
Family-friendly vacation rentals in Cumberland
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Top-rated family-friendly rentals in Cumberland
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

*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!

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.

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.

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

Spacious 4 BR Townhome near downtown Gettysburg
It's a battle out there! Relax & retreat to this stunning 4BR/2.5BA townhome located just outside downtown Gettysburg. Experience the comfort and convenience this home offers while you enjoy the battlefields, Gettysburg College, Liberty Ski Resort and numerous other local attractions. We aimed to create a space where modern meets history by highlighting several local pieces of art found in Gettysburg. This property is professionally owned and managed by Burkentine Property Management.

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 and living room areas are available as well. Relax on the back deck with a cocktail and grill or enjoy the garage complete with TV setup and workout equipment (Not in the Winter months). You can enjoy all Gettysburg has to offer with this perfectly located home.

Rebel Hollow
Come stay with us for the ultimate battlefield experience! The 1920s Farmhouse on 10 wooded acres on Willoughby Run directly across the street from the Herbst Woods where the first day's infantry battle occurred on July 1st, 1863. It is hard to get much closer, with less than a 2 minute drive to the battlefield and a 4 minute drive to historic downtown Gettysburg. On our property you will encounter our ducks, geese, chickens, Friday the cat, 2 goats and 2 friendly farm dogs

Gettysburg 2 Easy Times
Take a break and unwind at this peaceful oasis. In Rural Gettysburg but just 6 miles from the Gettysburg Square. Sit outside and enjoy one of the most Gorgeous Sunsets. 2 Small Bedrooms and open living room, dining room and kitchen area. Everything has been renovated. Very clean. Laundry room in breezeway. Front porch and adequate parking. Single family home on over .5 acre lot. Central to Hanover and Gettysburg and only 20 miles from York PA also

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!

Stoney Spring Overlook
This beautiful mountain home offers breathtaking views of the surrounding Catoctin Mountains. The area is rich with outdoor adventures and attractions. Though it feels like a peaceful retreat tucked away in the mountains, it’s only 30 minutes from Frederick, MD, historic Gettysburg, PA, and about an hour from the Washington, D.C. area. Whether you’re seeking a quiet escape or hoping to explore more of the Frederick County.

Cottage on our horse farm
"Dream on Farm" has a cottage that is cozy, airy and very spacious. It is very comfortable for 2 and can accommodate 6. Full kitchen, living area and bathroom. Bring your horses and/or dogs. 25 min. from Gettysburg, 5 min. from local golfing. 1 acre fenced in for monitored dog run area. Great internet and smart TV. No cleaning or dog Fees so we ask you to be considerate. Thank you.

Edward Menchey House
The Historic Edward Menchey House in Gettysburg, PA. Downtown attractions and restaurants are within easy walking distance. You will be staying on the first floor with a large bedroom and a queen bed, family room, kitchen, bathroom, and washer and dryer. The outside patio has chairs and a grill available. Free wifi, cable, and parking space in the rear of the building.
Popular amenities for Cumberland family-friendly rentals
Family-friendly home rentals with a hot tub

StayAround Dome ~ Unique & Tranquil Gem ~ Sauna

-The Pool Cottage at The Roundtop Estate-

Apple Blossom Cottage HT is extra$

Copper Flat Cottage

Mom's Cottage

Spectacular views, intimate dome

Brent Road Retreat

Beautiful, rustic/unique home near Gettysburg!
Family- and pet-friendly home rentals

The Emerald Roof, Historic Home Downtown Frederick

Sweet Gettysburg Area Cottage Close to Outdoor Fun

Charming vintage cabin in the ❤️ of Middletown.

Beautiful private home in the country

Steps to Winery & Battlefield – 1 Acre Retreat

Jewel Vinsota Artist's Guesthouse

Conewago Cabin #3

One-bedroom apartment with separate entrance.
Family-friendly home rentals with a pool

Harmony Lodge nestled in wooded tranquility!

Bear Pines Retreat ~ Game Room ~ Screened Porch

Cozy Secluded A-Frame Cabin Retreat

Splash by Hershey

Wizard's Escape | Sleep15+ | 2 Escape Rooms &Pool

Patterson Park Penthouse with Rooftop Deck!

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

Gunpowder Retreat
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- Family-friendly rentals Adams County
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- Family-friendly rentals United States
- M&T Bank Stadium
- Hersheypark
- Liberty Mountain Resort
- Baltimore Convention Center
- Whitetail Resort
- Oriole Park at Camden Yards
- Roundtop Mountain Resort
- Cunningham Falls State Park
- Codorus State Park
- Johns Hopkins University
- Cowans Gap State Park
- Caledonia State Park
- Hershey's Chocolate World
- Gambrill State Park
- CFG Bank Arena
- Baltimore Museum of Art
- South Mountain State Park
- Spooky Nook Sports
- National Aquarium
- Loyola University Maryland
- Harpers Ferry National Historical Park
- Merriweather Post Pavilion
- Big Cork Vineyards
- The Walters Art Museum




