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Kid-friendly vacation rentals in Frederick County

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Frederick County

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

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Cabin in Gerrardstown

4.89 out of 5 average rating, 209 reviews

Modern Eclectic Cabin with Views - Hot Tub - Creek

Our cabin in the treetops is the perfect place to rest, work remotely, or use as a basecamp for exploring the surrounding area. Our aesthetic is modern eclectic. We do our best to use only chemical/cruelty free products that are ethically and sustainably sourced. The cabin has many modern conveniences including an eco-friendly hot tub with epic views, high speed internet and chromecast for streaming your connected devices. Hot tub is available year round. Pellet stove is available Oct-March.

Cabin in High View

4.97 out of 5 average rating, 101 reviews

Mary's Cabin

Nestled on 2 acres in the woods of West Virginia, kick back and relax in this quiet, chic cabin. Soak in the oversized copper tub, read on the porch swing, or cuddle by the electric fireplace. All the amenities of home, but away from the hustle and bustle of daily life. Only 25 minutes to quaint Old Town Winchester, where there are unique shops, breweries, restaurants and history! The cabin is located 20 minutes from a variety of scenic hiking trails that provide opportunities for adventure.

Home in Winchester

4.97 out of 5 average rating, 190 reviews

Cameron Charmer pristine w/double master suites

Take a step into pure luxury in this newly renovated 1930's charmer in up and coming downtown area of Winchester. Owners have spared no expense to make this the kind of place where guests can come & forget about the rest of the world ! Incredible top of the line centralized dine in kitchen, wide open & inviting living areas, two master suites each with walk in closets & baths up lovely custom pine staircase. Come spoil yourself a bit at the Cameron Charmer, you are sure to enjoy your stay !

Rental unit in Winchester

5 out of 5 average rating, 174 reviews

Old Town Loft In Highly Desirable Area Downtown

Location, Location! A completely renovated apartment in the highly desirable center Winchester. You’ll still be able to see some of its original character throughout this historic building. The apartment has a fully stocked custom kitchen with reclaimed wood and quartz counters, coffee nook with Keurig, large tile shower with glass doors, hardwood floors, queen memory foam mattress, high speed Wi-Fi, 50’ smart TV, Xfinity HDTV with voice remote control, AC/Heat, Washer/Dryer, and dishwasher.

Cottage in Winchester

4.91 out of 5 average rating, 127 reviews

Lockley Cottage at Historic Perry Farm

Peace and tranquility await you at a quaint cottage on historic Perry Farm, where the original 19th century farmhouse still stands today. Stroll several acres of land and enjoy pastoral views while you unwind at this peaceful historic property in the hills of northern Shenandoah Valley. This rural retreat is easily accessed from I-81 and located a short 10-minute drive from historic downtown Winchester. Enjoy local wineries, breweries, farm markets, and the renowned Apple Blossom Festival.

Home in Winchester

4.97 out of 5 average rating, 234 reviews

City Charmer minutes from Old Town

Renovated 1950's cottage style home. Enjoy a small house with a great front porch and large backyard with patio. Just minutes to drive and about 10-15 minutes to walk to Historic Old Town Winchester which includes numerous restaurants, bars, shopping, and often some kind of event like the Shenandoah Apple Blossom Festival! Our house is located about 65 miles West of Washington D.C. if you're looking for a day trip to the big city or just sit back and relax right here in our small town.

Cabin in Star Tannery

4.99 out of 5 average rating, 113 reviews

Double Spur Outfitters' Brook Cabin

Relax and reconnect with nature at Double Spur Outfitters' Brook Cabin. Nestled in the woods by Cedar Creek, this beautiful pine wood cabin is ideal for those wanting to take in the beauty of the area. The cabin has 1 separate bedroom with a queen bed, an upstairs loft with a queen and a full bed, and a downstairs bunk bed. Includes a large front porch facing the creek. There is a downstairs bathroom and a fully equipped kitchen. Towels and Linens are provided. Feel free to contact.

Guest suite in Winchester

4.81 out of 5 average rating, 298 reviews

Safe, cozy oasis with private living & bath.

