A calm sea with a sailboat and rocky coastline.

Search B&B 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
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct
In one month
30 Oct - 1 Nov
In two months
27 Nov - 29 Nov

Our top choices for Great Diamond Island bed & breakfast

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

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, (1,147 reviews)
"Cute spot and very affordable."
United States
Tess
The price is SAR 476
SAR 519 total
includes taxes & fees
5 Oct - 6 Oct
Inn at St John Portland In-Town
A garden with a stone wall, various plants, and flowers.

2. Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast
3.0 star property
Rosemont
9.0 out of 10, Wonderful, (147 reviews)
"Breakfast was wonderful!"
United States
Karen
The price is SAR 860
SAR 975 total
includes taxes & fees
4 Oct - 5 Oct
Fleetwood House Bed & Breakfast
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, (99 reviews)
"Lovely property"
United States
Mary
The price is SAR 931
SAR 1,015 total
includes taxes & fees
28 Oct - 29 Oct
West End Collection at 146 Pine
A black front door with a light fixture above it, flanked by two potted evergreen trees.

4. The Orchard House: Inn & Cafe

The Orchard House: Inn & Cafe
3.0 star property
Freeport
9.6 out of 10, Exceptional, (181 reviews)
"Amazing stay in a perfect location! Would absolutely recommend to family and friends and will likely stay again!"
United States
Megan
The price is SAR 729
SAR 795 total
includes taxes & fees
29 Sep - 30 Sep
The Orchard House: Inn & Cafe
A covered patio with wicker furniture and a mosaic table, surrounded by greenery and a white building.

5. 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)
"Beautiful property a short walk from the beach and all the attractions make it an ideal place to stay"
United States
James
The price is SAR 437
SAR 532 total
includes taxes & fees
6 Oct - 7 Oct
Old Orchard Beach Inn
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, (490 reviews)
"Great stay in a historic home."
United States
Richard
The price is SAR 656
SAR 715 total
includes taxes & fees
30 Sep - 1 Oct
Candlebay Inn
A well-lit living room with a fireplace, comfortable seating, and a large mirror.

7. Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street
3.5 star property
West End
9.6 out of 10, Exceptional, (133 reviews)
"Beautiful place"
United States
Samuel
The price is SAR 1,189
SAR 1,296 total
includes taxes & fees
26 Oct - 27 Oct
Blind Tiger Portland – Carleton Street
A four-poster bed with a chandelier, a bedside table with books, and a view of a brick building through the windows.

8. Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.
3.5 star property
West End
9.6 out of 10, Exceptional, (193 reviews)
"Place was charming and quirky. Very comfortable and well located."
United States
Mary
The price is SAR 1,847
SAR 2,013 total
includes taxes & fees
29 Oct - 30 Oct
Blind Tiger Portland - Danforth Street.
A house with a sign for The James Place Inn, indicating a vacancy.

9. The James Place Inn B&B

The James Place Inn B&B
3.5 star property
Freeport
10.0 out of 10, Exceptional, (193 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 SAR 857
SAR 934 total
includes taxes & fees
5 Oct - 6 Oct
The James Place Inn B&B
A kitchen with a wooden table, bench, and a fireplace.

10. Experience the History of Portland - The Hope Island Room

Experience the History of Portland - The Hope Island Room
West End
The price is SAR 1,014
SAR 1,187 total
includes taxes & fees
29 Oct - 30 Oct
Experience the History of Portland - The Hope Island Room
A two-story house with a balcony, a front porch, and a snow-covered landscape.

11. The Nicholson Inn

The Nicholson Inn
3.0 star property
Freeport
10.0 out of 10, Exceptional, (2 reviews)
"The owners were amazing and so kind. The location is perfect, and the amenities feel so hoy and great."
United States
Meaghan
The price is SAR 962
SAR 1,048 total
includes taxes & fees
12 Oct - 13 Oct
The Nicholson Inn
A covered porch with white railings and a view of a well-maintained lawn and pathway.

12. The Kendall Inn

The Kendall Inn
3.5 star property
Freeport
9.8 out of 10, Exceptional, (162 reviews)
"The room was lovely and comfortable, including easy-to-adjust air conditioning. Breakfast was delicious as were the homemade cookies available each evening. Coffee and tea were available all the time."
United States
Kenneth and
The price is SAR 872
SAR 950 total
includes taxes & fees
12 Oct - 13 Oct
The Kendall Inn
A bedroom with a large bed, a wooden wardrobe, and a bench.

13. The Diamond Island Suite - Suite in Historic Home

The Diamond Island Suite - Suite in Historic Home
West End
The price is SAR 1,115
SAR 1,297 total
includes taxes & fees
29 Oct - 30 Oct
The Diamond Island Suite - Suite in Historic Home
A dining area with a round table, six chairs, and a floral centerpiece.

14. Experience the History of Portland - The Hope Island Room

Experience the History of Portland - The Hope Island Room
West End
The price is SAR 1,419
SAR 1,645 total
includes taxes & fees
27 Oct - 28 Oct
Experience the History of Portland - The Hope Island Room
A staircase with a wooden handrail and black steps, leading to a room with patterned wallpaper and a chandelier.

15. The Loft - private suite in historic home

The Loft - private suite in historic home
West End
The price is SAR 1,622
SAR 2,189 total
includes taxes & fees
29 Oct - 30 Oct
The Loft - private suite in historic home
An outdoor dining setup with a table set for two, featuring candles, glassware, and a vase of flowers.

16. Experience the History of Portland - Two Room Suite w/Private Bath

Experience the History of Portland - Two Room Suite w/Private Bath
West End
The price is SAR 1,521
SAR 1,764 total
includes taxes & fees
28 Oct - 29 Oct
Experience the History of Portland - Two Room Suite w/Private Bath
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

Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

10/10 Excellent
"The water pressure wasn’t the best and the pillows were pretty soft but other than that, it was a nice stay"
Steven Robert 1-night trip
Posted 2 hours ago
Hampton Inn Portland Downtown - Waterfront