
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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Cumberland family-friendly rentals
Family-friendly home rentals with a hot tub

"Whispering Pines"
Great place on the water! Great location, close enough to town for activities, far enough to be peaceful and private. Great amenities and plenty of space. The hot tub was a great place to unwind on a cool day with a great view.

Priv. Indoor Pool, Hot Tub, Free Golf&Mini,Tennis
Everything was phenomenal. Plenty of space to maneuver and have gatherings with loved ones.

Deep Creek Lake - Lakefront pup-friendly Chalet!
Cabin and location is in a prime location right on the lake. My family went there on a weekend that was snowy, rainy, dreary. We could not do outdoor activities, so we drove to Walmart ordered food and had an amazing weekend in the cabin. Ample space, stocked kitchen, clean bathrooms, pool table, plethora of games, large dining room table where we had a ball! Very peaceful and relaxing atmosphere, made for great pictures. Paul is an incredible host. Responsive, honest, reliable. I highly rec this location and my family and I will return.

Dock Holiday-Lake access with a boat slip
DockHoliday is a happy little place tucked between state parks. We enjoyed staying here for three nights. The house was suitable for our party, 4 adults and 3 small children. The amenities in the house were adequate to meet our needs. Keurig Coffee Maker, functioning Washer/Dryer, Foosball Table, and full size fridge to hold our groceries made our stay comfortable. Know that this house is on a two-lane road that serves as a main road around this western portion of Deep Creek Lake. The traffic isn’t constant, but the noise of passing cars and trucks can be disruptive to those seeking a vacation home that brings them closer to nature. Also, the living space in the house isn’t large, so noise travels easily. May be a problem for noise-sensitive people in your party. If sleeping in the master bedroom on the main level, I recommend bringing a white-noise machine to mask the noises of footsteps on the second level. We came to see the Lake and State Parks and this house was a nice base.

It's All Good @ Deep Creek Lake
Location was absolutely perfect for us. Close enough to everything, but with a private feel. House felt bigger than the pictures, which was a pleasant surprise! Loved having the basement floor for our boys to have their own sense of privacy as well. Would come back again 100%!

Wild, Wonderful Five-Bedrm Loghome
Susan's house was exactly what we wanted for our girl's weekend. We take this trip annually, and all we want to do is relax. We eat, drink and play games. Susan's house was perfect. The screened in porch was our favorite place to be. Susan was wonderful - gave detailed instructions ahead of time, left a ton of breakfast choices - eggs in the fridge, and bagels, muffins, etc. in the freezer. The kitchen had everything you could possibly need. The house is surrounded by beautiful trees and rocks. We will definitely return!

Emerald Overlook, Deep Creek Lake
We loved our stay at Maureen’s cabin. The views were stunning and the rooms were really cozy. It made us want to spend as much time as we could there. We would absolutely come back again.

Rock Haul
Great house and great location! John’s instructions were useful and precise.
Family- and pet-friendly home rentals

Mountaintop Retreat
What a gem of a place! My young girls enjoyed exploring the yard and going on walks, taking in the gorgeous views. The home is beautiful. We went to Orr’s Farmers Market and had everything we needed in the kitchen to make dinner with what we purchased there. The host provided all the necessary details and getting in and out was smooth.

Paddler's Lane Retreat - Riverside Chalet
Chalet was a great getaway spot for a few days for an annual fishing trip. Every detail was perfect for us, had everything you could think of and thoroughly thought through the details to make sure you had all amenities needed. Grounds were also beautiful. People mention trains in their reviews but honestly didn’t mind it one bit, if you wanted they even had ear plugs in each room. Thanks again and our guide this week said he has had others stay there as well Bruce

Rustic Paradise - Ohiopyle is only 7 miles away!
had a great stay at the cabin it was very clean and comforting. The fire place was great to sit in front of and watch a movie. its a easy place to find and get into; very quiet and great place to go on a hike just to relax. Thanks Joe

In the forest. Secluded. Glamping.
Great stay at Stephen’s. He advised us not to use our non 4WD vehicle to get up to the site but we tried anyway because we arrived after dark. He told us he could help get our car unstuck and patiently did so. It was a serene place and we tried some of his distillery items, which were tasteful and great (no hangover!!). Friendly and loving cat who follows him around as well.

Kaya Cabin on Deep Creek Lake
Fantastic weekend getaway for two + our new puppy. Would recommend this cabin to anyone looking to stay near Deep Creek with furry friend(s)!

Modern Escape with Cacapon Mountain View
The home was beautiful with a stunning view of the mountains from the porch. The house was pristine aside from a few bugs in the bathroom. The large living and dining room area comfortably fits 7-8 people. Overall, the accommodations exceeded our expectations. We would definitely go back!

Cabin G at Abrams Creek
Abrams Creek is a great place for a quiet, private, beautiful rustic cabin camping experience. The grounds were fantastic, from the moment you pass the check-in you are immediately in the woods. At the cabin itself you feel like you are alone in the woods next to a peaceful stream. The cabin was comfortable and plenty warm with the propane heating, and having a dedicated port-a-potty right next to our site made bio-breaks much more convenient than if you had to walk to a central bathhouse. Highly recommend Abrams Creek!

