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 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

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.
$223 nightly
The price is $226
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.
$340 nightly
The price is $370
Sep 22 - Sep 23
Total with taxes and fees
Full sized home
Living area

3. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.6 out of 10, Exceptional, (8 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
$265 nightly
The price is $282
Sep 13 - Sep 14
Total with taxes and fees
Mid Coast Getaway w/ water views
Living area

4. 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.
$271 nightly
The price is $288
Sep 7 - Sep 8
Total with taxes and fees
2 bedroom w/ expansive water views
Terrace/patio

5. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (65 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
$332 nightly
The price is $362
Sep 6 - Sep 7
Total with taxes and fees
Camp Forever cottage
House (2 Bedrooms) | Interior

6. 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
$249 nightly
The price is $271
Sep 23 - Sep 24
Total with taxes and fees
1 Mi to Maine Street! Mcm-style Home in Brunswick
Property grounds

7. Captain's 1BR Suite. Authenticity. Value. Walk to everything. Large yard.

Captain's 1BR Suite. Authenticity. Value. Walk to everything. Large yard.
Bath
8.0 out of 10, Very Good, (19 reviews)
"Cute but aging small space, Near attractions"
United States
michael
$149 nightly
The price is $162
Sep 7 - Sep 8
Total with taxes and fees
Captain's 1BR Suite. Authenticity. Value. Walk to everything. Large yard.
Outdoor dining

8. Guest room + bath in Bath!. Authenticity. Value. Large yard. Walk to everything.

Guest room + bath in Bath!. Authenticity. Value. Large yard. Walk to everything.
Bath
8.2 out of 10, Very Good, (29 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
$145 nightly
The price is $158
Sep 6 - Sep 7
Total with taxes and fees
Guest room + bath in Bath!. Authenticity. Value. Large yard. Walk to everything.
Room

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.
$424 nightly
The price is $429
Sep 9 - Sep 10
Total with taxes and fees
Fantastic Waterfront Views
Interior

10. Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath
Bath
10.0 out of 10, Exceptional, (11 reviews)
"Great location! We spent very little time in the room, but it was a great place to come back and crash! "
United States
Kristina M.
$215 nightly
The price is $234
Sep 8 - Sep 9
Total with taxes and fees
Modern style in historic building in downtown Bath
Exterior

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, (166 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 13 - Sep 14
Total with taxes and fees
Large suite/private bath/private entrance on quiet street near Thomas Bay
Property grounds

12. Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (69 reviews)
"Incredible home in a beautiful location!"
United States
Catherine G.
$415 nightly
The price is $452
Sep 7 - Sep 8
Total with taxes and fees
Centerview cottage
Property grounds

13. 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 8 - Sep 9
Total with taxes and fees
Modern cabin w/ full bath & kitchenette - 03
Dining

14. King Size Sun Rise Midcoast Lovely Stay

King Size Sun Rise Midcoast Lovely Stay
Topsham
9.6 out of 10, Exceptional, (18 reviews)
"Perfect for a my husband and I. Close to everything!"
United States
Tabcline S.
$257 nightly
The price is $260
Sep 28 - Sep 29
Total with taxes and fees
King Size Sun Rise Midcoast Lovely Stay
Property grounds

15. 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, (17 reviews)
"Hosts were very responsive with messages. The stay was clean and comfortable."
United States
Hana L.
$332 nightly
The price is $355
Sep 20 - Sep 21
Total with taxes and fees
Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean
Property grounds

16. 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 8 - Sep 9
Total with taxes and fees
Glamping cabin w/ full bath + spa access - 21
Honeymoon Studio

17. 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
$357 nightly
The price is $389
Sep 6 - Sep 7
Total with taxes and fees
Fortland Island Campground
Living area

18. Private Entrance Residential Portland

Private Entrance Residential Portland
Deering Center
8.8 out of 10, Excellent, (11 reviews)
"This was a great place to stay. Easy to get to all of our destinations. Place was clean and comfortable. Would stay here again. "
United States
Ameleah B.
$165 nightly
The price is $166
Sep 7 - Sep 8
Total with taxes and fees
Private Entrance Residential Portland
Outdoor dining

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

'Osprey Cottage' South Freeport Home on Casco Bay!
Freeport
8.8 out of 10, Excellent, (22 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.
$593 nightly
The price is $646
Sep 30 - Oct 1
Total with taxes and fees
'Osprey Cottage' South Freeport Home on Casco Bay!
Private kitchen

20. Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport

Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport
Freeport
10.0 out of 10, Exceptional, (11 reviews)
"Our whole family was impressed by this house!"
United States
Gary B.
$623 nightly
The price is $679
Sep 7 - Sep 8
Total with taxes and fees
Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport
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

Best Western Merry Manor Inn

Best Western Merry Manor Inn

10/10 Excellent
"The Merry Manor is conveniently located near airport and downtown. We stayed twice, once in a room that was ok and then got a nicer room when we returned. We liked that the shower and toilet were in a separate room with a sink and then an exterior sink accommodated the other person. There was a coffee maker, microwave and fridge with plenty of room for 2 suitcases. The breakfast was varied and surprisingly good for a motel. We used the hot tub and discovered that the pool is slightly heated as well, so a swim in cool weather was pleasant. All told, we enjoyed our stay."
Gail Swick 2-night trip
Posted less than an hour ago
Best Western Merry Manor Inn

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 $166 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.