B&B in Great Diamond Island
Maine
United States of America
B&B
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A calm sea with a sailboat and rocky coastline.

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your current months are November, 2026 and December, 2026.

November 2026

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Our top choices for Great Diamond Island bed & breakfast

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

A breakfast bar with various food items, a clock, and a mirror.

A hotel lobby with a reception desk, several armchairs, a patterned carpet, and a red wall with framed pictures.

A hotel room with a bed, a desk, a lamp, a television, and a brick wall.

1. Inn at St John Portland In-Town

Inn at St John Portland In-Town

2.5 star property

Valley Street

8.6 out of 10, Excellent, (1,179 reviews)

8.6/10

Excellent

(1,179 reviews)

"Great location and exactly what we needed for our time in Portland"

Darbi

The price is RM270

RM270

RM294 total

includes taxes & fees

22 Nov - 23 Nov

Inn at St John Portland In-Town

2. West End Collection at 146 Pine

West End Collection at 146 Pine

3.0 star property

West End

9.6 out of 10, Exceptional, (100 reviews)

9.6/10

Exceptional

(100 reviews)

"This was a super cute boutique inn and the location was ideal. The staff was super friendly!"

Stephanie

The price is RM877

RM877

RM956 total

includes taxes & fees

17 Nov - 18 Nov

West End Collection at 146 Pine

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

A red brick building with a classic facade, a front entrance with double doors, and a small porch area with potted plants.

A hotel room with a checkered bedspread, a large mirror above the bed, and two windows with curtains.

A staircase with a wooden handrail and a chandelier.

3. Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 star property

West End

9.6 out of 10, Exceptional, (137 reviews)

9.6/10

Exceptional

(137 reviews)

"Beautiful place"

Samuel

The price is RM866

RM866

RM944 total

includes taxes & fees

17 Nov - 18 Nov

Blind Tiger Portland – Carleton Street

A black front door with a light fixture above it, flanked by two potted evergreen trees.

A coastal landscape with a sandy beach, rocky outcrops, and grassy dunes.

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

4. The Orchard House: Inn & Cafe

The Orchard House: Inn & Cafe

3.0 star property

Freeport

9.6 out of 10, Exceptional, (185 reviews)

9.6/10

Exceptional

(185 reviews)

"Great place"

Mark

The price is RM635

RM635

RM692 total

includes taxes & fees

1 Dec - 2 Dec

The Orchard House: Inn & Cafe

A wooden deck with two wicker chairs and a small table, overlooking a brick building with ivy and a fire escape.

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

A living room with a fireplace, a sofa, a coffee table, and a bookshelf.

A cozy room with a brick fireplace, a bench, and a table.

5. Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 star property

West End

9.6 out of 10, Exceptional, (206 reviews)

9.6/10

Exceptional

(206 reviews)

"Very helpful and friendly staff"

paul k

The price is RM891

RM891

RM972 total

includes taxes & fees

17 Nov - 18 Nov

Blind Tiger Portland - Danforth Street.

A two-story house with a porch and a sign reading "Fleetwork House."

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

A dining table set with a fruit bowl, cutlery, and decorative elements like a pumpkin and autumn leaves.

A covered outdoor patio with a grill, seating area, and potted plants.

6. Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast

3.0 star property

Rosemont

9.0 out of 10, Wonderful, (150 reviews)

9.0/10

Wonderful

(150 reviews)

"Close location to airport. Sweet Neighbhorhood Good shower and breakfast was delish. Loved eating on the houses China"

caia

The price is RM929

RM929

RM1,054 total

includes taxes & fees

10 Nov - 11 Nov

Fleetwood House Bed & Breakfast

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

A living room with a beige sofa, a green armchair, a wooden coffee table, and a bookshelf.

A dining area with wooden tables and chairs, a chandelier, and a kitchen in the background.

A staircase with patterned carpet leading to a room with a desk, a map, and a basket of toys.

7. Candlebay Inn

Candlebay Inn

3.0 star property

Freeport

9.6 out of 10, Exceptional, (500 reviews)

9.6/10

Exceptional

(500 reviews)

"Great stay in a historic home."

Richard

The price is RM581

RM581

RM633 total

includes taxes & fees

10 Nov - 11 Nov

Candlebay Inn

A house with a porch, white railings, and hanging flower baskets.

A sign for the Old Orchard Beach Inn entrance.

