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
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

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, (1,179 reviews)
"Great location and exactly what we needed for our time in Portland"
United States
Darbi
The price is AED 244
AED 266 total
includes taxes & fees
22 Nov - 23 Nov
Inn at St John Portland In-Town
Exterior

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)
"This was a super cute boutique inn and the location was ideal. The staff was super friendly!"
United States
Stephanie
The price is AED 793
AED 865 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.

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)
"Beautiful place"
United States
Samuel
The price is AED 784
AED 854 total
includes taxes & fees
17 Nov - 18 Nov
Blind Tiger Portland – Carleton Street
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)
"Great place"
United States
Mark
The price is AED 483
AED 526 total
includes taxes & fees
3 Dec - 4 Dec
The Orchard House: Inn & Cafe
A spacious kitchen with a central island, wooden bar stools, and a long dining 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)
"Very helpful and friendly staff"
United States
paul k
The price is AED 807
AED 879 total
includes taxes & fees
17 Nov - 18 Nov
Blind Tiger Portland - Danforth Street.
A garden with a stone wall, various plants, and flowers.

6. Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast
3.0 star property
Rosemont
9.0 out of 10, Wonderful, (150 reviews)
"Close location to airport. Sweet Neighbhorhood Good shower and breakfast was delish. Loved eating on the houses China"
United States
caia
The price is AED 841
AED 954 total
includes taxes & fees
10 Nov - 11 Nov
Fleetwood House Bed & Breakfast
A hallway with patterned wallpaper, a wooden staircase, and two wooden chairs.

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

Experience the History of Portland - The Hope Island Room
West End
10.0 out of 10, Exceptional, (1 review)
"Really cool home and room was big and clean!"
United States
Daniel
The price is AED 628
AED 745 total
includes taxes & fees
15 Nov - 16 Nov
Experience the History of Portland - The Hope Island Room
A two-story house with a red roof, a front porch, and a well-maintained lawn.

8. Candlebay Inn

Candlebay Inn
3.0 star property
Freeport
9.6 out of 10, Exceptional, (500 reviews)
"Great stay in a historic home."
United States
Richard
The price is AED 526
AED 573 total
includes taxes & fees
10 Nov - 11 Nov
Candlebay Inn
A house with a porch, white railings, and hanging flower baskets.

9. 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)
"Really nice hotel"
United States
James
The price is AED 463
AED 560 total
includes taxes & fees
1 Dec - 2 Dec
Old Orchard Beach Inn
A covered porch with white railings and a view of a well-maintained lawn and pathway.

10. The Kendall Inn

The Kendall Inn
3.5 star property
Freeport
9.8 out of 10, Exceptional, (170 reviews)
"The breakfasts were so tasty! The Inn is so charming! We loved our stay and hope to return next year!"
United States
Justin Terry
The price is AED 610
AED 665 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.

11. The Nicholson Inn

The Nicholson Inn
3.0 star property
Freeport
10.0 out of 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.."
United States
alexandre
The price is AED 836
AED 912 total
includes taxes & fees
12 Nov - 13 Nov
The Nicholson Inn
A two-story house with a stone staircase leading to a front door, surrounded by a garden with potted plants and a seating area with chairs.

12. Diamond Island | King Room with Private Ensuite

Diamond Island | King Room with Private Ensuite
West End
The price is AED 713
AED 845 total
includes taxes & fees
10 Nov - 11 Nov
Diamond Island | King Room with Private Ensuite
A two-story house with a stone staircase leading to a front door, surrounded by a garden with potted plants and a seating area with chairs.

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

Experience the History of Portland - The Hope Island Room
West End
The price is AED 834
AED 989 total
includes taxes & fees
15 Nov - 16 Nov
Experience the History of Portland - The Hope Island Room
A house with a sign for The James Place Inn, indicating a vacancy.

14. 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)
"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 AED 920
AED 1,003 total
includes taxes & fees
10 Nov - 11 Nov
The James Place Inn B&B
A two-story house with a stone staircase leading to a front door, surrounded by a garden with potted plants and a seating area with chairs.

15. 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 AED 1,010
AED 1,193 total
includes taxes & fees
10 Nov - 11 Nov
Experience the History of Portland - Two Room Suite w/Private Bath
A two-story house with a stone staircase leading to a front door, surrounded by a garden with potted plants and a seating area with chairs.

16. The Loft - private suite in historic home

The Loft - private suite in historic home
West End
The price is AED 1,234
AED 1,790 total
includes taxes & fees
10 Nov - 11 Nov
The Loft - private suite in historic home
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

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
A calm sea with a sailboat and rocky coastline.

Top reviews in Great Diamond Island

A multi-story building with a stone facade, multiple windows, and awnings.
Inn at St John Portland In-Town

Inn at St John Portland In-Town

Inn at St John Portland In-Town
Valley Street

10/10 Excellent

My stay was great clean bathrooms parking great breakfast selection. Cookies and Tea Coffee available all day.
United States
Adela
Reviewed October 31, 2026
Inn at St John Portland In-Town

Explore a world of travel with Expedia