Casco Bay Islands Holiday Rentals, Maine: Private House Rentals

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

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

A beach with a wooden staircase leading down to the shore, surrounded by trees and a calm body of water.

1. Inn at Diamond Cove

Portland

Mikael

Rp4.834.651

Rp5.955.172 total

includes taxes & fees

8 Oct - 9 Oct

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 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 bedroom with a large bed, two bedside tables with lamps, a round table with chairs, and a grey sofa.

A wedding ceremony with guests seated on white chairs, a bride and groom walking down the aisle, and a grassy outdoor setting.

2. Inn On Peaks Island

Peaks Island

Alice

Rp2.407.444

Rp2.624.114 total

includes taxes & fees

2 Nov - 3 Nov

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

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

Tiffany N

Rp1.706.770

Rp1.860.379 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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.

4. Hampton Inn Freeport/Brunswick

Freeport

Steven

Rp1.870.979

Rp2.039.368 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

A dining area with a fireplace, a green sofa, and a table set with food and flowers.

5. The Harraseeket Inn & Event House Freeport Downtown

Freeport

Carol

Rp2.317.614

Rp2.526.199 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 hotel room with a large bed, a sofa, a small table, and a bench. There is a window with a view of the water.

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

6. AC Hotel Portland Downtown/Waterfront, ME

Downtown Portland

Paul

Rp2.191.852

Rp2.425.064 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 snack vending area with a Pepsi refrigerator and shelves stocked with various snacks.

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

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

7. The Freeport Hotel, an Ascend Collection Hotel

Freeport

Margaret

Rp1.675.689

Rp1.826.501 total

includes taxes & fees

26 Oct - 27 Oct

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

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

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

An indoor swimming pool with clear glass walls, blue cushioned chairs, and a tiled floor.

8. Hilton Garden Inn Freeport Downtown

Freeport

Moira

Rp1.885.711

Rp2.055.425 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 spacious lobby with multiple seating areas, a fireplace, and large windows.

A chef in a black uniform and white hat, holding a ladle and a bowl, with various dishes in front of him.

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

9. Embassy Suites by Hilton Portland Maine

Portland

Andrew

Rp2.275.574

Rp2.517.696 total

includes taxes & fees

1 Nov - 2 Nov

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

A bar area with stools, a counter, and a herringbone-patterned wall.

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".

10. Residence Inn by Marriott Portland Downtown/Waterfront

Downtown Portland

Tim

Rp2.119.988

Rp2.345.555 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 a large bed, a desk with a chair, a balcony with a view, and a modern design.

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

11. Best Western Freeport Inn

Freeport

Robert

Rp1.998.538

Rp2.178.407 total

includes taxes & fees

1 Nov - 2 Nov

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 hot tub area with a tiled floor, a wooden bench, a potted plant, and towels on a rack.

12. Portland Regency Hotel & Spa

Downtown Portland

SHELBY

Rp2.407.085

Rp2.663.280 total

includes taxes & fees

2 Nov - 3 Nov

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

A spacious living area with large windows, a staircase, and modern furniture.

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.

13. Portland Harbor Hotel

Downtown Portland

Teresa

Rp3.041.465

Rp4.050.480 total

includes taxes & fees

1 Nov - 2 Nov

A breakfast buffet with pastries, coffee, and condiments.

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

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.

14. Econo Lodge Freeport - Brunswick Area

Freeport

Margaret

Rp1.534.656

Rp1.672.775 total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a bed, a TV, a desk, and a view of a lighthouse through a mural.

A spacious lobby with a wooden floor, a reception desk, a blue sofa, and a chandelier.

An indoor swimming pool with a tiled floor, clear glass walls, and a few chairs.

A restaurant with wooden tables and chairs, a buffet counter, and a clock on the wall.

15. Clarion Pointe South Portland

Thorton Heights

Majella

Rp916.266

Rp998.730 total

includes taxes & fees

1 Nov - 2 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 dining area with a dark blue booth seating, wooden ceiling beams, and large windows providing natural light.

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

16. Cambria Hotel Portland Downtown-Old Port

Downtown Portland

Sharion

Rp1.997.819

Rp2.699.930 total

includes taxes & fees

1 Nov - 2 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 hotel room with a large bed, a desk with a computer, a TV, and a view of the city and water.

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

17. Courtyard Portland Downtown/Waterfront

Downtown Portland

Laura

Rp2.141.547

Rp2.369.408 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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.

18. Hilton Garden Inn Portland Downtown Waterfront

Downtown Portland

Jenna

Rp2.214.130

Rp2.449.713 total

includes taxes & fees

2 Nov - 3 Nov

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

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

A bar area with a polished granite countertop, a variety of liquor bottles, a fruit bowl, and blue upholstered bar stools.

