Family-friendly vacation rentals in Cumberland Township

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Top-rated family-friendly rentals in Cumberland Township

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

A spacious grassy yard is highlighted by a colorful playset, equipped with slides and climbing features. Sunlight filters through surrounding trees, casting gentle shadows on the lawn. The area is open and well-maintained, suitable for outdoor activities and play.

Apartment in Arnold

4.96 out of 5 average rating, 174 reviews

Celebrate Summer by Your Private Pool

Lovely 2 acre waterfront lower level attached apartment with separate private entrance. Exceptional amenities include an inground pool, a pier with kayaks and paddle boards, pickleball and basketball courts, a swing set with a rock wall for kids, a gas grill, and a pool table. This amazing water front home is conveniently located only seven miles from the Naval Academy and downtown Annapolis. We do not host parties or events. Only registered guests are permitted on the property.

Guest favorite

A cozy living area features soft lighting that highlights a colorful area rug with curved patterns. A welcoming orange couch and a matching armchair provide comfortable seating. A small round coffee table sits in the center, while a bookshelf filled with various items can be seen along the wall.

Cottage in Mount Gretna

4.89 out of 5 average rating, 269 reviews

Charming Cottage in the Heart of Mount Gretna

Whether you’re visiting for a quiet weekend, an artistic escape, or a nature-filled adventure, this one-of-a-kind cottage captures the spirit of Mount Gretna—where history, community, and natural beauty come together. Everything is within walking distance: local galleries, a pizza shop, the Hideaway Bar & Grill, scenic trailheads, the peaceful lake, the iconic Jigger Shop ice cream parlor, Mt Gretna Theater, making it the perfect base for exploring, relaxing, or catching a show.

Superhost

The cabin's living area features a warm wood interior with vaulted ceilings and large windows offering views of the lake. A comfortable brown leather sofa is positioned near a coffee table, complemented by two wooden armchairs. A cozy wood stove adds to the inviting atmosphere.

Cabin in Harpers Ferry

4.81 out of 5 average rating, 436 reviews

Cozy Cabin Hidden Away on a Lake!

MOUNTAIN MAMA VACATION HOMES The perfect getaway for any season! Enjoy the lake views inside next to a roaring fire, or in the summertime take the kids for a swim in the shallow water just off your private beach. Relax in the hot tub set in the back deck as the sun sets over the lake and the stars start to come out. Make every night movie night on the 50" 4k TV. Whether you want to stay in or see the area, this cabin has something for every member of the family!

Guest favorite

A cozy multi-bunk sleeping area features three built-in beds with plaid accents. A foosball table occupies the spacious hardwood floor, and large windows allow natural light to illuminate the room. Soft area rugs enhance the inviting atmosphere.

Farm stay in Ijamsville

4.96 out of 5 average rating, 292 reviews

Best Farm Stay Ever. Beautiful, affordable, fun!

Escape to our historic farm stay, where charm meets modern comfort. Enjoy the gourmet kitchen, unwind on the magnificent patio with a huge fire pit, and indulge in the infrared sauna. Perfect for families and friends, with an adorable kid's playhouse and games. Interact with friendly animals, immerse yourself in serenity, and experience the ultimate getaway near Whiskey Creek Golf Course in Ijamsville. Contact Fingerboard Farm directly for larger gatherings.

Guest favorite

A covered porch is supported by rustic wooden beams, featuring two green adirondack chairs and a circular coffee table. A hanging fern adds a touch of greenery above. Stone flooring complements the natural surroundings, which include lush shrubs and plants just beyond the porch.

Home in Fairfield

4.92 out of 5 average rating, 239 reviews

Brent Road Retreat

Rustic post and beam home rich with character. Five bedrooms and 2 full bath 2200 s/f sleeps up to 13. Cozy wood stove for heat with propane backup; a/c. House enjoys large yard and mature woodland surroundings. Relax on covered porch or large shaded deck and enjoy the biodiversity of your secluded surroundings. Five minutes to Liberty Resorts skiing and golf; 15 minutes to Gettysburg. Property features artwork from various local renowned artists.

Top guest favorite

A cozy sitting area is highlighted by natural light filtering through slatted windows. A sleek desk and dark wooden cabinet are positioned nearby, while a comfortable sofa is adorned with colorful cushions. A traditional rug adds warmth to the wooden floor.

Vacation home in Thurmont

4.94 out of 5 average rating, 182 reviews

"Breeches Pocket" C.Wr Log Cabin/House Getburg-DC

This Historic 4BR log Cabin (house) on "Saint Elizabeth" farm is a true gem. It is minutes from hiking and biking trails, ski resorts, history tours, and the Catoctin Mountains. It has exceptional architectural details and a gorgeous interior design. We have rented it for 14 years and maintain it at the highest level. We guarantee you will be thrilled with your stay. READ "show more" (below) to understand the layout of this house.

