
Cottage vacation rentals in Chebeague Island
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Top-rated cottage rentals in Chebeague Island
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chebeague Island cottage rentals
Cottage rentals with a hot tub

Cozy beach cottage with pool & hot tub
Lovely one night stay at this sweet little cottage! Grounds are well-kept, enjoyed morning coffee on the front porch. AC kept it nice and cool. Convenient location close to a great donut shop- Congdon’s and our favorite ice scream spot- Scoop Deck. Chloe is a gracious host and even granted us a late check-out!

Lakeside Cozy Cottage in Nature | Hot Tub
This trip was more than we could've ever wanted! The property was lovely and the hosts were more than accommodating and made sure everything was as comfortable as it could've been! I'd recommend anyone to book with these hosts and I will definitely be booking again!

Fully Renovated/4min to K-port/HotTub/Game Room
We had a great stay at Audrey & Seb's place. It was spacious, beautifully decorated, and extremely clean. The beds were super comfortable, the location was private and close to town, and there was so much thought put into all the little details. What an absolutely wonderful place. Thank you so much!

Beautifully renovated 2-bedroom cottage
Everything was so perfect !! thank you for hosting us !!

Megunticook Retreat
The perfect place to stay for a peaceful vacation - the home is extremely well appointed and had everything we could possibly need and more. The lake is even more beautiful than the photos and we enjoyed the kayaks and hot tub each day we were there. We would highly recommend.

Contemporary Cottage With Ocean View 13
Terrific stay! The cottage was modern, clean, convenient and lovely. The pools are great for kids, and the cottage is near to restaurants, beaches etc. Great place for a holiday.

Adorable cottage by Shorts Sands Beach
Above and beyond in every way! Everything was extremely clean, easy to access, and very dog friendly. The host was incredibly responsive, flexible, and kind! We plan to go back!

Owls Head Oceanview Cottage Cedar Hot Tub/Sauna
We had an amazing time! The location was perfect and the house was clean, quiet, and peaceful. The hot tub and sauna were an incredible addition, making our stay even more relaxing. Despite all the rain, we were happy to stay indoors, doing puzzles, reading, and playing Scrabble. Mary Jo was so responsive and the warm fire place w plenty of wood added a cozy touch! The pictures really don’t do it justice. We will definitely be back! Thank you so much!
Pet-friendly cottage rentals

Timeless Tides Cottage
The cottage was beautiful and comfortable, and the setting was gorgeous. We were very comfortable there and would definitely go back! Carlos and Karen left very helpful and thoughtful local recommendations for food and activities. This place is a gem!

Relax at this Pet Friendly, Lakefront Getaway
This was a great get away. Right on the lake with the convenience of using their kayaks, row boat, and peddleboat. Also had an array of life jackets for everyone to be safe. Scenery is beautiful, location is peaceful! We read, kayaked, played pinpong in their basement, sat around the firepit and listened to nature! The house is exactly how you see it in the pics, plus better! The home is spotless and has everything you need! Host Heidi is very responsive! They even have many board games and puzzles to play. I would highly recommend this property and plan to rent again. Thank you Heidi for sharing your home and for a lovely weekend. Jamie Hale

Cottage on Todd Bay
Our group of 4 had a wonderful stay here. It had everything we needed and John was extremely helpful. We cooked several meals and visited nearby attractions.

Osprey Cottage, peaceful setting, walk to beach
Elizabeth was a wonderful host and her home is perfect for a peaceful, relaxing vacation. The house was spotless, well appointed, and very cozy. The short walk to the beach and town market is really convenient. Her rental is a perfect home base if you’re visiting Portland or exploring the Maine coast nearby.

Lily Pond Studio Cabin #4
We loved our experience at our cozy, stand alone cabin. The room is spacious and has everything you need. We would stay again for sure!

Near Waterville | Lake Great Pond | Dog Friendly
The place was beautiful and exactly what we needed! I would definitely recommend staying here.

