
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.

Sweet Gettysburg Area Cottage Close to Outdoor Fun
Off the beaten path but close to it all, including historic Gettysburg, the Appalachian Trail, Caledonia State Park, and Michaux State Forest. Relax on a large screened-in porch, in the shade of our pines or on the banks of a mountain creek. Access your own streaming accounts through our TV/wifi. Great restaurants are nearby, or make use of our original 1950s efficiency kitchen and dine al fresco. You’re surrounded by wineries, farm markets and even a candy store. Central location to do it all!

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.

*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

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

Beautiful 3-bedroom home near downtown Gettysburg
Relax with the whole family and enjoy all Gettysburg has to offer in this quaint three-bedroom house. Located about 1.7 miles from the center of Gettysburg, this home boasts three bedrooms and two full baths. Full kitchen, dining room, and living room available as well as a spacious deck for sitting and garage area for enjoying time as well. You can enjoy all Gettysburg has to offer with this perfectly located home. Older house with some modern charm that will suit all your needs.

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!

Tiny A-Frame Retreat in the Woods
Beautiful, quiet woodland setting with a creek running through it, just 5 miles from downtown Frederick. Tucked away into the woods our tiny A-Frame has a comfortable queen bed(not an air mattress) for a rest and retreat fully immersed in the poplar woods. This is a camping style set up- so if you enjoy camping then this place is for you. No running water- but plenty of good clean mountain water available , no electricity, compost toilet. We do not allow dogs.

Home Away From Home - Apt in Historic Gettysburg
Come & explore Gettysburg while staying in a charming 1 bedroom, 1 bath apartment in the heart of downtown Gettysburg within walking distance of stores, restaurants & attractions. You'll have free private parking & private entrances (accessible by key), & a private back deck to relax and enjoy a view of the battlefield. During your stay, I'll only be a phone call or text away to help make your stay as comfortable as possible!

Top O' The Stairs
This charming and cozy second floor one bedroom apartment, which accommodates up to 3, is located in downtown Gettysburg within a five minute walk of major attractions, restaurants and the battlefield. We are located on a quiet residential street. Yet, within 5 minutes walk, you can be at the square where the action is or Baltimore St. where you can find ghost tours, carriage rides, and more....
Popular amenities for Cumberland family-friendly rentals
Family-friendly home rentals with a hot tub

Stoney Spring Overlook

StayAround Dome ~ Unique & Tranquil Gem ~ Sauna

The Glowing Logs Cabin

Apple Blossom Cottage HT is extra$

10 Mi. To Gettysburg Clean-HotTub Lakefront-Kayaks

The Frame ~ Charming Nature Escape ~ Hot Tub ~ BBQ

Mom's Cottage

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

Creekside Cabin - Pet Friendly

*Fully Fenced* Minutes to Gettysburg & Liberty Mtn

Cottage on our horse farm

Gettysburg 2 Easy Times

Lovely 2-bedroom apartment near McDaniel College

Spruce Run Cabin, a wooded retreat on the mountain

Beautiful private home in the country

Liberty Valley View - near ski slopes and golf
Family-friendly home rentals with a pool

Harmony Lodge nestled in wooded tranquility!

Cozy Secluded A-Frame Cabin Retreat

Civil War Farm House w/Heated (seasonal) Pool

Rollingside: Two-Room Guest Suite

All Seasons Retreat - Screened Porch - Fire Pit

*Cottage @ Firefly Cellars* VA Wine Country escape

Modern Cabin: Hot Tub, Arcade, FirePit, Pets+Pool

Master's Suite · 1920s Tudor Estate, Hunt Valley
Destinations to explore
- New York City Holiday rentals
- Philadelphia Holiday rentals
- Washington Holiday rentals
- Pittsburgh Holiday rentals
- Ocean City Holiday rentals
- Cleveland Holiday rentals
- Virginia Beach Holiday rentals
- Raleigh Holiday rentals
- Niagara Falls Holiday rentals
- Mississauga Holiday rentals
- Jersey City Holiday rentals
- Newark Holiday rentals
- Rentals with outdoor seating Cumberland
- House rentals Cumberland
- Rentals with a fireplace Cumberland
- Rentals with a patio Cumberland
- Rentals with breakfast Cumberland
- Apartment rentals Cumberland
- Pet-friendly rentals Cumberland
- Rentals with a washing machine and dryer Cumberland
- Bed and breakfasts Cumberland
- 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
- Merriweather Post Pavilion
- Harpers Ferry National Historical Park
- Cowans Gap State Park
- National Aquarium
- Caledonia State Park
- South Mountain State Park
- Baltimore Museum of Art
- Harbor East
- Whitetail Resort
- Loyola University Maryland
- Hersheypark Stadium
- Giant Center





