Search Vacation Homes in Chebeague Island

Upfront pricing

Our total price for your stay includes taxes and fees

Treat yourself

Save 10% or more on over 100,000 hotels worldwide with Member Prices

Learn about One Key

Be picky

Search almost a million properties worldwide

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Vacation Homes in Chebeague Island

Kitchen area with microwave, toaster, refrigerator, and sink.

"We enjoyed ourselves very much! Close to everything we wanted to do. Would stay again."

Stroll along the pier, taking in the serene views of the ocean and surrounding landscape.

"Mitchells home was PERFECT.Always quick to communicate and very accommodating. If you are looking for a great place to stay I cant say enough good things. Well stocked he has thought of everything people need when away. He even has games to play which was a nice surprise. You wont regret staying bere! Thanks again so much Mitchell!!!"

Cozy attic bedroom with a large bed, nightstands, and a window above.

"The house is in a wonderful location with great views of the ocean from several rooms. The listing photos really do tell the story of this beautiful home. The beach is just a few steps away from the property. Attention to detail was obviously put in to ensure a wonderful guest experience. The home is very clean, there are practical amenities throughout (4 smart TV’s), and our host was super communicative and accommodating. Portland & Saco being a short drive away is just icing on the cake. Can’t...

$768 nightly

Aug 31 - Sep 1

Total includes taxes and fees

"Clean, well maintained, slighly funky in an historical way . Very convenient to great breakfast spots and downtown Bath. Would stay there again."

$150 nightly

Aug 12 - Aug 13

Total includes taxes and fees

Enjoy a peaceful stay in this charming house with a porch, surrounded by a lush lawn and a majestic tree.

"Great stay in very clean house in a very quiet ocean side community. Perfect getaway!"

Relax on the spacious deck with a table and chairs, taking in views of the surrounding greenery.

"This apartment was very clean, modern, and fairly private, located on a quite street, but still close enough to walk to shops, cafes, breweries. Only about half a mile from downtown. Would definitely stay again!"

Enjoy a serene beach experience with gentle waves lapping against the shore.

"Perfect size home for a small group (we had 5). Great location for day trips to Bath, Boothbay, Freeport, and more. Host is super friendly and attentive! We loved being able to take advantage of the Resort restaurant and grounds. "

Stunning two-story home surrounded by lush greenery and trees, featuring a charming front porch and symmetrical facade.

"We had a great stay! Amazing weather and plenty of lobster."

Enjoy meals in the kitchen with a stove and dining area featuring a table and chairs.

$1,999 nightly

Aug 17 - Aug 18

Total includes taxes and fees

Relax in this stylish living room with a high ceiling, comfortable sofa, and flat-screen TV.

"We had a large group and had more than enough beds and plenty of space to hang out. Would recommend for a big group or a family looking to spread out!"

"We enjoyed this well kept property with beautiful gardens. It was very pet friendly with a nice back yard area. We cooked steak on the grill one night."

Relax in this serene bedroom with a large bed, a cozy reading nook, and a deck overlooking the forest.

"Our favorite part about our stay at this location was being able to look out the many sliding door windows to see the ocean view. It was a very relaxing place to stay. "

$468 nightly

Aug 12 - Aug 13

Total includes taxes and fees

Enjoy cooking in this well-equipped kitchen with oven, microwave, and refrigerator.

"We really enjoyed this property. It was very clean, and very comfortable. We will visit again. "

Relax on the porch with a round table and two Adirondack chairs, surrounded by lush greenery.

"Comfortable place to stay and enjoy time with family. We enjoyed exploring Peaks Island and Portland. Everything we needed."

Fully equipped kitchen with dishwasher, oven, refrigerator, sink, and kettle.

"This was our second stay at Beth’s home, and it certainly won’t be the last (as long as she’s willing to have us!) Everything is absolutely perfect. Beth is a thoughtful host, the location is perfect and the home is beautiful - you can’t go wrong!"