20 Best B&B in Bailey Island, ME - Bed and Breakfast from AED 244

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Our top choices for Bailey Island bed & breakfast

A breakfast setup with a tiered tray holding fruits, cups, and a coffee pot.

1. The Orchard House: Inn & Cafe

Freeport

Mark

AED 626 total

includes taxes & fees

1 Dec - 2 Dec

A two-story house with a red roof, a front porch, and a well-maintained lawn.

2. Candlebay Inn

Freeport

Richard

AED 573 total

includes taxes & fees

8 Nov - 9 Nov

A covered porch with white railings and a view of a well-maintained lawn and pathway.

3. The Kendall Inn

Freeport

Justin Terry

AED 757 total

includes taxes & fees

7 Nov - 8 Nov

A two-story house with a balcony, a front porch, and a snow-covered landscape.

4. The Nicholson Inn

Freeport

alexandre

AED 912 total

includes taxes & fees

12 Nov - 13 Nov

A multi-story building with a stone facade, multiple windows, and awnings.

5. Inn at St John Portland In-Town

Valley Street

Darbi

AED 266 total

includes taxes & fees

22 Nov - 23 Nov

A house with a sign for The James Place Inn, indicating a vacancy.

6. The James Place Inn B&B

Freeport

Kim

AED 1,003 total

includes taxes & fees

9 Nov - 10 Nov

An outdoor patio with a covered seating area, a brick pathway, and potted plants.

7. Benjamin F. Packard House

Bath

Tina

AED 779 total

includes taxes & fees

15 Nov - 16 Nov

A well-lit living room with a fireplace, comfortable seating, and a large mirror.

8. Blind Tiger Portland – Carleton Street

West End

Samuel

AED 854 total

includes taxes & fees

17 Nov - 18 Nov

A balcony with two wooden chairs and a small table, overlooking a body of water with houses in the background.

9. Harborage Inn on the Oceanfront

Boothbay Harbor

Michele

AED 659 total

includes taxes & fees

7 Nov - 8 Nov

10. West End Collection at 146 Pine

West End

Stephanie

AED 869 total

includes taxes & fees

30 Nov - 1 Dec

A spacious kitchen with a central island, wooden bar stools, and a long dining table.

11. Blind Tiger Portland - Danforth Street.

West End

paul k

AED 977 total

includes taxes & fees

8 Nov - 9 Nov

A garden with a stone wall, various plants, and flowers.

12. Fleetwood House Bed & Breakfast

Rosemont

caia

AED 954 total

includes taxes & fees

7 Nov - 8 Nov

A serene lakeside setting with two rocking chairs, a fire pit, and a view of boats on the water.

13. The Snug: Cozy Ground-Floor Queen at Admiral's Quarters, Boothbay Harbor

Boothbay Harbor

Rhonda L.

AED 933 total

includes taxes & fees

7 Nov - 8 Nov

A goat standing in a barn with wooden beams and a metal gate.

14. The Squire Tarbox Inn

Wiscasset

Oona

A wooden deck with three chairs and a table, overlooking a marina with boats and a lighthouse.

15. Tugboats at the Window: Direct Harbor-View King, Greenleaf Inn, Boothbay Harbor

Boothbay Harbor

Sara S.

AED 1,013 total

includes taxes & fees

7 Nov - 8 Nov

16. Ground-Level King with a Harbor-View Deck, Greenleaf Inn, Boothbay Harbor

Boothbay Harbor

Kaitlyn H.

AED 1,097 total

includes taxes & fees

7 Nov - 8 Nov

A deck with three chairs and a table, overlooking a marina with boats and a lighthouse.

17. Second-Floor King Suite with a Deck Toward the Harbor, Greenleaf Inn, Boothbay

Boothbay Harbor

Amy

AED 1,125 total

includes taxes & fees

27 Nov - 28 Nov

A balcony with a table set for two, a vase with flowers, and a view of a residential area.

18. Room to Breathe: 800 sq ft Harbor-View King Suite, Admiral's Quarters, Boothbay

Boothbay Harbor

Anonymous traveler

AED 1,521 total

includes taxes & fees

7 Nov - 8 Nov

A serene lakeside setting with two rocking chairs facing a calm body of water, a fire pit in the center, and a clear view of boats and distant land.

19. Fireside Corner King, Harbor Views, Electric Fireplace, Greenleaf Inn, Boothbay

Boothbay Harbor

AED 1,009 total

includes taxes & fees

7 Nov - 8 Nov

20. Your Own Deck Over the Harbor: Second-Floor King at Greenleaf Inn, Boothbay

Boothbay Harbor

AED 1,149 total

includes taxes & fees

7 Nov - 8 Nov

View all properties

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 wooden bridge over water with a yellow kayak, boats, and a motel in the background.

Top reviews in Bailey Island

Candlebay Inn

Freeport

10/10 Excellent

Sheree Lee

The Kendall Inn

Freeport

10/10 Excellent

Julia

The Nicholson Inn

Freeport

10/10 Excellent

David

The James Place Inn B&B

Freeport

10/10 Excellent

We booked a stay at the James Place Inn based on reviews that we read on a few travel sites. I can't even begin to express how well-deserved each and every one of those reviews actually is! Robin and Tori are incredible hosts, pleasant, friendly, easy to talk to, and made us feel right at home before we even got there! We drove up from NYC on a Friday afternoon and hit more traffic than we anticipated, so we called ahead to let the staff know we'd be late. Tori answered the phone and told us...

