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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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Top Guest favourite
A cottage exterior is presented, featuring blue siding and white trim. Decorative window boxes hold greenery beneath two gabled windows. A welcoming front porch is adorned with American flags. Lush grass and shrubs surround the home, contributing to its inviting appearance.
Cottage in Gettysburg

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.

FamilyIndoor spacesAccess

5.0 out of 5 average rating, 418 reviews
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

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.

Indoor spacesKitchenCleanliness

4.98 out of 5 average rating, 156 reviews
Top Guest favourite
A shaded seating area features a round table surrounded by four chairs beneath a large tree. Nearby, a picnic table provides additional seating, with an open grassy space visible in the background. A barn and fenced area are partially seen in the distance.
Home in Gettysburg

A "Suite" Place to Crash

NO CLEANING FEE. LG/SM FAMILIES, SCOUTS, REUNIONS, YTH GRPS. 1st bedrm-queen. 2nd bedrm-4 single beds and crib. If grp is larger, there are 4 queen hotel-quality sofabeds in the lg room, 1 rollaway and 1 mattress. Room on the floor for kids who bring their own sleeping bags. 2 bathrms/showers. Kitchen-340 sf attached to the suite seating 16+. You may also tent outside. 50 inch Smart TV. 2nd TV for DVD’s. Ping pong and fooseball inside. Strict $8/person/night over 5 people. NO DRUNKEN PARTIES!!

FamilyKitchenHeating

4.94 out of 5 average rating, 533 reviews
Top Guest favourite
The front facade of a historic brick home features a central door adorned with a decorative wreath. Flanking windows, accented by dark frames, showcase decorative panes. Colorful flower pots are placed on either side of the entrance, adding a touch of vibrancy to the exterior.
Home in Gettysburg

*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!

FamilyKitchenDecor

5.0 out of 5 average rating, 220 reviews
Top Guest favourite
A historic stone farmhouse from 1861 is set on a well-maintained lawn, surrounded by green shrubbery and trees. The two-story structure features red shutters on the windows and a welcoming front porch that invites relaxation.
Home in Gettysburg

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.

FamilyKitchenHeating

5.0 out of 5 average rating, 317 reviews
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.
Apartment in Gettysburg

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

Indoor spacesFamilyLayout

4.96 out of 5 average rating, 144 reviews
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

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.

Indoor spacesFamilySleep quality

4.85 out of 5 average rating, 189 reviews
Top Guest favourite
A spacious home is set on a green lawn, surrounded by tall trees. Mountain and valley views stretch in the background, capturing the serene countryside atmosphere. The home's exterior features a combination of siding and a metal roof, lending a rustic charm.
Home in Fairfield

Liberty Valley View - near ski slopes and golf

Relax in this completely renovated 3 bedroom home. Enjoy the peaceful quiet country scenery. Sleeps 6 people. Perfect for families or 3 couples. Enjoy the spectacular mountain and valley views from within the home and covered deck. Less than 2 miles from Liberty Mountain Resort with views of the back ski slopes. Multiple golf courses within a 15 minute drive. Approximately 8 miles from the Gettysburg National Park. Roku TV's in all bedrooms and family room ready for your apps.

FamilyIndoor spacesAccess

4.99 out of 5 average rating, 175 reviews
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.
Apartment in Gettysburg

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!

Indoor spacesFamilyCheck-in

4.94 out of 5 average rating, 165 reviews
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.
Apartment in Gettysburg

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!

Indoor spacesKitchenAir conditioning

4.83 out of 5 average rating, 124 reviews
Top Guest favourite
A charming two-story brick house stands with a red metal roof and black shutters. The front entrance features a multi-paned door, flanked by symmetrical windows. A small stone porch leads to the entrance, with neatly arranged landscaping and a partially visible carport on the left.
Home in Gettysburg

"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.

KitchenIndoor spacesParking

5.0 out of 5 average rating, 251 reviews
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

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

Indoor spacesFamilyWi-Fi

4.9 out of 5 average rating, 240 reviews

Popular amenities for Cumberland family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top Guest favourite
The spacious kitchen features gray cabinetry and a center island with a stone countertop. Stainless steel appliances complement the rustic wood accent wall. Open shelving holds various kitchenware, while natural light floods the room from nearby windows, creating a bright and inviting cooking space.
Home in Orrtanna

Relax near Gettysburg ski/wineries/fire pit!

