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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured B&B in Great Diamond Island and around

Inn at St John Portland In-Town
Classic building with a stone facade and commercial establishments on the ground floor.

Inn at St John Portland In-Town

2.5 star property
8.8 out of 10, Excellent, (1038)
"Quaint and fun old style place to stay. "
The price is €131
includes taxes & fees
1 Sept - 2 Sept
Inn at St John Portland In-Town
Old Orchard Beach Inn
Relax in a serene outdoor setting surrounded by lush greenery and comfortable seating.

Old Orchard Beach Inn

2.5 star property
8.2 out of 10, Very good, (1007)
"This historic inn was just what we wanted for our stay in OOB. "
Old Orchard Beach Inn
Blind Tiger Portland - Danforth Street.
Relax in a serene room with a four-poster canopy bed, featuring a table for reading and a decorative vase.

Blind Tiger Portland - Danforth Street.

3.5 star property
9.6 out of 10, Exceptional, (149)
"Everything was wonderful, we highly recommend staying here to anyone considering it."
The price is €347
includes taxes & fees
27 Aug - 28 Aug
Blind Tiger Portland - Danforth Street.
Fleetwood House Bed & Breakfast
Step up to the charming Fleecwood House, featuring a traditional facade with a welcoming porch and beautiful tree-lined surroundings.

Fleetwood House Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (120)
"We had a great time! The breakfast was wonderful! "
The price is €215
includes taxes & fees
11 Aug - 12 Aug
Fleetwood House Bed & Breakfast
The Orchard House & Cafe
Stylish entrance with a central door and potted evergreen trees.

The Orchard House & Cafe

3.0 star property
9.6 out of 10, Exceptional, (150)
"The place was perfect"
The price is €197
includes taxes & fees
10 Aug - 11 Aug
The Orchard House & Cafe
Blind Tiger Portland – Carleton Street
Relax in a stylish living room with a sofa, side table, and artwork, perfect for reading and unwinding.

Blind Tiger Portland – Carleton Street

3.5 star property
9.8 out of 10, Exceptional, (114)
"The Blind Tiger was a gem. It was convenient and private enough to enjoy with staff available 24/7 with and questions. The room, lobby and all areas were immaculate and brilliantly arranged. I would definitely go again!"
The price is €423
includes taxes & fees
20 Aug - 21 Aug
Blind Tiger Portland – Carleton Street
The James Place Inn B&B
Enjoy a romantic meal for two on the deck, surrounded by the house's charming facade.

The James Place Inn B&B

3.5 star property
10.0 out of 10, Exceptional, (173)
"Location to the busy areas of Freeport is steps away from this quiet oasis. Very nice innkeepers and staff will be there to make your stay pleasant while allowing you the privacy of a hotel guest. We stayed one night on our way home from mid coastal Maine and enjoyed our stay. "
The price is €286
includes taxes & fees
4 Aug - 5 Aug
The James Place Inn B&B
And. N B&B
Stroll up to the central entrance of this charming two-story house, featuring a gabled roof and a cozy porch.

And. N B&B

3.0 star property
9.8 out of 10, Exceptional, (65)
"Great breakfast with perfect homefries. Personable friendly hosts. Near town but wooded quiet sitting area out back. "
The price is €173
includes taxes & fees
21 Aug - 22 Aug
And. N B&B
Brewster House Bed & Breakfast
Escape to a serene garden oasis with a charming cottage nestled among vibrant flowers and lush greenery.

Brewster House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (112)
"Wonderful hosts. Enjoyed quiet evening and lovely gourmet breakfast. Truly memorable stay. We look forward to returning in the future."
The price is €244
includes taxes & fees
4 Aug - 5 Aug
Brewster House Bed & Breakfast
The Kendall Inn
Charming two-story house with a welcoming porch and a beautifully manicured lawn.

The Kendall Inn

3.5 star property
9.8 out of 10, Exceptional, (130)
"Quaint stay. Enjoyed our stay. "
The price is €198
includes taxes & fees
4 Aug - 5 Aug
The Kendall Inn
Candlebay Inn
Welcome to Candlebay Inn, a charming hotel surrounded by lush greenery and a well-manicured lawn.

Candlebay Inn

3.0 star property
9.6 out of 10, Exceptional, (432)
"Connie was extremely helpful and welcoming. The breakfast casserole, as many others have stated, was delicious. The room and bathroom were amply sized for our needs. We would stay here again!"
The price is €187
includes taxes & fees
5 Aug - 6 Aug
Candlebay Inn
West End Inn
Enjoy the view from this cozy corner bay window with a porch and brick facade.

West End Inn

3.0 star property
9.6 out of 10, Exceptional, (90)
"Extremely cozy and clean, perfect bed and breakfast in the West End for those looking for walkable access to the Old Port and downtown as well as a quiet retreat at night in the historic West End District. "
The price is €300
includes taxes & fees
1 Sept - 2 Sept
West End Inn
PineCrest Inn
Experience the charm of this traditional bed and breakfast, featuring a welcoming front porch and beautifully maintained grounds.

PineCrest Inn

4.0 star property
9.8 out of 10, Exceptional, (103)
"Lovely home, great breakfast. Kathy is a very gracious hostess and really helped us to thoroughly enjoy the Portland area."
PineCrest Inn
The Chadwick Bed & Breakfast
Terrace/patio

The Chadwick Bed & Breakfast

3.5 star property
9.8 out of 10, Exceptional, (48)
"Great getaway within Portland. The breakfast is first rate!"
The Chadwick Bed & Breakfast
Inn at Park Spring
Welcome to the Inn at Park Spring, featuring a traditional entrance with a red door and potted plants.

Inn at Park Spring

3.5 star property
10.0 out of 10, Exceptional, (48)
"Absolutely wonderful place! Room was spacious and comfortable. Breakfast was delicious. Everything was so clean. Buddy and Debbie were lovely hosts! Cannot wait to stay again! "
Inn at Park Spring
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

Old Orchard Beach Inn

Old Orchard Beach Inn

10/10 Excellent
"Absolutely gorgeous! Close to everything! Super clean! "
JILL 4-night trip
Posted 13 hours ago
Old Orchard Beach Inn