Casco Bay Islands Holiday Rentals, Maine: Private House Rentals

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Go beyond your typical stay in Casco Bay Islands

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Family friendly

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Our top choices for Casco Bay Islands hotels

A large, multi-story building with a central courtyard, featuring a fire pit and outdoor seating area.

A pool area with lounge chairs and a building with multiple levels and outdoor seating.

A spacious living room with a fireplace, two armchairs, a coffee table, and a dining area with chairs and a table.

A cozy lounge area with a fireplace, comfortable seating, and a bar with wooden stools.

1. Inn at Diamond Cove

Portland

Lisa

฿9,063

฿11,164 total

includes taxes & fees

8 Oct - 9 Oct

A hotel room with two beds, a small seating area, and a window with blinds.

A room with a sloped wooden ceiling, a round skylight, a television mounted on the wall, a sofa, a bed, a dining table with chairs, and a window with blinds.

A two-story hotel with a balcony on the second floor, a sign reading "The Inn on Peaks Island," and a flag in front.

A bedroom with a bed, bedside table, lamp, and a view of the dining area.

2. Inn On Peaks Island

Peaks Island

Alice

฿4,505

฿4,910 total

includes taxes & fees

5 Nov - 6 Nov

A Holiday Inn Express building with a covered entrance, multiple floors, and a clear sky.

A modern dining area with round tables and chairs, a coffee station, and a view of the city.

An indoor swimming pool with a clear water surface, surrounded by beige tiled walls and a blue accent wall.

A reception area with a modern design, featuring a seating area with yellow chairs, a reception desk, and a large wall mural.

3. Holiday Inn Express Hotel & Suites Freeport by IHG

Freeport

Marvin

฿3,194

฿3,481 total

includes taxes & fees

4 Nov - 5 Nov

A swimming pool with clear blue water, surrounded by large windows offering views of trees and a clear sky.

An outdoor patio with a row of tables and chairs, a green umbrella, and a wooden fence.

A dining area with a long table, multiple chairs, hanging lights, a fruit bowl, and a wall with a framed picture.

A spacious lobby with a blue wall, a reception desk, a large mirror, and seating areas with a patterned table and chairs.

4. Hampton Inn Freeport/Brunswick

Freeport

Steven

฿3,418

฿3,726 total

includes taxes & fees

1 Nov - 2 Nov

A brick building with a sign reading "WAYPOINT" and outdoor seating with tables, chairs, and a fire pit.

A swimming pool with clear blue water, surrounded by lounge chairs and a brick wall.

A hotel room with two beds, a stone-patterned wall, and a nightstand with a lamp.

A spacious lobby with multiple seating areas, a fireplace, and large windows.

5. Embassy Suites by Hilton Portland Maine

Portland

Robert

฿4,193

฿4,640 total

includes taxes & fees

1 Nov - 2 Nov

An outdoor patio area with wicker furniture, string lights, and a barbecue grill.

A hotel room with a bed, a TV, a nightstand, a window with a view of the water, and a wooden headboard.

A brick building with a large entrance and a sign that reads "Residence Inn Marriott".

A swimming pool with a tiled deck, lounge chairs, and a ceiling with recessed lighting.

6. Residence Inn by Marriott Portland Downtown/Waterfront

Downtown Portland

Tim

฿3,974

฿4,397 total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a large bed, a desk with a chair, a TV, and a window with curtains.

Outdoor seating with Adirondack chairs, a fire pit, and umbrellas.

A building with a sign reading "L.L.Bean" and a rock waterfall feature in front.

7. Hilton Garden Inn Freeport Downtown

Freeport

Leanne

฿3,528

฿3,846 total

includes taxes & fees

1 Nov - 2 Nov

A modern living room with a sofa, ottoman, and chairs, a kitchen area with a counter and pendant lights, and a large window with curtains.

A hotel room with two beds, a large framed picture of a lighthouse, and a view of boats.