Terrapin Cabin. A sunny, quiet cabin in the woods.
We had an amazing stay here, especially considering we got snowed in on Saturday and still had a great time! The area is beautiful, the neighborhood trail was fun to explore, and the history of Berkley Springs is fascinating. Jeff was kind and friendly, offered great recommendations, and very responsive to questions. The house was very clean and we were able to make use of the kitchen and pizza oven. Perfect little getaway spot!
Family-friendly home rentals with a pool

9118 Woodridge
We went for a ski trip and the place was great! Large, comfortable, clean house that was perfect for our group (6 friends). Finding the home was slightly challenging as GPS didn't take us to the correct location at first, but the host provided written instructions for how to get there when picking up the key at another location. One thing to note, while you can ski-on to this unit (back from the lifts), you cannot ski-off as it's about 0.5 miles downhill from the nearest trail. The host told us that it was ski-on when asked, so we were expecting this, but figure I'd share here. Additionally, the shuttle stop was very close by and ran continuously during the weekend (and was available by calling during the weekdays). Overall, we were thrilled with our stay, and had a great weekend skiing.

5⭐Cozy Condo at 7 Springs⭐
Great condo for a weekend ski trip to Seven Springs. The condo was comfortable and had everything we needed. It was located right on the shuttle line for the resort which was great, also a quick drive down if you don’t want to wait for the shuttle. Had a great stay and the price was excellent. Kim was also very easy to get in touch with and provided clear entry instructions at check in.

Deer Crossing at The Woods
This was our second stay at Janel's place and it was just as enjoyable as the first time. We loved the fireplace and views from the A frame windows. The hot tub wasn't working unfortunately, but things happen and Janel was communicative about it. Had a great weekend regardless. Also love that Janel is accommodating of dogs. Our fur babies were happy to join us on our getaway.

Walk to the Falls in Ohiopyle! Hot Tub,Fire Pit
Ohiopyle is one of our favorite places! House was clean & comfortable. Provided almost everything we needed, Excellent attention to details. Awesome set up in the backyard, we all enjoyed very much!!

Private-Pool Access-Deck Fireplace & Hot Tub-XTRAS
Loved staying at Lazy Bear Lodge. Beautiful home with privacy on big property. Hosts were super responsive and gave great local recommendations. Very accessible to hiking and white water rafting.

Hiking, WiFi, 4 Decks, King Suite, Community Pool
The location was nice, really quiet and private and right in the woods. There are hiking trails right there, so we could do a 2-3 mile hike in the morning before heading out to activities. It's just a 10 minute drive to Berkeley Springs. The views out of the picture windows in the living room, or on the deck, were great. The house is very spacious and clean, with a well stocked kitchen. Everyone found all the beds to be very comfortable with nice linens, features not always found in rental houses. The living room fireplace was welcome as it was chilly when we were there. I can't think of anything we needed that the house didn't have. One thing to note is that the driveway is graveled and there is a little slope to the door. Having said that our mid-80s parents had no issues; just something to keep in mind if you have someone with mobility issues. We enjoyed our stay and would recommend!

Cloud 10 at Deep Creek Lake
The house had so much to do which was fantastic for our kids. They were happy to spend the whole day being entertained by the arcade, pool, and other amenities. Thanks!

Big Savage Guest Cabin
I had a wonderful weekend at Al's place. The cabin was perfect for my peaceful time in Frostburg and surrounding areas. The hosts were informative and provided areas to see the sunset and sunrises. It was too cold to use the pool but the offer was there. I will be back.
Quick stats about vacation rentals that are family-friendly in Cumberland
Total rentals
40 properties
Nightly prices starting at
G$10,466 GYD before taxes and fees
Total number of reviews
2K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi
Destinations to explore
- Pittsburgh Vacation rentals
- Washington Vacation rentals
- Philadelphia Vacation rentals
- Pocono Mountains Vacation rentals
- Mississauga Vacation rentals
- Greater Toronto and Hamilton Area Vacation rentals
- South Jersey Vacation rentals
- Jersey Shore Vacation rentals
- New York Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Plainview Vacation rentals
- Rentals with a washer and dryer Cumberland
- Apartment rentals Cumberland
- Cabin rentals Cumberland
- Rentals with a patio Cumberland
- Rentals with outdoor seating Cumberland
- House rentals Cumberland
- Cottage rentals Cumberland
- Pet-friendly rentals Cumberland
- Family-friendly rentals Maryland
- Family-friendly rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Seven Springs Mountain Resort
- Fallingwater
- Flight 93 National Memorial
- Cacapon Resort State Park
- Hidden Valley Resort
- Ohiopyle State Park
- Wisp Resort
- Whitetail Resort
- Shawnee State Park
- Lodestone Golf Course
- Berkeley Springs State Park
- Laurel Mountain Ski Resort
- JayDee's Family Fun Center
- Blue Knob All Seasons Resort
- Clear Shade Creek
- Warden Lake
- Winter Experiences at The Peak