Kid-friendly holiday rentals in Frederick County

Find and book unique family-friendly rentals on Airbnb

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Popular amenities for Frederick County family-friendly rentals

Kid-friendly house rentals

Top guest favourite
Home in Winchester
4.96 out of 5 average rating, 124 reviews

Aunt Tim's Farmhouse

MarkRating, 5 stars2 weeks ago
Our ladies book club had a wonderful weekend away at Uncle Tim’s farm! We enjoyed the beautiful views all around the property. The inside welcomed us in like we were visiting grandma and grandpa! So much character and charm! It was our home away from home for a few days to relax in the living room, and front porch and play games and enjoy meals in the dining room and explore downtown Winchester. Thank you, Kay, for being a wonderful host!
Superhost
Home in Berkeley Springs
4.89 out of 5 average rating, 45 reviews

The Hidden Gem of of Berkeley Springs

ChristineRating, 5 stars6 days ago
The house has a fantastic layout and an incredible deck for enjoying the beautiful surroundings! So many birds singing, frogs calling at night, and a couple of turtles in the yard. Plenty of space for our dogs to run around. It was a great balance between a peaceful stay in the woods and still close enough to enjoy Berkeley Springs and Cacapon.
Guest favourite
Home in Winchester
4.94 out of 5 average rating, 153 reviews

Historic District Charm On Cameron Street

JohnRating, 5 stars2 weeks ago
We were thrilled to stay in this historic home and Elizabeth was highly attentive. Even if you don't love country music, a visit to Patsy Cline's house is well worth it because it is so close and you can learn how some Winchesterians lived in the early- to mid-20th century. We loved the easy walk to downtown and recommend Village Square and Antica Trattoria as restaurant stops. Our family made use of the outdoor basketball court and lovely deck at Elizabeth's and had great fun. Hopscotch records/coffee is walking distance from Elizabeth's as is Vibrissa beer. You'll need to get in your car to visit our favorite record store Ear Food, and you'll need to drive to the lovely Briede Family vineyard. We also recommend a lovely walk at the Third Winchester Battlefield Park. The Museum of the Shenandoah Valley is a true gem, and be sure to take a walk in the gardens included in the price of a museum ticket. Elizabeth's house is a launching point for many good and interesting times!
Guest favourite
Home in Gerrardstown
4.94 out of 5 average rating, 97 reviews

A-Frame Mountain Retreat

KirstenRating, 5 stars3 months ago
This place was great! Small, cozy location in the mountains! It was peaceful and just what we were looking for 😊 everything was nice and clean, and we felt right at home!
Superhost
Home in Middletown
4.62 out of 5 average rating, 13 reviews

Cozy Home with Valley Views

CherylRating, 5 stars4 weeks ago
My nieces and I had such a relaxing time at Julie's house! The place was super comfy and welcoming—perfect for lounging around and spending quality time together. Everything was clean, cozy, and thoughtfully set up, which made it really easy to feel at home. The location was great, we were able to find a local pizza place, diner and even a tea room. We will definitely be back!
Superhost
Home in Strasburg
4.76 out of 5 average rating, 266 reviews

Cedar Creek Wayside Castle

RogeRating, 5 stars2 weeks ago
It’s a private place to go and enjoy and famili kids are very happy with the pool and activities
Superhost
Home in Winchester
4.83 out of 5 average rating, 6 reviews

Sophisticated 4BR: Chef's Kitchen, Grill, Patio

PederRating, 5 stars1 month ago
We really enjoyed our stay in this house and Suranny was very responsive and helpful. The house was clean as can be and very spacious. Lots of natural sunlight and a wonderful covered porch to sit out on. The beds were very comfortable and the bathrooms were clean. We would certainly stay here again in the future.
Top guest favourite
Home in Winchester
5 out of 5 average rating, 33 reviews

Whole 3-bedroom house walkable to downtown.

GiniRating, 5 stars1 month ago
We thoroughly enjoyed our extended stay in this charming cottage! The location is ideal for walking—- either around the neighborhood or downtown. We loved the charm and cozy atmosphere and spent a lot of time on the sun porch too! Can’t recommend it highly enough and look forward to staying here again

Family-friendly apartment rentals

Top guest favourite
Flat in Winchester
4.98 out of 5 average rating, 104 reviews

Cozy Apartment located on our 5-acre property

MikeRating, 5 stars1 month ago
Excellent host. Very clean place, beautiful property. Laura was amazing. It was like staying with a good friend. We bought some of her eggs and delicious honey. We would definitely stay there again. My wife and I and our fur babies will miss Laura, Jerald, and Dasher.
Superhost
Flat in Stephens City
4.83 out of 5 average rating, 6 reviews

