
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.

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.
4.98 out of 5 average rating, 158 reviews
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.
5.0 out of 5 average rating, 420 reviews
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!!
4.94 out of 5 average rating, 536 reviews
*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!
5.0 out of 5 average rating, 223 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
4.88 out of 5 average rating, 280 reviews
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.
5.0 out of 5 average rating, 320 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
4.96 out of 5 average rating, 146 reviews
The Cock and Feather Guesthouse
AS OF 09/14/26 OUR DAILY RATE WILL INCREASE TO $11O. THIS INCREASE IS THE RESULT OF A 15.5% AIRBNB GUEST/HOST SERVICE CHARGE WHICH WILL NOW BE PAID ENTIRELY BY THE HOST. GUESTS WILL NO LONGER PAY AN AIRBNB SERVICE CHARGE. THE TOTAL PAYMENT FOR OUR GUESTS WILL REMAIN BASICALLY THE SAME AS IT HAS BEEN IN THE PAST. OUR CALENDAR IS OPEN THROUGH DECEMBER 19, AFTER WHICH WE WILL BE CLOSED UNTIL APRIL 1, 2027. PLEASE READ ALL OF THE HOUSE RULES BEFORE BOOKING YOUR RESERVATION
4.99 out of 5 average rating, 495 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!
4.93 out of 5 average rating, 166 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!
4.83 out of 5 average rating, 127 reviews
"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.
5.0 out of 5 average rating, 256 reviews
The Enchanting Lavender House
The Lavender House is an enchanting pre-Civil War farmhouse nestled in the middle of a working 600 acre farm. It was remodeled with love 18 years ago and became a cozy family home, where children grew and memories were created. Full of charm, The Lavender House boasts hand chosen antiques, beautiful wood beams, original hard wood flooring and a wood burning fireplace to warm your winter nights. We hope you enjoy your stay at The Lavender House!
4.93 out of 5 average rating, 317 reviewsPopular amenities for Cumberland family-friendly rentals
Family-friendly home rentals with a hot tub

Relax near Gettysburg ski/wineries/fire pit!
4.92 out of 5 average rating, 150 reviews
Brent Road Retreat
4.93 out of 5 average rating, 272 reviews
The Frame ~ Charming Nature Escape ~ Hot Tub ~ BBQ
5.0 out of 5 average rating, 489 reviews
Stoney Spring Overlook
4.95 out of 5 average rating, 156 reviews
Mom's Cottage
4.98 out of 5 average rating, 161 reviews
StayAround Dome ~ Unique & Tranquil Gem ~ Sauna
4.99 out of 5 average rating, 261 reviews
10 Mi. To Gettysburg Clean-HotTub Lakefront-Kayaks
5.0 out of 5 average rating, 135 reviews
Beautiful 5 star Mansion, Pool, Home Theater
4.85 out of 5 average rating, 193 reviewsFamily- and pet-friendly home rentals

Historic Downtown The Red Door- 1st floor
4.92 out of 5 average rating, 196 reviews
Rebel Hollow
4.98 out of 5 average rating, 246 reviews
*Fully Fenced* Minutes to Gettysburg & Liberty Mtn
5.0 out of 5 average rating, 134 reviews
Cabin in the Woods - Weekday Specials!
4.87 out of 5 average rating, 638 reviews
Liberty Valley View - near ski slopes and golf
4.99 out of 5 average rating, 178 reviews
Sweet Gettysburg Area Cottage Close to Outdoor Fun
4.9 out of 5 average rating, 164 reviews
The Ivy Loft in Westminster
4.99 out of 5 average rating, 102 reviews
A Place to make Memories
4.98 out of 5 average rating, 122 reviewsFamily-friendly home rentals with a pool

Historic Peace and Plenty Farm: Pool House
4.92 out of 5 average rating, 165 reviews
Rest and Recharge Retreat
4.96 out of 5 average rating, 114 reviews
POOL & Lrg Private Yard, Gazebo, Outdoor Kit/Bath!
4.89 out of 5 average rating, 102 reviews
The Master's Suite · King Suite, Hunt Valley
4.95 out of 5 average rating, 147 reviews
The Stone Cottage w-hot tub, a romantic escape
4.96 out of 5 average rating, 207 reviews
Quiet Antietam Cabin
4.82 out of 5 average rating, 129 reviews
Historic Farmhouse | Heated Plunge Pool, Billiards
4.96 out of 5 average rating, 221 reviews
4BR, 4BA, Amazing Indoor Pool, EV charger, ~10 acr
4.88 out of 5 average rating, 105 reviewsDestinations to explore
- New York Holiday rentals
- Philadelphia Holiday rentals
- Washington Holiday rentals
- Ocean City Holiday rentals
- Pittsburgh Holiday rentals
- Cleveland Holiday rentals
- Virginia Beach Holiday rentals
- Niagara Falls Holiday rentals
- Raleigh Holiday rentals
- Jersey City Holiday rentals
- Mississauga Holiday rentals
- Newark Holiday rentals
- Hersheypark
- M&T Bank Stadium
- Liberty Mountain Resort
- Johns Hopkins University
- Federal Hill Park
- Oriole Park at Camden Yards
- Hershey's Chocolate World
- CFG Bank Arena
- Baltimore Convention Center
- Harpers Ferry National Historical Park
- Spooky Nook Sports
- Roundtop Mountain Resort
- National Aquarium
- Cowans Gap State Park
- Cunningham Falls State Park
- Harbor East
- South Mountain State Park
- Caledonia State Park
- Baltimore Museum of Art
- Pennsylvania Farm Show Complex & Expo Center
- Greenbrier State Park
- Hersheypark Stadium
- Giant Center
- Broad Street Market





