
Family-friendly vacation rentals in Cumberland
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Top-rated family-friendly rentals in Cumberland
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Popular amenities for Cumberland family-friendly rentals
Family-friendly home rentals with a hot tub

Attitash Studio | 5min to Storyland| Pools
Was a nice peaceful stay for the most part. The pools were nice to swim in although it seems not everyone seemed to want to follow the pool rules. Doesn't help that there were no lifeguards to ensure kids remained safe other than the parents. A few times I saw individuals in the pool water with either glass or an open drink in hand. Saw kids diving into the pool and even witnessed a few hurt themself. But other than that, the hot tub was so lovely to soak in. The arcade room was fun to play in. It was cool to see there was a lot to be able to do in the area for yourself. Definitely wish there was more to do in the area other than the classic tourists spots. A lot of beautiful spots to hike. We ended up checking out Diana's Bath and it was a gorgeous spot to watch cascading waterfalls or have a tiny dip. Would definitely check out this space again and maybe spend a few more days to truly appreciate the environment and mountains ^-^

Coastal Maine & 10 Min to Portsmouth+ Hot Tub Too!
This is one of the best Air B&B experiences that we’ve had…beautiful place and surroundings, great amenities and personal touches, wonderful recommendations. Couldn’t have had a better time.

Falmouth 3br near Town landing
David and Valle’s house is welcoming, and it was just right for our family get-together. The kitchen is very well set up for cooking, and the counter is both beautiful and a great place for gathering and conversation. There are many lovely touches in the house. We appreciated the yard and gardens, and our dog loved the walking trail. The location is peaceful but just a few minutes from Portland. David communicated well and offered helpful ideas for our visit.

Tree Dwelling with Water Views & Cedar Hot Tub (2)
We had the most wonderful staying here! A peaceful and relaxing getaway is exactly what we needed, and exactly what we received. The hot tub was the perfect touch. We couldn’t recommend this place more! Can’t wait to go back!

Attitash Retreat
Had a great time peaceful get-away with great mountain views. Climbing,swimming,snowboarding, and all outdoor sports within close distance. I would definitely stay again

Cozy hot tub haven
Wendy’s place was really nice and the hot tub is very private.. we definitely got our usage out of it… Wendy herself was extremely kind and open minded. She didn’t rush us out come check out, instead, she encouraged us to stay a little longer and enjoy the hot tub before our long journey back home.. she gave us good tips about golden gems only locals know about 🥰 She did have a cool book to share reviews but I didn’t have a pen.. also we left grape soda in the fridge from Canada for the next person to try!! Thanks again Wendy 5⭐️

EPIC VIEWS, Hot Tub, Pond, River, 14 Acres A Frame
Property had amazing views. Inside was beautiful and very clean. Pond and river was nice. Host was quick with any question we had. would recommend.10/10

Seacoast Oasis (NH & ME)
Convenient location and easy to find. Great for an overnight stay like we needed. If you needed to cook at all, it would be tight but we didn’t need to. I highly recommend Bob’s Clam Hut while you are in the area!
Family- and pet-friendly home rentals

Private Hilltop Cabin, Lakes and Trails Abound..
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!!

McKeen's Riverside Retreat
We have stayed at Jackies place twice now and enjoyed it just as much this time as the last. Even though it rained for two days the house is plenty big enough to spread out. We had to change our reservation days twice because of circumstances and Jackie was very accomidating..

Private Hill Top Apartment/w One Car Driveway
Magical stay in a magical space. My family and I are do grateful for your hospitality.

Luxurious Mountainside Cabin! Fantastic Views!
The cabins location was secluded and private but not to far from activities everything you need is about a 25 minute drive away. The cabin had an amazing view and was stocked with everything we needed. The sauna was an amazing addition. We highly recommend. The house was spotless and the host was ver responsive. Overall we highly recommend this cabin and will most likely be returning ourselves.

Gorgeous Studio on the Kennebec
Perfect weekend retreat for a small family with a young one. Close to downtown, museum, and the firepit was so nice at night. 5 stars all around and will return in the future. Thanks Phillip!

