Casco Bay Islands Holiday Houses

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Our top choices for Casco Bay Islands holiday homes

A covered porch with a view of a lake and trees.

1. Mere Point Sunrise Views at Eastern Shore!

Brunswick

Michelle S.

A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

2. Mid Coast Getaway w/ water views

West Point

Rebecca

includes taxes & fees

3 Nov - 4 Nov

A grassy area with a picnic table and chairs, a body of water, and two trees in the background.

3. Orchid Harbor, Bailey Island 3BR

Harpswell

Jane D.

includes taxes & fees

16 Nov - 17 Nov

A living room with a sofa, armchair, wooden coffee table, and a potted plant.

4. Fully Updated Airy Historic Home in South Freeport

Freeport

boodu

includes taxes & fees

6 Nov - 7 Nov

A dining area with a wooden table and chairs, a red sofa, and a small round table with a decorative plate.

5. Quiet Spot in lovely Freeport neighborhood

Freeport

includes taxes & fees

3 Nov - 4 Nov

A window with a view of a snowy landscape and bare trees.

6. Tranquility between the Lakes & Sea

Westbrook

Bernie G.

includes taxes & fees

7 Nov - 8 Nov

A spacious room with a wooden floor, a dining area with chairs and a table, a sofa, a TV, and a balcony with a view of the sea.

7. 2 bedroom w/ expansive water views

West Point

Gregory M.

includes taxes & fees

8 Nov - 9 Nov

A wooden deck with outdoor seating and string lights.

8. Full sized home

Harpswell

Erika T.

includes taxes & fees

30 Nov - 1 Dec

A deck with white railings overlooking a body of water, boats, and a forested shoreline.

9. Captains Watch: A Coastal Escape

West Point

Holly G.

includes taxes & fees

3 Nov - 4 Nov

A spacious bedroom with a large bed, a rocking chair, and a view of a balcony with a white railing.

10. Fantastic Waterfront Views

West Point

Vanessa W.

includes taxes & fees

4 Nov - 5 Nov

A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

11. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

West End

Susan d.

includes taxes & fees

3 Nov - 4 Nov

A backyard with a red Adirondack chair, a barbecue grill, and a wooden treehouse.

12. Guest Room + Bath + Private Emtrance. Walk to everything, Large yard,

Bath

Esther

includes taxes & fees

3 Nov - 4 Nov

A spacious living room with a sofa, ottoman, and coffee table, a dining area with chairs, and a kitchen with cabinets and appliances.

13. Newly Renovated Luxury House with Game Room

Yarmouth

Michelle T.

A lush garden with a hammock, a variety of flowers, and a lake in the background.

14. Classic New England Waterfront House Big Lawn Beautiful Sunrise

Harpswell

Ashma B.

includes taxes & fees

30 Nov - 1 Dec

A silver convertible car parked in front of a red house with a garden.

15. 1BR Apt. Authenticity. Value. Walk to everything, Sundeck. Big yard. Treehouse.

Bath

michael

includes taxes & fees

3 Nov - 4 Nov

A spacious living room with a large window overlooking a lake, a flat-screen TV mounted on the wall, and a round wooden coffee table.

16. Casco Bay Oceanfront Retreat by Everrow

Freeport

"What can I say about my stay; peaceful, beautiful views, and relaxing! Home was clean with modern finishes but super comfortable for my four guests. The downstairs area is very private from the main floor. The yard was a great space where we had our outdoor fire looking up at the stars at night. The deck was perfect for our family lunch and dinners. We took chairs down to the beach area to sit closer to the water which was perfect. It's super close to town, Wolfe's Neck and other amenities....

Lisa E.

includes taxes & fees

3 Nov - 4 Nov

A building named Willard Square with a storefront and a red vehicle parked outside.

17. Willard Square Family Home

Willard Beach

David W.

includes taxes & fees

12 Nov - 13 Nov

A living room with a grey sofa, a coffee table, and a dining area with a wooden table and chairs.

18. Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Brunswick

Michaela M.

includes taxes & fees

1 Dec - 2 Dec

A cozy room with wooden flooring, wicker furniture, and a white brick wall.

19. Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard

Brunswick

Gary R.

A living room with a sofa, armchair, ottoman, and a colorful geometric rug.

