Family-friendly vacation rentals in Waterford

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Waterford

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

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Guest favorite

Guesthouse in Middletown

4.95 out of 5 average rating, 247 reviews

Indulge, Fresh Flowers, Frederick County Haven

2 bedroom, full kitchen and laundry, 1 level guesthouse beside detached garage (separate from main house). The front has a rose garden, birdbath and your own patio. An apple tree is beside the guesthouse. A farm is to the back. Asian cafe, Subway, Dempsey's Grill, Amvets, Main Cup bar and restaurant, Tapia's and 3 ice cream parlors are all a short walk away. More restaurants and grocery store are less than a mile. Farmer's market in season on Thursdays. Fresh flowers and coffee are provided.

Apr 5 – 12

R2,000 ZAR per night

Guest favorite

Cabin in Lovettsville

4.97 out of 5 average rating, 120 reviews

Rustic cabin + modern luxury in Lovettsville

Enjoy a one-of-a-kind stay in this restored 1800s cabin guest house with modern updates and beautiful decor. Off the beaten track but only about 1 hour from both DC and Baltimore. Located on a working farmstead and close to wine country, breweries, a goat cheese creamery, farm-to-table dining, and more. A favorite landing place for those out in the country enjoying Loudoun's Artists' Tour, Farm Tour, Wine Country Half Marathon, a wedding, a hiking trip, or just a weekend in the countryside.

Oct 24 – 31

R2,576 ZAR per night

Guest favorite

Guesthouse in Keedysville

4.98 out of 5 average rating, 191 reviews

City Dog Farm

Comfortable, light-filled one bedroom apartment on 10 acres in Maryland near Antietam battlefield and Harpers Ferry, WV. We have chickens, an organic garden, hills, woods and a stream. Apartment is 15 minutes from Harpers Ferry, Antietam battlefield, the C&O canal, river rafting on the Potomac or Shenandoah, vineyards, the Appalachian trail and small towns including Boonsboro and Shepherdstown, WV. 30 minutes to Frederick or Hagerstown/1.5 hours to DC or Baltimore. SORRY NO PETS

Jul 11 – 18

R2,375 ZAR per night

Guest favorite

Cottage in Winchester

4.97 out of 5 average rating, 425 reviews

Emma's Stone Cottage

Relax and unwind in the privacy of this wonderful stone cottage, which sits on 15 beautiful acres. In addition, it is located only 2.5 miles from I-81 and 14 minutes from Winchester Medical Center, Old Town Winchester, Shenandoah University and much more. Our cottage is fully furnished with all the comforts of home. From the full kitchen, central air, water softener, HD smart televisions, Wifi, outdoor firepit and more. It has everything you need for a peaceful and enjoyable stay.

Jul 30 – Aug 6

R2,318 ZAR per night

Guest favorite

Farm stay in Lovettsville

4.99 out of 5 average rating, 273 reviews

Wine Country Cottage!

Relax and enjoy the countryside! Historic 1796 Brookdale Farm Guesthouse nestled in the rolling hills of Northern Virginia’s wine country! This quaint cottage was formerly a schoolhouse located in Hillsboro, Va. In the early 1900's, this building was pulled 11 miles by mule to its current location. Residents of Lovettsville walked along side the mules to watch this local, historic event. The schoolhouse now sits in a neighborhood surrounded by horse farms and mountain views.

Apr 18 – 25

R2,936 ZAR per night

Guest favorite

Farm stay in Knoxville

4.97 out of 5 average rating, 262 reviews

Paradise Farm—Near Harpers Ferry

If you love animals and the country this is the place for you! Come visit our "paradise." Horses, cows, goats, donkey and a range of feathered exotics are right out your front door. Short drive to the Potomac river, C&O Canal, Harpers Ferry National Historic Park, Antietam Battlefield, Appalachian Trail, Shepherdstown, WV. Outfitters nearby offer rafting, kayaking/canoeing, tubing, ziplines. Vineyards all around. Hosts live in attached house and are nearby if needed.

Aug 1 – 8

R2,345 ZAR per night

Guest favorite

Home in Waterford

4.99 out of 5 average rating, 122 reviews

Restored 1820 Waterford Village Farm

We restored this 1820 village farmhouse in 2016. It is situated in the heart of the historic village of Waterford. It has 2 1/2 acres behind, with two barns, a herd of very friendly goats, chickens, and vegetable, herb and flower gardens. The house backs up to The Phillips Farm, 150 acres of preserved land and public walking trails. Beautiful sunset views from the back porch. The house, a work in progress, was featured in both Country Living and Preservation Magazines.

Jun 8 – 15

R6,094 ZAR per night

Guest favorite

Apartment in Leesburg

4.96 out of 5 average rating, 191 reviews

Heart of Loudoun Entire basement!

Guests love it here! Tucked away at the end of the lane yet right in the heart of Loudoun County. Private keyless entrance basement. Natural light filled fully equipped kitchen with full size appliances. King bed, full bath and a very spacious living room with 70" tv or movie screen...you choose! We have super fast Verizon Fios. Not your typical basement. Country living!!! There are many vineyards less than 10 minutes away and we are happy to make recommendations.

Sep 12 – 19

R3,042 ZAR per night

Guest favorite

Tiny home in Purcellville

4.96 out of 5 average rating, 314 reviews

Remote Tiny House in Purcellville

Nestled in the heart of Purcellville is a tiny home with a ton of charm. Less than 5 miles from vineyards, LOCO ale trail breweries, cideries, WO&D bike trail & 20 min to historic Leesburg, the Shenandoah river & Appalachian Trail. Our tiny house is a bit larger w/ 2 bedrooms, full kitchen & bath, family room & cozy front porch. Guests enjoy private parking & plenty of privacy. Enjoy a remote work getaway, (our broadband is about 8-10Mbps) relax & enjoy LOCO living!

Apr 21 – 28

R2,806 ZAR per night

Guest favorite

Guesthouse in Frederick

4.97 out of 5 average rating, 316 reviews

The Shady Bear Cabin

After a complete renovation, we decided the cabin would be perfect for Airbnb. It's completely separate from the main house and offers both of us a great deal of privacy. It is also warm and cozy yet extremely comfortable. Please be aware that we have dogs on the property. If you are not comfortable with dogs, please do not book this cabin. If you are, we hope to see you. DURING THE PANDEMIC WE WILL BE FOLLOWING AIRBNB'S ENHANCED CLEANING PROTOCOL.

Feb 16 – 23

R2,702 ZAR per night

Guest favorite

Cottage in Waterford

4.95 out of 5 average rating, 324 reviews

Grace Cottage, Unique Restored Church in Waterford

Grace Cottage has been expertly re-designed to be a unique studio-style living space. It has one California king bed, a living area, large library, dining area and a fully-stocked kitchen space with a stove (no oven). There are also two sofa beds and a grand piano ~ a wonderful place to explore Waterford, the surrounding vineyards, and an opportunity to stay in one of the village's beautifully preserved properties.

Oct 28 – Nov 2

R4,870 ZAR per night

Guest favorite

Apartment in Bluemont

4.96 out of 5 average rating, 140 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 and an occasional "woof" from our Golden Retriever. Gardens are plentiful with flowers and the smell of old boxwood.

Dec 2 – 9

R2,631 ZAR per night