Newtown Cozy Cottage Basement

LauraRating, 5 stars7 months ago
Thanks so much for having us, Amy! I loved all the colors and decorations. We apprecaited how you all took this space and made it something really special. We could tell how much TLC was poured into it. Thanks for the awesome communication before and during our stay. **I did want to make note of a few things for future guest** If you are much over 6 feet tall, there are a few places you'll need to duck. My husband hit his head on a pipe in the hallway a few times before he remembered it was there. Also, just remember that full beds aren't as long as queens and kings. The kitchen sink water gets REALLY hot, so use cation. The shower had wonderful pressure and great temps! The bed was comfortable. We did hear the animals upstairs some in the night. It didn't bother us, but if you are sensitive to sound, make note that this is a basement rental and you may hear some above you. The TV doesn't come with cable or rabbit ears, you must log into and log out. Overall, it's unique!
Top guest favourite
Flat in Winchester
5 out of 5 average rating, 203 reviews

Old Town Loft In Highly Desirable Area Downtown

JessicaRating, 5 stars2 weeks ago
We had such a great visit to Winchester for the Apple Blossom Festival & were so happy to find how convenient this location was to everything. The space was so clean and had every amenity we needed - like coffee for the keurig, creamer in the fridge, and toiletries for the bath. They even had umbrellas downstairs for the unexpected rain shower that hit during our stay. I loved the historic feel to the unit, like the exposed brick and wood floors, but also the modern comforts they added like the kitchen appliances and walk-in shower. We can't wait to come back next year.
Top guest favourite
Flat in Winchester
4.93 out of 5 average rating, 155 reviews

Modern Twist in Old Town! Rock n' Roll FUN!

AnnetteRating, 5 stars1 week ago
We very much enjoyed our stay at Basil! It was very clean and well equipped. The kitchen had a good supply of pots, pans, knives, silverware, dishes, etc. It was especially nice to have a full rack of spices available so that we could cook meals without having to purchase all of the little extras. The living space was comfortable and spotless. There were many little touches that made the stay quite comfortable. Basil's location is ideal. Just a block from the Old Town walking mall, it was so easy to wander about, get great food, people watch, and enjoy the street buskers. It is also less than 3/4 of a mile from the trails of the Shenandoah Museum. The area is very walkable. It's also under 30 minutes to get to trailheads along the Appalachian Trail and under 45 minutes to the Shenandoah National Park. We stayed for over a week and would definitely stay there again. We highly recommend Basil.
Top guest favourite
Flat in Winchester
4.97 out of 5 average rating, 273 reviews

Downtowner

SusanRating, 5 stars1 week ago
Gail and Sam's apartment on the 2nd floor of their home was very conveniently located! The Historic District was within easy walking distance and there was ample parking at the AirBNB. Gail did a great job explaining the check-in/check-out process via her email. Check-out was even easier as we didn't have a long list of "to-do's" on departure. We certainly enjoyed seeing some of the sites in Winchester and the surrounding area and we would stay at this AirBNB again. Thank you, Gail and Sam!
Top guest favourite
Flat in Stephens City
5 out of 5 average rating, 16 reviews

Spacious Charming Basement Apt

John and AlexisRating, 5 stars1 month ago
Great place to stay while visiting Stephens City, VA. The basement was spotless and we immediately noticed that it had been recently cleaned; fresh and airy. This location is easily walkable to the historic city center where you will find antique shops and restaurants. We contacted the hosts during our stay and they were very responsive to our questions. This would be an ideal location for a long-term stay.
Top guest favourite
Flat in Winchester
4.98 out of 5 average rating, 100 reviews

Historic Wisteria House on Old Town Walking Mall

KaterynaRating, 5 stars4 months ago
We liked the house very much. It`s an ancient historic house, though with all modern conveniences. Very comfortable bed, comfortable couch, convenient kitchen with all necessary kitchenware and utensils. The towels and bed linen are of good quality, all very clean and new. Good internet. Also the house appeared to be more spacious as it seemed on the pictures. Location is perfect, right in the center. We highly recommend this house for long-term stays.
Superhost
Flat in Winchester
4.82 out of 5 average rating, 11 reviews

"Cozy on Cameron!" - Historic Downtown Winchester

MatthiasRating, 5 stars4 months ago
Marks place is a delight in the heart of winchester, we're happy having been lucky enough to have it available at the dates we needed. It's a few walking minutes from the Old town center of winchester. The place is lovely and has all you'll need even for a few weeks stay. A private parking on top of that is just so nice to have. We'll definitely check in again the next time we're in winchester.

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