Guest favorite

A library featuring dark wooden furniture provides a serene reading space. A large bookshelf filled with books is complemented by a wooden desk with a lamp and a small potted plant. A vase of fresh flowers rests on a round coffee table, adding a touch of color.

Guesthouse in Frederick

4.98 out of 5 average rating, 179 reviews

Romantic Getaway - Heated Spa Open Year Round

Enjoy our beautifully decorated four bedroom home, furnished with unparalleled elegance and style. This tranquil guest house is located less than an hour from Washington DC and Baltimore, MD, and a half-hour from Gettysburg and Harper's Ferry and offers luxurious rooms with unparalleled elegance and style. For the ultimate pampered experienced, guests can arrange for in-house spa services such as a full-body therapeutic massage.

Top guest favorite

A park scene is visible, featuring a playground with colorful slides and climbing structures framed by several green trees. People are seen enjoying the space, with some pushing strollers on the grassy area. The setting appears to be family-friendly and inviting.

Townhouse in Federal Hill - Montgomery

4.96 out of 5 average rating, 196 reviews

Fed Hill & Inner Harbor / BEST Location & Reviews!

Walk to EVERYTHING! Steps to the Inner Harbor, museums, restaurants, stadiums, & parks. Charm City Circulator & Water Taxi nearby for access to the entire city! Bright home in Historic Federal Hill. Live like a local in an upscale setting! Quiet, comfortable 2 bedroom home perfect for families Preference for booking age to be 25 or older. Baltimore is thriving & evolving, see for yourself how beautiful the area is year round!

Top guest favorite

A charming multi-story home features a light-colored wooden exterior, complemented by stone pathways and a staircase. Flags adorn the exterior, and a spacious deck area is visible, surrounded by greenery. The building's architectural details showcase a blend of historical and modern design.

Home in Harpers Ferry

4.94 out of 5 average rating, 394 reviews

Gayte House Gay Owned, Liberal Oasis

Cozy and charming 1840's home in the heart of town. Steps from the National Park, feet from the Appalachian Trail. Relax by the fire, on the porch or on the river. We have something for every season and every age. Steve and I have lived here In HF 20 yrs., 13 of those at the Gaytehouse. We live right next door now and Love both our homes. Please, Check out the beautiful and cherished home we offer for your stay.

Guest favorite

The exterior view showcases a spacious driveway leading up to a two-story house, surrounded by lush greenery. Tall trees provide shade, while a manicured hedge adds to the landscape. The setting exudes tranquility, reflecting the peaceful mountain surroundings.

Apartment in Bluemont

4.94 out of 5 average rating, 154 reviews

Charming private apartment

"Magical." This second story apartment, surrounded by giant spruces, is sited at the top of the Blue Ridge mountains, with a long sweep of lawn guiding the eye to the Shenandoah Valley below. The view is stunning. Peace and quiet reign. Here it's quiet except for the chirp of birds. Gardens are plentiful with flowers and the smell of old boxwood.

Top guest favorite

A welcoming entryway displays a blue bench with a decorative chicken and a sign reading 'WELCOME.' A vintage suitcase is placed beside the bench, while the door opens to a view of the outdoors, framed by a rustic stone wall.

Cabin in Glen Rock

4.99 out of 5 average rating, 126 reviews

The Chicken Coop- Secluded log cabin

1840's log home with cozy rooms. Three season porch. Babbling brook. Hooting owls and stars at night. Claw foot tub. Games and puzzles. Line dried sheets and towels. Cleaned with environmentally friendly cleansers only. Farm-fresh eggs, yogurt, muffins, fruit for breakfast. Full 18 hole Disc Golf course on property for guests to enjoy.

Guest favorite

A single-story cottage is set against a backdrop of lush trees and greenery. The property features a large front yard, with a neatly trimmed lawn and shrubs framing the home. A gravel path is visible leading towards a wooded area.

Home in Enola

4.95 out of 5 average rating, 334 reviews

Whole Home, Wooded Serenity, Urban Proximity

Nestled on the base of Blue Mountain, this Central Pennsylvania cottage offers relaxing wooded serenity with urban proximity. Local Attractions Drive time (Minutes) 10-15: PA Farm Show Complex / Carlisle Fairgrounds / Appalachian Trail access 35-40: Hershey Park / Giant Center 55-60: Gettysburg / Lancaster Dutch Country