A modern kitchen with a herringbone wood floor, a central island with bar stools, and a built-in TV shelf.

A modern hotel lobby with wooden shelving, a Pepsi refrigerator, and a reception desk.

8. The Freeport Hotel, an Ascend Collection Hotel

Freeport

Margaret

฿3,135

฿3,418 total

includes taxes & fees

28 Oct - 29 Oct

A two-story building with a large glass conservatory and yellow umbrellas in the garden area.

A cozy living room with a wooden bench, a fireplace, and a large map on the wall.

An indoor swimming pool with lounge chairs and a view of the outdoors.

A stone staircase leading to a white house surrounded by lush greenery and autumnal decorations.

9. The Harraseeket Inn & Event House Freeport Downtown

Freeport

Carol

฿4,337

฿4,727 total

includes taxes & fees

1 Nov - 2 Nov

A modern bar area with a wooden bar counter, black bar stools, and a contemporary light fixture.

A modern reception area with a central desk, seating arrangements, and large windows offering views of the cityscape.

A black SUV parked in front of AC Hotel Portland, a modern building with a brick facade and large windows.

A modern living room with a sofa, two armchairs, a glass coffee table, and a decorative wall panel.

10. AC Hotel Portland Downtown/Waterfront, ME

Downtown Portland

Paul

฿4,101

฿4,538 total

includes taxes & fees

1 Nov - 2 Nov

A modern living room with dark blue walls, large windows, and a view of a landscaped garden.

A living room with two armchairs, a coffee table, and a TV. There is a door leading outside, a window with a view, and a patterned wall.

A hotel room with two beds, a desk, and a view of the outdoors.

A modern living room with a grey sofa, a coffee table, and a decorative plant.

11. Best Western Freeport Inn

Freeport

Robert

฿3,261

฿3,555 total

includes taxes & fees

1 Nov - 2 Nov

A spacious lobby with a reception desk, seating areas, and a 'Welcome to the Lobster State' sign.

A reception desk with a wooden design and a welcome sign for the Lobster State.

A snack and treat display area with shelves stocked with various snacks and a refrigerated section.

A spacious dining area with a long table, multiple chairs, and a sofa.

12. Hampton Inn & Suites Portland West

Nasons Corner

Michael

฿3,280

฿3,629 total

includes taxes & fees

4 Nov - 5 Nov

A rooftop terrace with a modern outdoor seating area, a fire pit, and a view of the cityscape.

A modern living room with a sofa, armchairs, a coffee table, and a rug.

A modern bar area with a long counter, multiple stools, and a variety of bottles and glasses on shelves.

A modern lobby with a geometric wall design, seating area, and a large abstract artwork.

13. Cambria Hotel Portland Downtown-Old Port

Downtown Portland

Sharion

฿3,738

฿5,052 total

includes taxes & fees

1 Nov - 2 Nov

A balcony with wooden flooring, striped cushioned chairs, and a glass railing overlooking a cityscape at night.

A bar area with a black countertop, blue bar stools, and a variety of bottles and glasses.

A modern hotel room with a large bed, a desk, and a TV.

A modern hotel with a dark facade, multiple windows, and a visible sign for 'Hyatt Place'.

14. Hyatt Place Portland Downtown - Old Port Square

Downtown Portland

Jeetindra

฿4,337

฿4,798 total

includes taxes & fees

2 Nov - 3 Nov

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 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.

15. Portland Regency Hotel & Spa

Downtown Portland

Julie

฿4,543

฿5,027 total

includes taxes & fees

2 Nov - 3 Nov

A hotel room with a bed, bedside table, TV, and a kitchenette in the background.

A hotel reception desk with a computer, a sign for Holiday Inn Express & Suites, and a display of snacks and beverages.

A compact kitchen with a built-in microwave, coffee maker, and dishwasher.

A modern hotel room with a blue sofa, a small round table, a desk with a chair, and two floor lamps.