KitchenIndoor spacesSleep quality

4.92 out of 5 average rating, 149 reviews
Top Guest favourite
Place to stay in Shippensburg

The Frame ~ Charming Nature Escape ~ Hot Tub ~ BBQ

FamilyKitchenView

5.0 out of 5 average rating, 485 reviews
Top Guest favourite
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

Brent Road Retreat

Indoor spacesFamilyHeating

4.93 out of 5 average rating, 272 reviews
Top Guest favourite
The exterior of a single-story cottage showcases a welcoming entrance with a wooden ramp leading to the front door. Lush green grass and light landscaping surround the home, which is framed by tall trees. A covered area is visible at the side of the structure.
Cottage in Fairfield

Mom's Cottage

Indoor spacesKitchenAccess

4.97 out of 5 average rating, 158 reviews
Top Guest favourite
A spacious mountain home is set against a backdrop of trees, with a gently sloping field leading to a small pond in the foreground. A wooden fence encircles the property, highlighting the serene outdoor environment that encompasses the house.
Home in Sabillasville

Stoney Spring Overlook

KitchenFamilyBathroom

4.95 out of 5 average rating, 154 reviews
Top Guest favourite
A warm living room is highlighted by wooden beams overhead and natural light streaming through French doors. A cozy sofa is positioned beside a rustic coffee table adorned with decorative items. Soft greenery is placed on surfaces, enhancing a serene environment.
Cabin in Railroad

The Creek House: Waterfront with Hot Tub & E-bikes

KitchenFamilyHot tub

5.0 out of 5 average rating, 140 reviews
Top Guest favourite
A spacious screened-in porch is shown, featuring wooden beams and skylights that allow natural light to flood in. Comfortable seating options are positioned to enjoy views of the surrounding trees and the lake, enhancing the serene environment.
Home in Fairfield

10 Mi. To Gettysburg Clean-HotTub Lakefront-Kayaks

KitchenFamilyCheck-in

5.0 out of 5 average rating, 132 reviews
Top Guest favourite
The unique dome structure is surrounded by lush trees, featuring large windows and a cozy entrance. An inviting outdoor seating area with a fire pit and black chairs is positioned on the wraparound deck, accompanied by a hammock and a hot tub.
Dome in Mercersburg

StayAround Dome ~ Unique & Tranquil Gem ~ Sauna

FamilyKitchenComfort

4.99 out of 5 average rating, 259 reviews

Family- and pet-friendly home rentals

Top Guest favourite
A historic stone building is featured, characterized by a red front door and multiple large windows. The entrance is framed by a low stone staircase and wrought iron railing. Trees are visible in the foreground, offering a natural touch to the urban setting.
Apartment in Gettysburg

Historic Downtown The Red Door- 1st floor

Indoor spacesFamilyAccuracy

4.92 out of 5 average rating, 195 reviews
Guest favourite
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

Gettysburg-Ski-Golf-AT Hikes-RoseSniffers LOFT

FamilyKitchenLayout

4.88 out of 5 average rating, 274 reviews
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.
Apartment in Gettysburg

Rebel Hollow

FamilyIndoor spacesCheck-in

4.98 out of 5 average rating, 241 reviews
Top Guest favourite
The log cabin features a spacious covered porch surrounded by trees. The wooden structure blends into the natural setting, while large windows invite natural light. The front yard is landscaped with shrubs, providing a warm and inviting entrance.
Home in Thurmont

Cabin in the Woods - Weekday Specials!

