Family-friendly vacation rentals in Winslow

Nicole’s home is a beautiful, quiet, and peaceful retreat. The home itself was clean, extremely comfortable, and a perfect place to relax with the family. Our toddler named it “the pretty house” and we couldn’t agree more! Nicole was an awesome host - responsive and helpful when we requested to open the hot tub early. The area around the house is private and quiet, perfect for people seeking solitude. We will definitely be going back if the opportunity come again!

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.

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.

I would recommend this place to anyone looking for a comfortable place to stay. It was my son’s wedding and I loved being able to come back from the activities to rest and relax . It was very homey.

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!

Marcia was wonderful . accommodated my wishes. It was like I was in a dream The place was pristine and beautiful would love to return again.

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!!!

This cabin was a wonderful place to spend the week, and I couldn’t be more happy. The hosts were communicative and friendly; offering great local recommendations. My girlfriend and I would be more than happy to stay here again!

My fiancée and I stayed here for a week with our dog, Lily. It was a great location - only a short drive to Portland and in a beautiful neighborhood. The area is wooded, peaceful and highly walkable. The amenities in the house were perfect - so convenient to have a washer and dryer. We were able to cook breakfast every morning before our day got started with the fully stocked kitchen. The bed was super comfortable! We slept great. Elizabeth was responsive and friendly. Would stay again and highly recommend her place.

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!

We absolutely loved our stay! We rented the house for 7 adults and 1 dog to celebrate a 31st bday! We loved being able to walk right down to the tasting room for a beer, cook a big dinner in the kitchen, play games, and watch the amazing vcr collection. Everything was clean and comfortable. So glad it’s a dog friendly space!

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.

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!

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!

Our stay here was amazing, the house is adorable and the views are stunning. The pool was the perfect temperature and the whole family was in the pool every day, plus the views from the pool were pretty remarkable. Sherri was a great host and super communicative and helpful. The house is set up perfectly for a large group with cute little restaurants a short car ride or boat ride away. We will definitely be back!

Great spot, would rent again!

The condo was very nice and comfortable. The host was responsive and provided good instructions ahead of time. The location is great, just a short slide to the condo lift. It is true ski in ski out, and provides a great Sugarloaf experience!