16. Holiday Inn Express Hotel & Suites South Portland by IHG

South Portland

Brian

฿3,395

฿3,701 total

includes taxes & fees

1 Nov - 2 Nov

A fire pit surrounded by wicker chairs in a garden setting.

A dining area with round tables and chairs, a view of the garden through large windows, and a cozy atmosphere.

A hotel room with a large bed, two bedside tables, a chair, a window with curtains, and a view of the city.

A living room with a fireplace, seating area, and a large window.

17. Portland Harbor Hotel

Downtown Portland

Teresa

฿5,691

฿7,579 total

includes taxes & fees

2 Nov - 3 Nov

A breakfast buffet with pastries, coffee, and condiments.

A hotel room with a large bed, a bedside table, a chair, a window with curtains, and a door.

A yellow motel with a two-story structure, a covered outdoor seating area, and a staircase leading to the upper floor.

A reception desk at Econolodge with a wooden finish, a framed picture on the wall, and a clock.

18. Econo Lodge Freeport - Brunswick Area

Freeport

John

฿2,872

฿3,130 total

includes taxes & fees

5 Nov - 6 Nov

A waterfront marina with boats docked, buildings with multiple windows, and a red building with a visible restaurant.

A hotel lobby with a bar area, seating arrangements, and a fireplace.

A large indoor swimming pool with clear water, tiled flooring, and a seating area with chairs and a plant.

A hotel room with two beds, a desk, a TV, and a view of a body of water.

19. Hilton Garden Inn Portland Downtown Waterfront

Downtown Portland

Jenna

฿4,760

฿5,266 total

includes taxes & fees

2 Nov - 3 Nov

The exterior of a Courtyard by Marriott hotel with a glass entrance, outdoor seating area, and a stone facade.

A modern hotel lobby with a reception desk, a seating area, and a large wall mural.

A restaurant with booths and tables, brick walls, and pendant lighting.

A modern bar area with leather seating, a bar counter, and a menu board.

20. Courtyard Portland Downtown/Waterfront

Downtown Portland

Laura

฿4,007

฿4,434 total

includes taxes & fees

1 Nov - 2 Nov

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Stay near popular Casco Bay Islands attractions

Mackworth Island State Park

This forested island sanctuary offers a 1.25-mile coastal trail with stunning Casco Bay views. Build tiny homes in the Fairy Village or visit Governor Baxter's pet cemetery while enjoying the tranquil shoreline.

See properties

Sand Beach

9.2/10 (22 reviews)

If a restful holiday is part of your travel plans, Sand Beach might be the perfect place to visit during your trip to Portland. Wander the area's waterfront or simply enjoy one of its seafood restaurants.

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Little John Island Preserve

Explore a coastal forest path leading to secluded rocky beaches at this 23-acre Maine preserve. Pause on shoreline benches to spot bald eagles while enjoying panoramic ocean views along the 1.3-mile loop trail.

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Fifth Maine Museum

This historic Queen Anne-style museum preserves both Civil War history and Peaks Island's local heritage. Explore two floors of exhibits while enjoying panoramic views of Casco Bay from the wrap-around porch.

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Little Diamond Island

Commune with nature and explore the great outdoors at Little Diamond Island during your travels in Portland. Stroll along the area's waterfront or experience its acclaimed theatre scene.

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Umbrella Cover Museum

You can spend time studying the exhibits at Umbrella Cover Museum in Peaks Island. Experience the area's entertainment choices and great live music.

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House Island

Commune with nature and explore the great outdoors at House Island during your travels in Portland. Stroll along the area's waterfront or experience its entertainment choices.

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Learn more about Casco Bay Islands

Check out sights like Little John Island Preserve and Sand Beach as you discover Casco Bay Islands—an area also known for its island views.

See all hotels in Casco Bay Islands

A beach with people sunbathing and swimming, boats in the water, and a rocky shoreline.

Top Casco Bay Islands Hotel Reviews

Cambria Hotel Portland Downtown-Old Port

10/10 Excellent

"The staff were nice, friendly, and accommodating. They offer a 25$ voucher per room per night which is nice"

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."

