Family-friendly holiday rentals in Orr's 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.

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 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.

Very nice stay! Cozy & felt like home. Lovely private hot tub space. Beautiful!!

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!

Jon’s cabin is a beautiful place to get away from it all. Very comfortable and well designed. We had everything we needed to cook and hole up for a few days. If you decide to drive to the lake, I would recommend 4WD. We had a truck but were not aware of how soft the ground was and ended up needing to be towed out. Still highly recommend! Enjoy your stay!

We had another wonderful stay at the Zen Den Yurt! Bob and Page are great hosts and very helpful and informative with communication. This is such a beautiful location and an excellent place to rest and recharge. We look forward to our next visit!

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.

Our son, his girlfriend, my husband and I enjoyed staying at the cottage in late October 2024. The location was quite scenic as it overlooked Casco Bay, near Portland, ME. The host made suggestions that we followed (bringing firewood & blankets). The kitchen was equipped with utensils & coffeemakers. The neighborhood was quiet. We enjoyed walking in the local preserve along the water and took advantage of visiting the Portland Museum of Art and eating at The Honey Paw, an Asian fusion restaurant.

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!

Super cute apartment in a great location and very responsive host! The apartment was clean and well stocked, and the Steve was very kind and responsive. He was also able to accommodate a very early check-in for us which was greatly appreciated. The location was great for getting around Portland. Our only complaint was that the free parking was not as easy/available as we had hoped, but the host did a great job compiling a list of other (paid) parking options. Overall loved it and highly recommend, just consider that you may have to pay for parking.

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

Aimee was wonderful to deal with. Her place was absolutely beautiful. we definitely picked the right place. the sunrises were so awesome. Rockland was a gorgeous little town.

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.

Maryann is SUCH a treasure! She really is the hostess with the mostest! Gives great recommendations, homemade coffee and treats, and if you mention you like something, she might get it for you! Making this Philly girl a wannabe Maine resident! Couldn’t recommend more.

Our stay here was amazing, the house is adorable and the views are stunning. The pool was the perfect temperature and the whole family was in the pool every day, plus the views from the pool were pretty remarkable. Sherri was a great host and super communicative and helpful. The house is set up perfectly for a large group with cute little restaurants a short car ride or boat ride away. We will definitely 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 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.