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
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Bailey Island vacation rentals

Exterior

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, (153 reviews)
"The place was lovely, communications with the host were helpful and friendly. Dinner restaurant recommendations were great as well. "
United States
Jane T.
$133 nightly
The price is $145
Jun 29 - Jun 30
Total with taxes and fees
Large suite/private bath/private entrance on quiet street near Thomas Bay
Outdoor dining

Captain's Guest Room. Authenticity. Value. Near everything. No fees.

Captain's Guest Room. Authenticity. Value. Near everything. No fees.
Bath
8.2 out of 10, Very Good, (22 reviews)
"Great location and a beautiful property. Great walking/driving distance from town and the waterfront, we had a great stay and would do it again! "
United States
Nina P.
$134 nightly
The price is $146
Jun 29 - Jun 30
Total with taxes and fees
Captain's Guest Room. Authenticity. Value. Near everything. No fees.
House (2 Bedrooms) | Interior

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
$286 nightly
The price is $312
Jul 16 - Jul 17
Total with taxes and fees
1 Mi to Maine Street! Mcm-style Home in Brunswick
TV, fireplace, books

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

1 Mi to Maine Street! MCM-Style Home in Brunswick
Brunswick
9.4 out of 10, Exceptional, (9 reviews)
"There were a number of great details, snacks, art, pottery and the story of the house and owner (worth reading)."
United States
Seraphina E.
$293 nightly
The price is $317
Jul 16 - Jul 17
Total with taxes and fees
1 Mi to Maine Street! MCM-Style Home in Brunswick
2 bedrooms, WiFi, bed sheets

Large, luxurious geodesic dome - 04

Large, luxurious geodesic dome - 04
Freeport
10.0 out of 10, Exceptional, (3 reviews)
"Pet friendly and the experience is just amazing. Thank you for having us! "
United States
Rene B.
$388 nightly
The price is $423
Jun 29 - Jun 30
Total with taxes and fees
Large, luxurious geodesic dome - 04
Dining

King Size Sun Rise Midcoast Lovely Stay

King Size Sun Rise Midcoast Lovely Stay
Topsham
10.0 out of 10, Exceptional, (15 reviews)
"Great location surroundings a little unkept but tis the spring cleanup season. Excellent accommodation and located near town shopping but quiet neighborhood"
United States
Douglas H.
$381 nightly
The price is $415
Jul 1 - Jul 2
Total with taxes and fees
King Size Sun Rise Midcoast Lovely Stay
TV

Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.4 out of 10, Exceptional, (6 reviews)
"Second time we have stay in this cottage. The perfect location for a Maine vacation. "
United States
chuck c.
$263 nightly
The price is $279
Jun 30 - Jul 1
Total with taxes and fees
Mid Coast Getaway w/ water views
Interior

Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath
Bath
9.8 out of 10, Exceptional, (10 reviews)
"Clean comfortable and right downtown"
United States
stephen e.
$225 nightly
The price is $245
Jun 29 - Jun 30
Total with taxes and fees
Modern style in historic building in downtown Bath
Property grounds

Modern, Luxurious Cabin in the Woods - 03

Modern, Luxurious Cabin in the Woods - 03
Freeport
10.0 out of 10, Exceptional, (7 reviews)
"This was a perfect little cabin. It was clean, well equipped with a nice kitchen and bathroom, quiet and wooded location, and comfy bed. "
United States
Chris B.
$408 nightly
The price is $445
Jul 5 - Jul 6
Total with taxes and fees
Modern, Luxurious Cabin in the Woods - 03
Terrace/patio

Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (58 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
$336 nightly
The price is $366
Jun 27 - Jun 28
Total with taxes and fees
Camp Forever cottage
Interior

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (27 reviews)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
$368 nightly
The price is $401
Jul 6 - Jul 7
Total with taxes and fees
Sunny Spot with Private Parking.
Outdoor dining

Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.6 out of 10, Exceptional, (10 reviews)
"Apartment was very cute, clean, and just what I was looking for. Jennifer was very accommodating and understanding "
United States
Jolee S.
$303 nightly
The price is $330
Jun 29 - Jun 30
Total with taxes and fees
Peaceful & minutes from the Old Port with private parking
TV

Private Entrance Residential Portland

Private Entrance Residential Portland
Deering Center
8.4 out of 10, Very Good, (7 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.
$206 nightly
The price is $209
Jun 30 - Jul 1
Total with taxes and fees
Private Entrance Residential Portland
3 bedrooms, premium bedding, iron/ironing board, travel crib

Cozy 3BR | Pet Friendly | Near Portland | Parking

Cozy 3BR | Pet Friendly | Near Portland | Parking
Westbrook
10.0 out of 10, Exceptional, (13 reviews)
"We had a great stay here. It was very clean and conveniently located."
United States
Angela B.
$504 nightly
The price is $549
Jul 9 - Jul 10
Total with taxes and fees
Cozy 3BR | Pet Friendly | Near Portland | Parking
Honeymoon Studio | Egyptian cotton sheets, premium bedding, down comforters, bed sheets

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
$384 nightly
The price is $419
Jul 21 - Jul 22
Total with taxes and fees
Fortland Island Campground
Interior

East end. Walk to food, beer and downtown fun.

East end. Walk to food, beer and downtown fun.
Munjoy Hill
9.8 out of 10, Exceptional, (38 reviews)
"Clean, great location, excellent communication with host, perfectly furnished for our group"
United States
Elizabeth P.
$343 nightly
The price is $366
Jun 28 - Jun 29
Total with taxes and fees
East end. Walk to food, beer and downtown fun.
Interior

Downtown Brunswick New Look Old Charm Next to Bowdoin

Downtown Brunswick New Look Old Charm Next to Bowdoin
Brunswick
9.8 out of 10, Exceptional, (21 reviews)
"We really enjoyed our visit with family and friends and the location was perfect for what we needed. "
United States
Eliza
$324 nightly
The price is $353
Jun 30 - Jul 1
Total with taxes and fees
Downtown Brunswick New Look Old Charm Next to Bowdoin
Property grounds

First Floor Little Cozy Studio with King Size Bed Downtown

First Floor Little Cozy Studio with King Size Bed Downtown
Brunswick
8.8 out of 10, Excellent, (6 reviews)
"We loved the simplicity of the residence as well as location "
United States
Joel
$392 nightly
The price is $427
Jul 19 - Jul 20
Total with taxes and fees
First Floor Little Cozy Studio with King Size Bed Downtown
Terrace/patio

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (53 reviews)
"Wonderful stay!"
United States
Erika T.
$341 nightly
The price is $371
Jul 1 - Jul 2
Total with taxes and fees
Full sized home
TV

2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
10.0 out of 10, Exceptional, (3 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.
$384 nightly
The price is $411
Jun 27 - Jun 28
Total with taxes and fees
2 bedroom w/ expansive water views
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

Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

8/10 Good
"average hotel near the airport"
Harold 1-night trip
Posted less than an hour ago
Fireside Inn & Suites Portland

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 $146 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. Our travelers also rate Johnson Homestead. One level living, ocean view with semi-private beach access. as a favorite home for rent in Bailey Island.

How many vacation rentals are there in Bailey Island?

With 31 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.