TOP Historic Hotels in Casco Bay Islands, ME for 2026

A dock with a small building, people, and colorful items.

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Our top choices for Casco Bay Islands 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 restaurant with a brick fireplace, white chairs, and tables set for dining.

A bar area with multiple seating options, including bar stools and chairs, and a bar counter with a variety of bottles and glasses.

1. Portland Regency Hotel & Spa

Downtown Portland

Brian

£113

includes taxes & fees

1 Nov - 2 Nov

A street lined with buildings, one with a red door and a sign that reads "MINATO".

A cozy room with a wooden table, a sofa, a bookshelf, and a window with a view.

A kitchen with a wooden island, two stools, a refrigerator, and a hanging light fixture.

A restaurant interior with tables and chairs, a bar area, and shelves with bottles.

2. Adorable Portland getaway on the Eastern Promenade

Munjoy Hill

Kiernan

£222

includes taxes & fees

20 Oct - 21 Oct

A wooden staircase with a wooden railing, surrounded by green foliage.

A bedroom with a navy blue bedspread, two matching pillows, a navy blue and white anchor-patterned rug, and two bedside tables with lamps.

A living room with a wooden chair, a blue patterned sofa, a television, and bookshelves.

A porch with a rocking chair and a metal bench with decorative plates.

3. 1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!

Bath

michael

£138

includes taxes & fees

13 Oct - 14 Oct

A modern kitchen with a dishwasher, a dining area with chairs, and a red refrigerator.

A bedroom with a bed, a nightstand, a lamp, and a door.

A bridge over a river with a building on the right.

A modern kitchen with white cabinets, stainless steel appliances, and a wooden dining area.

4. 2King Bed BR Private Apt Downtown Brunswick

Brunswick

caralyn g.

£235

includes taxes & fees

13 Oct - 14 Oct

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.

5. Glorious getaway on Portland's Eastern Promenade.

Munjoy Hill

William

£354

includes taxes & fees

14 Oct - 15 Oct

A modern kitchen with white cabinetry, a central island with stools, a refrigerator, and a microwave.

A modern kitchen with white cabinets, a central island with stools, a microwave, and a large window.

A bedroom with two beds, a desk, and a chair. There are windows with blinds, a painting on the wall, and a vase with dried plants.

A modern kitchen with a central island, a dining area with a sofa, and a living room with a coffee table.

6. Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)

Brunswick

Britta M.

£311

includes taxes & fees

2 Nov - 3 Nov

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 staircase with wooden steps and white walls, leading to an upper floor.

A cabin room with a bed, a chair, a desk, and large windows with blinds.

7. Centerview cottage

Harpswell

Catherine G.

£356

includes taxes & fees

13 Oct - 14 Oct

A staircase with wooden railings and carpeted steps leading to an upper floor.

A dining area with a wooden table and four chairs, surrounded by wooden walls and a window with curtains.

A wooden dining room with a round table and six chairs, large windows with lace curtains, and a chandelier.

A cozy, wooden-floored living room with a pool table, leather sofa, and a piano.

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

Downtown Saco

Bob Z.

£677

includes taxes & fees

13 Oct - 14 Oct

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Top Casco Bay Islands Hotel Reviews

Clarion Hotel Portland Airport ME

10/10 Excellent

"Very convenient to the airport for an early morning flight."

Clarion Pointe South Portland

8/10 Good

"The hotel was good overall and a convenient option for our needs. We only stayed one night, but it was a good choice for a short stay. I would consider staying here again."

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent

"We were in Portland for three (3) days on the tail end of our 2-week east coast trip. While the hotel is showing some signs of age, it did not disappoint and fully met our needs. The breakfast was great, especially the cook to order omelets. The hotel is not in the Old Port area but is still a comfortable 15-minute walk to get to the harbor area for dinner, bay tours and site seeing. The only negative was our last day and being awakened with two (2) room attendant staffers arguing in the hall. It lasted about 5 minutes until we came out into the hallway and glared at both of the participants. We will definitely stay here again when we come back either in 27 or 28."