A house with a porch, a flag, and outdoor furniture.

8. Old Orchard Beach Inn

Old Orchard Beach Inn

2.5 star property

Old Orchard Beach

8.2 out of 10, Very good, (1,002 reviews)

8.2/10

Very good

(1,002 reviews)

"Really nice hotel"

James

The price is RM544

RM544

RM654 total

includes taxes & fees

10 Nov - 11 Nov

Old Orchard Beach Inn

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

A two-story yellow house with a front porch, a flag, and a well-maintained garden.

A wooden porch with white railings and potted plants.

A living room with a fireplace, a patterned armchair, a blue blanket, and a framed picture on the wall.

9. The Kendall Inn

The Kendall Inn

3.5 star property

Freeport

9.8 out of 10, Exceptional, (170 reviews)

9.8/10

Exceptional

(170 reviews)

"The breakfasts were so tasty! The Inn is so charming! We loved our stay and hope to return next year!"

Justin Terry

The price is RM682

RM682

RM743 total

includes taxes & fees

10 Dec - 11 Dec

The Kendall Inn

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

A covered porch with wicker chairs, a small table, and a potted plant.

A garden with purple flowers, outdoor furniture, and a statue.

A dining table set with white tableware, a pitcher, and salt and pepper shakers.

10. The Nicholson Inn

The Nicholson Inn

3.0 star property

Freeport

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"We had a fantastic and lovely, although quick, stay. The Inn is very charming and John and Loretta are so kind and helpful. Would love to go back and stay with them again.."

alexandre

The price is RM1,050

RM1,050

RM1,145 total

includes taxes & fees

17 Nov - 18 Nov

The Nicholson Inn

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

A house with a front porch, a fire pit, and two Adirondack chairs.

A dining area with a checkered tablecloth, a chandelier, and a view of the outdoors through large windows.

A bedroom with a wooden bed, a nightstand, a desk, a chair, a floor lamp, and a window with curtains.

11. The James Place Inn B&B

The James Place Inn B&B

3.5 star property

Freeport

10.0 out of 10, Exceptional, (196 reviews)

10/10

Exceptional

(196 reviews)

"Sean was amazingly helpful and friendly. The house itself is so well maintained, and the blue room was adorable. Loved the fact that we were within walking distance of all the shops. Would definitely recommend and will plan on staying again the next time we’re in town."

Kim

The price is RM1,017

RM1,017

RM1,109 total

includes taxes & fees

10 Nov - 11 Nov

The James Place Inn B&B

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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Learn more about Great Diamond Island

Check out Sand Beach and East End Beach—just a couple of the sights around Great Diamond Island.

See all hotels in Great Diamond Island

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Aparthotels in Lincoln County
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Cottages in Old Orchard Beach
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Flights to New Gloucester
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Flights to Poland
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Flights from Portland Intl. Jetport
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Flights from Billund (BLL) to Portland (PWM)
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Flights from London (LHR) to Auburn (LEW)
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Flights from Raleigh (RDU) to Auburn (LEW)
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Flights from Fort Myers (RSW) to Portland (PWM)
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Flights from Sanford (SFM) to Auburn (LEW)
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Big 20 Bowling Center
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Bowdoin College Museum of Art
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Cathedral Church of Saint Luke
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Fitzpatrick Stadium
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Happy Wheels Skate Center
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Harrington House
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Hollis Center Holidays
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Maine Military Museum
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Maine State Music Theater
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Maine Street
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Merrill Auditorium
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Monkey Trunks Extreme Aerial Adventure Park
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Monument Square
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Visit Ocean Park
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Popham Beach State Park
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Portland Head Light
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Visit Old Port
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Quarry Run Dog Park
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Visit Saco
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Spring Point Ledge Lighthouse
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Car hire near Funtown Splashtown USA
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Car hire Lisbon Falls
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Search B&B in Great Diamond Island

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Great Diamond Island bed & breakfast

1. Inn at St John Portland In-Town

2. West End Collection at 146 Pine

3. Blind Tiger Portland – Carleton Street

4. The Orchard House: Inn & Cafe

5. Blind Tiger Portland - Danforth Street.

6. Fleetwood House Bed & Breakfast

7. Candlebay Inn

8. Old Orchard Beach Inn

9. The Kendall Inn

10. The Nicholson Inn

11. The James Place Inn B&B

Learn more about Great Diamond Island

Explore a world of travel with Expedia