Pet Friendly Audubon Bring Your Fishing Gear!
What an amazing setting! Right on the water. We saw seals, osprey, and, we think, an eagle.Also the most beautiful sunrise. The house is cozy and comfortable and really really clean. We found everything we needed and some thoughtful extras. Tamara is an excellent host!

Our charming,oceanfront, Bradford point cottage
Just amazing!! This is the second time we have stayed at this air bnb! The cabin is quaint. You cannot beat the views!! It is just absolutely perfect!
Private cottage rentals

Tranquil waterfront cottage
This Lakeside Retreat was a perfect weekend escape for two couples. In late September, we seemed to have the pond to ourselves and enjoyed sharing time around the firepit overlooking the lake. The Bathroom was spacious and one level up from the bedrooms downstairs. The kitchen had everything needed to prepare an excellent meal. I would highly recommend this cabin to a a small group of friends or family looking for a great location near Portland and Lake area attractions.Our host Bobbi was very responsive.

Cobb Cottage: Lake Beachfront Fri-Fri Jul-Aug
My husband and I spent 6 days here for our anniversary. I wanted a location on the water and close to visit all the major coastal towns in Maine. This was perfect! The home, felt like home, and everything was clean and beautiful. Adam was very helpful whenever I had any questions. Sipping coffee every morning on the back porch and watching the sunrise over the lake was so peaceful. Grocery store close by and great hiking/walking areas right out the front door. Can’t wait to come back and bring the family.

Cozy cottage
We absolutely loved our stay at Cal’s place! We were impressed by all of the personal touches to this home that make you feel right at home and ready to plan your next stay there! Cal’s home was spotless, had comfortable beds, and had everything you need and more. There was even detergent, dishwashing products, and a cute travel size mouthwash in the bathroom. Cal definitely wants his visitors to feel right at home. We will definitely be back!

Big Sebago Lake Rentals Waterfront w Private Beach
Beautiful location, perfect stay with amazing hosts! This was the perfect getaway for our family and we cannot wait to go back! The location can't be beat and Kate and Barry went above and beyond to make sure we had everything we needed. Highly recommend!

Relax by a Quiet Lake
Was a great place to get away from the city hustle and bustle and was a nice way to recharge and recenter

Seaside Escape
The location was amazing. Just a few steps to Crescent Beach. I actually took my coffee down there and watched the sunrise in the morning. So beautiful. The cottage was clean and comfortable. Kristin was very responsive and helpful. Don't miss out on the clam chowder at the Lobster Pound less than 100 meters away. We'd definitely come again.

Saco Cozy Cottage! Minutes From Old Orchard Beach
The cottage was perfect for our needs and had everything! Auria was extremely helpful and responded to us quickly! I would definitely stay there again!

Peaceful Cottage on Maine Flower Farm
Perfect fall cottage so close to Portland! The cottage is so peaceful and quiet. But so close to Portland but you wouldn’t even know it. The farm is lovely and we took a walk down to the river on the property, it was so peaceful and so much land! If you are looking for a get away from a city, but want to be able to explore Portland and Kennybunks, this was the perfect spot. I don’t know if I’ve slept that good all year. Would definitely come back again. And we love Trooper the dog!
Quick stats about cottage rentals in Chebeague Island
Total rentals
50 properties
Nightly prices starting at
$120 before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Ogunquit Beach
- Wells Beach
- Sebago Lake
- Scarborough Beach
- York Harbor Beach
- Ogunquit Playhouse
- Long Beach
- Surfside Beach
- Fox Ridge Golf Club
- Brunswick Golf Club
- Long Sands Beach
- Popham Beach State Park
- Purity Spring Resort
- East End Beach
- King Pine Ski Area
- Palace Playland
- Dunegrass Golf Club
- Pemaquid Beach
- Middle Beach
- Laudholm Beach
- Ferry Beach
- Mothers Beach
- Parsons Beach
- Portland Museum of Art
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