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
9.0 out of 10, Wonderful, (8 reviews)
"Wonderful views. Comfortable. "
United States
Susy K.
The price is CA $104
CA $274 total
includes taxes & fees
Nov 10 - Nov 11
Sunset Hideaway on Bailey Island

2. Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR
Harpswell
10.0 out of 10, Exceptional, (13 reviews)
"Lovely property, close to what we needed and wanted, host communicated promptly. Would definitely stay there again."
United States
Jane D.
The price is CA $199
CA $551 total
includes taxes & fees
Oct 27 - Oct 28
Orchid Harbor, Bailey Island 3BR

3. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (78 reviews)
"Wonderful stay!"
United States
Erika T.
The price is CA $284
CA $517 total
includes taxes & fees
Oct 27 - Oct 28
Full sized home

4. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (12 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 $147
CA $300 total
includes taxes & fees
Nov 2 - Nov 3
Mid Coast Getaway w/ water views

5. 2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
9.8 out of 10, Exceptional, (6 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 $177
CA $338 total
includes taxes & fees
Nov 1 - Nov 2
2 bedroom w/ expansive water views

6. Captains Watch: A Coastal Escape

Captains Watch: A Coastal Escape
West Point
The price is CA $231
CA $262 total
includes taxes & fees
Oct 25 - Oct 26
Captains Watch: A Coastal Escape

7. 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 $207
CA $555 total
includes taxes & fees
Nov 17 - Nov 18
Mere Point Sunrise Views at Eastern Shore!

8. Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.6 out of 10, Exceptional, (21 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is CA $221
CA $251 total
includes taxes & fees
Nov 2 - Nov 3
Fantastic Waterfront Views

9. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (72 reviews)
"We had a really nice day in communication and check-in were very easy. Overall, it was a lovely day and we would definitely consider returning."
United States
Len B.
The price is CA $294
CA $510 total
includes taxes & fees
Nov 1 - Nov 2
Camp Forever cottage

10. 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, (176 reviews)
"This is a really lovely place to stay. Clean and very comfortable with lovely hosts."
United Kingdom
Lucinda
The price is CA $133
CA $176 total
includes taxes & fees
Nov 3 - Nov 4
Large suite/private bath/private entrance on quiet street near Thomas Bay

11. Three bedroom in United States of America, Freeport

Three bedroom in United States of America, Freeport
Freeport
10.0 out of 10, Exceptional, (13 reviews)
"What can I say about my stay; peaceful, beautiful views, and relaxing! Home was clean with modern finishes but super comfortable for my four guests. The downstairs area is very private from the main floor. The yard was a great space where we had our outdoor fire looking up at the stars at night. The deck was perfect for our family lunch and dinners. We took chairs down to the beach area to sit closer to the water which was perfect. It's super close to town, Wolfe's Neck and other amenities....
United States
Lisa E.
The price is CA $546
CA $1,291 total
includes taxes & fees
Nov 8 - Nov 9
Three bedroom in United States of America, Freeport

12. 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 $210
CA $453 total
includes taxes & fees
Nov 1 - Nov 2
1 Mi to Maine Street! Mcm-style Home in Brunswick

13. Cabin w/ bath + kitchenette | Hot tub add-on - 03

Cabin w/ bath + kitchenette | Hot tub add-on - 03
Freeport
9.8 out of 10, Exceptional, (10 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 $305
CA $505 total
includes taxes & fees
Oct 28 - Oct 29
Cabin w/ bath + kitchenette | Hot tub add-on - 03

14. Modern dome w/ full bath | Hot tub add-on - 04

Modern dome w/ full bath | Hot tub add-on - 04
Freeport
10.0 out of 10, Exceptional, (5 reviews)
"Pet friendly and the experience is just amazing. Thank you for having us! "
United States
Rene B.
The price is CA $266
CA $470 total
includes taxes & fees
Oct 25 - Oct 26
Modern dome w/ full bath | Hot tub add-on - 04

15. King Size Sun Rise Midcoast Lovely Stay

King Size Sun Rise Midcoast Lovely Stay
Topsham
9.6 out of 10, Exceptional, (19 reviews)
"Perfect for a my husband and I. Close to everything!"
United States
Tabcline S.
The price is CA $133
CA $314 total
includes taxes & fees
Nov 2 - Nov 3
King Size Sun Rise Midcoast Lovely Stay

16. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (127 reviews)
"Really nice room and location"
United States
Victoria
The price is CA $267
CA $396 total
includes taxes & fees
Nov 18 - Nov 19
The Weldon Hotel

17. 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 $156
CA $248 total
includes taxes & fees
Oct 25 - Oct 26
Perfect stopover, getaway, base to explore the area, or to simply stay in town.

18. Beautiful Delightful 3BR Downtown Brunswick All King Beds

Beautiful Delightful 3BR Downtown Brunswick All King Beds
Brunswick
10.0 out of 10, Exceptional, (26 reviews)
"This was just what we needed and close to everything we were doing!"
United States
Darryl T.
The price is CA $231
CA $757 total
includes taxes & fees
Oct 25 - Oct 26
Beautiful Delightful 3BR Downtown Brunswick All King Beds

19. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (16 reviews)
"This is a very nice hotel in a great location. It’s new and wonderfully appointed. Everything about it is first class."
United States
Rick
The price is CA $411
CA $659 total
includes taxes & fees
Nov 10 - Nov 11
Evalina Hotel

20. Willard Beach–Apartment Near Portland & Parks

Willard Beach–Apartment Near Portland & Parks
Willard Beach
10.0 out of 10, Exceptional, (10 reviews)
"Location and parking were perfect for our first visit to Portland"
United States
Linda
The price is CA $174
CA $403 total
includes taxes & fees
Oct 25 - Oct 26
Willard Beach–Apartment Near Portland & Parks
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 34 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.