Cozy Guest Suite in White Mountain National Forest
Mary's place was great. Everything was exactly as described and Mary gave very clear instructions for check in and responded quickly to text messages. It was a very enjoyable stay.

Island Glamping in a Luxury Tent in Maine
Incredible place. The island is beautiful, and everything is ready for you so you don't have much to do. Kent was great at communicating, gave us all the information we needed and was quick to help us, making the whole experience very easy. We will be back

True Maine Artist Cottage with Outdoor Shower
We had such a great time staying at Emily's awesome retreat. It was our first mini-vacation with our dog and we were looking for some peaceful, wide open space to let her roam free. We absolutely got that with this home and thoroughly enjoyed the town, as well. Emily was super responsive whenever we did have a question and provided us with a great list of places to check out around town. Would absolutely stay again. Thanks!
Family-friendly home rentals with a pool

Upscale retreat w/ panoramic White Mountain views
We really enjoyed our stay at Lisa’s house in our white mountains foliage trip. Very quiet and stunning views of the mountains in color right in the living room. Secluded location but very short drive to Jackson and Conway. We would be happy to return again. Highly recommended!

Slopeside Sunday River Condo Brookside 2A210
Great place to stay with an awesome view of white heat!

Storyland, golf, hiking, kayak and more
We had a lovely stay at the condo. It was the most comfy place to get snowed in. We received about a foot of snow the night we checked in and Seasons was very helpful to continually plow and shovel walkways. We explored the property and had fun sledding down hills with our tube. The condo is very clean and comfortable and has everything you may need. It was still decorated for the holidays which was a nice touch as well. The electric fireplaces worked great and were so pretty to look at. All of the furniture was very cozy and comfortable. The carpet throughout is great on cold days. We highly recommend a sleigh ride at Nestlenook farm if staying in the winter. Living Shores Aquarium is down the block and a great place to visit with kids. Diana’s Baths is a short drive away and beautiful to explore in the snow. Our daughter loved seeing the frozen waterfall. There are lots of restaurants nearby. We can’t wait to come back and see it during the summer months.

Two-Bedroom Condo on the Wells/Ogunquit town-line
Christopher was a helpful host and his place was perfect! Clean, fully stocked, great location. It was close to lots of beaches and restaurants and the pool was great for the little ones

Across from Storyland & in the Heart of the Mtns
Beautiful place, has everything you might need. Very convenient location , close to storyland, restaurants and convenience stores . The restaurant recommendations from the host were great

Intimate Garden Style Condo with Mountain Views
We had a wonderful stay here! We were up for a weekend to enjoy the snow and mountains and appreciated how close it was to everything we planned. We had a snow storm the second night and the grounds maintenance was perfect, we had no problem walking right out the door. We would recommend heading for a stay!

Bartlett N. Conway, NH condo ski near Storyland
We loved our stay and couldn't have felt more at home. Condo has everything you need and the hosts were so kind. Plenty of space for our family of 4 but could easily fit 6. Location is ideal for families to explore all Bartlett has to offer. Highly recommend and can't wait to come back!

Peaceful Condo Near Storyland & Attitash Skiing
We had a great time staying at this condo. Had all amenities needed and very clean! Close to downtown North Conway and scenic areas. We also enjoyed checking out the pool.
Quick stats about vacation rentals that are family-friendly in Cumberland
Total rentals
110 properties
Total number of reviews
4.2K reviews
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Wifi availability
110 properties include access to wifi
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- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Scarborough Beach
- York Harbor Beach
- Long Beach
- Popham Beach State Park
- Surfside Beach
- Long Sands Beach
- Pemaquid Beach
- Brunswick Golf Club
- Fox Ridge Golf Club
- Coastal Maine Botanical Gardens
- East End Beach
- Cranmore Mountain Resort
- Palace Playland
- Ferry Beach
- Cliff House Beach
- Pemaquid Point Lighthouse
- King Pine Ski Area
- Purity Spring Resort
- Diana's Baths
- Laudholm Beach
- Ogunquit Playhouse