Kid-friendly holiday rentals in Milton

Staying at Michael's lake house was the perfect retreat for our family. The first thing that stood out: The quiet. The house is on a cove just off the main lake, and it's so peaceful. We started our mornings with coffee on the screened in porch (yay no mosquitoes to worry about with kids!) and then spent the days kayaking, paddleboarding, and lying in the hammock. The lake itself is gorgeous and there's a sandbar that our girls loved! Meals were a breeze. The kitchen had everything we needed and was a lovely space to cook in (not to mention clean!). We grilled a couple of times too, which, for us, is a vacation must. It rained a little bit while we were there, but the house was well stocked with board games and honestly, everything was so beautifully decorated, it was just as relaxing indoors as outside. We'd totally come back here again. Thanks for a wonderful stay! Joel

We had a wonderful stay at this beautiful beachfront home with our extended family, including a total of 6 adults and 5 kids. We had two additional adults spend one night, there was plenty of room for everyone. The house was spacious, comfortable, and perfectly suited for a group of our size. The location is unbeatable, right on Drakes Island Beach, with incredible views and direct access to the sand. While we didn’t go in the water, we spent plenty of time relaxing on the beach, walking along the shore, and enjoying the peaceful setting. The home was clean, well-maintained, and stocked with everything we needed. The large deck and open living spaces gave us plenty of room to spend time together and unwind. This was a perfect spot for a relaxing family getaway, and we’d absolutely return again. Highly recommended!

It was a great location for a quick getaway. Close to Portland and plenty of places to eat in town. I only met Clarishell but she was lovely!

We would definitely go back for another stay. Carl is a wonderful host and was very responsive and helpful. The house is beautiful and is located in such a tranquil and scenic location. We are a family of 6 along with our black lab and everyone fit comfortably. I highly recommend this place for a family get away.

This was an excellent stay! The house was beautifully situated on a peaceful lake, clean, and the location was perfect for relaxing weekend away. Plenty of space for seven adults. Wether it was roasting marshmallows by the fire or lounging in the hot tub, this house had something for everyone. The host was incredibly responsive and helpful throughout my entire stay. I would highly recommend this listing to anyone!

My family and I had a serene experience staying here. Although the weather was mostly rainy or cloudy, we loved the lake location and maximized the indoor, outdoor, and nearby activity options. The hosts were so responsive, regardless of the question, and made this a truly delightful visit. This was my parents’ first Airbnb experience and it set the bar higher than I could have imagined! My family and I are already talking about coming back!!

This house was absolutely fantastic, even better than we hoped! Everything was spotless and brand new, and it's in a beautiful peaceful spot on the lake. The hosts thought of everything from sound machines in the bedrooms, games for all ages, water toys, beach gear, and more! It made our stay easy and fun. We can't wait to come back!

We enjoyed our stay at this beautiful home. Lots of amenities and the hosts are very friendly and quick to respond to any questions. It was roomy for our family of 5 and the beds were really comfortable. I’d say it easily accommodates 6-7 people. If you are adventurous and don’t mind sleeping in a small loft or a basement setting you could fit 10-11.

A beautiful home with a very short walk to the beach. We enjoyed our stay at this historic home. Very cozy and clean.

Visited Feb '25 Steep stairs {a delightful New England quirk} lead to a comfortable bed, quaint views out the window. Soft cottage core vibes. Eclectic design steeping in a life well lived. Wonderful kitchen, well stocked and easy to cook in. Shower pressure is adequate. Bathroom is clean and filled with an array of books and tchotchkes. Your eyes always have something to wander and examine. It's a maximalists dream. The book shelf in the living room is filled with old books some titles are expected due to surroundings and some are just plain fun. May I recommend a game of I spy Nina is quite fantastic. A spit fire. An attentive host. Hospitable and kind. She gave it a welcoming vibe. Meeting her animals was truthfully a highlight. They are even tempered and kind. Her horse is stunning & social. The donkey a goof. The mule is oh so friendly. Sheep a bit shy but non the less beautiful. Chickens? fluffy feet! The ducks were personable. The goats, joyful. Cat, adorable. Good workin dogs.

We absolutely loved staying here! It was only an overnight trip and we wished we could have stayed longer. Very friendly hosts, lots of room, nice character within the Airbnb- the main bedroom was beautiful and both bedrooms had great views of the farm on one side and the mountains on the other. They called down the cows so we could feed them bread and it was such a fun experience! Would definitely stay here again if in the area.

I booked Bog Mountain Retreat for a personal getaway for a few nights. It truly is a lovely and peaceful retreat, which was exactly what I needed. The place is beautifully designed and decorated. It's tasteful, comfortable, clean, and full of unique, creative touches. The location is very quiet and surrounded by nature. Dave and Donna were responsive and helpful. They've thought of everything you need for a comfortable stay and recommended good local places to hike. I highly recommend the hike up Bog Mountain, right up the road. (And you can see the mountain from the living room skylight!) I had a wonderful stay and hope to return soon!

Stayed alone for a week and it was very nice. The surrounding area had lots of neighbors/ people walking around w their dog or family or just going for a jog felt very safe. I had some issues with the wifi but Travis responded within 30 minutes and helped me with it. The only thing is that the walls are thin so you can hear almost everything but besides that everything else was very nice!

Always a great stay at Jeff and Jayne's cabin. I think this was our 8th stay here and as always, a wonderful place to stay near Gunstock and Lake Winnipesauke.

If you are looking for a place to relax and unwind, look no further - this is everything you could want and more. While our stay was brief, we left feeling completely rejuvenated and restored before heading back to our busy city lives. We hope we are able to return for many years to come to this beautiful, magical place!

I'm very thankful to have found Christine's place! I had a short but great stay and would love to go back. Everything was as described and there was such attention to detail to make the apartment feel like home--from homemade cookies at check-in and all the needed kitchen amenities to extra towels and tissues and the AC left on for arrival on a hot day. I highly recommend staying here!

The condo was very beautiful and homey. We spent most of our stay indoors because it rained, and we enjoyed every second! Everything was as described and well taken care of. Basia and Bradley checked in on us throughout our stay and gave us plenty of recommendations. Looking forward to staying there again!

Great stay

We had a great time! The place was very clean, nicely maintained, and in a perfect location—just a short drive to local coffee shops and great restaurants. The surrounding nature was absolutely beautiful and made the whole trip feel relaxing and refreshing. Highly recommend!

I really enjoyed staying at Christine’s place on the lake. The condo was clean and the view by the water was great. It was super easy to check in / out. Christine was always very responsive. I would definitely consider staying again.

Great would do it again and recommend to a friend

The place was great. Quiet with beautiful views. Lots of games which was helpful because it rained a lot during our stay. 10/10 would recommend and stay again. Host was very helpful and kind. The woman that cleaned the pool was also very sweet. My 8 year old was itching to swim in the freezing pool when it wasn’t quite ready and she offered to come to our room and let us know when she was done. Thank you for having us!

Great place. The deck overlooking the lake was great! The large deck over the water was a great place to hang out, and everyone we meet were friendly. Only 3 steps off the deck/dock to get into the refreshing water. The game room pool table and pool accessories were all in great shape ( Remember to bring quarters, $1.00 per a game). The internet works great we had 4 people working on laptops in the morning and no issues were observed. Will stay at again!

Although it is a condo, it's 1st floor and extremely private with an awesome view! Very relaxing! It's just off the main road with many bars, restaurants, and ice cream within a 2 minute walk. Bob was a wonderful host... I would HIGHLY recommend this rental!