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Holiday Homes in Chebeague Island

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Chebeague Island holiday homes

A compact kitchen with a dishwasher, microwave, and coffee maker on the countertop.

1. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
Quiet Spot in lovely Freeport neighborhood
A living room with a sofa, armchair, wooden coffee table, and a potted plant.

2. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
10.0 out of 10, Exceptional, (1 review)
"Great property well kept and close to everything we wanted to do"
United States
boodu
The price is €428
includes taxes & fees
26 Oct - 27 Oct
Fully Updated Airy Historic Home in South Freeport
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

Orchid Harbor, Bailey Island 3BR
Harpswell
10.0 out of 10, Exceptional, (13 reviews)
"Lovely property, close to what we needed and wanted, host communicated promptly. Would definitely stay there again."
United States
Jane D.
Orchid Harbor, Bailey Island 3BR
A wooden deck with outdoor seating and string lights.

4. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (78 reviews)
"Wonderful stay!"
United States
Erika T.
The price is €331
includes taxes & fees
27 Oct - 28 Oct
Full sized home
A covered porch with a view of a lake and trees.

5. Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (10 reviews)
"Lovely location "
United States
Michelle S.
The price is €344
includes taxes & fees
17 Nov - 18 Nov
Mere Point Sunrise Views at Eastern Shore!
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

Classic New England Waterfront House Big Lawn Beautiful Sunrise
Harpswell
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful stay! "
United States
Ashma B.
The price is €1,493
includes taxes & fees
23 Nov - 24 Nov
Classic New England Waterfront House Big Lawn Beautiful Sunrise
A room with a sliding glass door leading to an outdoor deck with Adirondack chairs and a table.

7. Three bedroom in United States of America, Freeport

Three bedroom in United States of America, Freeport
Freeport
10.0 out of 10, Exceptional, (13 reviews)
"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....
United States
Lisa E.
The price is €819
includes taxes & fees
8 Nov - 9 Nov
Three bedroom in United States of America, Freeport
A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

8. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (12 reviews)
"The location and views from the cottage are quintessential coastal Maine. Small community with lobster pound and Maine Oyster Company across the street. John is a welcoming host and eager to make sure you enjoy your stay. The cottage is great for 2 people, equipped with the basics and has a great deck to enjoy the views. Planning to return next year. Great spot!"
United States
Rebecca
The price is €196
includes taxes & fees
4 Nov - 5 Nov
Mid Coast Getaway w/ water views
A spacious living room with a sofa, ottoman, and coffee table, a dining area with chairs, and a kitchen with cabinets and appliances.

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

Luxe 5 Bed/ 3 Bath with Game Room & AC
Yarmouth
10.0 out of 10, Exceptional, (4 reviews)
"What a great place to stay! The home is very clean and very quiet. Our host was very responsive to any questions we had. We would book this one over and over again."
United States
Michelle T.
The price is €955
includes taxes & fees
26 Oct - 27 Oct
Luxe 5 Bed/ 3 Bath with Game Room & AC
A lakeside property with a deck, picnic table, and barbecue grill.

10. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (72 reviews)
"We had a really nice day in communication and check-in were very easy. Overall, it was a lovely day and we would definitely consider returning."
United States
Len B.
The price is €328
includes taxes & fees
1 Nov - 2 Nov
Camp Forever cottage
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

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.4 out of 10, Very good, (63 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is €324
includes taxes & fees
29 Oct - 30 Oct
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
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.

Chic 3-bedroom house in Munjoy Hill with off-street parking.
Munjoy Hill
10.0 out of 10, Exceptional, (10 reviews)
"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...
United States
Maris P.
Chic 3-bedroom house in Munjoy Hill with off-street parking.
A spacious living room with large windows, a sofa, a chair, and a small table.

13. 1 Mi to Maine Street! MCM-Style Home in Brunswick

1 Mi to Maine Street! MCM-Style Home in Brunswick
Brunswick
9.6 out of 10, Exceptional, (13 reviews)
"Quiet, clean, well appointed house close to Maine St Brunswick and convenient to both Portland and points north. "
United States
Kendra G.
The price is €300
includes taxes & fees
1 Nov - 2 Nov
1 Mi to Maine Street! MCM-Style Home in Brunswick
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.

14. 2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
9.8 out of 10, Exceptional, (6 reviews)
"Place was clean, beautiful and the photos do not do it justice. The perfect get away vacation from the rat race."
United States
Gregory M.
The price is €222
includes taxes & fees
1 Nov - 2 Nov
2 bedroom w/ expansive water views
A deck with white railings overlooking a body of water, boats, and a forested shoreline.

15. Captains Watch: A Coastal Escape

Captains Watch: A Coastal Escape
West Point
The price is €171
includes taxes & fees
25 Oct - 26 Oct
Captains Watch: A Coastal Escape
A building named Willard Square with a storefront and a red vehicle parked outside.

16. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (13 reviews)
"Thoroughly enjoyed this house! "
United States
David W.
The price is €593
includes taxes & fees
23 Nov - 24 Nov
Willard Square Family Home
A room with a large sliding glass door leading to a balcony with chairs and potted plants.

17. Modern & Sunny House Steps from the Promenade.

Modern & Sunny House Steps from the Promenade.
Munjoy Hill
10.0 out of 10, Exceptional, (48 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is €460
includes taxes & fees
23 Nov - 24 Nov
Modern & Sunny House Steps from the Promenade.
A modern kitchen with a large island, dark cabinetry, and a view of a lake.

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

The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury
Harpswell
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful property, well equipped, lots of amenities, plenty of space for our large group."
United States
Edwin M.
The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury
A house with a wooden front door, a stone staircase, and a porch with a wooden railing.

19. Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
East Deering
10.0 out of 10, Exceptional, (84 reviews)
"Absolutely perfect rental!Great location with an amazing view!"
United States
Mike G.
The price is €984
includes taxes & fees
26 Oct - 27 Oct
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
A spacious bedroom with a large bed, a rocking chair, and a view of a balcony with a white railing.

20. Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.6 out of 10, Exceptional, (21 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is €164
includes taxes & fees
1 Nov - 2 Nov
Fantastic Waterfront Views
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chebeague Island Hotel Reviews

Clarion Pointe South Portland

Clarion Pointe South Portland

8/10 Good
"Great staff very helpful. Clean enough space. The room and hallways and building in general showed some age, but that isnt important to me so I was happy. Very affordable and the breakfast was pretty good."
Cole 2-night trip
Posted 1 hour ago
Clarion Pointe South Portland

Find out more about Chebeague Island

Chebeague Island Holiday Homes information

Number of reviews
393
Accommodation
639 Holiday Homes
Lowest Price
€164
Highest Price
€1,493