20. Modern & Sunny East End House.

Munjoy Hill

stacey p.

includes taxes & fees

30 Nov - 1 Dec

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Top Casco Bay Islands Hotel Reviews

Portland Regency Hotel & Spa

10/10 Excellent

"Great location. Clean and nice room. Reliable staff"

Clarion Hotel Portland Airport ME

10/10 Excellent

"Hotel was close to the airport, about a 10-minute drive in a safe and quiet area. Staff was courteous and helpful and check-in was straightforward and quick. The room was clean and bed was comfortable. I didn't need much of anything else. Breakfast is not included, but there's a Holy Donut store nearby. The drive to Old Port area for sightseeing is less than 15 minutes away. Totally recommended for a no-frills affordable hotel that's outside the pricey downtown area."

Hilton Garden Inn Portland Downtown Waterfront

8/10 Good

"Everything was great for our 2 nights girls trip of 3 of us staying in Portland. The staff was very friendly and helpful, even helping us choose a couple of restaurants. The rooms were very clean and the beds surprisingly comfortable. Not too hard and not too soft but on the firm side. We paid a little extra for our stay on breakfast which was ok for some of the choices, but also more than we expected. The coffee, however, was awful which was a big disappointment because we all want our coffee in the morning! My big complaint, which was a really big one for me and one of my friends, was this strong odor of either cleaning product or freshener or both in the rooms and hallways. If you have any allergies to scents or chemicals, please beware. We were suffering from headaches, burning eyes and ears and generally feeling a little ill and it was better when we were outside. It was a real drag considering the otherwise wonderful stay. I mentioned it to the front desk checking out and they were very gracious about it. Don’t know if things will change but thought I’d mention it because it was pretty bad."

Find out more about Casco Bay Islands

Casco Bay Islands Holiday Homes information

Number of reviews	383
Accommodation	701 Holiday Homes
Lowest Price	NZ$299
Highest Price	NZ$2,760

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Activities in Portland

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Casco Bay Islands holiday homes

1. Mere Point Sunrise Views at Eastern Shore!

2. Mid Coast Getaway w/ water views

3. Orchid Harbor, Bailey Island 3BR

4. Fully Updated Airy Historic Home in South Freeport

5. Quiet Spot in lovely Freeport neighborhood

6. Tranquility between the Lakes & Sea

7. 2 bedroom w/ expansive water views

8. Full sized home

9. Captains Watch: A Coastal Escape

10. Fantastic Waterfront Views

11. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

12. Guest Room + Bath + Private Emtrance. Walk to everything, Large yard,

13. Newly Renovated Luxury House with Game Room

14. Classic New England Waterfront House Big Lawn Beautiful Sunrise

15. 1BR Apt. Authenticity. Value. Walk to everything, Sundeck. Big yard. Treehouse.

16. Casco Bay Oceanfront Retreat by Everrow

17. Willard Square Family Home

18. Private Home w/ Office Year Round in town Brunswick next to Bowdoin

19. Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard

20. Modern & Sunny East End House.

Find holiday rentals that suit your style

Top Casco Bay Islands Hotel Reviews

Portland Regency Hotel & Spa

Clarion Hotel Portland Airport ME

Portland Harbor Hotel

Cambria Hotel Portland Downtown-Old Port

Clarion Pointe South Portland

Hilton Garden Inn Portland Downtown Waterfront

Hampton Inn Portland Downtown - Waterfront

Find out more about Casco Bay Islands

Casco Bay Islands Holiday Homes information

Explore a world of travel with Expedia

Holiday Homes in Casco Bay Islands

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Casco Bay Islands holiday homes

1. Mere Point Sunrise Views at Eastern Shore!

2. Mid Coast Getaway w/ water views

3. Orchid Harbor, Bailey Island 3BR

4. Fully Updated Airy Historic Home in South Freeport

5. Quiet Spot in lovely Freeport neighborhood

6. Tranquility between the Lakes & Sea

7. 2 bedroom w/ expansive water views

8. Full sized home

9. Captains Watch: A Coastal Escape

10. Fantastic Waterfront Views

11. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

12. Guest Room + Bath + Private Emtrance. Walk to everything, Large yard,

13. Newly Renovated Luxury House with Game Room

14. Classic New England Waterfront House Big Lawn Beautiful Sunrise

15. 1BR Apt. Authenticity. Value. Walk to everything, Sundeck. Big yard. Treehouse.

16. Casco Bay Oceanfront Retreat by Everrow

17. Willard Square Family Home

18. Private Home w/ Office Year Round in town Brunswick next to Bowdoin

19. Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard

20. Modern & Sunny East End House.

Find holiday rentals that suit your style

Top Casco Bay Islands Hotel Reviews

Portland Regency Hotel & Spa

Find out more about Casco Bay Islands

Casco Bay Islands Holiday Homes information

Explore a world of travel with Expedia