Family-friendly holiday rentals in Bailey 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.

David and Valle’s house is welcoming, and it was just right for our family get-together. The kitchen is very well set up for cooking, and the counter is both beautiful and a great place for gathering and conversation. There are many lovely touches in the house. We appreciated the yard and gardens, and our dog loved the walking trail. The location is peaceful but just a few minutes from Portland. David communicated well and offered helpful ideas for our visit.

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.

The house was beautiful and worked perfectly for our group! Check in was very easy, and the house was spotless when we arrived. My favorite part it was the yard - perfect for a big barbecue with a large group.

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.

Possibly the nicest Airbnb I’ve ever stayed in. This house was in spotless condition and looks even better than it does in the pictures. There’s a beautiful view from the back deck. It is the perfect place for a ski getaway and has so much character inside. From the hot tub to the pool table to the pinball machine, we were constantly having fun. Also didn’t have a single issue for the entire stay. 10/10.

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!

I had a wonderful stay at Julia’s place! From the moment I arrived, everything was exactly as described — clean, cozy, and thoughtfully prepared. Julia was a fantastic host: responsive, kind, and attentive to every detail, which made the whole experience smooth and enjoyable. The location was perfect, and the space felt like a true home away from home. I would absolutely stay here again and highly recommend it to anyone visiting the area. Thank you, Julia, for your hospitality!

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.

What stood out the most to me was how responsive Jennifer was, even before booking. It just showed how much she cares about her rental. Her and her family were very accommodating, the rental was clean and had everything we needed, and the location was perfect for a trip to Freeport! Would highly recommend! 😊

Thoughtfully designed and appointed place - has all the things you need and Marcia makes it very easy to get in and check out. Easy to get to Lewiston, Brunswick, Portland and everywhere in between!

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.

Our stay at Margaret's home was very relaxing and comfortable. Pristine bathroom, kitchen and bedding. The lake view was so much more than we anticipated. It was serene, peaceful, and breathtaking. She went out of her way to answer questions for us about the area, and we left feeling like we just gained a new friend. Jeff and Donna

The perfect house! Beautiful and just like the photos. The location is perfect and just a short walkable distance to the beach. The home was roomy, clean, and had great amenities.

Super cute cottage! I really enjoyed a few peaceful days there on my own, it was exactly what I was looking for. It's very charming and has everything you need. Like others have mentioned, you can definitely hear the road noise so it doesn't feel totally secluded but that didn't detract from my stay. Emily was a great host, provided lots of helpful information, and very quick to respond.

My husband and in-laws and I and our two dogs stayed for a long MDW. The weather did not cooperate but did not hinder us. Especially staying at this Airbnb on the beautiful Oxbow Brewing property. In fact the coziness of the space made a rainy day even more fun. We were visiting for the racetrack and location was excellent for privacy and also close to local attractions. Wish we had more of a group to experience the space with us, it was really special!

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

We had a wonderful experience staying at the White Cap A condos. Our place was peaceful, clean, and the surrounding area offers many activities and beautiful views.

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!

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.

The home was beautiful and exactly as pictured. We especially loved the hot tub and the outdoor fire pit, such great touches for a relaxing stay. The space had everything we needed, and we felt right at home. We’d absolutely stay again in the future if welcomed back!

Great home for our large family gathering. Great location near Sunday River skiing, Downtown and snowmobile trails right outside the door. We had a great time and will be back.

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!