Family-friendly vacation rentals in Winslow

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.

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.

We loved our time at Dwayne and Patti’s place! It definitely felt like a home rather than a hotel, which is exactly what we want when we book an Airbnb over a hotel. The musical instruments and hot tub were a hit with our group :) The location is amazing, close to both Bar Harbor (Acadia) and Bangor. We got to go to a concert and hiking during our stay, and we loved returning to our home base. I can’t want to be back!!

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.

Beautiful spot to stay at, we didn’t get so lucky with how weather panned out but it didn’t take away from the experience we had. Would recommend to anyone!

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!

Wendy’s place was really nice and the hot tub is very private.. we definitely got our usage out of it… Wendy herself was extremely kind and open minded. She didn’t rush us out come check out, instead, she encouraged us to stay a little longer and enjoy the hot tub before our long journey back home.. she gave us good tips about golden gems only locals know about 🥰 She did have a cool book to share reviews but I didn’t have a pen.. also we left grape soda in the fridge from Canada for the next person to try!! Thanks again Wendy 5⭐️

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.

Perfect weekend retreat for a small family with a young one. Close to downtown, museum, and the firepit was so nice at night. 5 stars all around and will return in the future. Thanks Phillip!

Charming little cottage on the lake! Had a lot of fun, easy to get to town and the lake was serene and peaceful. Great place to stay!

Words literally cannot explain the feeling you get when you step onto this property. Picture perfect piece of heaven. I've never cried leaving a place before, that's the impact it had on me. I left a piece of my heart in that cabin. Already planning to go back. 🤙✌️💚

Wonderful stay, the place was in a beautiful location, walkable to Wolfe’s Neck Farm where we love to walk. My husband and I were there the first few days, then our adult daughter joined us for two nights. The place is small (described accurately) but the three of us found it very workable. The king bed was very comfortable. There was plenty of outside patio space to lounge and soak up the sun when it was out. This was a work trip for us as we were getting a property in a nearby town ready for sale. We didn’t have time to use the provided kayaks but hope to in a future stay. The hosts very friendly and accommodating, highly recommended this property.

Great cabin for my family of 4 and our dog for a quick ski trip. I have 2 boys aged 14 and 11 who loved the loft area. We stayed to ski at Saddleback for 2 days, so was in the cabin l for just breakfast and then evening. Is described accurately in listing. Enjoyed our time!

My husband and I stayed here with our dogs and loved it! The cottage was quaint and lovely …. And the location is perfect! Amanda was so kind and responsive! We will definitely be back when in Camden again 🌸🌲🌊

The Strawberry house was such an amazing place for my wife and I to spend our first anniversary. We go to midcoast Maine every year and this was certainly a special one for us. Comfortable, thoughtfully designed and accessible to town. Highly recommend!

Beautiful setting on the lake with a modern, updated home complete with so many thoughtful amenities and touches - would love to return!! Spectacular sunsets and a private dock, too - did some late summer fishing on the Kennebago and the Magalloway - spectacular!

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!

Property had amazing views. Inside was beautiful and very clean. Pond and river was nice. Host was quick with any question we had. would recommend.10/10

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!

My husband and I, and our two pups had a fantastic time in the Carriage House for a week. Part of a breathtaking private/secret compound on the water…with the most incredible private tidal pool. The place is so authentic, which is what we love about staying in ME when we can escape. We were so blessed to find Margaret’s place last minute. Margaret’s mother, Sally, and her husband were in the main Kate’s house. So so sweet they were to us and our girls. A dog paradise. We are foodies. Plenty of good restaurants around - just a few minutes to the adorable village of Stonington. Around the corner is one of the best restaurants in the country - Aragosta. We can’t wait to return…hopefully, in the Fall. A trip we will always remember. Thank you, Margaret & Family.