Casco Bay Islands Historic Hotels, Maine: Casco Bay Islands Hotel Guide

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 restaurant with a brick fireplace, white chairs, and tables set for dining.

A reception area with two wooden reception desks labeled 'eighteen95 restaurant' and 'Valet'.

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

€133

includes taxes & fees

8 Nov - 9 Nov

A wooden house with a deck and a stone pathway leading to a grassy area.

A bedroom with a wooden bed, two bedside tables, a nightstand, a wooden desk, and a door.

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

A cozy living room with a brown sofa, a small kitchenette with a microwave and refrigerator, and a window with a view of trees.

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

Freeport

Hana L.

€295

includes taxes & fees

20 Oct - 21 Oct

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 corner room with large windows offering a city view.

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

3. Adorable Portland getaway on the Eastern Promenade

Munjoy Hill

Kiernan

€262

includes taxes & fees

26 Oct - 27 Oct

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

A kitchen with a GE microwave, a coffee maker, and a kettle on the counter.

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.

4. 1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!

Bath

michael

€164

includes taxes & fees

18 Oct - 19 Oct

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.

5. Glorious getaway on Portland's Eastern Promenade.

Munjoy Hill

William

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

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

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.

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

Brunswick

Britta M.

€354

includes taxes & fees

2 Nov - 3 Nov

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.

7. Centerview cottage

Harpswell

Catherine G.

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 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.

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

Downtown Saco

Bob Z.

€783

includes taxes & fees

18 Oct - 19 Oct

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Top Casco Bay Islands Hotel Reviews

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent

"The breakfast is great and the staffs are very friendly!"

DoubleTree by Hilton Hotel Portland

8/10 Good

"Great airport shuttle convenient location comfortable room"

Portland Harbor Hotel

10/10 Excellent

"From the moment we arrived, the Hilton Garden Inn Portland Downtown Waterfront exceeded every expectation. The room was spotless, spacious, beautifully appointed, and in the heart of the tourist section. Tour boats and trolleys, wonderful shops and restaurants are right there. This hotel is quiet, well designed and the bed was incredibly comfortable. We slept like babies. Beginning with a warm greeting at check, every staff member made us feel welcome and valued. We were especially moved by the front desk and management’s attentiveness — they went above and beyond to accommodate our needs. After we checked out, I realized I had left my wallet in the room. I can honestly say that I did not panic. I had a strong belief that the staff would retrieve it and send it to me. Two days later it arrived at my home with every ID, credit card and cash money still in it. This level of care and personalization is rare and truly memorable. Breakfast on site was how we started our day with traditional and continental fare that was fresh and satisfying. Our boat and trolley tours mentioned nearby famous restaurants that we happily tried for lunch and dinner. We went to relax, spend money, see a part of the country we had not visited before, witness the fall foliage, eat seafood and sleep. This ideal location satisfied our every whim, and I highly recommend it to anyone seeking a luxurious yet welcoming stay in the heart of the city."

Hampton Inn Portland Downtown - Waterfront

10/10 Excellent

"The rooms were spacious and clean. We couldn’t have found a better breakfast by eating out! Each morning the staff had an immaculate breakfast bar! The location was great for walking to the shops and eating out at night."

Clarion Pointe South Portland

10/10 Excellent

"Clean Room. Great Stay."

Spark by Hilton Portland Airport Maine Mall

8/10 Good

"Clean room, convenient location"

Portland Regency Hotel & Spa

8/10 Good

"Great location. Comfy bed. No included breakfast unfortunately but there's a restaurant downstairs where you can get lovely food."

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!"

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Scarborough Holiday Rentals

Casco Bay Islands Hotel Guide - Historic Hotels in Casco Bay Islands, Maine

Change your mind

Treat yourself

Be picky

Check availability on Casco Bay Islands Historic Hotels

Our top choices for Casco Bay Islands historic hotels

1. Portland Regency Hotel & Spa

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

3. Adorable Portland getaway on the Eastern Promenade

4. 1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!

5. Glorious getaway on Portland's Eastern Promenade.

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

7. Centerview cottage

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

Top Casco Bay Islands Hotel Reviews

Holiday Inn Portland-By the Bay by IHG

DoubleTree by Hilton Hotel Portland

Portland Harbor Hotel

Hampton Inn Portland Downtown - Waterfront

Clarion Pointe South Portland

Spark by Hilton Portland Airport Maine Mall

Portland Regency Hotel & Spa

Inn at St John Portland In-Town

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