A rocky shoreline with a boat, a house, and a forest in the background.

Bailey Island Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Bailey Island vacation rentals

Terrace/patio

1. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (60 reviews)
"Wonderful stay!"
United States
Erika T.
$341 nightly
The price is $371
Aug 12 - Aug 13
Total with taxes and fees
Full sized home
TV

2. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.6 out of 10, Exceptional, (7 reviews)
"Second time we have stay in this cottage. The perfect location for a Maine vacation. "
United States
chuck c.
$284 nightly
The price is $303
Aug 28 - Aug 29
Total with taxes and fees
Mid Coast Getaway w/ water views
House (2 Bedrooms) | Interior

3. 1 Mi to Maine Street! Mcm-style Home in Brunswick

1 Mi to Maine Street! Mcm-style Home in Brunswick
3.0 star property
Brunswick
$267 nightly
The price is $291
Aug 25 - Aug 26
Total with taxes and fees
1 Mi to Maine Street! Mcm-style Home in Brunswick
TV, fireplace, books

4. 1 Mi to Maine Street! MCM-Style Home in Brunswick

1 Mi to Maine Street! MCM-Style Home in Brunswick
Brunswick
9.6 out of 10, Exceptional, (11 reviews)
"Quiet, clean, well appointed house close to Maine St Brunswick and convenient to both Portland and points north. "
United States
Kendra G.
$275 nightly
The price is $300
Aug 25 - Aug 26
Total with taxes and fees
1 Mi to Maine Street! MCM-Style Home in Brunswick
Exterior

5. Large suite/private bath/private entrance on quiet street near Thomas Bay

Large suite/private bath/private entrance on quiet street near Thomas Bay
Brunswick
10.0 out of 10, Exceptional, (159 reviews)
"Susan and Jeff were amazing hosts! There were so kind, thoughtful and welcoming. The suite was extremely spacious, well decorated and very comfortable. We were very close to the Air Show which was the reason for our trip. They gave us great instructions for a short cut to the airfield and amazing dinner recommendations. We could not have chosen a better place to stay. We highly recommend this place!"
United States
Asha
$152 nightly
The price is $166
Aug 16 - Aug 17
Total with taxes and fees
Large suite/private bath/private entrance on quiet street near Thomas Bay
Interior

6. Sweet comfy cottage on Small Point Road

Sweet comfy cottage on Small Point Road
Small Point
9.4 out of 10, Exceptional, (3 reviews)
"Lovely home with plenty of space and seating. Not the most comfortable of beds but we enjoyed the space. Perfect location and would love to stay again. "
United States
Liz J.
$514 nightly
The price is $560
Aug 31 - Sep 1
Total with taxes and fees
Sweet comfy cottage on Small Point Road
Smart TV, fireplace, foosball, books

7. Cozy and charming coastal retreat

Cozy and charming coastal retreat
West Point
9.8 out of 10, Exceptional, (33 reviews)
"My family and I had an amazing time at the schoolhouse. It is much bigger than the pictures show! Great beds, the couches will force you to nap, and we had so much fun exploring the area. They had everything you need for fun at the beach, and lots of options for kids to keep busy. Highly recommend!"
United Kingdom
Byrony S.
$566 nightly
The price is $617
Aug 23 - Aug 24
Total with taxes and fees
Cozy and charming coastal retreat
TV

8. 2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
10.0 out of 10, Exceptional, (4 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.
$373 nightly
The price is $399
Sep 7 - Sep 8
Total with taxes and fees
2 bedroom w/ expansive water views
Outdoor dining

9. Captain's Guest Room. Authenticity. Great Value. Walk to everything.

Captain's Guest Room. Authenticity. Great Value. Walk to everything.
Bath
8.4 out of 10, Very Good, (27 reviews)
"A charming, quiet, and clean room with separate bathroom close to everything downtown. Felt a bit like staying at my grandparent’s house in a good way - it’s very homey. Dmitri is very nice and communication was thorough and easy!"
United States
Esther
$164 nightly
The price is $179
Sep 10 - Sep 11
Total with taxes and fees
Captain's Guest Room. Authenticity. Great Value. Walk to everything.
Interior

10. Three bedroom in United States of America, Freeport

Three bedroom in United States of America, Freeport
Freeport
10.0 out of 10, Exceptional, (5 reviews)
$922 nightly
The price is $1,005
Sep 1 - Sep 2
Total with taxes and fees
Three bedroom in United States of America, Freeport
Interior

11. Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath
Bath
9.8 out of 10, Exceptional, (10 reviews)
"Clean comfortable and right downtown"
United States
stephen e.
$219 nightly
The price is $239
Sep 8 - Sep 9
Total with taxes and fees
Modern style in historic building in downtown Bath
Coffee/tea maker, fridge, microwave, oven

12. Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport

Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport
Freeport
10.0 out of 10, Exceptional, (10 reviews)
"Incredible location right in downtown Freeport, and an even better host. We will definitely be staying with Jared again."
United States
Jake P.
$618 nightly
The price is $644
Aug 14 - Aug 15
Total with taxes and fees
Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport
Property grounds

13. Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.

Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.
Bath
8.0 out of 10, Very Good, (16 reviews)
"We stayed for two nights. Good location."
United States
Maryanne E.
$160 nightly
The price is $174
Aug 24 - Aug 25
Total with taxes and fees
Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.
Dining

14. King Size Sun Rise Midcoast Lovely Stay

King Size Sun Rise Midcoast Lovely Stay
Topsham
9.6 out of 10, Exceptional, (17 reviews)
"Great location surroundings a little unkept but tis the spring cleanup season. Excellent accommodation and located near town shopping but quiet neighborhood"
United States
Douglas H.
$303 nightly
The price is $330
Aug 18 - Aug 19
Total with taxes and fees
King Size Sun Rise Midcoast Lovely Stay
Coffee/tea maker, fridge, microwave, oven

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

Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
Brunswick
9.6 out of 10, Exceptional, (33 reviews)
"Wonderful location. It’s right next to Bowdoin. There is a great coffee shop a block away and a grocery store within easy walking distance. The place was spotless. "
United States
Mike S.
$406 nightly
The price is $443
Aug 11 - Aug 12
Total with taxes and fees
Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
Property grounds

16. Modern cabin w/ full bath & kitchenette - 03

Modern cabin w/ full bath & kitchenette - 03
Freeport
10.0 out of 10, Exceptional, (7 reviews)
"Easy check in process. More than clean, it looked brand new. Overall a great stay. Kitchen was well stocked with plates, utensils, and cookware. "
United States
Michael H.
$473 nightly
The price is $516
Sep 2 - Sep 3
Total with taxes and fees
Modern cabin w/ full bath & kitchenette - 03
Honeymoon Studio | Egyptian cotton sheets, premium bedding, down comforters, bed sheets

17. Fortland Island Campground

Fortland Island Campground
1.0 star property
Portland
10.0 out of 10, Exceptional, (3 reviews)
"It was very quiet and liked the experience of staying in a camp like setting."
United States
leela srinivas
$357 nightly
The price is $390
Aug 23 - Aug 24
Total with taxes and fees
Fortland Island Campground
TV

18. Private Entrance Residential Portland

Private Entrance Residential Portland
Deering Center
8.6 out of 10, Excellent, (8 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.
$130 nightly
The price is $132
Aug 30 - Aug 31
Total with taxes and fees
Private Entrance Residential Portland
TV

19. Brunswick Downtown Sugar Cube next to Bowdoin

Brunswick Downtown Sugar Cube next to Bowdoin
Brunswick
8.6 out of 10, Excellent, (9 reviews)
"Had a great overnight here with my mother as a Mother’s Day trip. Size was perfect for the two of us. Easy walk to town. Had a lovely stay!"
United States
Andrea L.
$326 nightly
The price is $355
Aug 30 - Aug 31
Total with taxes and fees
Brunswick Downtown Sugar Cube next to Bowdoin
1 bedroom, WiFi, bed sheets

20. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.2 out of 10, Very Good, (13 reviews)
"A perfectly decent place to stay, plenty of restaurants and bars within reasonable walking distance. Neighborhood is a bit rough, as the listing mentioned, but no problems while I was there. Response time on questions to the host could be better."
Canada
Brian
$166 nightly
The price is $167
Aug 11 - Aug 12
Total with taxes and fees
Studio Apartment near downtown Walkable!
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

HomeAwhile

HomeAwhile

10/10 Excellent
"One of the best hotels I’ve stayed at. Spotless, comfortable; a perfect experience."
Nadia 1-night trip
Posted less than an hour ago
HomeAwhile

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 $167 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?

Spacious 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. Our travelers also rate Johnson Homestead. One level living, ocean view with semi-private beach access. as a favorite home for rent in Bailey Island.

How many vacation rentals are there in Bailey Island?

With 31 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.