Kid-friendly vacation rentals in Oakland

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.

One of my favorite experiences with AirBnB So comfy and had many items that other hosts don't offer

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.

Second stay at the farm house. Two weeks this time. We just love it here. Plenty of space yet cozy, everything you need, lovely outdoors space. We enjooed watching the chickens, dicks and horse next door. I wish we could stay for months. Thank you, Amy and family!

This was the perfect rental for our family of 4 for the thanksgiving holiday. The home had everything we needed and wanted, great location within walking distance of so many great places in Rockland, and was clean and comfortable. Alicia went out of her way to provide recommendations for our stay! This is probably the best Airbnb we’ve stayed at and the most helpful host we’ve encountered. Highly recommend and thank you to Alicia and family for making our week so enjoyable while spending time with our kids on their college break.

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.

We had an amazing time over valentines day weekend. There was a snow storm and Kent snow blowed around our vehicle to make sure we could get out. The house is very comfortable and peaceful, amazing view of the river and just off the road enough to not be bothered by passing traffic. Definitely recommend!!!!

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.

Great stay with Dom. Exactly what we were looking for. Short walk to everything. Comfy beds.

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 is an excellent host, friendly and helpful. Her apartment is spotlessly clean, and Marie is thoughtful in providing amenities such as tea and coffee. The location is on a quiet street in the village of Rangeley within easy walking distance of several restaurants and shops and the lake. It's a short drive to Saddleback Mountain. All in all, very convenient.

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.

I stayed for 2 nights and had a great weekend. The apartment is the bottom floor of a 2-unit house but it was quiet, VERY clean, and a large space. There's one review on here from 2024 that had several negative criticisms, that must be a one time thing or a bad tenant bc my friends and I had a perfect experience. The apartment is a 5 minute walk through a family friendly neighborhood to the main drag. Brunswick is basically a 1-mile road with everything within 10 minutes. We loved parking the car and only using it for a trip to get games from the goodwill. But we walked comfortably to dinner, diners, drinks, and the Hannaford.**The location is perfect and convenient, worth staying here exclusively just for the easy walk everywhere!!**** Bring books/ games, as there's none. Bedrooms are comfortable and got warm quickly. Plenty of clean and thick bedding. The 10am check-out time, and 4pm check-in was the only inconvenience. Would have liked to check in sooner. Had a wonderful stay!

Super fun place. Great for 1-3 People. I thought this place was perfect… no washer and dryer on site but there is a place down the street. Also no freezer which for me wasn’t a huge deal. I really loved the place great location. I would definitely book again.

This spacious place was perfect for a getaway! So close to restaurants , shops and Belfast Harbor walk, yet so quiet at night.

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.

Perfect place super close to sugarloaf mountain. Place was so cute and clean. Melissa was a great host :)

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

Great stay at this conveniently located condo at Sugarloaf. Condo was very clean and listing pictures were accurate. Lots of info provided by the host made the stay seamless. Great choice for the two of us, but more than 2 would be tight, in my opinion…unless you have very young children!

She made cookies the moment we checked in and delivered them to us with warm milk. Wonderful host with great knowledge of the beautiful Pemaquid region

The condo was very clean, charming and had everything we needed. The option to walk over to the lift and ski back into the neighborhood was excellent. We didn't use the shuttle, but noticed it stopped right next to the condo building at the expected times. This is our third stay in the area - once at the Inn and another time at a studio condo - and this is by far our favorite!

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.