Bailey Island Vacation Rentals

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Check prices for these dates

Tonight
Nov 25 - Nov 26
Tomorrow
Nov 26 - Nov 27
This weekend
Nov 28 - Nov 30
Next weekend
Dec 5 - Dec 7

Vacation Rentals in Bailey Island

Beach
Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR

Harpswell
9.8 out of 10, Exceptional, (7)
"Orchid Harbor was perfect for my 3 week escape from life. Bailey Island is quiet and the house is comfortable and accommodating for family and friends.The outdoor seating along the ocean was our favorite place to be."
United States
Karen T.
The price is ￥25,648
￥65,058 total
includes taxes & fees
Nov 26 - Nov 27
Orchid Harbor, Bailey Island 3BR
Property grounds
Sunset Hideaway on Bailey Island

Sunset Hideaway on Bailey Island

Harpswell
8.0 out of 10, Very Good, (4)
"We really enjoyed our stay on Bailey Island. The apartment was clean and comfortable. The kitchen was well stocked and former renters had even left some food in the fridge.The house is in a sweet little, quiet community. Would recommend. Thanks"
United States
Reen and Gordon H.
Sunset Hideaway on Bailey Island
Property grounds
Modern, Luxurious Cabin in the Woods - 03

Modern, Luxurious Cabin in the Woods - 03

Freeport
10.0 out of 10, Exceptional, (6)
"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.
The price is ￥18,197
￥36,421 total
includes taxes & fees
Dec 1 - Dec 2
Modern, Luxurious Cabin in the Woods - 03
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, (144)
"Lovely space, comfortable bed, very convenient to downtown Brunswick."
United States
Kimberly G.
The price is ￥14,118
￥18,808 total
includes taxes & fees
Nov 26 - Nov 27
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
Interior
Captain's Quaters 1BR Apt. Quiet. Walk to everything. No fees. Pets stay free!

Captain's Quaters 1BR Apt. Quiet. Walk to everything. No fees. Pets stay free!

Bath
7.6 out of 10, Good, (12)
"Quaint and historic old house in a quiet neighborhood. The location was very convenient to the sights around Bath."
United States
Ricky R.
The price is ￥11,295
￥15,731 total
includes taxes & fees
Dec 1 - Dec 2
Captain's Quaters 1BR Apt. Quiet. Walk to everything. No fees. Pets stay free!
Dining
Sunny Spot with Private Parking.

Sunny Spot with Private Parking.

2.0 star property
Knightville
9.8 out of 10, Exceptional, (24)
"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 ￥14,589
￥30,778 total
includes taxes & fees
Dec 1 - Dec 2
Sunny Spot with Private Parking.
Property grounds
Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome

Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome

Boothbay
9.2 out of 10, Wonderful, (69)
"Everything was perfect. It’s an amazing home and the area is peaceful. The house was clean and it has everything you need. I will definitely be back. Thanks for a wonderful stay."
United States
Luis Correa
The price is ￥15,687
￥48,567 total
includes taxes & fees
Nov 30 - Dec 1
Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome
Interior
Brunswick Downtown Sugar Cube next to Bowdoin

Brunswick Downtown Sugar Cube next to Bowdoin

Brunswick
8.4 out of 10, Very Good, (7)
"Stayed for one night. Very convenient to campus"
United States
Lin-Lin R.
The price is ￥14,118
￥40,866 total
includes taxes & fees
Dec 3 - Dec 4
Brunswick Downtown Sugar Cube next to Bowdoin
Dining
Escape to Positive Outlook

Escape to Positive Outlook

West Point
10.0 out of 10, Exceptional, (2)
"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 ￥16,471
￥33,993 total
includes taxes & fees
Dec 1 - Dec 2
Escape to Positive Outlook
Fridge, microwave, oven, stovetop
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)
"We loved the simplicity of the residence as well as location "
United States
Joel
The price is ￥11,138
￥28,384 total
includes taxes & fees
Nov 30 - Dec 1
First Floor Little Cozy Studio with King Size Bed Downtown
Microwave, oven, stovetop
Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath

Bath
10.0 out of 10, Exceptional, (8)
"Property was nice little apartment with what I needed"
United States
stephen e.
The price is ￥15,687
￥34,711 total
includes taxes & fees
Nov 26 - Nov 27
Modern style in historic building in downtown Bath
TV
Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!

