Family-friendly vacation rentals in Oakland

A beautiful rustic cabin in an amazing spot. Lori is a great host and is always near in her farmhouse to communicate and get you what you need. Appleton is not far from Camden / Rockland but has that rustic getaway feel. The option of adding a wonderful soak in the hot tub, wood fired sauna, massage and breakfast are available as well. I’ll be back next year! Thank you for everything, Lori!

We really enjoyed our stay at Woolwich. There is a peaceful nature vibe to the house and a beautiful view and location. The Bald Eagles live in a tree right on the edge of the backyard and were visible numerous times during our stay. The location to various towns and locations in Maine is convenient.

We had the most wonderful staying here! A peaceful and relaxing getaway is exactly what we needed, and exactly what we received. The hot tub was the perfect touch. We couldn’t recommend this place more! Can’t wait to go back!

Just returned from the most fantastic 2 weeks exploring the US which included a weeks stay at Kiwi Lodge. Where to start? This was exactly as described and the perfect base for exploring Maine. The property was spotless and has all the amenities needed for a comfortable stay. 3 beautiful bedrooms, 2 great sized bathrooms, wonderful living area and kitchen and fantastic games room. Hot tub was brilliant. The location on the lake is just perfect, we had the lake to ourselves and took the canoe out. Nearest town of Farmington has all the shops and cafes you’d need. The communication from Kay was great from the day we booked, and recommendations we took her up on were all absolutely spot on. Thank you Kay and thank you Kiwi Lodge for a holiday to remember!

I was happy to return to stay at Deb's, this time around in the studio loft. It was very spacious and comfortable and included anything that you might want or need. It was a perfect spot for me to rest while watching ski races at Black Mountain for the weekend. Thanks for being a wonderful host once again, Deb!

Great place. The bed was really comfortable. Hot tub was nice and private and relaxing.

If you like the outdoors, seasonal activities and have several guest, then this is the place for you! The kitchen is restaurant quality and well stocked with spices and cooking utensils. The property has plenty of amenities, games and the fire place and hot tub gives you a resort vibe - overall a great experience.

This was our second time staying here, my family and I love the tranquility of this little piece of heaven. Christopher’s home was beautiful, clean and well maintained.

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!

Great communication, easy to work with, great place, great location. Exactly how described.

This house is awesome! Located in waking distance to nature’s incredible beauty -Popham Beach. If you’re never been but are looking for a great Maine beach experience, this place is for you. The house is beautifully decorated, comfortable, cozy, and well stocked. We enjoyed multiple beach walks, hiked nearby Morse Mountain, improved our sand dollar collection, and watched the sea lions frolic during dinner at nearby Spinney’s restaurant. The fire pit and snores were a terrific ending to a great celebration of our Bowdoin College graduate We can’t wait to return!

As our last stay everything was very accommodating and comfortable. Great music, books, art and an expansive beautiful landscape. The stars at night are beyond amazing. Highly recommended.

We have visited this spot many times and are never disappointed. Great house with lots of extras for kids and families. Many great games in the game room including pool and foozball, very spacious and lovely amenities

Great retreat to feel relaxed and inspired. The location suits our needs for comfort and accessibility to surrounding disc golf courses and is great for travelers looking to escape screens, and the stress of cluttered and busy lifestyles. It feels like home as soon as you arrive .

Great place, great location and has a view of the water on one side of the apartment. Close to Portland and very convenient with a washer and dryer and parking. Comfortable place! Would definitely book again!

The moment we walked into this amazing home we felt so welcome. Phil and Jill left a nice bottle of wine and tray of baked delicious cookies. The home had great amenities including the indoor basketball hoop which was a great hit with our grand kids. This home was a lovely representation of family. Phil was so gracious he came twice to snowblow out the driveway and we had a chance to chat confirming that he is a wonderful host . We look forward to spending next year at this great vacation destination. A million thank you’s

Beautiful and peaceful place! Just admiring the surroundings let the peace and tranquility set in and consume you. Highly recommend! Teresa is a wonderful host and flexible to your needs. Will definitely visit again, thank you Teresa!

Jonathan and Lisa were wonderful hosts! We stayed 3 nights to enjoy some Spring skiing at Saddleback. The home was close to town and a quick drive to Saddleback mountain. The house is perched high on a hill overlooking Rangeley lake. The downside is that the driveway is steep and icy (this time of year due to the recent March thaws) but the view and sunsets are breathtaking!! For an additional fee, you can enjoy their newly built sauna and whirlpool. So relaxing after a day of skiing that we booked it twice. The house has all the comforts of home. Being culinary masters, we had a bit of a struggle in the small kitchen. But certainly most everything you need to prepare great meals. Communication with the hosts was excellent and timely.

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!

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 spot, would rent again!

We had such an enjoyable stay we didnt want to leave! All agreed we would stay here again - such a beautiful quiet retreat. Steve was a responsive host with detailed instructions for checkin/checkout. It made everything perfect for my family.

Great place to stay for a family of 4. Very close to Snubber for skiing and hiking. Hope to stay again. Thank you!

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