A calm sea with a sailboat and rocky coastline.

Search Bed and Breakfast in Great Diamond Island

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
23 Oct - 25 Oct
In two weeks
30 Oct - 1 Nov
In one month
13 Nov - 15 Nov
In two months
11 Dec - 13 Dec

Our top choices for Great Diamond Island bed & breakfast

A building with a sign reading "The Inn At St. John."

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, (1,161 reviews)
"It was a cool place to stay. Plenty of space in the room. Would stay here again."
United States
Steven
The price is S$106
includes taxes & fees
26 Oct - 27 Oct
Inn at St John Portland In-Town
A well-lit living room with a fireplace, comfortable seating, and a large mirror.

2. Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street
3.5 star property
West End
9.6 out of 10, Exceptional, (135 reviews)
"Fantastic property, full of character in a great location. Walkable location, we will be back next time we are in Portland."
United States
Ryan
The price is S$338
includes taxes & fees
1 Nov - 2 Nov
Blind Tiger Portland – Carleton Street
Exterior

3. 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)
"This was a super cute boutique inn and the location was ideal. The staff was super friendly!"
United States
Stephanie
The price is S$306
includes taxes & fees
1 Nov - 2 Nov
West End Collection at 146 Pine
A garden with a stone wall, various plants, and flowers.

4. Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast
3.0 star property
Rosemont
9.0 out of 10, Wonderful, (148 reviews)
"A wonderful experience with Jim and Linda. Fantastic breakfast every morning, in the cutest old house just outside of the city. Definitely recommend!"
United States
Tyler
The price is S$332
includes taxes & fees
18 Oct - 19 Oct
Fleetwood House Bed & Breakfast
A four-poster bed with a chandelier, a bedside table with books, and a view of a brick building through the windows.

5. Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.
3.5 star property
West End
9.6 out of 10, Exceptional, (198 reviews)
"Place was charming and quirky. Very comfortable and well located."
United States
Mary
The price is S$368
includes taxes & fees
9 Nov - 10 Nov
Blind Tiger Portland - Danforth Street.
A white building with a red roof, a sign indicating a vacancy at Candlebay Inn, and an American flag.

6. Candlebay Inn

Candlebay Inn
3.0 star property
Freeport
9.6 out of 10, Exceptional, (495 reviews)
"Great stay in a historic home."
United States
Richard
The price is S$200
includes taxes & fees
1 Nov - 2 Nov
Candlebay Inn
A covered porch with white railings and a view of a well-maintained lawn and pathway.

7. The Kendall Inn

The Kendall Inn
3.5 star property
Freeport
9.8 out of 10, Exceptional, (164 reviews)
"I really enjoyed The Kendall Inn. Elegant and comfortable, super clean rooms, friendly staff and delicious breakfasts (and home baked cookies in the evening). Definitely would love to stay there again"
United States
Katherine
The price is S$271
includes taxes & fees
1 Nov - 2 Nov
The Kendall Inn
A covered patio with wicker furniture and a mosaic table, surrounded by greenery and a white building.

8. Old Orchard Beach Inn

Old Orchard Beach Inn
2.5 star property
Old Orchard Beach
8.2 out of 10, Very good, (1,006 reviews)
"Really nice hotel"
United States
James
The price is S$191
includes taxes & fees
15 Oct - 16 Oct
Old Orchard Beach Inn
A black front door with a light fixture above it, flanked by two potted evergreen trees.

9. The Orchard House: Inn & Cafe

The Orchard House: Inn & Cafe
3.0 star property
Freeport
9.6 out of 10, Exceptional, (184 reviews)
"Great place"
United States
Mark
The price is S$274
includes taxes & fees
3 Nov - 4 Nov
The Orchard House: Inn & Cafe
A two-story house with a balcony, a front porch, and a snow-covered landscape.

10. The Nicholson Inn

The Nicholson Inn
3.0 star property
Freeport
10.0 out of 10, Exceptional, (4 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.."
United States
alexandre
The price is S$332
includes taxes & fees
21 Oct - 22 Oct
The Nicholson Inn
A house with a sign for The James Place Inn, indicating a vacancy.

11. The James Place Inn B&B

The James Place Inn B&B
3.5 star property
Freeport
10.0 out of 10, Exceptional, (195 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."
United States
Kim
The price is S$350
includes taxes & fees
9 Nov - 10 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Great Diamond Island Hotel Reviews

Clarion Pointe South Portland

Clarion Pointe South Portland

8/10 Good
"Rooms were clean, but did have a cleaning solution smell. Lobby and property was dated, but the location and breakfast were perfect for what we needed."
Jeffrey 1-night trip
Posted 1 hour ago
Clarion Pointe South Portland

Find out more about Great Diamond Island

Great Diamond Island B&B information

Number of reviews
3,790
Accommodation
16 B&B
Lowest Price
S$106
Highest Price
S$368

Explore a world of travel with Expedia