Sarah

Inn at St John Portland In-Town

Valley Street

10/10 Excellent

Adela

Benjamin F. Packard House

Bath

10/10 Excellent

Lori

Harborage Inn on the Oceanfront

Boothbay Harbor

10/10 Excellent

George

Blind Tiger Portland – Carleton Street

West End

10/10 Excellent

Monica

West End Collection at 146 Pine

West End

10/10 Excellent

Constance

Blind Tiger Portland - Danforth Street.

West End

10/10 Excellent

John

Fleetwood House Bed & Breakfast

Rosemont

10/10 Excellent

C

The Squire Tarbox Inn

Wiscasset

10/10 Excellent

A little slice of Heaven tucked away on a most peaceful and natural setting as can be imagined! Walking the grounds or exploring the natural bounty of the island can"t be more cathartic than this. Extremely comfortable beds and very clean rooms leave little to be desired if you are looking for that non plugged in experience.The stars at nite are what's showing and there is no intermission!!Chef Mario and crew are top notch , I've worked at the Ritz, and they perform w/o a hitch! Wish I had...

Christopher

Frequently Asked Questions

Searching for B&Bs in Bailey Island?

If you're looking for something a little more offbeat than the traditional hotel experience, a bed and breakfast could be a great option for your trip. If you'd like to learn more about Bailey Island through its top sites and landmarks, Bailey Island Bridge and Cobwork Bridge are some notable monuments to check out.

Are you thinking about a B&B for your stay?

With attentive service, opportunities to meet guests from other places, and of course a full breakfast, B&Bs provide a one-of-a-kind setting.

What are the best bed and breakfasts in Bailey Island?

Below are some well-liked B&Bs in the surrounding area: Inn at St John Portland In-Town: 15.3 mi (24.7 km) from the heart of Bailey Island.Blind Tiger Portland - Danforth Street.: 9 rooms. 14.7 mi (23.7 km) from the downtown core. The Orchard House: Inn & Cafe: 5 rooms. Situated 10.6 mi (17 km) from the heart of Bailey Island. Blind Tiger Portland – Carleton Street: 6 rooms. 15 mi (24.2 km) from the heart of downtown. Enjoy the unique décor and patio area. West End Collection at 146 Pine: 6 rooms. Located 15.1 mi (24.4 km) from the core of Bailey Island. Enjoy the local cuisine breakfast and deli.

What's the best time of year to stay at a B&B in Bailey Island?

When you're dreaming of a getaway to Bailey Island, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Bailey Island are January, March, February, and December, with each month seeing an average of 7 inches of snowfall.

What is there to do in Bailey Island?

When you want to spend some time in the great outdoors, Mackerel Cove and Ragged Island are some notable spots. You might put Bailey Island Bridge and Land's End Gift Shop on your list if you want to see more of the area.

How can I get to and around Bailey Island?

You can plan your excursions in and around Bailey Island ahead of time with these transportation options. Fly into Portland Intl. Jetport Airport (PWM), which is located 17 mi (27.3 km) away from the city center. Otherwise, you can search for flights to Wiscasset, ME (ISS), which is 21.1 mi (33.9 km) away. If you'd like to venture out around the area, consider renting a car to take in more sights.

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Search B&B in Bailey Island

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Bailey Island bed & breakfast

1. The Orchard House: Inn & Cafe

2. Candlebay Inn

3. The Kendall Inn

4. The Nicholson Inn

5. Inn at St John Portland In-Town

6. The James Place Inn B&B

7. Benjamin F. Packard House

8. Blind Tiger Portland – Carleton Street

9. Harborage Inn on the Oceanfront

10. West End Collection at 146 Pine

11. Blind Tiger Portland - Danforth Street.

12. Fleetwood House Bed & Breakfast

13. The Snug: Cozy Ground-Floor Queen at Admiral's Quarters, Boothbay Harbor

14. The Squire Tarbox Inn

15. Tugboats at the Window: Direct Harbor-View King, Greenleaf Inn, Boothbay Harbor

16. Ground-Level King with a Harbor-View Deck, Greenleaf Inn, Boothbay Harbor

17. Second-Floor King Suite with a Deck Toward the Harbor, Greenleaf Inn, Boothbay

18. Room to Breathe: 800 sq ft Harbor-View King Suite, Admiral's Quarters, Boothbay

19. Fireside Corner King, Harbor Views, Electric Fireplace, Greenleaf Inn, Boothbay

20. Your Own Deck Over the Harbor: Second-Floor King at Greenleaf Inn, Boothbay

Learn more about Bailey Island

Top reviews in Bailey Island

Candlebay Inn

10/10 Excellent

Frequently Asked Questions

Searching for B&Bs in Bailey Island?

Are you thinking about a B&B for your stay?

What are the best bed and breakfasts in Bailey Island?

What's the best time of year to stay at a B&B in Bailey Island?

What is there to do in Bailey Island?

How can I get to and around Bailey Island?

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