A calm sea with a sailboat and rocky coastline.

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Check prices for these dates

Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11
In one month
Oct 23 - Oct 25
In two months
Nov 20 - Nov 22

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, (1,136 reviews)
"Cute spot and very affordable."
United States
Tess
The price is ₩152,647
₩166,389 total
includes taxes & fees
Sep 28 - Sep 29
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 ₩312,807
₩354,620 total
includes taxes & fees
Sep 28 - Sep 29
Fleetwood House Bed & Breakfast

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 ₩405,693
₩442,205 total
includes taxes & fees
Oct 26 - Oct 27
West End Collection at 146 Pine
A well-lit living room with a fireplace, comfortable seating, and a large mirror.

4. Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street
3.5 star property
West End
9.6 out of 10, Exceptional, (132 reviews)
"Beautiful place"
United States
Samuel
The price is ₩442,575
₩482,407 total
includes taxes & fees
Oct 26 - Oct 27
Blind Tiger Portland – Carleton Street
A black front door with a light fixture above it, flanked by two potted evergreen trees.

5. 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 ₩308,205
₩335,944 total
includes taxes & fees
Oct 7 - Oct 8
The Orchard House: Inn & Cafe
A four-poster bed with a chandelier, a bedside table with books, and a view of a brick building through the windows.

6. 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 ₩721,643
₩786,591 total
includes taxes & fees
Oct 25 - Oct 26
Blind Tiger Portland - Danforth Street.
A white building with a red roof, a sign indicating a vacancy at Candlebay Inn, and an American flag.

7. 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 ₩238,373
₩259,821 total
includes taxes & fees
Oct 5 - Oct 6
Candlebay 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, (1,003 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 ₩170,883
₩206,752 total
includes taxes & fees
Sep 27 - Sep 28
Old Orchard Beach Inn
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 ₩311,755
₩339,811 total
includes taxes & fees
Oct 5 - Oct 6
The James Place Inn B&B
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, (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 ₩317,011
₩345,545 total
includes taxes & fees
Oct 5 - Oct 6
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, (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 ₩388,591
₩423,564 total
includes taxes & fees
Oct 5 - Oct 6
The Nicholson Inn
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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Top Great Diamond Island Hotel Reviews

Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine

10/10 Excellent
"Everything about our stay at the Embassy suites Hotel in Portland Maine was excellent staff food amenities property all of it great experience"
Sheila 2-night trip
Posted 1 hour ago
Embassy Suites by Hilton Portland Maine

Find out more about Great Diamond Island

Great Diamond Island B&B information

Number of reviews
2,733
Accommodation
16 B&B
Lowest Price
₩166,389
Highest Price
₩786,591