Family-friendly holiday rentals in Winthrop

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!

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.

The house was perfect for our group of 12. It was spacious and well-cared for. While not located in downtown Portland, it was just minutes away by car. There was ample parking in the driveway and on the street. Meghan was a very responsive and flexible host. We had a great time.

We love staying at the Brownie. It’s a great home for any active family that appreciates a quiet surrounding. Great home and so close to SR. It can’t be beat.

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!

Nice stay, nice host, lots of recommendations in binder for things to do. Nice hot tub. Cozy place and location. DQ right across the street.

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!

I had a wonderful stay at Julia’s place! From the moment I arrived, everything was exactly as described — clean, cozy, and thoughtfully prepared. Julia was a fantastic host: responsive, kind, and attentive to every detail, which made the whole experience smooth and enjoyable. The location was perfect, and the space felt like a true home away from home. I would absolutely stay here again and highly recommend it to anyone visiting the area. Thank you, Julia, for your hospitality!

Elia's cabin is magical. What a beautiful and peaceful place. We had everything we needed, but be sure to bring bug spray.

Colby’s cabin was everything I expected and more. The location was fantastic so private and quiet, even during Memorial Day weekend I didn’t see or hear anyone. The cabin is two miles up a dirt road, nestled into the woods on the side of a hill it’s the perfect weekend hideaway. My camping car (2012 crv, 250k miles) made it up no problem in May even with heavy rain the day before. The cabin has everything you could need just pack food and clothes. This could easily be more rustic but a lot of work was put into the little touches that take this place to the next level like wood stove, well pump, refrigerator and stove, and clean comfortable furniture. Lots to do in the area check out mt blue, tumbledown and Webb lake. Can’t wait to come back soon!

We stayed at a few of Spencer's places while our child was at Bowdoin college. The places are lovely and convenient and made visiting our child a pleasure.

Super cute cottage! I really enjoyed a few peaceful days there on my own, it was exactly what I was looking for. It's very charming and has everything you need. Like others have mentioned, you can definitely hear the road noise so it doesn't feel totally secluded but that didn't detract from my stay. Emily was a great host, provided lots of helpful information, and very quick to respond.

This cabin is perfect for a peaceful Maine getaway. Tucked right on the water’s edge, the views are absolutely breathtaking. The cabin itself is cozy. We loved having morning coffee on the dock and taking out the row boat provided. My dog enjoyed being able to swim in the lake. Devon was incredibly welcoming and responsive. If you're looking for a quiet, rejuvenating escape with unbeatable lakefront access, this is it. We can’t wait to come back next season!

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!

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 🌸🌲🌊

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!

Great place to stay with an awesome view of white heat!

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!

The home was beautiful and exactly as pictured. We especially loved the hot tub and the outdoor fire pit, such great touches for a relaxing stay. The space had everything we needed, and we felt right at home. We’d absolutely stay again in the future if welcomed back!

Great on mountain accommodation. Clean and well appointed for all the basic things you will need. Bethel has some nice dining and museum options for when the weather doesn't cooperate.

Great spot, would rent again!

Home is very expansive with room for multiple families to reside together. Lots of games and activities for all ages. Amazing location within minutes to airport and short drive to downtown