Wonderfully comfortable basement apartment. We are less than a mile from Winchester Medical Center.... ideal for traveling doctors/nurses. Close to other area attractions. You will have your own living room, bathroom and bedroom. Private entrance. Digital lock. You will get instructions prior to check in. You will be in the basement however it has natural light in the bedroom. There may be some noise from upstairs, but it is generally quiet.

Townhouse in Winchester

4.93 out of 5 average rating, 211 reviews

Modern Elegance in Historic Old Town Winchester

Just a block and a half from the Old Town Winchester pedestrian mall, this historic beauty with modern elegance is sure to please. You are within walking distance of quaint shops, great restaurants, The Brightbox Theater, and The Shenendoah Discovery Museum. Spend the day touring the areas great wineries or enjoying Skyline Drive, and then return to enjoy a great night out, or an evening at home making dinner in the spacious modern kitchen.

Cottage in Winchester

4.97 out of 5 average rating, 465 reviews

Emma's Stone Cottage

Relax and unwind in the privacy of this wonderful stone cottage, which sits on 15 acres. In addition, it is located only 2.5 miles from I-81 and approx 10 miles from Winchester Medical Center, Old Town Winchester, Shenandoah University and much more. Our cottage has everything you need for a peaceful and enjoyable stay including full kitchen, central air, water softener, HD smart televisions, Wifi, outdoor firepit and more.

Home in Winchester

4.96 out of 5 average rating, 107 reviews

Aunt Tim's Farmhouse

Our farmhouse is located approximately 5 miles west of Historic Winchester, VA. The house is situated on 106 acres of an operational farm. You may see family members and friends tending honey bee hives, working in the detached garage, gardening, and completing other farm chores. The house is solely occupied by our guests. Come on out to enjoy some peace and quiet and take advantage of all Mother Nature has to offer!

Home in Winchester

4.97 out of 5 average rating, 213 reviews

Full basement with private entrance. Hot tub

Cozy movie themed basement is exactly what you are looking for. Classic AirBnB-we are opening our house to you! Space is completely private. Bedroom with queen bed. High speed internet. Private bath w/shower. Small refrigerator, microwave. flat screen, table and chairs and couch in a large family room w/Sofa bed. 1000 square feet of space! Home 2 miles outside of the city of Winchester in Frederick County.

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Popular amenities for Frederick County kid-friendly rentals

Free parking on premises

Air conditioning

Kid-friendly house rentals

Home in Winchester

5 out of 5 average rating, 14 reviews

Great house 3 bedrooms, 3 beds

Home in Winchester

4.94 out of 5 average rating, 139 reviews

Historic District Charm On Cameron Street

Home in High View

4.95 out of 5 average rating, 113 reviews

Mtn. View, Creek, 50 Ac, ATV Trails, Near Wash. DC

Home in Winchester

5 out of 5 average rating, 24 reviews

Downtown Chic Condo w/parking

Home in Winchester

5 out of 5 average rating, 41 reviews

Large Historic Stone Home in the Heart of Old Town

Home in Winchester

5 out of 5 average rating, 15 reviews

Bear Drop Inn on Chestnut Hill with walking trails

Home in Winchester

4.95 out of 5 average rating, 39 reviews

Misty Meadow has quite setting in the country.

Home in Winchester

5 out of 5 average rating, 5 reviews

Enchanting Forest Retreat with Lake Views

Kid-friendly apartment rentals

Rental unit in Winchester

4.94 out of 5 average rating, 32 reviews

Easy like a Sunday Morning 1 BR apt great location

Rental unit in Winchester

4.97 out of 5 average rating, 248 reviews

Downtowner

Rental unit in Winchester

4.81 out of 5 average rating, 21 reviews

The Flat of Old Town Winchester

Rental unit in Winchester

4.94 out of 5 average rating, 80 reviews

Newly repurposed Historic Home in Winchester VA!

Rental unit in Winchester

4.98 out of 5 average rating, 93 reviews

Historic Wisteria House on Old Town Walking Mall

Rental unit in Winchester

5 out of 5 average rating, 37 reviews

Peaceful Family Retreat in the Heart of Winchester

Rental unit in Winchester

4.89 out of 5 average rating, 95 reviews

Last Minute Deals! Luxe 2 BD Apt in OT Winchester

Rental unit in Winchester

5 out of 5 average rating, 5 reviews

The Queen of Winchester

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