
Family-friendly holiday 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.

Sleepy Hollow Log Cabin
Sleepy Hollow Log Cabin at Beechnut Springs is nestled in the majestic Blue Ridge Mountains. A short distance from Rt 70 as you travel down scenic route 17 following a bustling trout stream to Beechnut Springs entrance. After you arrive & settle into your secluded cabin, you will find many unique activities & quiet places in this serene setting amid the wonders of quiet waterfalls, easy walking paths, a wildlife haven, natural running streams & "The Bog Shack". Welcome to Sleepy Hollow Log Cabin

A Hub for History Buffs!
A very private, brand new apartment all for you! New furnishings make it comfortable, antique pieces make it quaint! Both will make your stay with us enjoyable and peaceful. A kid and adult friendly space. Enjoy the deck in the morning and the electric fireplace in the evening. A quiet home-base for your visit to historic Gettysburg! We are a HUB for HISTORY BUFFS and more! Entrance is no longer through the garage! PS: In the winter, we are 15 min from Ski Liberty and have garage storage!

Country Cottage Nestled on a 20 acre Horse Farm
Relax with the whole family at this peaceful cottage nestled on a horse farm. Enjoy roasting marshmallows in the outdoor firepit or sit back on the porch to watch the wildlife. We are located only minutes from the battlefields and town center. Enjoy local restaurants, breweries, specialty shops, & wineries. Liberty Mountain Ski Resort is only a 20 minute drive. Take advantage of nearby golfing, scenic views, historical sites, ghost tours, museums, or take a guided bus tour of the battlefields.

Rebel Hollow
Come stay with us at our beautiful Gettysburg battlefield farm. Our secluded apartment is attached to a charming 1920s farmhouse and features a private entrance, porch, and windows overlooking historic Willoughby Run. Set on 10 peaceful acres , the property offers a true countryside escape. Guests are welcome to enjoy our 2-acre pond with fishing access, walking trail around the property as well as our friendly hobby farm home to ducks, chickens, goats, emus, and welcoming farm dogs and cats.

Serene 3BR Cottage with Creekside View Gettysburg
Voted #1 rental 2021–2025, & in the top 1% of AirBnb’s, Blue Coat Cottage is nestled between 2 picturesque farms directly across from Marsh Creek in historic Gettysburg. It perfectly blends battlefield access with peaceful country living. This home away from home is ideal for families & friends. Enjoy a fully equipped home with thoughtfully designed spaces, hidden kids’ nook, scenic views, a hammock, chiminea, front porch overlooking the creek, and a private backyard for relaxing & unwinding.

Old Orchard House in Historic Gettysburg
Welcome to the Old Orchard House in Historic Gettysburg. This lovely Federal-style home was built in 1866 and maintains the charm of that era while offering modern conveniences to guests. With 3 bedrooms, a fully-equipped kitchen, and a backyard garden, this location is the perfect place to vacation with family or friends. Walk to the civil war battlefields, Gettysburg College, museums, shops, and restaurants. Take a short drive through the countryside to visit local wineries or Ski Liberty.

*Pre-Civil War & Downtown~The Garlach House~c.1830
At this pre-Civil War home, you will find yourself within walking distance of restaurants, ice cream parlors, shops, museums & battlefields. Feel comfort in our home as you will be able to step back in time, but with modern day amenities. Enjoy our private fenced in backyard with a cup of coffee in the morning & a glass of wine in the evening as it is dimly lit, you can still see the stars! Take a short drive to local wineries, golf courses & Ski Liberty to enjoy skiing/snowboarding/tubing!

Gettysburg-Ski-Golf-AT Hikes-RoseSniffers LOFT
Calling all RoseSniffers!! Stop and Smell the Roses in this stylish boutique studio with private entrance and free parking. Although you will wake up to a bird's eye view of mountains and farms, you will be close to four-season adventures: Skiing, Antiquing, Vineyards, History, Gettysburg Military Park, 5-Star Golfing, Performing Arts, and Dining are all minutes away! 4 mi to GBurg Battlefield 2 mi to Liberty Mtn 8 miles to 5+ AT access points Across street to GBurg National Golf Course

Quiet Country Setting
The apartment is approximately 3 miles from downtown Gettysburg and Gettysburg College and about 12 minutes from the Gettysburg National Military Park Museum & Visitors Center on Baltimore Street. It is only 5 minutes from the reenactment site on Pumping Station Rd and also about 12 minutes from Liberty Mountain Resort. Other popular wedding venues nearby: Hauser Estate Winery, Adams County Winery, Lodges, Rock Creek Farm, Links. The apartment is close to everything yet in a quiet setting.

