Bailey Island Holiday Rentals, Maine: Private House Rentals

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

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Go beyond your typical stay in Bailey Island

Pet friendly

Apartment

Pool

Condo

Hot tub

Family friendly

Waterpark

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Bailey Island hotels

1. Travelers Inn

Brunswick

Susan

2.842.502 ₫

3.098.327 ₫ total

includes taxes & fees

2 Sept - 3 Sept

2. Embassy Suites by Hilton Portland Maine

Portland

Tiffany

5.119.571 ₫

5.664.294 ₫ total

includes taxes & fees

3 Sept - 4 Sept

3. Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

South Portland

Heidi

2.948.118 ₫

3.213.449 ₫ total

includes taxes & fees

30 Aug - 31 Aug

4. Holiday Inn Express Hotel & Suites Freeport by IHG

Freeport

Bethann

2.999.545 ₫

3.269.504 ₫ total

includes taxes & fees

2 Sept - 3 Sept

5. La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

Portland

Corey

3.691.341 ₫

4.084.100 ₫ total

includes taxes & fees

31 Aug - 1 Sept

6. Days Inn by Wyndham Brunswick Bath Area

Brunswick

Stephen

2.999.545 ₫

3.269.504 ₫ total

includes taxes & fees

31 Aug - 1 Sept

Standard Double Room, 2 Double Beds, Non Smoking

7. Comfort Inn South Portland Airport

South Portland

Reneen

2.886.052 ₫

3.145.797 ₫ total

includes taxes & fees

31 Aug - 1 Sept

8. Hampton Inn Freeport/Brunswick

Freeport

Karen

3.614.582 ₫

3.939.894 ₫ total

includes taxes & fees

7 Sept - 8 Sept

9. Fairfield Inn & Suites by Marriott Brunswick Freeport

Brunswick

Aaron

3.414.265 ₫

3.721.549 ₫ total

includes taxes & fees

7 Sept - 8 Sept

10. The Brunswick Hotel

Brunswick

Elisa

4.606.675 ₫

5.021.276 ₫ total

includes taxes & fees

8 Sept - 9 Sept

11. Spark by Hilton Brunswick

Brunswick

Tammy

2.972.940 ₫

3.240.505 ₫ total

includes taxes & fees

7 Sept - 8 Sept

12. Clarion Hotel Portland Airport ME

Portland

Barbara

2.859.453 ₫

3.163.698 ₫ total

includes taxes & fees

7 Sept - 8 Sept

13. The Freeport Hotel, an Ascend Collection Hotel

Freeport

Karin

2.501.881 ₫

2.727.051 ₫ total

includes taxes & fees

6 Sept - 7 Sept

14. Tru by Hilton Portland Airport Area

South Portland

Ioannis

3.186.821 ₫

3.473.635 ₫ total

includes taxes & fees

7 Sept - 8 Sept

15. Hyatt Place Portland Downtown - Old Port Square

Downtown Portland

Leanna

5.451.347 ₫

6.031.371 ₫ total

includes taxes & fees

30 Aug - 31 Aug

16. TownePlace Suites by Marriott Portland Airport ME

South Portland

Michael

4.408.027 ₫

4.804.750 ₫ total

includes taxes & fees

30 Aug - 31 Aug

17. The Harraseeket Inn & Event House Freeport Downtown

Freeport

Carol

4.668.857 ₫

5.089.054 ₫ total

includes taxes & fees

1 Sept - 2 Sept

18. Hilton Garden Inn Freeport Downtown

Freeport

Toni

4.042.343 ₫

4.406.154 ₫ total

includes taxes & fees

13 Sept - 14 Sept

19. SpringHill Suites by Marriott Freeport Brunswick

Freeport

Vilma

3.589.282 ₫

3.912.450 ₫ total

includes taxes & fees

30 Aug - 31 Aug

Suite, 1 Queen Bed, Non Smoking, Jetted Tub

20. Best Western Plus Brunswick Bath

Brunswick

Anna

3.732.738 ₫

4.068.684 ₫ total

includes taxes & fees

6 Sept - 7 Sept

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Stay near popular Bailey Island attractions

Bailey Island Bridge

9.2/10 (10 reviews)

The world's only cribstone bridge connects Bailey Island with unique granite slabs that allow tides to flow freely. Drive or walk across this 1926 engineering marvel for spectacular coastal views.

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Land's End Gift Shop

10.0/10 (1 review)

Perched at Bailey Island's southern tip, this charming shop offers an array of Maine-made treasures. Browse two levels of local crafts and speciality foods while enjoying Casco Bay views from the rocky coastline.

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Cobwork Bridge

10.0/10 (1 review)

The Bailey Island Bridge's unique granite cribstone design allows tides to flow freely through its structure. Drive across this engineering marvel for stunning Casco Bay views—America's only bridge of its kind.

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Learn more about Bailey Island

Hike the Giant's Stairs trail along the rocky coastline for dramatic views of Casco Bay. Seafood lovers shouldn't miss lobster rolls at Cook's Lobster & Ale House on the island's southern tip.

See all hotels in Bailey Island

A green netted buoy attached to a wooden post by a curved metal hook, with a wooden fence and a body of water in the background.

Top Bailey Island Hotel Reviews

Comfort Inn South Portland Airport

8/10 Good

"Hotel was clean and modern. Bed was very comfortable. Only downside was I was unable to close the curtain all the way to block the highway lights and the hotel is so close to the highway it was a bit noisy."

Embassy Suites by Hilton Portland Maine

8/10 Good

"I was annoyed at check in when they said there was a parking fee ($13/night, but still- annoying and unexpected). The “happy hour” was not as great as others we had had at the same hotel chain. The room was lovely and clean and the breakfast was EXCELLENT!"

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

10/10 Excellent

"Clean and quiet room. Bed and pillows were comfortable."

Best Western Merry Manor Inn

10/10 Excellent

"Pool and breakfast are the highlights, though the room and staff are standouts too. We've stayed many times and will always know it's a great experience"

HomeAwhile

10/10 Excellent

"An apartment with a washer dryer was A great mid point in our trip. Comfortable and in a great location close to downtown Portland. Loved the property and really good deal. Highly recommend!"

Quality Inn & Suites South Portland

8/10 Good

"This was a comfortable clean place to stay, though a bit rough around the edges. Front desk had surveillance views of the outside so it felt quite secure."

Clarion Hotel Portland Airport ME

8/10 Good

"It's a decent hotel in the process of doing some renovations. The restaurant does not appear to be open at the moment which was not a hardship for us. The cleaning staff was friendly and helpful. The front desk folks were great during the day. At night, while trying to call for the shuttle one night the desk did not answer at all. The next night, the clerk gave us a bit of a runaround. But the shuttle drivers were awesome and made sure we were not left stranded downtown. Would stay here again."

Clarion Pointe South Portland

10/10 Excellent

"Vacances"

Spark by Hilton Portland Airport Maine Mall

8/10 Good

"The fan in the bathroom, which is always on when the light is on, is very noisy and irritating in such a small room. There are quieter fans that would be better."

More cheap stays in Bailey Island

Clarion Pointe South Portland

675 Main Street I-95 South Portland ME

1.773.304 ₫

1.932.901 ₫ total

27 Sept - 28 Sept

includes taxes & fees

7.2/10 Good! (740 reviews)

Quality Inn & Suites South Portland

738 Main Street South Portland ME

1.972.801 ₫

2.150.353 ₫ total

7 Sept - 8 Sept

includes taxes & fees