Bailey Island Vacation Rentals

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Our top choices for Bailey Island vacation rentals

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.
$221 nightly
The price is $234
May 3 - May 4
Total with taxes and fees
2 bedroom w/ expansive water views

HomeAwhile

HomeAwhile
4.0 star property
Scarborough
9.2 out of 10, Wonderful, (30 reviews)
"It was a perfect stay!"
United States
Armando
$125 nightly
The price is $136
May 27 - May 28
Total with taxes and fees
HomeAwhile

Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (5 reviews)
"Second time we have stay in this cottage. The perfect location for a Maine vacation. "
United States
chuck c.
$203 nightly
The price is $215
May 3 - May 4
Total with taxes and fees
Mid Coast Getaway w/ water views

Modern, Luxurious, Cabin in the Woods - 17

Modern, Luxurious, Cabin in the Woods - 17
Freeport
10.0 out of 10, Exceptional, (3 reviews)
"Awesome camping in a great, quiet campground. The staff is very responsive and all the little details make this place special."
United States
Miranda K.
$282 nightly
The price is $308
May 3 - May 4
Total with taxes and fees
Modern, Luxurious, Cabin in the Woods - 17

Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath
Bath
10.0 out of 10, Exceptional, (8 reviews)
"Clean comfortable and right downtown"
United States
stephen e.
$201 nightly
The price is $219
May 8 - May 9
Total with taxes and fees
Modern style in historic building in downtown Bath

Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (58 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
$309 nightly
The price is $337
May 1 - May 2
Total with taxes and fees
Camp Forever cottage

Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.8 out of 10, Exceptional, (16 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
$280 nightly
The price is $281
May 3 - May 4
Total with taxes and fees
Fantastic Waterfront Views

Private Entrance Residential Portland

Private Entrance Residential Portland
Deering Center
8.8 out of 10, Excellent, (6 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.
$144 nightly
The price is $145
May 3 - May 4
Total with taxes and fees
Private Entrance Residential Portland

Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
Brunswick
10.0 out of 10, Exceptional, (148 reviews)
"Lovely space, comfortable bed, very convenient to downtown Brunswick."
United States
Kimberly G.
$110 nightly
The price is $120
May 14 - May 15
Total with taxes and fees
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Captain's House 2BR Guest Suite. Discover the authenticity & best value in Bath!

Captain's House 2BR Guest Suite. Discover the authenticity & best value in Bath!
Bath
8.6 out of 10, Excellent, (10 reviews)
"Clean rooms. Quiet location walkable to much of downtown Bath "
United States
randy k.
$231 nightly
The price is $251
May 11 - May 12
Total with taxes and fees
Captain's House 2BR Guest Suite. Discover the authenticity & best value in Bath!

Large, luxurious geodesic dome - 04

Large, luxurious geodesic dome - 04
Freeport
10.0 out of 10, Exceptional, (2 reviews)
"We didn’t get enough time to evaluate but from the short visit, we can say that this is the small paradise within the Main area. Best camp ground facilities we have ever seen or experienced. Looking forward to visit with friends and extended families as well. "
United States
Hrishi K.
$368 nightly
The price is $401
May 10 - May 11
Total with taxes and fees
Large, luxurious geodesic dome - 04

Brunswick Downtown Sugar Cube next to Bowdoin

Brunswick Downtown Sugar Cube next to Bowdoin
Brunswick
8.4 out of 10, Very Good, (7 reviews)
"We ahd a great stay in Maine over the 4th visiting family, eating good food and walking around in great weather. Great stay in Brunswick, easy in and easy out and all sorts of things Maine accessible. Would recommend for anyone looking for a hassle-free weekend in coastal Maine. "
United States
Tjorvi P.
$248 nightly
The price is $270
May 3 - May 4
Total with taxes and fees
Brunswick Downtown Sugar Cube next to Bowdoin

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (25 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
$237 nightly
The price is $258
May 4 - May 5
Total with taxes and fees
Sunny Spot with Private Parking.

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, (9 reviews)
"This well- appointed apartment was perfect for our stay in the Portland area. Jennifer was always quick to answer any questions. We would definitely recommend this listing."
United States
Lynn E.
$253 nightly
The price is $276
May 6 - May 7
Total with taxes and fees
Peaceful & minutes from the Old Port with private parking

2King Bed BR Private Apt Downtown Brunswick

2King Bed BR Private Apt Downtown Brunswick
Brunswick
8.4 out of 10, Very Good, (12 reviews)
"Small place in a great location. Easily walk to several shops and restaurants. "
United States
Jillian B.
$278 nightly
The price is $303
May 5 - May 6
Total with taxes and fees
2King Bed BR Private Apt Downtown Brunswick

Little Lincoln beautiful home

Little Lincoln beautiful home
Brunswick
9.0 out of 10, Wonderful, (16 reviews)
"The host was very welcoming and responsive when we had a question. We would stay here again when we come back to Brunswick. "
United States
Michael S.
$256 nightly
The price is $279
May 25 - May 26
Total with taxes and fees
Little Lincoln beautiful home

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, (32 reviews)
"Clean, great location, excellent communication with host, perfectly furnished for our group"
United States
Elizabeth P.
$349 nightly
The price is $372
May 4 - May 5
Total with taxes and fees
East end. Walk to food, beer and downtown fun.

Luxury on Back Cove - Three Gables

Luxury on Back Cove - Three Gables
Rosemont
10.0 out of 10, Exceptional, (9 reviews)
"GoodLocation, very clean. Would stay again "
United States
Carly B.
$335 nightly
The price is $365
May 4 - May 5
Total with taxes and fees
Luxury on Back Cove - Three Gables

Willard Beach–Private Apt Near Portland & Parks

Willard Beach–Private Apt Near Portland & Parks
Willard Beach
10.0 out of 10, Exceptional, (5 reviews)
"Excellent in every way."
United States
Robert B.
$233 nightly
The price is $254
May 6 - May 7
Total with taxes and fees
Willard Beach–Private Apt Near Portland & Parks

Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (59 reviews)
"Great spot to relax and enjoy the beautiful outdoors. Very quiet and amazing views of the water. Everything needed for a comfortable and relaxing getaway. Highly recommend if coming to the area! "
United States
Erin
$434 nightly
The price is $473
May 1 - May 2
Total with taxes and fees
Centerview cottage
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

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 $136 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.

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?

New 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 30 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.