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

19. Hyatt Place Portland Downtown - Old Port Square

Downtown Portland

Jeetindra

Rp2.317.614

Rp2.564.208 total

includes taxes & fees

2 Nov - 3 Nov

A spacious lobby with a sofa, chairs, a coffee table, and a TV.

A bar area with wooden bar stools, a television, and a liquor display. There are red chairs and a small table with a glass top.

An indoor swimming pool with clear lane markings, a seating area with chairs, and potted plants.

A lobby with a reception desk, a clock, a plant, and a round table.

20. Clarion Hotel Portland Airport ME

Portland

Leonard

Rp1.272.083

Rp1.407.434 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.

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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

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

8/10 Good

"Nice Hôtel to stayed. Recommend to come back"

The Westin Portland Harborview

10/10 Excellent

"We really liked the Westin property. We were able to check in early which made it so helpful. Room was very clean and ready. Breakfast was fantastic. I loved that there was a Peloton bike in good working order in the workout room. If we go back to Portland I would stay there again."

Portland Regency Hotel & Spa

10/10 Excellent

"Visited Portland for the first time, the Regency is in the perfect location. It’s a great food town, do your homework before you go and make reservations."

Fireside Inn & Suites Portland

8/10 Good

"Everything was great except Restaurant was closed, and the hot tub was nice, but inconvenient since it was on other side of building from pools."

Clarion Pointe South Portland

10/10 Excellent

"Everything was very nice clean very comfortable love having the two sinks one in the bathroom and one in the adjoining area"

Quality Inn & Suites South Portland

10/10 Excellent

"Good place to crash"

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent

"Very friendly and professional staff in the lobby. Portland Wharf has great restaurants and beautiful views in Downtown"

Inn at St John Portland In-Town

10/10 Excellent

"We had a lovely stay at The Inn on St. John! It’s a very unique hotel with a lot of character, both inside and out. Our room was comfortably spacious and featured a fantastic shower—plus, having a jet bath was a wonderful bonus! The complimentary morning breakfast was a great touch to start the day. Parking was a little tricky, but we lucked out with a spot right under our room window, which was super convenient. Overall, a charming and very enjoyable stay in Portland!"

More cheap stays in Casco Bay Islands

Clarion Pointe South Portland

675 Main Street I-95 South Portland ME

Rp916.266

Rp998.730 total

1 Nov - 2 Nov

includes taxes & fees

Quality Inn & Suites South Portland

738 Main Street South Portland ME

Rp1.236.061

Rp1.347.307 total

1 Nov - 2 Nov

includes taxes & fees

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME

Rp1.272.083

Rp1.407.434 total

1 Nov - 2 Nov

includes taxes & fees

8.2/10 Very good! (1,734 reviews)

Spark by Hilton Portland Airport Maine Mall

461 Maine Mall Rd South Portland ME

Rp1.311.159

Rp1.429.163 total

25 Oct - 26 Oct

includes taxes & fees

Comfort Inn South Portland Airport

90 Maine Mall Rd South Portland ME

Rp1.324.094

Rp1.443.262 total

1 Nov - 2 Nov

includes taxes & fees

Inn at St John Portland In-Town

939 Congress St Portland ME

Rp1.603.466

Rp1.747.732 total

1 Nov - 2 Nov

includes taxes & fees

8.6/10 Excellent! (1,128 reviews)

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Book Hotels in Casco Bay Islands on Expedia.com

Find hotels in Casco Bay Islands, ME from Rp998.730

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. The Harraseeket Inn & Event House Freeport Downtown

6. AC Hotel Portland Downtown/Waterfront, ME

7. The Freeport Hotel, an Ascend Collection Hotel

8. Hilton Garden Inn Freeport Downtown

9. Embassy Suites by Hilton Portland Maine

10. Residence Inn by Marriott Portland Downtown/Waterfront

11. Best Western Freeport Inn

12. Portland Regency Hotel & Spa

13. Portland Harbor Hotel

14. Econo Lodge Freeport - Brunswick Area

15. Clarion Pointe South Portland

16. Cambria Hotel Portland Downtown-Old Port

17. Courtyard Portland Downtown/Waterfront

18. Hilton Garden Inn Portland Downtown Waterfront

19. Hyatt Place Portland Downtown - Old Port Square

20. Clarion Hotel Portland Airport ME

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

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

The Westin Portland Harborview

Portland Regency Hotel & Spa

Fireside Inn & Suites Portland

Clarion Pointe South Portland

Quality Inn & Suites South Portland

Holiday Inn Portland-By the Bay by IHG

Inn at St John Portland In-Town

More cheap stays in Casco Bay Islands

Clarion Pointe South Portland

Quality Inn & Suites South Portland

Clarion Hotel Portland Airport ME

Spark by Hilton Portland Airport Maine Mall

Comfort Inn South Portland Airport

Inn at St John Portland In-Town

Explore a world of travel with Expedia

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