A calm sea with a sailboat and rocky coastline.

Find Historic Hotels in Great Diamond Island, ME

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Great Diamond Island Historic Hotels

Tonight
6 Oct - 7 Oct
Tomorrow
7 Oct - 8 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 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 bar area with multiple seating options, including bar stools and chairs, and a bar counter with a variety of bottles and glasses.
A reception area with two wooden reception desks labeled 'eighteen95 restaurant' and 'Valet'.
A hot tub area with a tiled floor, a wooden bench, a potted plant, and towels on a rack.

1. Portland Regency Hotel & Spa

Portland Regency Hotel & Spa
Downtown Portland
United States
Susan
AED 496
AED 549 total
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 restaurant interior with tables and chairs, a bar area, and shelves with bottles.
A kitchen with a wooden island, two stools, a refrigerator, and a hanging light fixture.
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
AED 650
AED 1,009 total
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 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.
A neatly made bed with white linens and pillows, a bedside lamp, and a framed artwork on the wall.

3. Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
United States
William
AED 1,091
AED 1,702 total
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 living room with a gray sofa, two pink armchairs, a wooden coffee table, and a colorful rug.
A dining area with a wooden table, four chairs, a hanging light fixture, and a window with curtains.
A house with a black front door, white trim, and a number '106' above the door. There are two flower pots on the steps.

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.
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 wooden hallway with built-in shoe racks and a metal coffee table.

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.
AED 387
AED 827 total
includes taxes & fees
20 Oct - 21 Oct
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 living room with a sofa, a green couch, a coffee table, a fireplace, and a staircase.
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.

6. Centerview cottage

Centerview cottage
Harpswell
United States
Catherine G.
AED 1,084
AED 1,738 total
includes taxes & fees
9 Oct - 10 Oct
Centerview cottage
A staircase with wooden railings and carpeted steps leading to an upper floor.
A wooden dining room with a round table and six chairs, large windows with lace curtains, and a chandelier.
A kitchen with a large island, white cabinets, and a stainless steel refrigerator.
A cozy, wooden-floored living room with a pool table, leather sofa, and a piano.

7. The Gregory House in Southern Maine close to many beaches & popular destinations

The Gregory House in Southern Maine close to many beaches & popular destinations
Downtown Saco
United States
Bob Z.
AED 2,057
AED 3,911 total
includes taxes & fees
8 Oct - 9 Oct
The Gregory House in Southern Maine close to many beaches & popular destinations
View all properties

Top Great Diamond Island Hotel Reviews

Clarion Pointe South Portland

Clarion Pointe South Portland

10/10 Excellent
"Clean room and nice staff."
Nathan 1-night trip
Posted 1 hour ago
Clarion Pointe South Portland
Inn at St John Portland In-Town

Inn at St John Portland In-Town

8/10 Good
"The inn itself was beautifully kept. The water pressure was great. There was plenty of hot water except very early in the morning (before 6am). I didn’t walk in the area but if I had too, I wouldn’t feel comfortable in the evening. There was parking behind the hotel and I was lucky to get a spot both nights that I was there otherwise you would have to park in their other lot somewhere around the corner. They had lemon water, fruit, cookies, tea and coffee out all the time. The included breakfast was just an easy grab a toasted bagel and go. Nothing special but it was a nice offer. The beds were soft, the AC worked well and our room was very large. Our room was on the second floor, no elevator and extremely steep steps, but staff was always available to help with bags or luggage. Overall, a very nice stay and less expensive than closer to town."
Jane 2-night trip
Posted 4 hours ago
Inn at St John Portland In-Town
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

8/10 Good
"This was my first stay, I was surprised at how nice and big the lobby area was. The hallway to my room smelled really nice, and a staff member was in the hall and asked me if I needed help finding my room. I fly out of Portland often and the airport shuttle is a must. This was the first time I did not have to wait for my arrival pick-up. The young man that was the driver, was the most personable and respectful. He is truly an asset to your organization, I apologize for not getting his name."
Diane 1-night trip
Posted 6 hours ago
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

8/10 Good
"The staff was friendly, and the room was clean. There is a restaurant on site, and the location is fantastic and close to everything."
Angela M 1-night trip
Posted 8 hours ago
Portland Regency Hotel & Spa
The Westin Portland Harborview

The Westin Portland Harborview

8/10 Good
"Wonderful, historic building. Clean room. Great staff. Design starting to look a bit dated."
Robert 1-night trip
Posted 10 hours ago
The Westin Portland Harborview
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

8/10 Good
"S for"
David 2-night trip
Posted 13 hours ago
Fireside Inn & Suites Portland
Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

10/10 Excellent
"Good for the cost"
Robert 2-night trip
Posted 2 days ago
Quality Inn & Suites South Portland

Explore a world of travel with Expedia