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

Bailey Island Vacation Rentals

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Our top choices for Bailey Island vacation rentals

1. Sunset Hideaway on Bailey Island

Sunset Hideaway on Bailey Island
Harpswell
8.8 out of 10, Excellent, (6 reviews)
"Wonderful views. Comfortable. "
United States
Susy K.
The price is CA $122
CA $295 total
includes taxes & fees
Sep 30 - Oct 1
Sunset Hideaway on Bailey Island

2. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (10 reviews)
"The location and views from the cottage are quintessential coastal Maine. Small community with lobster pound and Maine Oyster Company across the street. John is a welcoming host and eager to make sure you enjoy your stay. The cottage is great for 2 people, equipped with the basics and has a great deck to enjoy the views. Planning to return next year. Great spot!"
United States
Rebecca
The price is CA $134
CA $287 total
includes taxes & fees
Sep 29 - Sep 30
Mid Coast Getaway w/ water views

3. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (71 reviews)
"The house was lovely and well kept and in a great location."
United States
Angela M.
The price is CA $286
CA $519 total
includes taxes & fees
Oct 5 - Oct 6
Full sized home

4. 2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
10.0 out of 10, Exceptional, (5 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 $193
CA $364 total
includes taxes & fees
Sep 29 - Sep 30
2 bedroom w/ expansive water views

5. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (68 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is CA $297
CA $515 total
includes taxes & fees
Oct 3 - Oct 4
Camp Forever cottage

6. Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean

Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean
Freeport
10.0 out of 10, Exceptional, (17 reviews)
"Hosts were very responsive with messages. The stay was clean and comfortable."
United States
Hana L.
The price is CA $441
CA $682 total
includes taxes & fees
Oct 10 - Oct 11
Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean

7. Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.6 out of 10, Exceptional, (20 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is CA $223
CA $257 total
includes taxes & fees
Oct 4 - Oct 5
Fantastic Waterfront Views

8. 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, (172 reviews)
"What a beautiful place to stay. Jeff and Susan made your stay a very special experience."
United States
DENESE
The price is CA $182
CA $230 total
includes taxes & fees
Sep 29 - Sep 30
Large suite/private bath/private entrance on quiet street near Thomas Bay

9. Perfect stopover, getaway, base to explore the area, or to simply stay in town.

Perfect stopover, getaway, base to explore the area, or to simply stay in town.
Bath
8.0 out of 10, Very good, (31 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 $171
CA $265 total
includes taxes & fees
Oct 1 - Oct 2
Perfect stopover, getaway, base to explore the area, or to simply stay in town.

10. Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath
Bath
9.8 out of 10, Exceptional, (13 reviews)
"Great location! We spent very little time in the room, but it was a great place to come back and crash! "
United States
Kristina M.
The price is CA $141
CA $311 total
includes taxes & fees
Sep 29 - Sep 30
Modern style in historic building in downtown Bath

11. King Size Sun Rise Midcoast Lovely Stay

King Size Sun Rise Midcoast Lovely Stay
Topsham
9.6 out of 10, Exceptional, (18 reviews)
"Perfect for a my husband and I. Close to everything!"
United States
Tabcline S.
The price is CA $177
CA $367 total
includes taxes & fees
Sep 29 - Sep 30
King Size Sun Rise Midcoast Lovely Stay

12. Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (10 reviews)
"Lovely location "
United States
Michelle S.
The price is CA $228
CA $583 total
includes taxes & fees
Oct 5 - Oct 6
Mere Point Sunrise Views at Eastern Shore!

13. 1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!

1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!
Bath
8.2 out of 10, Very good, (21 reviews)
"Cute but aging small space, Near attractions"
United States
michael
The price is CA $175
CA $267 total
includes taxes & fees
Oct 5 - Oct 6
1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!

14. 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 $144
CA $384 total
includes taxes & fees
Oct 20 - Oct 21
1 Mi to Maine Street! Mcm-style Home in Brunswick

15. Portland 1-bedroom with enclosed porch & parking

Portland 1-bedroom with enclosed porch & parking
Deering Center
8.0 out of 10, Very good, (13 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 $119
CA $150 total
includes taxes & fees
Sep 29 - Sep 30
Portland 1-bedroom with enclosed porch & parking

16. Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (73 reviews)
"Incredible home in a beautiful location!"
United States
Catherine G.
The price is CA $417
CA $672 total
includes taxes & fees
Sep 29 - Sep 30
Centerview cottage

17. Glamping cabin w/ full bath + spa access - 21

Glamping cabin w/ full bath + spa access - 21
Freeport
10.0 out of 10, Exceptional, (1 review)
The price is CA $318
CA $519 total
includes taxes & fees
Oct 4 - Oct 5
Glamping cabin w/ full bath + spa access - 21

18. Great suburban location close to town!

Great suburban location close to town!
Deering Center
The price is CA $106
CA $137 total
includes taxes & fees
Oct 25 - Oct 26
Great suburban location close to town!

19. 2BR Apt. Authenticic value, Walk to everything, Large yard, Treehouse. No fees.

2BR Apt. Authenticic value, Walk to everything, Large yard, Treehouse. No fees.
Bath
9.0 out of 10, Wonderful, (27 reviews)
"Clean, walkable to town, nice backyard to sit and talk."
United States
Kathleen
The price is CA $322
CA $402 total
includes taxes & fees
Oct 1 - Oct 2
2BR Apt. Authenticic value, Walk to everything, Large yard, Treehouse. No fees.

20. King size Bed Big Smile Big Sunshine 1st FL Washer&Dryer

King size Bed Big Smile Big Sunshine 1st FL Washer&Dryer
Topsham
9.4 out of 10, Exceptional, (6 reviews)
"Perfect place and location for visiting Bowdoin."
United States
Kristen S.
The price is CA $212
CA $433 total
includes taxes & fees
Oct 28 - Oct 29
King size Bed Big Smile Big Sunshine 1st FL Washer&Dryer
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

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.

How many vacation rentals are there in Bailey Island?

With 33 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.