Brunswick
9.8 out of 10, Exceptional, (7)
"Such a beautiful home and peaceful location. We loved our stay and the host was responsive and helpful with any questions we had!"
United States
Diana H.
The price is ￥24,280
￥64,374 total
includes taxes & fees
Dec 2 - Dec 3
Mere Point Sunrise Views at Eastern Shore!
Interior
The Outlet House, Comfortable Cottage

The Outlet House, Comfortable Cottage

Freeport
9.8 out of 10, Exceptional, (49)
"Awesome little house perfect for our family of 4, also big bonus they had kids toys and books! Very walkable to downtown freeport, very driveable to Portland."
United States
Emily N.
The price is ￥19,060
￥35,139 total
includes taxes & fees
Dec 7 - Dec 8
The Outlet House, Comfortable Cottage
Smart TV, books
Little Lincoln beautiful home

Little Lincoln beautiful home

Brunswick
9.0 out of 10, Wonderful, (14)
"Simon was very easy to communicate with, the place was clean, the bed was quite comfortable, and we were right by Main Street in Brunswick which made for easy access to food and things to do. Wonderful place to stay!"
United States
Jessica B.
The price is ￥13,961
￥40,695 total
includes taxes & fees
Dec 1 - Dec 2
Little Lincoln beautiful home
Fridge, microwave, oven, stovetop
2King Bed BR Private Apt Downtown Brunswick

2King Bed BR Private Apt Downtown Brunswick

Brunswick
8.4 out of 10, Very Good, (10)
"Small place in a great location. Easily walk to several shops and restaurants. "
United States
Jillian B.
The price is ￥14,903
￥37,618 total
includes taxes & fees
Dec 15 - Dec 16
2King Bed BR Private Apt Downtown Brunswick
Living area
Nancy Cottage - Spacious retreat on Popham Beach with A/C!

Nancy Cottage - Spacious retreat on Popham Beach with A/C!

Phippsburg
9.4 out of 10, Exceptional, (3)
" Close walk to beach"
United States
John H.
The price is ￥28,080
￥40,183 total
includes taxes & fees
Nov 26 - Nov 27
Nancy Cottage - Spacious retreat on Popham Beach with A/C!
Iron/ironing board, free WiFi
Studio Apartment in Freeport

Studio Apartment in Freeport

2.0 star property
Freeport
The price is ￥9,883
￥22,036 total
includes taxes & fees
Dec 8 - Dec 9
Studio Apartment in Freeport
1 bedroom, iron/ironing board, free WiFi
Solitude @ The Offshore House

Solitude @ The Offshore House

Boothbay
9.8 out of 10, Exceptional, (7)
"Managers were very responsive and helpful. Condo was very clean and comfortable and close to the town of Boothbay Harbor and Ocean Point and the Botanic Gardens. "
United States
Linda O.
The price is ￥24,707
￥47,205 total
includes taxes & fees
Nov 26 - Nov 27
Solitude @ The Offshore House
Fridge, microwave, oven, stovetop
King Size Sun Rise Midcoast Lovely Stay

King Size Sun Rise Midcoast Lovely Stay

Topsham
10.0 out of 10, Exceptional, (14)
"Very pretty studio with a full modern kitchen. Very comfortable and close to everything "
United States
WEndy D.
The price is ￥14,118
￥33,906 total
includes taxes & fees
Nov 30 - Dec 1
King Size Sun Rise Midcoast Lovely Stay
Interior
Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade

Munjoy Hill
9.6 out of 10, Exceptional, (125)
"So clean! Loved all the little notes, very helpful. Such a great location close to the water and would definitely recommend this place in the future."
United States
Lorena
The price is ￥13,648
￥27,700 total
includes taxes & fees
Dec 1 - Dec 2
Adorable Portland getaway on the 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

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:

  • View our selection of featured holiday rentals in Bailey Island
  • Use the map to find apartments and other holiday homes in the Bailey Island neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Bailey Island while they last

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 23 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.