A calm sea with a sailboat and rocky coastline.

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Check prices for these dates

Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13
In one month
Sep 25 - Sep 27
In two months
Oct 23 - Oct 25

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, (1,112 reviews)
"Room was clean, bed was comfortable, staff were helpful. Would stay here again!"
United States
Caleb
The price is ￥26,956
￥29,381 total
includes taxes & fees
Aug 30 - Aug 31
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, (143 reviews)
"Breakfast was wonderful!"
United States
Karen
The price is ￥36,493
￥41,371 total
includes taxes & fees
Sep 6 - Sep 7
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, (96 reviews)
"Wonderful staff and scrumptious breakfast "
United States
Elena
The price is ￥34,900
￥38,041 total
includes taxes & fees
Aug 30 - Aug 31
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, (129 reviews)
"Beautiful place to stay in the middle of a quiet street and walking distance to many spots. The rooms and common areas were clean and beautifully maintained. Staff was ready to answer any questions you had via phone or text. I loved this inn and would choose it again. Definitely recommend it !"
United States
Adriana Cecilia
The price is ￥50,601
￥55,155 total
includes taxes & fees
Sep 10 - Sep 11
Blind Tiger Portland – Carleton Street
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, (1,001 reviews)
"This place was amazing. The staff were so friendly and the breakfast was delicious!"
United States
Samantha
The price is ￥17,946
￥21,951 total
includes taxes & fees
Aug 31 - Sep 1
Old Orchard Beach Inn
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, (192 reviews)
"Perfect location & beautiful stay! Very unique property. Great recommendations & lovely hospitality. We will definitely come back the next time we’re in Portland! :)"
United States
Ariana A De
The price is ￥66,931
￥72,955 total
includes taxes & fees
Sep 1 - Sep 2
Blind Tiger Portland - Danforth Street.
A black front door with a light fixture above it, flanked by two potted evergreen trees.

7. The Orchard House: Inn & Cafe

The Orchard House: Inn & Cafe
3.0 star property
Freeport
9.6 out of 10, Exceptional, (179 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 ￥35,256
￥38,429 total
includes taxes & fees
Sep 15 - Sep 16
The Orchard House: Inn & Cafe
A hotel room with a bed, a fireplace, a door, and a painting on the wall.

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

Experience the History of Portland - The Hope Island Room
West End
The price is ￥38,724
￥48,289 total
includes taxes & fees
Sep 9 - Sep 10
Experience the History of Portland - The Hope Island Room
A white building with a red roof, a sign indicating a vacancy at Candlebay Inn, and an American flag.

9. Candlebay Inn

Candlebay Inn
3.0 star property
Freeport
9.6 out of 10, Exceptional, (485 reviews)
"Great location, quiet room, great breakfast......"
United States
Keith
The price is ￥27,824
￥30,328 total
includes taxes & fees
Aug 31 - Sep 1
Candlebay Inn
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, (1 review)
The price is ￥41,742
￥45,499 total
includes taxes & fees
Sep 28 - Sep 29
The Nicholson Inn
A covered porch with white railings and a view of a well-maintained lawn and pathway.

11. The Kendall Inn

The Kendall Inn
3.5 star property
Freeport
9.8 out of 10, Exceptional, (159 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 ￥34,249
￥38,264 total
includes taxes & fees
Sep 15 - Sep 16
The Kendall Inn
A house with a sign for The James Place Inn, indicating a vacancy.

12. The James Place Inn B&B

The James Place Inn B&B
3.5 star property
Freeport
10.0 out of 10, Exceptional, (190 reviews)
"Fabulous hosts, beautiful property, excellent breakfast, walking distance to the main street of Freeport but still quiet. Highly recommend!"
United States
Carol
The price is ￥43,792
￥47,733 total
includes taxes & fees
Aug 30 - Aug 31
The James Place Inn B&B
A bedroom with a large bed, a bedside table, a chair, and a window.

13. The Diamond Island Suite - Suite in Historic Home

The Diamond Island Suite - Suite in Historic Home
West End
The price is ￥47,330
￥57,496 total
includes taxes & fees
Sep 8 - Sep 9
The Diamond Island Suite - Suite in Historic Home

14. Charming Top-Floor Queen Room with Sloped Ceilings, Walk to the Beach

Charming Top-Floor Queen Room with Sloped Ceilings, Walk to the Beach
Old Orchard Beach
10.0 out of 10, Exceptional, (1 review)
"Definitely worth a visit! Beach just down the road!"
United States
Matt S.
The price is ￥28,278
￥35,339 total
includes taxes & fees
Sep 18 - Sep 19
Charming Top-Floor Queen Room with Sloped Ceilings, Walk to the Beach
A hotel room with a bed, a fireplace, a door, and a painting on the wall.

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

Experience the History of Portland - The Hope Island Room
West End
The price is ￥55,935
￥67,917 total
includes taxes & fees
Sep 20 - Sep 21
Experience the History of Portland - The Hope Island Room
A hotel room with a large bed, a fireplace, a window with curtains, and two framed pictures on the wall.

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 ￥64,541
￥78,514 total
includes taxes & fees
Sep 27 - Sep 28
Experience the History of Portland - Two Room Suite w/Private Bath
A bedroom with a brick wall, a wooden ceiling beam, a bed with white bedding, a nightstand with a lamp, and a window with curtains.

17. The Loft - private suite in historic home

The Loft - private suite in historic home
West End
The price is ￥77,449
￥108,564 total
includes taxes & fees
Sep 8 - Sep 9
The Loft - private suite in historic home

18. Bright Character Studio Near the Beach with Outdoor Seating & Parking

Bright Character Studio Near the Beach with Outdoor Seating & Parking
Old Orchard Beach
8.0 out of 10, Very Good, (1 review)
"served its purpose as between residences; nice place with all necessities; time of year issue was not enough heat; host attentive to any questions"
United States
Beth W.
The price is ￥29,952
￥37,165 total
includes taxes & fees
Aug 29 - Aug 30
Bright Character Studio Near the Beach with Outdoor Seating & Parking
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

8/10 Good
"I was annoyed at check in when they said there was a parking fee ($13/night, but still- annoying and unexpected). The “happy hour” was not as great as others we had had at the same hotel chain. The room was lovely and clean and the breakfast was EXCELLENT!"
Debbie 1-night trip
Posted less than an hour ago
Embassy Suites by Hilton Portland Maine

Find out more about Great Diamond Island

Great Diamond Island B&B information

Number of reviews
3,381
Accommodation
15 B&B
Lowest Price
￥21,951
Highest Price
￥72,955

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