Family-friendly vacation rentals in Cumberland

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Cumberland

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite

Apartment in East End

4.96 out of 5 average rating, 558 reviews

Peaceful Oasis on Munjoy Hill -1st flr/3BR+parking

Spacious, light-filled 3 Bedroom/1 bath 1st-floor apartment with tasteful art, contemporary furnishings, + a well-appointed kitchen. Fantastic location! -A 5-minute walk to the Eastern Promenade with its food trucks, beach & scenic trails -Nearby are bakeries, cafes, world-class restaurants and popular breweries -Relax in the serene garden w/ outdoor seating -A 15-minute walk takes you to the Old Port. Discover the best of Portland, then return to A Peaceful Oasis, a place to truly call home.

Superhost

Home in Conway

4.83 out of 5 average rating, 114 reviews

A Large Vacation Home with hot tub, game room +

My place is close to family-friendly activities, skiing, snowboarding, golf, shopping, hiking, restaurants, night life, shoe shoeing, ice skating, sleigh rides, tubing, Saco River tubing/canoeing, Echo Lake, Gondloa rides to summit, mini golf much more. You’ll love my place because of the quiet neighborhood, comfy beds, the kitchen, the hot tub and fireplaces and the space for large reunions and gatherings . My place is good for couples, business travelers, families (with kids), and big groups.

Guest favorite

Cabin in Carroll County

4.84 out of 5 average rating, 745 reviews

The Overlook/Cozy 2 bed/Hot Tub/Wood Stove/Firepit

Great location! .5 mile to scenic overlook! Central to all attractions, private yard, fire pit, wood stove, outdoor space, hot tub, new furniture, cozy mattresses & linens. Walk to ice cream & scenic overlook, less than 5 mins to Saco River path, Golf, North Conway Village, Whitaker Woods, scenic train station, coffee shops, shopping, skating, nightlife, restaurants, kayaking, skiing, adventure parks, sleigh rides (discounts available), skiing, story land, hiking, Outlets, snowshoeing, etc.

Top guest favorite

Apartment in Falmouth

4.9 out of 5 average rating, 195 reviews

Falmouth 3br near Town landing

Enjoy the rocky coast of Maine with lobster rolls on Town Landing pier. Watch the Lobster fishers work and buy fresh lobster right off the boat. With Portland Maine’s iconic Foodie city with artisan brewers and fun dining and night life just down the road. (6.6 miles) Our classic New England Cape home is the perfect place to meet family and cook and eat around the counter in our amateur chef’s kitchen. Crack some fresh Lobster from Shaws on Rt One they are happy to cook them for you.

Guest favorite

Home in Conway

4.87 out of 5 average rating, 130 reviews

Hot tub with country setting, close to village.

Must bring Bathing & hot tub towels We will supply everything else. ALL Major 3 day holiday weekends is a min of 3 nights!! Now close to the new Mt Washington Recreation Path. Country setting, quiet, three bedroom home close to village. All major ski resorts are minutes away. Hiking paths as well as TAX FREE OUTLETS. Brand new hot tub and wood stove works, wood is mostly supplied Storyland and Santa's village is also minutes away. Great country feeling in a good location.

Guest favorite

Townhouse in Kennebunkport

4.94 out of 5 average rating, 167 reviews

Great get away spot,historic home in Kennebunkport

Located 1.8 mi-dock square, 2.6 mi- Colony Beach, .7 mi -Cape Arundel Golf Course. Plenty of onsite parking, beach pass provided for Kbunk Beaches, a large back yard for fun and relaxation. Just on the outside of town in a country setting. Comfortable setting for relaxation. This is a daily reservation from Oct.1st-June. I love to make sure my guests have as much fun as they can while they are visiting and will help out in anyway possible. No dogs of any kind are allowed

Guest favorite

Chalet in Bartlett

4.92 out of 5 average rating, 277 reviews

Chalet in the Sky| NorthConway+StoryLand| Outlets

This gorgeous 2-bedroom chalet, styled by the Homme team, is the ultimate mountain escape! Tucked away in North Conway’s White Mountains, it’s great for families, friends, or ski enthusiasts. Take in stunning views, free onsite parking, modern comforts, and quick access to top area attractions for a getaway to remember! 🌿✨ 🎢 Story Land - 10 min 🌿 Diana’s Baths - 10 min 🚠 Mt. Washington Auto Rd - 35 min 🏞️ Echo Lake State Park - 15 min See below to learn more!

Top guest favorite

Home in Intervale

4.97 out of 5 average rating, 179 reviews

Spacious 3 level family friendly home.Dog friendly

Private home 3 Levels Sleeps 14 Plus! Large fire pit! Great for family gatherings! rustic weddings and celebrations. close to Cranmore, Story Land, Local Breweries, skiing & shopping. Amazing view of the Moat mountains Close to great local restaurants. Dishwasher, Wi-Fi PacMan Arcade, Washer/Dryer, Lg backyard, deck, BBQ grill Spacious Family Room! Full home generator! We are proud of our great reviews and as a host I look forward to hosting you. Dog friendly

Guest favorite

Home in Kennebunk

4.95 out of 5 average rating, 151 reviews

Quiet cozy cottage close to restaurants, beach

Winter-wonderland, close to skiing and a walk from great dining. In the summer, enjoy the quiet backyard or walk to the beach! No need to find parking, my place is 3/10 of a mile from downtown Kennebunkport and 7/10 of a mile to Gooch's Beach. You will love my place because of the kitchen, the coziness, and the location. My place is good for couples. It has a tempurpedic king-sized bed and a queen sized pull out bed in the living room.

