
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
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Quiet Escape with Creek, Chiminea & Kids Nook
Voted #1 rental 2021–2026, & 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.
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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.
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*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!
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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
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Civil War Farm House w/Heated (seasonal) Pool
Welcome to this historical Civil War Farm House. This stone home built in 1861 by Christian Shriver and was actively used as a field hospital during the war. Mrs Shriver prepared General Reynolds his breakfast on the first day of the battle (which he was killed). The Durboraw's moved here in the early 1890's and have remained here on the farm ever since. Please note, pool is open seasonally mid-May through mid- Sept. Please inquire to its opening/closing if booking around these times.
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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.
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The Frame ~ Charming Nature Escape ~ Hot Tub ~ BBQ
Escape to the charming 2BR 1Bath A-frame on a secluded wooded property just 10 mins away from Shippensburg, PA. Whether you're looking to savor nature‘s tranquility from the luxurious hot tub, share stories around the fire pit, or explore picturesque Cumberland Valley, this will be the ideal starting point for your adventures. *2 Comfortable BRs *Open Design Living *Full Kitchen *Smart TV *Backyard (Hot Tub, Sauna, Fire Pit, BBQ, Outdoor shower) *High-Speed Wi-Fi *Free Parking *EV charger
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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
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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!
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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!
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"The Historic Rowe House" Circa 1819
This charming, battle-scarred home sits in the heart of Gettysburg’s historic downtown, just a short walk from unique shops and the main square. Nearby, you’ll find popular spots like the Dobbin House, Garryowen, and Blue & Gray Grille, along with attractions such as the newly restored Lincoln Train Station, battlefield tours, museums, and more. Don’t miss the chance to stay in a witness house that stood right in the middle of the Confederate battle line.
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Popular amenities for Cumberland family-friendly rentals
Family-friendly home rentals with a hot tub

Mom's Cottage
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Relax near Gettysburg ski/wineries/fire pit!
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StayAround Dome ~ Unique & Tranquil Gem ~ Sauna
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Apple Blossom Cottage HT is extra$
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The Glowing Logs Cabin
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The Creek House: Waterfront with Hot Tub & E-bikes
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Spectacular views, intimate dome
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10 Mi. To Gettysburg Clean-HotTub Lakefront-Kayaks
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Family- and pet-friendly home rentals

Sweet Gettysburg Area Cottage Close to Outdoor Fun
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Liberty Valley View - near ski slopes and golf
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Gettysburg 2 Easy Times
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The Crooked Cottage: a Cozy, Curated Escape
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Historic Downtown The Red Door- 2nd floor
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Cabin in the Woods - Weekday Specials!
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The Ivy Loft in Westminster
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Apartment on Peace Ridge Farm
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Family-friendly home rentals with a pool

Rest and Recharge Retreat
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Stoney Spring Overlook
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Historic Peace and Plenty Farm: Pool House
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Quiet Antietam Cabin
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The Master's Suite · King Suite, Hunt Valley
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Poolside Paradise in Monrovia, Maryland.
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Container Pool, Hot Tub, Games, Espresso Machine
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Rollingside: Two-Room Guest Suite
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Destinations to explore
- New York City Holiday rentals
- Philadelphia Holiday rentals
- Washington Holiday rentals
- Ocean City Holiday rentals
- Pittsburgh Holiday rentals
- Cleveland Holiday rentals
- Virginia Beach Holiday rentals
- Raleigh Holiday rentals
- Niagara Falls Holiday rentals
- Jersey City Holiday rentals
- Mississauga Holiday rentals
- Baltimore Holiday rentals
- Hersheypark
- M&T Bank Stadium
- Baltimore Convention Center
- Johns Hopkins University
- Oriole Park at Camden Yards
- Federal Hill Park
- Liberty Mountain Resort
- Hershey's Chocolate World
- Spooky Nook Sports
- CFG Bank Arena
- Merriweather Post Pavilion
- Harpers Ferry National Historical Park
- Roundtop Mountain Resort
- Cunningham Falls State Park
- Cowans Gap State Park
- National Aquarium
- Harbor East
- South Mountain State Park
- Caledonia State Park
- Hersheypark Stadium
- Whitetail Resort
- Baltimore Museum of Art
- Pennsylvania Farm Show Complex & Expo Center
- Greenbrier State Park