Cozy West Virginia Treehouse
Thanks for checking out our treehouse! It’s 4 minutes from downtown Shepherdstown and 15 minutes from downtown Harpers Ferry. We are excited to share it with other fun-loving folks! The treehouse has heat and AC, a tiny kitchen with a mini fridge, stove top, toaster oven, gravity-fed sink and kitchenware. There’s a bathhouse built on the back of the host’s home with a conventional toilet and shower. There’s also an outhouse with a light and essentials. We provide wood for the fire pit also.

Heart of Gettysburg Walk to Everything!
Walking distance to shops, museums, restaurants, and the battlefield. Situated where federal troops were positioned on July 2-3, 1863 and steps from the site where Lincoln gave his immortal Gettysburg address. Parking for two vehicles on site. Amenities include: - King Bed - Wi-Fi - Off street parking for guests - Netflix - TV lots of channels - Shampoo and Conditioner - Body Wash - Keurig and Coffee Pods - Washer and Dryer - Pinball Machine (Fun!) - Refrigerator - Dishwasher

Summer Kitchen
This renovated ‘summer kitchen’ is close to Gettysburg battle field and Gettysburg university. There are a set of fairly steep steps that lead to the bedroom, so please ensure that you are able to climb these (see pics). There is a small sitting room, bathroom and kitchenette on the first floor, and the bedroom is the only thing on the 2nd floor. There is plenty to do in historic Gettysburg, or if you like to ski or snowboard, Ski Liberty is only about 20 mins away!
Popular amenities for Cumberland family-friendly rentals
Family-friendly home rentals with a hot tub

StayAround Dome ~ Unique & Tranquil Gem ~ Sauna

The Glowing Logs Cabin

Apple Blossom Cottage HT is extra$

10Mi. To Gettysburg Clean-HotTub Lakefront-Kayaks

All Seasons Retreat - Screened Porch - Fire Pit

The Frame ~ Charming Nature Escape ~ Hot Tub ~ BBQ

Mom's Cottage

Spectacular views, intimate dome
Family- and pet-friendly home rentals

Creekside Retreat at the Jewel Vinsota

*Fully Fenced* Minutes to Gettysburg & Liberty Mtn

Cottage on our horse farm

Sweet Gettysburg Area Cottage Close to Outdoor Fun

Gettysburg 2 Easy Times

Country 2-Bed/2-Bath Barndominium w/Beautiful View

Beautiful private home in the country

Steps to Winery and Battlefield – 1 Acre Retreat
Family-friendly home rentals with a pool

Stoney Spring Overlook

4BR, 4BA, Amazing Indoor Pool, EV charger, ~10 acr

The Grey Wolf (studio-style loft suite)

Civil War Farm House w/Heated (seasonal) Pool

Starcatcher Chalet, The Woods Resort

Master's Suite · 1920s Tudor Estate, Hunt Valley

The Cottage at Nestled Inn

Historic Peace and Plenty Farm: Pool House
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- Family-friendly rentals Adams County
- Family-friendly rentals Pennsylvania
- Family-friendly rentals United States
- Hersheypark
- M&T Bank Stadium
- Baltimore Convention Center
- Oriole Park at Camden Yards
- Federal Hill Park
- Liberty Mountain Resort
- Johns Hopkins University
- Spooky Nook Sports
- Hershey's Chocolate World
- CFG Bank Arena
- Roundtop Mountain Resort
- Cunningham Falls State Park
- Harpers Ferry National Historical Park
- Cowans Gap State Park
- Merriweather Post Pavilion
- National Aquarium
- Caledonia State Park
- South Mountain State Park
- Baltimore Museum of Art
- Whitetail Resort
- Harbor East
- Pennsylvania Farm Show Complex & Expo Center
- Loyola University Maryland
- Hersheypark Stadium





