
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

Raven's Crossing - Kate's Cottage
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!

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!

Luxury 6 bedroom Beach House 50 ft from beach
The house was beautiful and worked perfectly for our group! Check in was very easy, and the house was spotless when we arrived. My favorite part it was the yard - perfect for a big barbecue with a large group.

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⭐️

Owl-Pine Ski Lodge: Rustic Cabin w/Hot Tub
The cabin was beautiful and spacious. Definitely can see all the updates and renovations that have been made. Rustic but with all the modern comforts. We were only there a couple of days but fit in an outdoor fire pit and hot tub! Wish we had a few more days off to enjoy more- but we made the most of it. I take any family time i can get! Thank you!

Maine Lakes Region house (private hot tub)
The spot was perfect for a weekend of skiing and riding snowmobiles. Exactly what we were looking for in a vacation home. Paul was great at recommending places and his response time was great. Also the wood burning stove made the weekend cozy and perfect.

awesome private cabin
Dave was an amazing host and he provided the best possible get away for our first wedding anniversary. It was private there is so much beautiful outdoor art to look at and the hot tub was the perfect way to wind down after the day. If there was a 6 star option I would give it this was everything we wanted and needed and then some
Family- and pet-friendly home rentals

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

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..

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

Sunset Haven - Little Sebago Lake
second year in a row staying here and looking forward to our next trip back! Another amazing stay

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!

Unique artist's sun filled farmhouse meets loft
This was a great experience for us, the artist cottage was outfitted like home with everything we needed. We cooked on an amazing stove, fridge was large and works well for food storage. Tanja was gracious and helpful. We enjoyed meeting her. I would love to stay here again. Highly recommend. You must do stairs as all bedrooms are upstairs. One room has en-suite bath with tub. The other shower and bathroom is downstairs and both have great water pressure and temp. Enjoy this jewel which is close to everything but still super private.
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!

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

Main Street for 6!
I’ve been to North Conway many times and this one was one of my favorites. The location is perfect and the space is wonderful. You’re at the center of everything and it’s a great location for families. I will definitely use this location again the next time I come to North Conway.

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

Beach Dreaming
A nice private cottage in a quiet community that was super handy for us to stay until we secured our house in New England. Everything is in place for comfortable living. We lived there for a month long and the hosts were always responsible.

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

The Hill's on Buttonwood
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

*Chalet in the Sky|NorthConway+StoryLand|Outlets
Krysten's chateau was perfect for a family trip with my girlfriend, my sister and my sister's husband! The two bedrooms were very tidy and cozy and both bathrooms had plenty of towels and soaps. Krysten left thoughtful touches through the space such as a guide book with recommendations for places to visit, restaurants, and instructions for check in, check out, and how to use all of the amenities. the view from the back porch was beautiful and this made for a very cozy, yet spacious, place to rest after long days of hiking various trails (and Mt. Monroe) and visiting the surrounding areas, including North Conway. This space would be especially great for families with kids because there are board games included by the owner(s), bunk beds in the second bedroom as well as a second queen bed, and you would be in arms reach or Story Land! Overall, I would 10/10 recommend this AirBnb to anyone looking for an affordable, renovated, clean, and beautiful space for their trip to New Hampshire!
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