Bailey Island Vacation Rentals

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Our top choices for Bailey Island vacation rentals

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, (145 reviews)
"Lovely space, comfortable bed, very convenient to downtown Brunswick."
United States
Kimberly G.
$110 nightly
The price is $120
Feb 10 - Feb 11
Total with taxes and fees
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Brunswick Downtown Sugar Cube next to Bowdoin

Brunswick Downtown Sugar Cube next to Bowdoin
Brunswick
8.4 out of 10, Very Good, (7 reviews)
"Stayed for one night. Very convenient to campus"
United States
Lin-Lin R.
$232 nightly
The price is $253
Feb 16 - Feb 17
Total with taxes and fees
Brunswick Downtown Sugar Cube next to Bowdoin

The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (91 reviews)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
$256 nightly
The price is $273
Mar 1 - Mar 2
Total with taxes and fees
The Weldon Hotel

Port City Nest: Beautiful 2bd w/ Balcony & Parking

Port City Nest: Beautiful 2bd w/ Balcony & Parking
Parkside
10.0 out of 10, Exceptional, (2 reviews)
"Very nice apartment. Had everything we needed. "
United States
Bob S.
$222 nightly
The price is $242
Feb 10 - Feb 11
Total with taxes and fees
Port City Nest: Beautiful 2bd w/ Balcony & Parking

Cozy 1-bedroom apartment in awesome Portland with WiFi, AC

Cozy 1-bedroom apartment in awesome Portland with WiFi, AC
Parkside
8.0 out of 10, Very Good, (4 reviews)
"Everything was perfect."
United States
Edward J.
$136 nightly
The price is $148
Feb 17 - Feb 18
Total with taxes and fees
Cozy 1-bedroom apartment in awesome Portland with WiFi, AC

Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
9.0 out of 10, Wonderful, (27 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
$145 nightly
The price is $158
Feb 10 - Feb 11
Total with taxes and fees
Beautiful 1st Floor Apartment & Amazing Shower

Little Lincoln beautiful home

Little Lincoln beautiful home
Brunswick
9.2 out of 10, Wonderful, (15 reviews)
"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.
$225 nightly
The price is $245
Mar 11 - Mar 12
Total with taxes and fees
Little Lincoln beautiful home

Bright & Spacious Apartment with Amazing Shower

Bright & Spacious Apartment with Amazing Shower
Parkside
8.4 out of 10, Very Good, (18 reviews)
"Super cute. Enjoyed our stay"
United States
Amber T.
$145 nightly
The price is $158
Feb 10 - Feb 11
Total with taxes and fees
Bright & Spacious Apartment with Amazing Shower

Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (128 reviews)
"Tidy place in a great location! "
United States
Mary M.
$188 nightly
The price is $205
Feb 11 - Feb 12
Total with taxes and fees
Adorable Portland getaway on the Eastern Promenade

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
$168 nightly
The price is $184
Feb 10 - Feb 11
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
9.8 out of 10, Exceptional, (7 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.
$180 nightly
The price is $197
Feb 10 - Feb 11
Total with taxes and fees
Peaceful & minutes from the Old Port with private parking

Walk to Old Port ♦ West End Condo ♦ Parking

Walk to Old Port ♦ West End Condo ♦ Parking
West End
9.6 out of 10, Exceptional, (80 reviews)
"Great location and very spacious! Easy commutation - must stay! "
United States
Courtney H.
$249 nightly
The price is $272
Feb 16 - Feb 17
Total with taxes and fees
Walk to Old Port ♦ West End Condo ♦ Parking

Top floor loft apartment in downtown Bath

Top floor loft apartment in downtown Bath
Bath
9.8 out of 10, Exceptional, (6 reviews)
"Great location!"
United States
James E.
$203 nightly
The price is $221
Feb 14 - Feb 15
Total with taxes and fees
Top floor loft apartment in downtown Bath

Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.4 out of 10, Very Good, (7 reviews)
"Maine Oyster Company was a highlight of the trip! "
United Kingdom
Tyler P.
$154 nightly
The price is $156
Feb 19 - Feb 20
Total with taxes and fees
Studio Apartment near downtown Walkable!

Escape to Positive Outlook

Escape to Positive Outlook
West Point
10.0 out of 10, Exceptional, (3 reviews)
"The host was welcoming. The home was clean, comfortable and the views were outstanding. "
United States
Rachel K.
$205 nightly
The price is $217
Feb 10 - Feb 11
Total with taxes and fees
Escape to Positive Outlook

Bird Watching Paradise @ Waterfront Harpswell with Private Deck

Bird Watching Paradise @ Waterfront Harpswell with Private Deck
Harpswell
10.0 out of 10, Exceptional, (2 reviews)
"Super location, very private, responsive host, lovely, clean. Very lucky to have been able to stay here!"
United States
Kate K.
$279 nightly
The price is $304
Feb 10 - Feb 11
Total with taxes and fees
Bird Watching Paradise @ Waterfront Harpswell with Private Deck

Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.6 out of 10, Exceptional, (15 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
$261 nightly
The price is $276
Mar 11 - Mar 12
Total with taxes and fees
Fantastic Waterfront Views

Classic New England 1st Floor 3 BR Downtown Brunswick

Classic New England 1st Floor 3 BR Downtown Brunswick
Brunswick
9.6 out of 10, Exceptional, (9 reviews)
"We had a good time in Brunswick.... great location and jumping off point to explore."
United States
Karin S.
$305 nightly
The price is $332
Feb 10 - Feb 11
Total with taxes and fees
Classic New England 1st Floor 3 BR Downtown Brunswick

Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)

Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
Brunswick
9.8 out of 10, Exceptional, (28 reviews)
"This property is newly renovated and is in a great location--right across from the Brunswick Hotel and next to campus. Parking is easy (in the driveway) and the apartment is really spacious!"
United States
Jill C.
$305 nightly
The price is $332
Feb 10 - Feb 11
Total with taxes and fees
Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)

Charming Studio apartment with WiFi, AC in welcoming Portland

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.6 out of 10, Exceptional, (11 reviews)
"A great location and a comfortable place to stay!"
United States
Andrew K.
$197 nightly
The price is $214
Feb 10 - Feb 11
Total with taxes and fees
Charming Studio apartment with WiFi, AC in welcoming Portland
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 $124 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 26 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.