A calm sea with a sailboat and rocky coastline.

Great Diamond Island Hotel Guide - Historic Hotels in Great Diamond Island, Portland

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Check availability on Great Diamond Island Historic Hotels

Tonight
1 Oct - 2 Oct
Tomorrow
2 Oct - 3 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Great Diamond Island historic hotels

A balcony with a table and chairs, overlooking a street with buildings and parked cars.
A hot tub area with a tiled floor, a wooden bench, a potted plant, and towels on a rack.
A bar area with multiple seating options, including bar stools and chairs, and a bar counter with a variety of bottles and glasses.
A restaurant with a brick fireplace, white chairs, and tables set for dining.

1. Portland Regency Hotel & Spa

Portland Regency Hotel & Spa
Downtown Portland
United States
SHELBY
€132
includes taxes & fees
1 Nov - 2 Nov
Portland Regency Hotel & Spa
A street lined with buildings, one with a red door and a sign that reads "MINATO".
A kitchen with a wooden island, two stools, a refrigerator, and a hanging light fixture.
A cozy room with a wooden table, a sofa, a bookshelf, and a window with a view.
A corner room with large windows offering a city view.

2. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
United States
Kiernan
€260
includes taxes & fees
20 Oct - 21 Oct
Adorable Portland getaway on the Eastern Promenade
A street lined with buildings, one with a red door and a sign that reads "MINATO".
A neatly made bed with white linens and pillows, a bedside lamp, and a framed artwork on the wall.
A living room with a sofa, armchairs, a coffee table, and a potted plant.
A living room with a white sofa, a small table with a potted orchid, a bookshelf, and a radiator.

3. Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
United States
Cynthia
€413
includes taxes & fees
14 Oct - 15 Oct
Glorious getaway on Portland's Eastern Promenade.
A two-story house with a balcony, a covered patio, and a fenced yard.
A house with a black front door, white trim, and a number '106' above the door. There are two flower pots on the steps.
A wooden console table with a wine bottle, glasses, and framed pictures.
A dining area with a wooden table, four chairs, a hanging light fixture, and a window with curtains.

4. The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries
Munjoy Hill
United States
Richard D.
€576
includes taxes & fees
6 Oct - 7 Oct
The Globe House on Munjoy Hill - Walk to Breweries
A wooden house with a deck and a stone pathway leading to a grassy area.
A cozy living room with a brown sofa, a small kitchenette with a microwave and refrigerator, and a window with a view of trees.
An aerial view of a two-story house with a large deck, surrounded by dense forest.
A bedroom with a wooden bed, two bedside tables, a nightstand, a wooden desk, and a door.

5. Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean

Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean
Freeport
United States
Hana L.
Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean
A wooden deck with a view of a lake, surrounded by trees and shrubs.
A cabin room with a bed, a chair, a desk, and large windows with blinds.
A kitchen with wooden cabinets, a stove, a refrigerator, and a dining table with chairs.
A staircase with wooden steps and white walls, leading to an upper floor.

6. Centerview cottage

Centerview cottage
Harpswell
United States
Catherine G.
€431
includes taxes & fees
11 Oct - 12 Oct
Centerview cottage
View all properties

Top Great Diamond Island Hotel Reviews

Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

8/10 Good
"Everything was great except Restaurant was closed, and the hot tub was nice, but inconvenient since it was on other side of building from pools."
Roderic 1-night trip
Posted less than an hour ago
Fireside Inn & Suites Portland
Clarion Pointe South Portland

Clarion Pointe South Portland

10/10 Excellent
"Everything was very nice clean very comfortable love having the two sinks one in the bathroom and one in the adjoining area"
James 1-night trip
Posted less than an hour ago
Clarion Pointe South Portland
Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

10/10 Excellent
"Good place to crash"
Hariharan 2-night trip
Posted 2 hours ago
Quality Inn & Suites South Portland
Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent
"Very friendly and professional staff in the lobby. Portland Wharf has great restaurants and beautiful views in Downtown"
CHARLES 1-night trip
Posted 3 hours ago
Holiday Inn Portland-By the Bay by IHG
Comfort Inn South Portland Airport

Comfort Inn South Portland Airport

10/10 Excellent
"Very accessible and quiet location. The property is well maintained, but is dated - a renovation would improve business opportunities I believe from my past hospitality experiences. Thank You for a wonderful relaxing stay. Best Regards- Jeff"
Jeffery 4-night trip
Posted 19 hours ago
Comfort Inn South Portland Airport
Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine

10/10 Excellent
"Great location near airport with free airport shuttle and breakfast. Only 15 minute drive to Old Port restaurants, shops and activities. Clean, spacious rooms. Friendly service. Great choice!"
Bertha 1-night trip
Posted 20 hours ago
Embassy Suites by Hilton Portland Maine
Inn at St John Portland In-Town

Inn at St John Portland In-Town

10/10 Excellent
"We had a lovely stay at The Inn on St. John! It’s a very unique hotel with a lot of character, both inside and out. Our room was comfortably spacious and featured a fantastic shower—plus, having a jet bath was a wonderful bonus! The complimentary morning breakfast was a great touch to start the day. Parking was a little tricky, but we lucked out with a spot right under our room window, which was super convenient. Overall, a charming and very enjoyable stay in Portland!"
Igor 1-night trip
Posted 21 hours ago
Inn at St John Portland In-Town

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