Bailey Island Vacation Rentals

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Check prices for these dates

In two weeks
May 15 - May 17
In two months
Jun 26 - Jun 28
In three months
Jul 24 - Jul 26
In four months
Aug 21 - Aug 23

Our top choices for Bailey Island vacation rentals

TV

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.
The price is ￥13,404
￥30,057 total
includes taxes & fees
Apr 30 - May 1
Mid Coast Getaway w/ water views
Interior

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.
The price is ￥15,941
￥35,273 total
includes taxes & fees
May 14 - May 15
Modern style in historic building in downtown Bath
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.
The price is ￥20,086
￥37,325 total
includes taxes & fees
May 5 - May 6
2 bedroom w/ expansive water views
Exterior

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.
The price is ￥14,347
￥19,113 total
includes taxes & fees
Apr 30 - May 1
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
3 bedrooms, WiFi

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.
The price is ￥25,107
￥45,218 total
includes taxes & fees
May 4 - May 5
Fantastic Waterfront Views
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.
The price is ￥30,159
￥53,745 total
includes taxes & fees
Apr 30 - May 1
Camp Forever cottage
Outdoor dining

Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (8 reviews)
"Lovely location "
United States
Michelle S.
The price is ￥60,702
￥107,052 total
includes taxes & fees
May 27 - May 28
Mere Point Sunrise Views at Eastern Shore!
TV

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.
The price is ￥15,941
￥43,092 total
includes taxes & fees
May 3 - May 4
Brunswick Downtown Sugar Cube next to Bowdoin
TV

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.
The price is ￥11,717
￥23,163 total
includes taxes & fees
May 5 - May 6
Private Entrance Residential Portland
Interior

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
The price is ￥17,090
￥34,108 total
includes taxes & fees
Apr 30 - May 1
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, (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.
The price is ￥17,226
￥36,170 total
includes taxes & fees
Apr 30 - May 1
Peaceful & minutes from the Old Port with private parking
Living area

Fred Cottage - Spacious retreat on Popham Beach!

Fred Cottage - Spacious retreat on Popham Beach!
Phippsburg
9.6 out of 10, Exceptional, (4 reviews)
"Off the beaten path, easy access to beach and Spinneys"
United States
Sean B.
The price is ￥31,667
￥44,605 total
includes taxes & fees
May 4 - May 5
Fred Cottage - Spacious retreat on Popham Beach!
Outdoor dining

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.
The price is ￥34,611
￥55,467 total
includes taxes & fees
May 12 - May 13
Modern, Luxurious, Cabin in the Woods - 17
2 bedrooms, WiFi, bed sheets

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.
The price is ￥35,903
￥60,528 total
includes taxes & fees
May 3 - May 4
Large, luxurious geodesic dome - 04
Property grounds

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.
The price is ￥32,648
￥40,108 total
includes taxes & fees
May 11 - May 12
Captain's House 2BR Guest Suite. Discover the authenticity & best value in Bath!
Interior

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.
The price is ￥16,738
￥44,482 total
includes taxes & fees
May 25 - May 26
Little Lincoln beautiful home
Property grounds

Pond Cabin: Private Sauna+Near Beach+FirePit+Pond

Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
Georgetown
The price is ￥36,880
￥66,203 total
includes taxes & fees
May 3 - May 4
Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
Property grounds

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
The price is ￥47,026
￥75,411 total
includes taxes & fees
May 3 - May 4
Centerview cottage
Smart TV

Beautiful Delightful 3BR Downtown Brunswick All King Beds

Beautiful Delightful 3BR Downtown Brunswick All King Beds
Brunswick
10.0 out of 10, Exceptional, (23 reviews)
"Great place, super convenient to downtown."
United States
Heather C.
The price is ￥25,531
￥85,922 total
includes taxes & fees
May 26 - May 27
Beautiful Delightful 3BR Downtown Brunswick All King Beds
Smart TV

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.
The price is ￥19,110
￥43,766 total
includes taxes & fees
May 6 - May 7
Willard Beach–Private Apt Near Portland & Parks
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

Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent
"The shuttle driver and the service they offered was great. They took us to dinner on the waterfront,then picked us up and took us to the State theater. They also picked us up after the show. The staff and breakfast buffet was awesome I'm just beware,they have cutback and breakfast was no longer free.that said it was delicious and well worth the price"
John 1-night trip
Posted 1 hour ago
Holiday Inn Portland-By the Bay by IHG

Find out more about Bailey Island

Search for holiday rentals in Bailey Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Bailey Island using one of the methods below:

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Look no further and take a look at our great range of rental properties in Bailey Island!

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.