Clarion Hotel Portland Airport ME

8/10 Good

"Nice hotel and near the airport."

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."

The Westin Portland Harborview

8/10 Good

"Wonderful, historic building. Clean room. Great staff. Design starting to look a bit dated."

Fireside Inn & Suites Portland

8/10 Good

"S for"

DoubleTree by Hilton Hotel Portland

10/10 Excellent

"I liked that it had an indoor pool, bar and restaurant."

Quality Inn & Suites South Portland

10/10 Excellent

"Good for the cost"

More cheap stays in Casco Bay Islands

Clarion Pointe South Portland

675 Main Street I-95 South Portland ME

฿1,714

฿1,869 total

5 Nov - 6 Nov

includes taxes & fees

Quality Inn & Suites South Portland

738 Main Street South Portland ME

฿2,178

฿2,374 total

5 Nov - 6 Nov

includes taxes & fees

Comfort Inn South Portland Airport

90 Maine Mall Rd South Portland ME

฿2,390

฿2,605 total

4 Nov - 5 Nov

includes taxes & fees

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME

฿2,380

฿2,634 total

3 Nov - 4 Nov

includes taxes & fees

8.2/10 Very good! (1,755 reviews)

Spark by Hilton Portland Airport Maine Mall

461 Maine Mall Rd South Portland ME

฿2,543

฿2,772 total

25 Oct - 26 Oct

includes taxes & fees

7.8/10 Good! (1,825 reviews)

Inn at St John Portland In-Town

939 Congress St Portland ME

฿2,748

฿2,996 total

19 Oct - 20 Oct

includes taxes & fees

8.6/10 Excellent! (1,145 reviews)

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Book Hotels in Casco Bay Islands on Expedia.com

Find hotels in Casco Bay Islands, ME from ฿1,869

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Casco Bay Islands

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Casco Bay Islands hotels

1. Inn at Diamond Cove

2. Inn On Peaks Island

3. Holiday Inn Express Hotel & Suites Freeport by IHG

4. Hampton Inn Freeport/Brunswick

5. Embassy Suites by Hilton Portland Maine

6. Residence Inn by Marriott Portland Downtown/Waterfront

7. Hilton Garden Inn Freeport Downtown

8. The Freeport Hotel, an Ascend Collection Hotel

9. The Harraseeket Inn & Event House Freeport Downtown

10. AC Hotel Portland Downtown/Waterfront, ME

11. Best Western Freeport Inn

12. Hampton Inn & Suites Portland West

13. Cambria Hotel Portland Downtown-Old Port

14. Hyatt Place Portland Downtown - Old Port Square

15. Portland Regency Hotel & Spa

16. Holiday Inn Express Hotel & Suites South Portland by IHG

17. Portland Harbor Hotel

18. Econo Lodge Freeport - Brunswick Area

19. Hilton Garden Inn Portland Downtown Waterfront

20. Courtyard Portland Downtown/Waterfront

Stay near popular Casco Bay Islands attractions

Mackworth Island State Park

Sand Beach

Little John Island Preserve

Fifth Maine Museum

Little Diamond Island

Umbrella Cover Museum

House Island

Learn more about Casco Bay Islands

Top Casco Bay Islands Hotel Reviews

Cambria Hotel Portland Downtown-Old Port

Inn at St John Portland In-Town

Clarion Hotel Portland Airport ME

Portland Regency Hotel & Spa

The Westin Portland Harborview

Fireside Inn & Suites Portland

DoubleTree by Hilton Hotel Portland

Quality Inn & Suites South Portland

More cheap stays in Casco Bay Islands

Clarion Pointe South Portland

Quality Inn & Suites South Portland

Comfort Inn South Portland Airport

Clarion Hotel Portland Airport ME

Spark by Hilton Portland Airport Maine Mall

Inn at St John Portland In-Town

Explore a world of travel with Expedia

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