Chebeague Island Holiday Homes from £137: Search Holiday Homes in Chebeague Island

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Our top choices for Chebeague Island holiday homes

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

1. Quiet Spot in lovely Freeport neighborhood

Freeport

includes taxes & fees

27 Oct - 28 Oct

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

2. Fully Updated Airy Historic Home in South Freeport

Freeport

boodu

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 covered porch with a view of a lake and trees.

4. Mere Point Sunrise Views at Eastern Shore!

Brunswick

Michelle S.

includes taxes & fees

17 Nov - 18 Nov

A wooden deck with outdoor seating and string lights.

5. Full sized home

Harpswell

Erika T.

includes taxes & fees

27 Oct - 28 Oct

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

6. Classic New England Waterfront House Big Lawn Beautiful Sunrise

Harpswell

Ashma B.

includes taxes & fees

23 Nov - 24 Nov

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

7. Mid Coast Getaway w/ water views

West Point

Rebecca

includes taxes & fees

27 Oct - 28 Oct

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.

8. 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

28 Oct - 29 Oct

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

9. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

West End

Susan d.

includes taxes & fees

29 Oct - 30 Oct

A lakeside property with a deck, picnic table, and barbecue grill.

10. Camp Forever cottage

Harpswell

Len B.

includes taxes & fees

1 Nov - 2 Nov

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

11. Luxe 5 Bed/ 3 Bath with Game Room & AC

Yarmouth

Michelle T.

includes taxes & fees

1 Nov - 2 Nov

A living room with a sofa, coffee table, and a large rug. There is a dining area with chairs and a table. The room has a mural on the wall depicting a landscape.

12. Chic 3-bedroom house in Munjoy Hill with off-street parking.

Munjoy Hill

"Wow, wow, wow! My family and I all agree that this has been the best rental home we have ever stayed in. The interior design is so chic, we were truly wowed by the attention to detail in this place. The beds and pillows are also extremely comfy, we all had a great two nights of sleep here. The location of this place is phenomenal, it neighbors the Portland Observatory, many bars/cafes, and is a short walk down to the eastern promenade. We will absolutely stay here again the next time we’re in...

Maris P.

includes taxes & fees

11 Nov - 12 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.

13. 2 bedroom w/ expansive water views

West Point

Gregory M.

includes taxes & fees

1 Nov - 2 Nov

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

14. Captains Watch: A Coastal Escape

West Point

includes taxes & fees

27 Oct - 28 Oct

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

15. Willard Square Family Home

Willard Beach

David W.

includes taxes & fees

12 Nov - 13 Nov

A modern kitchen with dark cabinetry, stainless steel appliances, and a large island.

16. Gorgeous 3-bedroom house in charming Portland

North Deering

Bridget M.

includes taxes & fees

31 Oct - 1 Nov

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

17. Tranquility between the Lakes & Sea

Westbrook

Bernie G.

includes taxes & fees

30 Oct - 31 Oct

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

18. Fantastic Waterfront Views

West Point

Vanessa W.

includes taxes & fees

1 Nov - 2 Nov

A room with a large sliding glass door leading to a balcony with chairs and potted plants.

19. Modern & Sunny House Steps from the Promenade.

Munjoy Hill

stacey p.

includes taxes & fees

27 Oct - 28 Oct

A modern kitchen with a large island, dark cabinetry, and a view of a lake.

20. The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury

Harpswell

Edwin M.

includes taxes & fees

27 Oct - 28 Oct

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Top Chebeague Island Hotel Reviews

Tru by Hilton Portland Airport Area

10/10 Excellent

"Very efficient staff. Hotel easy for parking. Decent breakfast included. Quiet room and comfortable bed. Slept well."

Ramada Plaza by Wyndham Portland

8/10 Good

"I was there for 2 nights and was told when I checked in housekeeping would not be cleaning my room but if I needed anything just ask. I was fine with that. Room was clean, bed was comfortable, and there was a fridge in the room. The shower head was adjustable for different water flows but the pressure made them all seem about the same. The shower covering over the old tub felt weird as there was some give to the floor as you moved around in the shower. The bathroom was clean and they provided facecloths as well as towels. There was a sink in the bathroom as well as one outside the bathroom door. Room had a balcony. I would definitely stay hear again for the combination location, affordability, cleanliness and friendliness of staff."