Kid-friendly holiday rentals in Winthrop

Comfortable and convenient. We were minutes from restaurants and skiing which was perfect. The rental really felt like a hime. Check in was easy and Julia and Peter were proactive with messages about check in and trash. Rooms and beds were comfortable and clean.

We chose Jeff's house in Hallowell for our first trip to Maine because it is conveniently located near the Maine Cabin Masters' Kennebec Cabin Company store and Woodshed Restaurant, the town of Hallowell is quaint, and it's easy to get to Waterville, Cape Elizabeth, Portland, and Camden. We visited all of these places and were fortunate to have beautiful weather for late April. While we didn't use the hot tub and only tried the sauna once, we can definitely recommend this house for skiers. I can only imagine how good the sauna and the electric blankets on the comfortable beds would feel after a cold day on the slopes! Jeff is very friendly and provided recommendations. All around great visit and would stay again on our next trip to Maine.

We had a wonderful stay at Roy’s house. We know the neighborhood well because we have family that lives there and we love it! The house was very clean and had everything we needed. Our kids really enjoyed movie night downstairs. We would definitely stay here again if we are in the area. Thank you!

I went with my friends and it was fantastic! The surrounding area as beautiful and the added amenities really made the stay special for us.

Julie was fantastic and always responded in minutes to any questions we had. I love their home manual which is so easy to navigate and has answers for everything. The home is super cozy and the large gas fireplace downstairs was a treat on cooler April mornings. The weather wasn't on our side for 1/2 of short stay, but we had a family olympics inside, using their ping pong table, foosball and connect 4 game. We did get out on kayaks one day - lovely lake, larger than you think! tons of hiking nearby too.

We had a wonderful girl's trip staying in Diana's house! We walked to the beach and to Scratch bakery (twice). The house was perfect for the five of us with a great sitting area to hang out and chat. The house was clean and the instructions for cleaning up were easy to follow.

We had a wonderful stay at this Maine house--Barb, the property manager was incredibly responsive, helped with a heating issue while we were there and had the repairs done same day--The house was well equipped with everything you need for a family getaway at the beach! puzzles and games galore, kitchen was fully stocked with everything needed for family meals (including lobster cooking essentials--bibs, crackers, steam pots) Great little fire pit out front which we enjoyed, and fenced in back yard area so pets or kids can be safely contained :) Linens, towels, all clean and provided--truly a wonderful home away from home, perfect for our family trip to the beach!

Spent the weekend here with friends and really appreciated the host’s hospitality! They accommodated an earlier check in, responded to messages promptly, and the space had comfortable beds and great linens. Would stay here again in a heartbeat!

The apartment was just as described by the host, and was very comfortable for a two night stay, for two couples. Excellent, proactive, communication by the host prior to check-in. Very clear instructions. The kitchen was well equipped for breakfast (which is the only meal we ate at the apartment during our stay). A serrated knife would be a nice addition. All of the appliances were very clean, and in good working order. Entry to the building was easy. Be comfortable climbing stairs. Five minute drive, or 15 minute walk to downtown. Quiet and peaceful neighborhood. Would definitely return, and recommended it to others. Thank you for a nice stay, Susan.

Margaret’s place is very homey with all the necessities for a family gathering. The neighborhood is beautiful and close to beautiful trails

Super walkable and great for a weekend stay!

Great place to stay. Deck is nice and overlooks the water. Warm during cold weather. Host is kind and very helpful.

Ian's place was great for a girls trip ti Portland. He was a great communicator if I had any questions or cleaning instructions. Will definitely stay again for any future trips to Portland.

I highly recommend staying here if you are visiting Portland! The apartment was adorable, very clean and in a perfect location. Alex had an entire list of recommendations that we found very helpful! We will definitely be back!

Sadie and Laughlin are the best Airbnb hosts we have come across. We could not have asked for a better place to stay. The apartment is very clean, has lovely furnishings, is nicely decorated and had everything we needed for a very comfortable 3 and a half day stay in Portland. Both bedrooms are a good size and have incredibly comfortable beds. When we needed help with something, our hosts came around fast to help us. If we are ever back in Portland, we shall gladly book again with them. I would highly recommend this apartment!

Very well located apartment, with large living room and bed room, small kitchen and tiny bathroom. Communication with Sharon was easy and responsive.

We enjoyed our stay! The place was very clean. The hosts were responsive and helpful. The train does go right behind the place at an intersection. The horn is very loud, which was hard for our toddler. Just something to consider if you’re traveling with infants/toddlers. Overall, would definitely recommend!

Had an excellent stay at this wonderful condo on the mountain. Clean, easily accessible and well furnished! (The chocolates were a nice touch!)

The ski in ski out at Pleasant Mountain is hard to beat for families. The hosts were super responsive and our party of 8 had a great time.

A beautiful condo, just 20 minutes away from the heart of North Conway. Everything was in pristine condition and it is always amazing to have a kitchen at our fingertips. Beautiful views of the woods out back. Would definitely recommend to those coming to visit the North Conway, New Hampshire area and surroundings!!!!

Great location between southridge and north peak express with a view of the southway trail that passes between buildings 1 and 2.

Our 3rd time staying here....great location and reasonably priced. Love the view out back to the trees and a peek of some mountains. Also great snow cleanup - we were here for a big storm and the plows cleared the car park and the paths were shoveled quickly.

We had a fantastic stay at this condo! It’s cozy and well-equipped, with a lovely fireplace that made our evenings so relaxing. The location is unbeatable—just minutes from Attitash Ski Resort, which made getting to the slopes super easy. Our kids absolutely loved the selection of games, keeping them entertained after a day of skiing. Check-in was seamless, and the hosts were great with communication, making sure everything was smooth from start to finish. Overall, a wonderful experience, and we’ll definitely be back!

A good ski in ski out location. Perfect for us. Thank you.