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 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

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.
The price is CA $284
CA $516 total
includes taxes & fees
Aug 12 - Aug 13
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.
The price is CA $258
CA $442 total
includes taxes & fees
Aug 28 - Aug 29
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
The price is CA $168
CA $408 total
includes taxes & fees
Aug 25 - Aug 26
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
9.4 out of 10, Exceptional, (10 reviews)
"Quiet, clean, well appointed house close to Maine St Brunswick and convenient to both Portland and points north. "
United States
Kendra G.
The price is CA $116
CA $420 total
includes taxes & fees
Aug 25 - Aug 26
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
The price is CA $185
CA $232 total
includes taxes & fees
Aug 11 - Aug 12
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.
The price is CA $420
CA $782 total
includes taxes & fees
Aug 8 - Aug 9
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, (31 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.
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.
The price is CA $368
CA $570 total
includes taxes & fees
Sep 7 - Sep 8
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
The price is CA $160
CA $251 total
includes taxes & fees
Aug 9 - Aug 10
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)
The price is CA $602
CA $1,360 total
includes taxes & fees
Sep 1 - Sep 2
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.
The price is CA $161
CA $335 total
includes taxes & fees
Sep 2 - Sep 3
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.
The price is CA $371
CA $997 total
includes taxes & fees
Aug 9 - Aug 10
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.
The price is CA $200
CA $248 total
includes taxes & fees
Aug 11 - Aug 12
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.
The price is CA $231
CA $460 total
includes taxes & fees
Aug 18 - Aug 19
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.
The price is CA $287
CA $614 total
includes taxes & fees
Aug 10 - Aug 11
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.
The price is CA $481
CA $716 total
includes taxes & fees
Sep 6 - Sep 7
Modern cabin w/ full bath & kitchenette - 03
Honeymoon Studio

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
The price is CA $479
CA $522 total
includes taxes & fees
Aug 23 - Aug 24
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.
The price is CA $155
CA $185 total
includes taxes & fees
Aug 30 - Aug 31
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.
The price is CA $231
CA $498 total
includes taxes & fees
Aug 30 - Aug 31
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
The price is CA $147
CA $249 total
includes taxes & fees
Aug 11 - Aug 12
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

Clarion Pointe South Portland

Clarion Pointe South Portland

10/10 Excellent
"At first some of the reviews were a little bit scary not going to lie but this place was really great me and my children and husband loved using the pool. Parking and air conditioning was great, we decide not to have our room cleaned because we were only there for two nights but they were constantly cleaning rooms around us and doing such a great job."
Molly 2-night trip
Posted less than an hour ago
Clarion Pointe South Portland

Find out more about Bailey Island

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Bailey Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.