Bailey Island Vacation Rentals

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Vacation Rentals in Bailey Island

Property grounds
Modern, Luxurious Cabin in the Woods - 03

Cabin in 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.
$209 nightly
The price is $228
Nov 30 - Dec 1
Total with taxes and fees
Modern, Luxurious Cabin in the Woods - 03
Dining
Sunny Spot with Private Parking.

Apartment in Knightville

2.0 star property
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
$164 nightly
The price is $179
Dec 1 - Dec 2
Total with taxes and fees
Sunny Spot with Private Parking.
Interior
Captain's Quaters 1BR Apt. Quiet. Walk to everything. No fees. Pets stay free!

Vacation Home in 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.
$83 nightly
The price is $90
Dec 1 - Dec 2
Total with taxes and fees
Captain's Quaters 1BR Apt. Quiet. Walk to everything. No fees. Pets stay free!
Exterior
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Apartment in Brunswick

10.0 out of 10, Exceptional, (144)
"Lovely space, comfortable bed, very convenient to downtown Brunswick."
United States
Kimberly G.
$110 nightly
The price is $120
Nov 30 - Dec 1
Total with taxes and fees
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
Outdoor dining
Seabed @ The Offshore House

Condo in Boothbay

9.8 out of 10, Exceptional, (14)
"Our room was excellent!!! Everything was clean and organized and looked beautiful. Location was just far enough from all the attractions to make it very comfortable. Will definitely return next time we are in the area. "
United States
Steve G.
$284 nightly
The price is $301
Nov 30 - Dec 1
Total with taxes and fees
Seabed @ The Offshore House
Interior
Brunswick Downtown Sugar Cube next to Bowdoin

Apartment in Brunswick

8.4 out of 10, Very Good, (7)
"Stayed for one night. Very convenient to campus"
United States
Lin-Lin R.
$239 nightly
The price is $261
Dec 3 - Dec 4
Total with taxes and fees
Brunswick Downtown Sugar Cube next to Bowdoin
Dining
Escape to Positive Outlook

Vacation Home in 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.
$205 nightly
The price is $217
Dec 1 - Dec 2
Total with taxes and fees
Escape to Positive Outlook
Property grounds
Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome

Vacation Home in 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
$284 nightly
The price is $310
Nov 30 - Dec 1
Total with taxes and fees
Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome
Fridge, microwave, stovetop, coffee/tea maker
The Outlet Studio, Rustic Comfort w Fireplace

Vacation Home in Freeport

10.0 out of 10, Exceptional, (11)
"Very comfortable and homey Great location to the outlets. "
United States
Patricia C.
$151 nightly
The price is $164
Dec 1 - Dec 2
Total with taxes and fees
The Outlet Studio, Rustic Comfort w Fireplace
TV
Mere Point Sunrise Views at Eastern Shore!

Vacation Home in 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.
$387 nightly
The price is $391
Dec 3 - Dec 4
Total with taxes and fees
Mere Point Sunrise Views at Eastern Shore!
Fridge, microwave, oven, stovetop
First Floor Little Cozy Studio with King Size Bed Downtown

Apartment in Brunswick

8.8 out of 10, Excellent, (6)
"We loved the simplicity of the residence as well as location "
United States
Joel
First Floor Little Cozy Studio with King Size Bed Downtown
Smart TV
Shipwright @ The Offshore House

Condo in Boothbay

9.4 out of 10, Exceptional, (13)
"Great location. Easy location to town and Dunkin Donuts accros street. "
United States
Steven
$284 nightly
The price is $301
Nov 30 - Dec 1
Total with taxes and fees
Shipwright @ The Offshore House
Interior
The Outlet House, Comfortable Cottage

Cottage in Freeport

9.8 out of 10, Exceptional, (49)
"Fantastic house in a great location! Will definitely be back"
United States
Brandon G.
$195 nightly
The price is $212
Dec 7 - Dec 8
Total with taxes and fees
The Outlet House, Comfortable Cottage
Interior
Adorable Portland getaway on the Eastern Promenade

Apartment in 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
$149 nightly
The price is $162
Dec 1 - Dec 2
Total with taxes and fees
Adorable Portland getaway on the Eastern Promenade
Smart TV, books
Little Lincoln beautiful home

Apartment in 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.
$238 nightly
The price is $259
Dec 1 - Dec 2
Total with taxes and fees
Little Lincoln beautiful home
Fridge, microwave, oven, stovetop
2King Bed BR Private Apt Downtown Brunswick

Apartment in 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.
$220 nightly
The price is $240
Dec 15 - Dec 16
Total with taxes and fees
2King Bed BR Private Apt Downtown Brunswick
Microwave, oven, stovetop
Modern style in historic building in downtown Bath

Apartment in Bath

10.0 out of 10, Exceptional, (8)
"Clean comfortable and right downtown"
United States
stephen e.
$203 nightly
The price is $221
Nov 30 - Dec 1
Total with taxes and fees
Modern style in historic building in downtown Bath
Private kitchen
Classic New England 1st Floor 3 BR Downtown Brunswick

Apartment in Brunswick

9.6 out of 10, Exceptional, (9)
"We had a good time in Brunswick.... great location and jumping off point to explore."
United States
Karin S.
$313 nightly
The price is $341
Dec 7 - Dec 8
Total with taxes and fees
Classic New England 1st Floor 3 BR Downtown Brunswick
Iron/ironing board, free WiFi
Studio Apartment in Freeport

Apartment in Freeport

2.0 star property
$128 nightly
The price is $135
Dec 2 - Dec 3
Total with taxes and fees
Studio Apartment in Freeport
Fridge, microwave, oven, stovetop
King Size Sun Rise Midcoast Lovely Stay

Apartment in 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.
$214 nightly
The price is $216
Nov 30 - Dec 1
Total with taxes and fees
King Size Sun Rise Midcoast Lovely Stay
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

Portland Harbor Hotel

Portland Harbor Hotel

10/10 Excellent
"Lovely old hotel in the heart of Portland. Loved the pantry, the staff were friendly and our room was quiet and comfortable. We got a great price from Hotels.com. We would love to stay here again but the normal rate is too steep for us. "
Irene 1-night trip
Posted 3 days ago
Portland Harbor Hotel

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 $156 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?

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.