Family-friendly holiday rentals in Chebeague Island

Sometimes photos just don't do the real thing justice, and this is the case with this property. The property and the views are truly spectacular! The home is huge and has everything you could ever need to live for a week or more. The porch, especially the screened in portion are magnificent and the hot tub was a perfect way to finish up a great day. We had so many plans to adventure out, but found ourselves wanting to stay and enjoy the pristine yard or just sit on the porch and enjoy each others company, we didn't want or need to leave. Having coffee and watching eagles fly by over the river was truly spectacular. Judy is one of the nicest, easiest hosts we have had the pleasure to work with and truly appreciates your patronage. And Hugh's journal on all things Graywood is a lifesaver. Not only would we return again, but we look forward to it.

The house was perfect for our group of 12. It was spacious and well-cared for. While not located in downtown Portland, it was just minutes away by car. There was ample parking in the driveway and on the street. Meghan was a very responsive and flexible host. We had a great time.

We love staying at the Brownie. It’s a great home for any active family that appreciates a quiet surrounding. Great home and so close to SR. It can’t be beat.

We spent a lovely few days at this property enjoying the winter weather at its finest. The house is close to everything but still felt private and cozy. A great choice for families!

Nice stay, nice host, lots of recommendations in binder for things to do. Nice hot tub. Cozy place and location. DQ right across the street.

What an awesome place to stay! Lori was incredibly gracious and accommodating with out late arrival. The cabin towards the back of the property was so cozy. Fantastic stay and would definitely recommend!

The spot was perfect for a weekend of skiing and riding snowmobiles. Exactly what we were looking for in a vacation home. Paul was great at recommending places and his response time was great. Also the wood burning stove made the weekend cozy and perfect.

Dave was an amazing host and he provided the best possible get away for our first wedding anniversary. It was private there is so much beautiful outdoor art to look at and the hot tub was the perfect way to wind down after the day. If there was a 6 star option I would give it this was everything we wanted and needed and then some

Jennifer was a phenomenal host. She was very accommodating (we were traveling with our 8 month old) which was extremely helpful. The place was spotless, quiet and very peaceful. We felt right at home and you can easily walk right to downtown Freeport. Highly recommend this host and this location!

This was a perfect stay for our 2 days in Portland. We could walk everywhere from the apartment. There were plenty of options for restaurants nearby.

We have stayed at Jackies place twice now and enjoyed it just as much this time as the last. Even though it rained for two days the house is plenty big enough to spread out. We had to change our reservation days twice because of circumstances and Jackie was very accomidating..

Easy 5 stars! Phillip was kind, proactive and responsive. The space, while quaint and simple, was clean, had all the essentials and, it was perfect for a week visiting my grandparents/ working remote! Not to mention my dogs loved being a half mile from the Bath dog park. Highly recommend if you’re looking for a Maine mid-coast getaway!

A beautiful and cozy space with lovely natural light and generous room to spread out. The full kitchen is equipped like a real home, with everything from basic pots and pans to whisks and even nut crackers! A great place for cooking full meals. A nice quiet location, even with its relative proximity to a regularly-traveled road. I'm sensitive to noise and was never bothered by sounds of traffic. Pettengill Farm is only a few minutes up the road, a beautiful place to walk for both dogs and humans and really easy to access multiple times a day. Mandana was always very responsive to communication, and when there was a glitch with Airbnb's fee calculation she was extremely helpful and approachable and took care of it immediately.

Elia's cabin is magical. What a beautiful and peaceful place. We had everything we needed, but be sure to bring bug spray.

We stayed at a few of Spencer's places while our child was at Bowdoin college. The places are lovely and convenient and made visiting our child a pleasure.

We did not want to leave this home! It was stunning and had everything we could possibly need. Close to the beach. Spinney’s restaurant was right up the road. It was quiet and peaceful. It was good for the soul. We will definitely be back!

Great place to stay with an awesome view of white heat!

Our stay at the beach house was great! You couldn't be closer to the water! So much fun kayaking, floating and swimming in the lake! House is much better than the pictures do it justice. For a 2 bedroom house its very big and spacious, beds were extremely comfortable. The no wifi was a little bit of a downer but there were plenty of board games to play. There is some street noise but not bad at all. Would most definitely recommend if you are looking for waterfront property. The access to the resort pool was a plus too for the kiddos!

Christopher was a helpful host and his place was perfect! Clean, fully stocked, great location. It was close to lots of beaches and restaurants and the pool was great for the little ones

A nice private cottage in a quiet community that was super handy for us to stay until we secured our house in New England. Everything is in place for comfortable living. We lived there for a month long and the hosts were always responsible.

Home is very expansive with room for multiple families to reside together. Lots of games and activities for all ages. Amazing location within minutes to airport and short drive to downtown

We had a lovely time at the cabin. Close to skiing yet peaceful and relaxing. We thoroughly enjoyed our stay ! Thank you!

We found the home clean and welcoming. There was plenty of room for all of us and we enjoyed the back deck very much. The kitchen was well equipped and although we did not do any cooking, if we had, everything was there for us. We really liked how private the home was. Had the weather been warmer we definitely would have checked out the pool. It is also very close to Thomaston, Rockland and Owls Head. So much to do in this area. We would recommend this home to anyone who wants a quiet retreat in Maine that is close to the coast.

We had a great time at Jim and Gwens place in Knight's Hill. The amenities were great and the location provided us with everything we were looking for near Moose Pond. Would highly recommend.