Kid-friendly holiday rentals in Oakland

Scott's place was perfect for our small family's ski trip! It was exactly as pictured, had everything we needed for our stay, and was so close to Sunday River (~10 minutes) and right down the road from restaurants in Bethel Village. We would love to stay again on our next ski trip!

We thoroughly enjoyed our stay at Samantha's place in Cushing. To say that she is "very responsive" would be an understatement. She typically responded within 10 minutes no matter what my question was. She lives a short distance away which really helped facilitate things. We had a minor issue with the Internet which required communication with the service provider, but she coordinated everything and resolved it right away. The house is totally charming - old, a bit creaky and adorable - and well maintained (no issues there). We imagined how great it would be to visit in wintertime and snuggle up to a roaring fire. They have an expansive yard with gardens great for a short evening stroll. Forest habitat behind the property was great for bird watching. The area is absolutely beautiful - quintissential coastal Maine. The Olson House (local attraction) is a few minutes drive from the house. The grounds have a walking trail along the water with fantastic views of the coast.

This is my favorite AirBnB So comfortable, clean, relaxing atmosphere Has everything you could possibly need and more Set up is so cozy and welcoming... Other places dont offer so many amenities and often they seem like left overs or an after thought...not Jeff's place...very top notch will be there for a third stay for sure

This is a perfect place to have a great time with your loved one, very comfortable , spacious and easy to access, the house is clean and and had everything we needed, I recommend for everyone, I loved our stay at the house.

We chose this adorable house in Rockland for our second annual book retreat! It was the perfect size for the three of us with comfortable accommodations and lots of places to sit and relax and read. The beds gave us some of the best nights sleep we’d had in a while and the living room was great for late night conversations and movies! The location was perfect and we walked into town every day for a little adventure! Alicia provided us with so many incredible recommendations for spots to try in town. One week here just wasn’t enough, and we’re already looking for reasons to come back! Maybe for the Lobster Festival?! Overall, this was a fantastic stay with a wonderful host!

My stay was in between two large snow storms, and Arthur had the driveway plowed for us, and checked in on us during the stay.

The home was very welcoming and accommodating for our family of 5. The views were spectacular at sunrise, sunset and during the snowstorm. Bald Eagles and hawks would land in the trees right in front of the house. Also, there was a skating pond down the street my family love to visit almost each evening. There was an alarm going off as soon as we arrived, Debbi was incredibly fast responding and sending someone to check it out clear it up. On the plus someone came and plowed the driveway after the snowstorm it was great. She left a basket of local food and my family ate it up. We are so thankful for our relaxing week and would love to return.

We had a wonderful stay at this Maine house--Barb, the property manager was incredibly responsive, helped with a heating issue while we were there and had the repairs done same day--The house was well equipped with everything you need for a family getaway at the beach! puzzles and games galore, kitchen was fully stocked with everything needed for family meals (including lobster cooking essentials--bibs, crackers, steam pots) Great little fire pit out front which we enjoyed, and fenced in back yard area so pets or kids can be safely contained :) Linens, towels, all clean and provided--truly a wonderful home away from home, perfect for our family trip to the beach!

We sent our children to school, we chose to stay here, close to the main road, also very quiet, the room looks bigger than the photos, there are amenities such as refrigerator microwave oven induction stove, convenient for us to cook instant noodles, burn some hot water, you can see squirrels outside in the snow on the bed, very comfortable, can live in this historic old house, very lucky, some small problems, the host will respond in time, if we have the chance, we will stay here again.

Loved this place!! Very cute & comfortable stay! Can’t wait to come back in the future!

My family and I had another great stay at Kathleen’s. We arrived and were so grateful for a clean and comfortable stay. We cooked lobster and were so happy to see that Kathleen’s kitchen had everything we needed. Excited to go back a third time!

Marie met me at the door to greet me as I arrived early. I was only there for one night but felt right at home. the apartment is spacious, clean, nicely set up, has a nice view of the nearby pond, and is in walking distance to main Street. perfect spot for a stay in town.

This sweet apartment was a true haven during a challenging time for our family. It was clean, comfortable, and thoughtfully appointed—just what we needed while navigating medical appointments nearby. The host was kind, responsive, and flexible, which made a world of difference. We’re so grateful for the peaceful space and support.

Not only is Nicole a gracious host and cheerily responsive to questions, the space is adorable! Everything you need to be comfortable, in a great neighborhood, within walking distance to EVERYTHING downtown, including a very sweet harbor! 🌟🌟🌟🌟🌟🌟🌟🌟🌟🌟🌟🌟

We had a wonderful time at Diane’s place. Very convenient to Belfast and a great value for the price.

This was an excellent place to stay that exceeded my expectations! Michelle and Nick went above and beyond to ensure we were comfortable during our stay. Very clean and felt right at home. Will definitely stay here again next time I am in Freeport, ME!

My family really enjoyed our stay at Ambers place! It was very spacious yet cozy, clean, and in a great location with a short walk to Snubber lift. With four floors our party of 7 had plenty of room to spread out during the trip. Any questions we had for Amber were answered quickly

Wonderful stay at this ski in ski out condo, perfect for a long weekend. Super nice that it was dog friendly. Having access to ski locker was convenient. Had just what we needed in kitchen. Sofa bed was just ok, and I think an upgrade on the sheets would be welcome but those things are minor. We would love to stay here again and again.

Good location, easy access to the hill by either driving or shuttle. The condo was fine for our group of four. Kitchen had everything to cook for that many. Very comfortable. thanks

Had an excellent stay at this wonderful condo on the mountain. Clean, easily accessible and well furnished! (The chocolates were a nice touch!)

The ski in ski out at Pleasant Mountain is hard to beat for families. The hosts were super responsive and our party of 8 had a great time.

Great location between southridge and north peak express with a view of the southway trail that passes between buildings 1 and 2.

We had a great stay at this unit. Long weekend skiing at Sunday River and this condo was small but had absolutely everything we needed and was only a few short minutes to the mountain. Would definitely stay here again.

A family of four stayed in mid-April for spring skiing at Sugarloaf. Our arrival was late in the evening, and Dan was receptive and helpful in accessing the unit in the evening. The unit was clean and comfortable for a family of four. Sugarloaf was a short, three-minute walk away to the nearest lodge from the unit, and many of the restaurants/shops were still open. We cooked lunch and dinner one day, and the unit had everything we needed. Overall, we highly recommend this unit.