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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured B&B in Great Diamond Island

Inn at St John Portland In-Town
Front of property - evening/night

Inn at St John Portland In-Town

2.5 star property
8.8 out of 10, Excellent, (1060)
"Quaint and fun old style place to stay. "
The price is AU$233
includes taxes & fees
24 Aug - 25 Aug
Inn at St John Portland In-Town
Old Orchard Beach Inn
Exterior

Old Orchard Beach Inn

2.5 star property
8.2 out of 10, Very good, (1021)
"Nice place and was a great breakfast "
Old Orchard Beach Inn
Fleetwood House Bed & Breakfast
Property entrance

Fleetwood House Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (123)
"The breakfasts and friendly conversations were amazing. We thoroughly enjoyed our stay at the Fleetwood Bed and Breakfast "
The price is AU$384
includes taxes & fees
25 Aug - 26 Aug
Fleetwood House Bed & Breakfast
Candlebay Inn
Porch

Candlebay Inn

3.0 star property
9.6 out of 10, Exceptional, (440)
"Great location and hospitality."
The price is AU$333
includes taxes & fees
20 Aug - 21 Aug
Candlebay Inn
The Kendall Inn
Exterior

The Kendall Inn

3.5 star property
9.8 out of 10, Exceptional, (134)
"Quaint stay. Enjoyed our stay. "
The price is AU$353
includes taxes & fees
20 Aug - 21 Aug
The Kendall Inn
The Orchard House & Cafe
Front of property - evening/night

The Orchard House & Cafe

3.0 star property
9.6 out of 10, Exceptional, (151)
"The place was perfect"
The price is AU$350
includes taxes & fees
21 Aug - 22 Aug
The Orchard House & Cafe
Blind Tiger Portland - Danforth Street.
Baxter

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 AU$601
includes taxes & fees
26 Aug - 27 Aug
Blind Tiger Portland - Danforth Street.
Blind Tiger Portland – Carleton Street
Stovall | Living area

Blind Tiger Portland – Carleton Street

3.5 star property
9.8 out of 10, Exceptional, (115)
"Loved the place "
The price is AU$648
includes taxes & fees
27 Aug - 28 Aug
Blind Tiger Portland – Carleton Street
And. N B&B
Front of property

And. N B&B

3.0 star property
9.8 out of 10, Exceptional, (67)
"Lovely place to stay. Sweet staff and delicious breakfast. "
The price is AU$304
includes taxes & fees
10 Sept - 11 Sept
And. N B&B
The James Place Inn B&B
Outdoor dining

The James Place Inn B&B

3.5 star property
10.0 out of 10, Exceptional, (175)
"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 AU$509
includes taxes & fees
20 Aug - 21 Aug
The James Place Inn B&B
West End Inn
Exterior

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. "
West End Inn
PineCrest Inn
Street view

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
Brewster House Bed & Breakfast
Garden

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 AU$501
includes taxes & fees
20 Aug - 21 Aug
Brewster House Bed & Breakfast
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
Exterior

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

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

10/10 Excellent
"Great location. We had such a blast. You can walk to tons of fun restaurants, and places to shop. Our room was very nice and we enjoyed using the spa facilities."
Christopher 2-night trip
Posted 9 hours ago
Portland Regency Hotel & Spa