Indoor spacesFamilyHospitality

4.87 out of 5 average rating, 635 reviews
Top Guest favourite
A porch area is depicted featuring a decorative green wall with illuminated dog-themed accents. Black outdoor chairs and a coffee table are arranged on a wooden floor, complemented by a patterned blue rug. A ceiling fan provides an additional comfort feature.
Home in Gettysburg

*Fully Fenced* Minutes to Gettysburg & Liberty Mtn

Indoor spacesKitchenOutdoor spaces

5.0 out of 5 average rating, 133 reviews
Guest favourite
A charming cottage exterior features a gray metal roof and a welcoming entry with blue trim. A covered porch invites relaxation, while two wooden chairs and a small table provide a cozy outdoor seating area. Lush green grass surrounds the property.
Cottage in Orrtanna

Sweet Gettysburg Area Cottage Close to Outdoor Fun

KitchenIndoor spacesValue

4.89 out of 5 average rating, 160 reviews
Top Guest favourite
A living area is presented with a soft blue couch and a dark coffee table resting on a patterned area rug. Natural light enters through multiple windows, and a pair of neutral curtains frame them. Additional doors lead to other spaces within the home.
Home in Gettysburg

Gettysburg 2 Easy Times

KitchenIndoor spacesQuiet

4.92 out of 5 average rating, 146 reviews
Top Guest favourite
A rustic barn is positioned against a backdrop of barren trees during winter. The scene is accentuated by a gentle blanket of snow, creating a calm landscape. A sign in the distance indicates the property entrance, adding to the serene outdoor setting.
Home in New Oxford

A Place to make Memories

KitchenFamilyQuiet

4.98 out of 5 average rating, 122 reviews

Family-friendly home rentals with a pool

Guest favourite
Home in New Market

Historic Peace and Plenty Farm: Pool House

FamilyKitchenValue

4.92 out of 5 average rating, 163 reviews
Guest favourite
A spacious backyard features a large in-ground pool with two fountains, surrounded by a concrete deck. Lounge chairs are positioned around the pool, and vibrant flowers add color. A screened gazebo is visible in the background, providing shaded seating for relaxation.
Home in Mechanicsburg

POOL & Lrg Private Yard, Gazebo, Outdoor Kit/Bath!

FamilyIndoor spacesLong stay

4.89 out of 5 average rating, 101 reviews
Top Guest favourite
Farm stay in Cockeysville

The Master's Suite · King Suite, Hunt Valley

Indoor spacesKitchenCheck-in

4.95 out of 5 average rating, 145 reviews
Guest favourite
An expansive outdoor pool is set against a backdrop of lush greenery and trees. Warm lighting from the stone cottage bathes the area in a soft glow, creating a tranquil ambiance in the early evening. The pool's water reflects blue hues, inviting a sense of relaxation.
Cottage in Wrightsville

The Stone Cottage w-hot tub, a romantic escape

Indoor spacesKitchenAccuracy

4.96 out of 5 average rating, 205 reviews
Guest favourite
A wooden deck extends from the cabin, surrounded by lush green trees. A striped awning provides shade over a picnic table, creating a space for outdoor dining or relaxation. The natural ambiance enhances the secluded feel of the property.
Cabin in Keedysville

Quiet Antietam Cabin

Indoor spacesFamilyBarbecue

4.82 out of 5 average rating, 129 reviews
Guest favourite
The exterior of the farmhouse is showcased at dusk, highlighting the blend of historic and modern architecture. A stone path leads to the welcoming entry, framed by glowing flower pots. The wraparound porch features multiple illuminated windows, reflecting a cozy and inviting ambiance.
Home in Harpers Ferry

Historic Farmhouse | Heated Plunge Pool, Billiards

Indoor spacesFamilyBackyard

4.96 out of 5 average rating, 219 reviews
Guest favourite
A heated pool is surrounded by a stone wall and lush greenery, offering a serene atmosphere. The lodge features large windows and a balcony overlooking the pool area, seamlessly connecting indoor and outdoor spaces.
Guest suite in Myersville

Harmony Lodge nestled in wooded tranquility!

KitchenFamilyAccuracy

4.92 out of 5 average rating, 343 reviews
Guest favourite
A compact kitchen features dark wooden cabinetry and a granite countertop. Modern appliances include a stainless steel stove and a dishwasher, with a sink positioned beneath a window allowing natural light. A small plant adds a touch of greenery to the countertop.
Apartment in Hershey

5 Minutes from Hershey Park/ Hershey Giant Center!

Indoor spacesKitchenCondition

4.9 out of 5 average rating, 124 reviews

Destinations to explore