Family-friendly holiday 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.

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Guest favourite
A comfortable living area is presented, featuring a light-colored sofa with a decorative pillow. Two dark armchairs flank a rustic wooden coffee table, and a vintage rug adds warmth to the wood flooring. A framed photo and a door provide additional detail.
Flat in Gettysburg
4.94 out of 5 average rating, 158 reviews

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!

Top guest favourite
A single-story cottage features a red metal roof and a welcoming porch with seating. Lush greenery surrounds the property, and an American flag is displayed near the entrance. A gravel driveway leads up to the house, adding to the tranquil rural setting.
Cottage in Gettysburg
4.98 out of 5 average rating, 141 reviews

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.

Top guest favourite
A winding gravel driveway leads towards a wooden gate, framed by lush greenery and tall trees. The driveway is flanked by a wooden fence, providing a sense of privacy and seclusion. Soft natural light filters through the leaves overhead.
Flat in Gettysburg
4.99 out of 5 average rating, 211 reviews

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.

Superhost
A decorative wreath is displayed on a door, featuring an assortment of flowers and foliage in warm hues. The background consists of a textured glass door, allowing soft light to filter through, and the words 'WELCOME to The LOFT' are prominently featured.
Guest suite in Fairfield
4.87 out of 5 average rating, 259 reviews

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

Top guest favourite
The exterior of a spacious brick and stone house is shown, featuring multiple gabled windows and a prominent American flag. A circular driveway leads to a landscaped front yard, surrounded by lush green grass and mature trees.
Flat in Gettysburg
4.98 out of 5 average rating, 424 reviews

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.

Top guest favourite
The treehouse is perched among tall trees, featuring a wooden deck that wraps around its structure. A gentle staircase leads to the entrance. In the foreground, purple flowers bloom beside a rock outcropping, enhancing the natural landscape under a bright blue sky.
Treehouse in Shepherdstown
4.97 out of 5 average rating, 415 reviews

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.

Top guest favourite
Place to stay in Shippensburg
5 out of 5 average rating, 464 reviews

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

Top guest favourite
A well-appointed king bedroom features a tufted beige headboard and soft white bedding. Flanking the bed, two bedside tables with lamps provide illumination. A rounded ottoman sits at the foot of the bed, complemented by a light-colored area rug with subtle patterns.
Flat in Gettysburg
4.95 out of 5 average rating, 128 reviews

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

Guest favourite
A charming single-story house features a brick and siding exterior, accented by a red metal roof. A paved driveway leads to a two-car garage. Lush green grass surrounds the property, complemented by mature trees and shrubs, creating a welcoming entrance.
Home in Gettysburg
4.87 out of 5 average rating, 172 reviews

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.

Superhost
A cozy bedroom features a spacious bed complemented by a neutral-colored blanket. Wooden flooring and a rustic dresser add warmth, while an angled ceiling showcases natural wood panels. Soft light filters through the window, enhancing the tranquil atmosphere.
Flat in Gettysburg
4.86 out of 5 average rating, 109 reviews

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!

Top guest favourite
Holiday home in Gettysburg
4.96 out of 5 average rating, 103 reviews

New The Ridge is a Cozy 2-bedroom apartment

The Ridge is a Cozy 2 Q Bedrooms, 1 bath with walk in shower first floor apartment. It is located in Historic Gettysburg, Pa. just 2 blocks to downtown Gettysburg and 4 blocks to Gettysburg College. It is also located within walking distance to Restaurants, Wineries, Museums and Quaint shops and everything else that Gettysburg has to offer. We have everything to make you feel right at home. Early check in and late checkout (if possible) is $25.00 an hour.

Top guest favourite
The exterior of the Ertter House is displayed, featuring a white facade with six evenly spaced windows. A sturdy railing lines the entrance, highlighted by two front doors. The roof is topped with light-colored shingles, and power lines run along the street in front.
Townhouse in Gettysburg
4.9 out of 5 average rating, 232 reviews

The Ertter House

The Ertter House was built in 1843 by John and Mary Ertter." Mrs Shriver looked out her kitchen window in direction of the house and saw hundreds of Calvary riding by." Located one block off Baltimore Street within a 5 minute walk to restaurants, shopping, museums and a grocery store. Free Wifi -Roku TV to use for streaming. Within driving distance to Lancaster/ Amish country 1hr 30 mins Washington DC 1 hr 45 mins Antietam Battlefield 55 mins

Popular amenities for Cumberland family-friendly rentals