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Family-friendly vacation rentals in Cumberland

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Cumberland family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Cabin in Swanton
4.8 out of 5 average rating, 97 reviews

"Whispering Pines"

SusanRating, 5 stars3 weeks ago
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.
Home in Swanton
4.62 out of 5 average rating, 110 reviews

Priv. Indoor Pool, Hot Tub, Free Golf&Mini,Tennis

ChristopherRating, 5 stars9 months ago
Everything was phenomenal. Plenty of space to maneuver and have gatherings with loved ones.
Top guest favorite
Chalet in Swanton
4.83 out of 5 average rating, 60 reviews

Deep Creek Lake - Lakefront pup-friendly Chalet!

ConstanceRating, 5 stars4 months ago
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.
Cottage in Oakland
4.88 out of 5 average rating, 81 reviews

Dock Holiday-Lake access with a boat slip

AdamRating, 5 stars10 months ago
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.
Chalet in Accident
4.81 out of 5 average rating, 149 reviews

It's All Good @ Deep Creek Lake

KellyRating, 5 stars3 weeks ago
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%!
Top guest favorite
Cabin in Berkeley Springs
4.96 out of 5 average rating, 310 reviews

Wild, Wonderful Five-Bedrm Loghome

GailRating, 5 stars1 week ago
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!
Guest favorite
Home in McHenry
4.93 out of 5 average rating, 113 reviews

Emerald Overlook, Deep Creek Lake

CathleenRating, 5 starstoday
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.
Cabin in Swanton
4.82 out of 5 average rating, 38 reviews

Rock Haul

LaiaRating, 5 stars3 months ago
Great house and great location! John’s instructions were useful and precise.

Family- and pet-friendly home rentals

Chalet in Martinsburg
4.92 out of 5 average rating, 295 reviews

Mountaintop Retreat

AdrienneRating, 5 stars3 months ago
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.
Guest favorite
Chalet in Confluence
4.92 out of 5 average rating, 222 reviews

Paddler's Lane Retreat - Riverside Chalet

BruceRating, 5 stars2 weeks ago
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
Guest favorite
Cabin in Confluence
4.86 out of 5 average rating, 72 reviews

Rustic Paradise - Ohiopyle is only 7 miles away!

Joseph T.Rating, 5 stars4 months ago
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
Guest favorite
Tent in Purgitsville
4.97 out of 5 average rating, 140 reviews

In the forest. Secluded. Glamping.

GraceRating, 5 stars20 months ago
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.
Guest favorite
Cabin in McHenry
5 out of 5 average rating, 14 reviews

Kaya Cabin on Deep Creek Lake

BillyRating, 5 stars1 week ago
Fantastic weekend getaway for two + our new puppy. Would recommend this cabin to anyone looking to stay near Deep Creek with furry friend(s)!
Guest favorite
Chalet in Berkeley Springs
4.83 out of 5 average rating, 66 reviews

Modern Escape with Cacapon Mountain View

JenniferRating, 5 stars1 month ago
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!
Guest favorite
Cabin in Elk Garden
4.81 out of 5 average rating, 101 reviews

Cabin G at Abrams Creek

DanielRating, 5 stars8 months ago
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!
Guesthouse in Berkeley Springs
4.83 out of 5 average rating, 299 reviews

Terrapin Cabin. A sunny, quiet cabin in the woods.

JaclynRating, 5 stars4 months ago
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

Superhost
Condo in Champion
4.88 out of 5 average rating, 33 reviews

9118 Woodridge

DavidRating, 5 stars16 months ago
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.
Superhost
Townhouse in Champion
4.71 out of 5 average rating, 135 reviews

5⭐Cozy Condo at 7 Springs⭐

BreaRating, 5 stars4 months ago
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.
Superhost
Cabin in Hedgesville
4.88 out of 5 average rating, 225 reviews

Deer Crossing at The Woods

LauraRating, 5 stars5 months ago
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.
Superhost
Home in Ohiopyle
4.82 out of 5 average rating, 158 reviews

Walk to the Falls in Ohiopyle! Hot Tub,Fire Pit

JodiRating, 5 stars2 weeks ago
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!!
Top guest favorite
Cabin in Oakland
4.95 out of 5 average rating, 219 reviews

Private-Pool Access-Deck Fireplace & Hot Tub-XTRAS

BenRating, 5 stars1 month ago
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.
Guest favorite
Cabin in Berkeley Springs
4.89 out of 5 average rating, 76 reviews

Hiking, WiFi, 4 Decks, King Suite, Community Pool

MaryRating, 5 stars3 weeks ago
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!
Guest favorite
Cabin in McHenry
4.86 out of 5 average rating, 44 reviews

Cloud 10 at Deep Creek Lake

RachelRating, 5 stars4 months ago
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!
Guest favorite
Cabin in Frostburg
4.92 out of 5 average rating, 139 reviews

Big Savage Guest Cabin

SheriRating, 5 stars7 months ago
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