Kid-friendly holiday rentals in Frederick County

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Popular amenities for Frederick County family-friendly rentals

Kid-friendly house rentals

Guest favourite
Home in Berkeley Springs
4.9 out of 5 average rating, 48 reviews

The Hidden Gem of of Berkeley Springs

MaryannRating, 5 stars2 weeks ago
We thoroughly enjoyed our stay at Matthew’s retreat. The home is spacious across both levels, making it perfect for our large family. It’s beautifully furnished-comfortable, tasteful and uncluttered. The kitchen is generously equipped. The massive deck is a real highlight. With plenty of seating, two heaters and a grill. The peaceful surroundings made it easy to connect with nature and truly unwind. Check-in and check-out were easy. The house is exactly as advertised- no surprises, just a great experience. Five stars, Matthew, we are so glad we found your place/
Top guest favourite
Home in Yellow Spring
4.98 out of 5 average rating, 41 reviews

River Perch on the Cacapon River in Capon Bridge

AlexandraRating, 5 stars6 days ago
My husband, two young children and I stayed for a weekend, and it was amazing! The house and area was beautiful. There was a fire pit within walking distance, and Glenn gave great details on the best place to go kayaking and tubing along the river. Glenn was an amazing host, and he gave great recommendations on what to do in that area. If you have smaller kids who just love to run around outside this is a great place!
Guest favourite
Home in Winchester
4.94 out of 5 average rating, 155 reviews

Historic District Charm On Cameron Street

StaceyRating, 5 stars3 weeks ago
I’ve had the wonderful opportunity to stay at Elizabeth’s place a few times and it’s one of my favorites! It is so homey, spacious, and the location is fantastic! Elizabeth is a fabulous host…great communication and very personable. This last stay in late May was very special because my son graduated from Shenandoah Conservatory. Highly recommend to stay here!
Guest favourite
Home in High View
4.94 out of 5 average rating, 138 reviews

Mtn. View~Cave Hot Tub~50 Ac~ATV Trails~Fishing

SeanRating, 5 stars2 weeks ago
Our family loved our stay at Ken's place. The house was extremely clean, the listing gave us a great feeling going into the rental, and we were not disappointed upon arrival. The property and scenery were fantastic. Our kids loved going out onto trails, creek, hot tub, local lake, and feeding the animals. We all wish we booked a longer stay and we will be back in the near future.
Superhost
Home in Middletown
4.63 out of 5 average rating, 16 reviews

Cozy Home with Valley Views

StephenRating, 5 stars2 weeks ago
central location for NP and surrounding towns, clean and accommodating. Would stay again.
Superhost
Home in Strasburg
4.76 out of 5 average rating, 269 reviews

Cedar Creek Wayside Castle

TraceyRating, 5 stars3 weeks ago
I needed a place that my family, from out of state, could stay while attending a graduation. The house was perfect! I told Bob what I wanted to do and he was encouraging and helpful. He made sure we had propane for grilling and answered all my questions. He was very prompt when I reached out to him. We had an amazing time. I would stay there again.
Superhost
Home in Winchester
4.86 out of 5 average rating, 7 reviews

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

PederRating, 5 stars2 months 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 stars2 months 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 stars2 months 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
4.86 out of 5 average rating, 7 reviews

Newtown Cozy Cottage Basement

SandraRating, 5 stars2 weeks ago
I enjoyed my stay. Very convenient to nearby restaurants and shopping. I would recommend this place to others.
Superhost
Flat in Winchester
4.69 out of 5 average rating, 35 reviews

The Flat of Old Town Winchester

TheresaRating, 5 stars1 week ago
The room was just as pictured and described. It was easy to find. The directions were clear. The room had a guest binder that made it easy to find a restaurant and I even enjoyed reading through the town history book. When we drove around town I pointed out buildings I had just learned about! There are motion activated lights in the hallways that I thought were a great touch! I loved the designated parking in the back.
Top guest favourite
Flat in Stephens City
5 out of 5 average rating, 16 reviews

Spacious Charming Basement Apt

John and AlexisRating, 5 stars3 months 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.
Superhost
Flat in Winchester
4.8 out of 5 average rating, 10 reviews

Historic French Modern Downtown

PeterRating, 5 stars4 weeks ago
We had a great stay in Old Town Winchester! The apartment was very cute and just full of character, and an easy walk to anywhere we wanted to go. Kim was an outstanding host, providing us with very detailed instructions on how to find the place and how to get in. She also recommended some great local restaurants and attractions.
Superhost
Flat in Winchester
4.77 out of 5 average rating, 13 reviews

"Cozy on Cameron!" - Historic Downtown Winchester

MatthiasRating, 5 stars5 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.
Top guest favourite
Flat in Winchester
5 out of 5 average rating, 47 reviews

Peaceful Family Retreat in the Heart of Winchester

KristenRating, 5 stars1 day ago
Maryssa’s place was great for our family of 5! Our 7 year old and toddler loved the bunk bed, and we appreciated how quiet it was for our 5 month old. Super clean and comfortable. The oversized chair was my favorite part!
Superhost
Flat in Winchester
4.83 out of 5 average rating, 23 reviews

The Queen of Winchester - Three Bedroom Apartment

ShelleyRating, 5 stars2 weeks ago
Sean’s place was perfect for our stay. Sean was responsive and the house was very well maintained.

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