Family-friendly vacation rentals in Oakland

Lori’s is exactly what we need while visiting family over a holiday. She is very gracious to host us over Thanksgiving as the last occupants of the year. Even during a snow storm, her place is cosy and beautiful. This is our second year coming, and we love it every time. We would recommend it for those looking for a charming getaway from busy life. Thanks Lori!

We couldn’t have asked for a better stay at Latham blueberry farm. Doug and Brenda were incredibly helpful and friendly- they introduced us to the house and farm as soon as we checked in and were always available if needed. The beds were comfy, the kitchenette stocked, and the grounds were gorgeous. Their beautiful 1826 farm house was an authentic experience of staying on a farm- our kids loved feeding the animals (especially Ernie the pig and Moses the horse); picking fresh blueberries; and swimming and paddleboating in the private pond. Our hosts had great recommendations for local outings, and we loved chatting with them and playing with their puppy Jackie. Our family made lifetime memories.

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 amazing stay at Madawaska! Amazing views from the bedroom and hot tub in a beautiful, peaceful, and private location overlooking the water. And such a wonderful design of the cabin. We will definitely be 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!

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.

Paul's house was wonderful! It smelled so fresh when we arrived and was very clean. The house was more spacious than i expected. It was just us two of but could absolutely fit another couple and a few kids with plenty of privacy. We really enjoyed fires in the wood stove with firewood provided. The soaks in the hot tub were amazing! The beach towels were greatly appreciated for wrapping up in to hurry in from the cold! We had fun grilling in the snow and found everything we needed in the kitchen. We felt right at home. Our dog had a blast playing in the big backyard too! Paul has great communication and was very fast to respond. Paul's vacation home is perfect place to relax and unwind! Thank you for sharing your beautiful Maine getaway Paul!

We had the absolute best time at MJ’s place, highly recommend !! The house is spatious yet very cozy and quiet, with a nice back porch to sit and enjoy the surrounding woods! Home is also very close to town and to Poryland/coastline, and the cleanest lake to swim in that we’ve ever been to! MJ was very helpful and quick to respond. Stay here! We hope to return sometime soon!!

My boyfriend and I had a great stay with our dog. It is a short walk to the shops. It was great having access to a backyard area where I could take my dog out to use the bathroom. The place was cozy with great natural lighting and Jennifer was super approachable and responded promptly to any questions. We forgot a tool for cooking so we reached out to her and she brought it over to us. SO kind!! Highly recommend a stay at Freeport at Jennifers place.

The cabin was just as advertised. A quiet clean space!!

This trip was a very last minute thing for us. Our 4 year old pup was diagnosed with cancer and we just want him to be happy whether he has to leave us tomorrow or in two years. Kent made everything so perfect for us. With our dog going through chemo, he’s been “off” lately. We Didn’t know how he’d be with other people or dogs, he’s been weird when I HUG him sometimes… just going through it, ya know? Kent arranged times for us to go on the ferry with no other guests just to help us and our pup feel comfortable. It was the best trip ever. I cannot tell you how badly you need this trip😂. It couldn’t have been better. Make sure to use bug spray (or just have a fire going all the time, the bugs don’t like that haha), bring at least two books if you’re a reader, it’s AMAZING! GO OUT ON THE KAYAKS! Check out stars at night! Our first night we were stargazing and I saw THREE shooting stars and I finally looked up why I saw so many in such a short time and there was a meteor shower happening!

Cozy and comfortable place to stay while exploring the area. Close to most anything you’d want to do in Southern Maine.

I loved this place! Enjoying coffee and meals outside on the deck overlooking the lake and beautiful surroundings of nature. I felt safe there and was a charming neighborhood. I loved that there were boats to use and a dock to watch sunset an autumn harvest moon over lake! Jess was the perfect host and made sure everything was great when I arrived. She was very helpful when I had any questions and I am looking so forward to going back there again! Thank you Jess for sharing this wonderful place!!!

We have rented this adorable log cabin many times and look forward to our next visit! The host is very responsive and friendly and we can not recommend this lovely stay enough.

Absolutely loved our stay at this lake cabin! It's nestled right on the water, making it a perfect spot for peaceful mornings and unbeatable fishing. The sunsets over the lake are absolutely stunning — a real highlight of the trip. The cabin itself has a rustic charm, filled with unique vintage touches that make it feel cozy and full of character. It's quiet, far enough from the city to truly relax, but still conveniently close to town if you need anything. A wonderful place to unwind and make lasting memories with family. Can't wait to come back!

Great 2-level apartment with terrific deck and beautiful view overlooking the river. Quiet and pretty. Owners were very responsive and the kitchen is very well stocked. Nice rustic touches and great running/walking trail along the river, just down the road. WiFi works well. Recommend upgrading the beds as they are small and not very comfortable. Otherwise a great property!

Great house and good location, it was warm during our stay. Enough space for our company. Not far away from the city. Overall it was nice staying there.

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!

A few times while wandering around midcoast Maine in late March, we were asked if this is when we usually came to vacation here. Yes, we are educators from the Southwest, and this was our spring break, so this is when we came to visit, but honestly, it is so peaceful this time of year. Especially Boothbay Harbor, and what we imagined while walking around the very quiet town would be a very different place in July! Our experience at Abby’s space was absolutely wonderful and serene in the spring. The thoughtful touches (thank you for the bottle of Maine wine and jar of blueberry jelly!) made it even more special. Thank you, we hope to be back one day.

Perfect little spot on Frye Island! Great location, walking distance to our favorite beach on island as well as the general store. House was clean, comfortable, just as described. We enjoyed our stay!

Great spot, would rent again!