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
15 Oct - 16 Oct
Tomorrow
16 Oct - 17 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 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 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
Brian
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 corner room with large windows offering a city view.
A kitchen with a wooden island, two stools, a refrigerator, and a hanging light fixture.

2. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
United States
Kiernan
AED 650
AED 1,061 total
includes taxes & fees
26 Oct - 27 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 white sofa, a small table with a potted orchid, a bookshelf, and a radiator.
A living room with a sofa, armchairs, a coffee table, and a potted plant.

3. Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
United States
William
AED 1,017
AED 1,625 total
includes taxes & fees
18 Oct - 19 Oct
Glorious getaway on Portland's Eastern Promenade.
A wooden house with a deck and a stone pathway leading to a grassy area.
A wooden hallway with built-in shoe racks and a metal coffee table.
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.

4. 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 725
AED 1,251 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 cabin room with a bed, a chair, a desk, and large windows with blinds.
A staircase with wooden steps and white walls, leading to an upper floor.
A living room with a sofa, a green couch, a coffee table, a fireplace, and a staircase.

5. Centerview cottage

Centerview cottage
Harpswell
United States
Catherine G.
Centerview cottage
A staircase with wooden railings and carpeted steps leading to an upper floor.
A cozy, wooden-floored living room with a pool table, leather sofa, and a piano.
A dining area with a wooden table and four chairs, surrounded by wooden walls and a window with curtains.
A kitchen with a large island, white cabinets, and a stainless steel refrigerator.

6. 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 1,579
AED 3,315 total
includes taxes & fees
18 Oct - 19 Oct
The Gregory House in Southern Maine close to many beaches & popular destinations
View all properties

Top Great Diamond Island Hotel Reviews

Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

8/10 Good
"Basic room...comfy bed....sauna and whirlpool area was nice....small very basic gym area but ok...nice grab and bag breakfast small but basic and tasty...staff was very nice tried to help with wi fi sign in but my outlook was not operating there....parking ample...close to amenities ie eateries....shopping...and road access...."
William 2-night trip
Posted 1 hour ago
Fireside Inn & Suites Portland
Clarion Pointe South Portland

Clarion Pointe South Portland

8/10 Good
"Super comfy beds, nice sized bathroom and vanity area. Close to convenience store, staff was friendly and helpful."
Tina 1-night trip
Posted 1 hour ago
Clarion Pointe South Portland
Spark by Hilton Portland Airport Maine Mall

Spark by Hilton Portland Airport Maine Mall

10/10 Excellent
"Good for a nights stay"
Gary 1-night trip
Posted 2 hours ago
Spark by Hilton Portland Airport Maine Mall
Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

10/10 Excellent
"Staff was very helpful & friendly"
Mike 1-night trip
Posted 2 hours ago
Hampton Inn Portland Downtown - Waterfront
Inn at St John Portland In-Town

Inn at St John Portland In-Town

10/10 Excellent
"We love to stay at historic places when we travel, and we were not disappointed with this one! So cute and cozy!"
Vicki 1-night trip
Posted 4 hours ago
Inn at St John Portland In-Town
Portland Harbor Hotel

Portland Harbor Hotel

10/10 Excellent
"This was our favorite hotel on our trip. The property is very clean and well maintained. The restaurant food was delicious. Valet service was great. Location in town was perfect very close to shopping and activities."
Garrett 3-night trip
Posted 8 hours ago
Portland Harbor Hotel
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

8/10 Good
"Extremely well located in Portland, in the heart of the old town and central to everything. I'm glad we chose this hotel rather than others that were mostly newer. The breakfast and bar options were good."
shaun 2-night trip
Posted 17 hours ago
Portland Regency Hotel & Spa
Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent
"The room was beautiful, clean and comfortable. The most comfortable hotel beds we have slept in this trip. Front desk staff was extremely helpful and kind. Loved that they have a shuttle to take you to the hotspots so you don’t have to move your car and pay for parking."
James 1-night trip
Posted 1 day ago
Holiday Inn Portland-By the Bay by IHG

Explore a world of travel with Expedia