621
Sep 30 - Oct 1
Total with taxes and fees
'Osprey Cottage' South Freeport Home on Casco Bay!
Honeymoon Studio | Egyptian cotton sheets, premium bedding, down comforters, bed sheets

11. Fortland Island Campground

Fortland Island Campground
1.0 star property
Portland
10.0 out of 10, Exceptional, (3 reviews)
"It was very quiet and liked the experience of staying in a camp like setting."
United States
leela srinivas
Fortland Island Campground
Property grounds

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

Modern cabin w/ full bath & kitchenette - 03
Freeport
10.0 out of 10, Exceptional, (8 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.
$264 nightly
The price is $288
Sep 15 - Sep 16
Total with taxes and fees
Modern cabin w/ full bath & kitchenette - 03
Exterior

13. 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, (169 reviews)
"What a beautiful place to stay. Jeff and Susan made your stay a very special experience."
United States
DENESE
$152 nightly
The price is $166
Sep 15 - Sep 16
Total with taxes and fees
Large suite/private bath/private entrance on quiet street near Thomas Bay
Property grounds

14. 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)
$264 nightly
The price is $288
Sep 15 - Sep 16
Total with taxes and fees
Glamping cabin w/ full bath + spa access - 21
Interior

15. Lush Coastal Downtown Home - Beaches & Shopping

Lush Coastal Downtown Home - Beaches & Shopping
Freeport
10.0 out of 10, Exceptional, (6 reviews)
"Our stay was very comfortable and easy to navigate. The host was very communicative. We had everything we needed and more. It was nice to be in walking distance from downtown Freeport. Although the price was higher than we wanted, our family of four (2 teens) enjoyed having a clean, comfortable and seamless stay."
United States
Alana K.
$555 nightly
The price is $605
Sep 17 - Sep 18
Total with taxes and fees
Lush Coastal Downtown Home - Beaches & Shopping
Front of property

16. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (11 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
$617 nightly
The price is $673
Sep 13 - Sep 14
Total with taxes and fees
Evalina Hotel
Interior

17. 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, (4 reviews)
"Great location and super clean house"
United States
Gary R.
$650 nightly
The price is $709
Sep 14 - Sep 15
Total with taxes and fees
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
Exterior

18. Ocean View East End Studio in a Historic Victorian

Ocean View East End Studio in a Historic Victorian
Portland
10.0 out of 10, Exceptional, (111 reviews)
"Fantastic host, fantastic place, fantastic location. 30 second walk out to a massive green lawned park overlooking the water. Easy stroll downtown. Dan was a very friendly, welcoming, and accommodating host. We had a great stay and would return again."
United States
Ryan S.
$423 nightly
The price is $461
Sep 14 - Sep 15
Total with taxes and fees
Ocean View East End Studio in a Historic Victorian
Beach

19. City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (131 reviews)
"Wonderful place! Owner very responsible! Would stay again! Great choice for place to stay away from home."
United States
Arlene L.
$376 nightly
The price is $409
Sep 22 - Sep 23
Total with taxes and fees
City Amenities, Casco Bay Sunrises and Natural Beauty
Exterior detail

20. Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (183 reviews)
"Wonderful experience with exceptional hosts!"
United States
Cynthia
$425 nightly
The price is $463
Sep 16 - Sep 17
Total with taxes and fees
Glorious getaway on Portland's Eastern Promenade.
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

Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

10/10 Excellent
"Beautiful and relaxing! Definitely would return."
Joseph 2-night trip
Posted 1 hour ago
Cambria Hotel Portland Downtown-Old Port

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 $161 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 32 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.