Superhost

Apartment in East End

4.83 out of 5 average rating, 140 reviews

Fall in LOVE With PORTLAND, MAINE

Portland and its surrounding areas is a FOODIE's paradise. Our comfortable home is perfect for Family or Friends to enjoy Portland's charm. Approx 3 miles from Portland Jetport and 90 miles from Boston Logan airport. Walk to downtown or the Old Port on the waterfront. The surrounding areas offer fine beaches and beautiful scenic towns guaranteed to make you want to come back and visit this best kept secret again!

Guest favorite

Home in Kennebunk

4.91 out of 5 average rating, 111 reviews

A Great Space in a Great Place

This Lindal Cedar Home overlooks the tidal marsh. Walking distance to beach and Kennebunkport. Second story duplex with master bedroom loft. Complete kitchen. Children's play park, pitch and putt golf, kayak and bike rentals, bakery, restaurants, market, antiquing, whale watching, Shipyard brewery and retail shopping; all within walking distance. Owners on site.

Guest favorite

Chalet in Intervale

4.91 out of 5 average rating, 246 reviews

Spacious, air-conditioned condo next to Storyland!

Large, mountainside condo just minutes to Storyland and all attractions in the Mt Washington Valley! Features king BR with en suite bathroom and a queen BR on the 1st fl. The 2nd level features a giant bedroom with 4 twins. Brand new ductless AC system. Perfect for families or groups! Use the condo as home base for all of your vacation adventures.

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What guests are saying

Cozy 2BR Across from Storyland! Near Attitash

4.91 out of 5 average rating, 92 reviews7 months ago

This may not be the most picturesque airbnb you've laid eyes on, but it was HANDS DOWN the best accommodation I have EVER stayed in with my toddlers (we have been on 10 trips in the last 3 years!) Dan's place was cozy and the right amount of space for my family of four, but the thing that made it really stand out is that they had everything you could need for young kids. Not only the standard pack and play and highchair, but also a sound machine, stroller, and best of all- a box of toys that my two (4 and 1.5) played with CONSTANTLY every spare moment we were in the airbnb. We stayed a week and they didn't get bored of them, which, if you've ever had two energetic kids running circles around the living room, you know REALLY says something. The kitchen had everything we could possibly need as well, which was so helpful. This place is priced fantastically for families and I would whole heartedly recommend it.

Condo in Bartlett

What guests are saying

Old Orchard Beach House

4.94 out of 5 average rating, 88 reviews8 months ago

Perfect location for a family vacation. The extras in the shed such as beach toys, tumbling mats, and wagons to carry beach gear made all the difference. Our group consisted 6 adults and 3 children ages 5 and under. There was plenty of room for everyone and the kids were never bored. The fenced in yard and deck were perfect for relaxing.

Home in Old Orchard Beach

What guests are saying

Incredible Views * Private * pet friendly

4.91 out of 5 average rating, 86 reviews2 months ago

We were a group of 9, 3 couples and 3 babies under the age of 2. Molly’s place was great for all of us to space out and the backyard scenery was gorgeous. The home was stocked with everything you could ask for in a kitchen and more. Would definitely consider staying here again if we make another trip up here!

Home in Conway

What guests are saying

Private apt, 5 minute walk to the beach!

4.81 out of 5 average rating, 68 reviews2 months ago

This place was immaculate. Squeaky clean. Super comfortable. Everything we needed. It was easy to find, Kate was so kind and the space felt like a home away from home. We will definitely be coming back. The beach is very close, and it’s a very peaceful setting.

Apartment in York

What guests are saying

Great place to stay for multiple families all year

4.79 out of 5 average rating, 75 reviews1 month ago

This is the second year that we stayed at Michael’s and we love it. It fits our family of 4, another family of 3 and 1 more random adult perfectly. We liked the bunks downstairs so the kids could sleep in and there was plenty of space for all of our ski gear.

Condo in Bartlett

What guests are saying

The "Happy Hen House" cottage in lakes region

4.7 out of 5 average rating, 67 reviews6 months ago

As Mainer living across the country, it is always nice to come. Unfortunately this trip was to attend my Mom's funeral. Pam's home was the right level of closeness to the rest of my family to make visiting easy. The place was the peaceful retreat I needed to visit with myself. Five minutes to most things a person living out of a suitcase could need. Also less then 5 minutes walk puts one at the boat launch for personal watercraft. A great place to sit for a few. The amenities were plentiful at the house and the character was Maine charming. Pam was wonderful and easy to communicate with at all stages. I will be back in the future. Matt

Home in Windham

What guests are saying

Lakeside Cottage on Great East Lake - Smoke Free

5 out of 5 average rating, 30 reviews10 months ago

Our stay at Dave's cabin on Great East Lake was even more wonderful than i thought it would be! My daughter's and I just loved our adorable cabin. We enjoyed having camp fires at night, the waterfront game room with pool table, ping pong and more. We enjoyed the SUPs, kayaks and swimming to the raft. Fun and relaxing describes our stay. Thank you Dave, MB, dogs Tini, and Biker. We will recommend this place again and again!

Cabin in Wakefield