Family-friendly holiday rentals in Cumberland County

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.

This place was great for our group (3 couples). It had plenty of room for us to hang out in the mornings, with several breakfast options within walking distance. It was a short ride to the downtown area where we spent most of our days. Then we'd come back to the house where we had plenty of room to eat the take-out food we'd bring back, and then hang out some more regretting the massive amounts of food we'd just eaten! Tim was great to deal with and was responsive to our needs. We would stay here again if we return to the area.

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.

This place has gorgeous views. Amazing for morning coffee!

We had the absolute best time at MJ’s place, highly recommend !! The house is spatious yet very cozy and quiet, with a nice back porch to sit and enjoy the surrounding woods! Home is also very close to town and to Poryland/coastline, and the cleanest lake to swim in that we’ve ever been to! MJ was very helpful and quick to respond. Stay here! We hope to return sometime soon!!

We arrived and saw either the hosts or prior renters had left a few key basic unopened items in the fridge to help ease us into our stay: items like half and half, some eggs and butter were present. The hosts had also made the effort to leave a small welcome and departing treat for me and the family that was a nice touch. The building was older but with that comes the charms of different features liked slightly raised floors at times and other anomalies. The rooms were freshly painted and we never saw any signs of pests inside.The location was close to the shore and walkable to the pier and attractions. The beach was extremely clean and though we only went at off hours (late night or sunrise) it was always relaxing. There is an active set of train tracks nearby so don't be alarmed, it's about a mile off I'd guess but you will hear them pass through.The roads were pretty quiet in the neighborhood and kids plays on the inactive street for hours. Thanks for the enjoyable stay, The Hornes

Jennifer was a phenomenal host. She was very accommodating (we were traveling with our 8 month old) which was extremely helpful. The place was spotless, quiet and very peaceful. We felt right at home and you can easily walk right to downtown Freeport. Highly recommend this host and this location!

This was a perfect stay for our 2 days in Portland. We could walk everywhere from the apartment. There were plenty of options for restaurants nearby.

Our son, his girlfriend, my husband and I enjoyed staying at the cottage in late October 2024. The location was quite scenic as it overlooked Casco Bay, near Portland, ME. The host made suggestions that we followed (bringing firewood & blankets). The kitchen was equipped with utensils & coffeemakers. The neighborhood was quiet. We enjoyed walking in the local preserve along the water and took advantage of visiting the Portland Museum of Art and eating at The Honey Paw, an Asian fusion restaurant.

Can’t say enough about how great our stay was! Andrew was incredibly responsive, let us check in early and check out late without even asking. It was a great location on the island, very walkable, even for my mother with a bad knee (she was exhausted after the first day though). Would absolutely stay again!! 10/10

This home was fabulous! The space was clean, lovely, and so comfortable. Additionally the neighborhood offered but walks in nature and restaurants/stores. I wish I could go back next month!

We really enjoyed Elizabeth's house. It was beautiful and peaceful. The dock and beach were great. Communication was awesome! would loved to stay stay again.

We had such a wonderful week-long stay at Suzanne’s place. We spent our days skiing at pleasant Mountain (only a five minute drive away) and our evenings relaxing by the fireplace. The space was super clean, comfortable, and cozy, and the perfect layout for our family. Would highly recommend a stay here, we hope to be back again next year!

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!

This place had everything we needed. The view was spectacular! We really enjoyed seeing fireworks from the deck. The home was very clean, kitchen fully stocked. We loved hearing live music each day and night. So much walkable fun for the kids. We had a wonderful 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!

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!

Maryann is SUCH a treasure! She really is the hostess with the mostest! Gives great recommendations, homemade coffee and treats, and if you mention you like something, she might get it for you! Making this Philly girl a wannabe Maine resident! Couldn’t recommend more.

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

My family and I had a awesome time enjoyed the quiet and relaxing days. Michael was very helpful and very quick responses to any questions we had.The cabin was very nice it felt like home was very comfortable slept very well. Everything about the cabin and the island was well worth going looking forward to going again in the future.