
Kid-friendly holiday rentals in Jefferson County
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Top-rated family-friendly rentals in Jefferson County
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Popular amenities for Jefferson County family-friendly rentals
Kid-friendly house rentals

Newly renovated - Walk to Harpers Ferry NP
Really nice place off a quiet street in Bolivar/Harper’s Ferry. Very clean and exactly as advertised. Hosts provided great instructions and it was easy to access and enter. Convenient to hiking trails and sight seeing. Would stay here again and recommend.

Hot Tub, Wi-fi, Rural Setting, Smrtv, Convenient
This is our second time staying at one of Laura's properties and each time has been terrific! What you see is what you get... a large fully functioning home with easy check-in, nice amenities, responsive host and easy check out! My family and I had a great time, thank you Laura!

Eclectic & Romantic - Walk to Historic Downtown!
This home in Harper's Ferry was everything and more as described in the listing. We had plenty of room. The beds are roomy and comfortable. The bathrooms are spacious. I loved the polished cement floors as well as the eclectic artwork and decorations. We enjoyed mornings on the deck and our walks to visit Harper's Ferry.

The Dorothy Historical home in Shepherdstown, WV
We had a wonderful few days at “The Dorothy.” The house was very spacious and comfortable. The kitchen had everything we needed, the bed was super comfortable, the place was very clean and inviting and the decor is very charming. Jo Ann was very quick to respond to our questions. I would highly recommend staying here. There is plenty to do and see in the surrounding areas, but coming back every evening was very relaxing and we felt at home. A++! Thanks!

Small Town Living: Historic District Guesthouse
Amy's place is in a great location in the heart of the charming town of Shepherdstown. It was easily walkable to numerous restaurants and shops. The ice cream shop around the corner was a huge hit with our teenage son who declared it has "the best ice cream [he's] ever had!" The parking was also great to have. The place itself is quite large with very spacious rooms. The beds were comfy and we all slept great. We wanted for nothing. This was a great location to explore nearby Harper's Ferry and Antietam.

Steps to Winery & Battlefield-Pvt Acre w/ Hot Tub!
We loved our stay here. Super comfortable and cozy, beautiful patio and garden and such a pretty view! Highly recommend!

Outdoor Basecamp at Tiny Hidden Ridge
Tara and Shawn were great hosts! The place was comfy, they were easy to communicate with, and great of all, we got to hang out with their awesome goats and feed them snacks!

Harpers Ferry House for Family Events
I can’t say enough about how absolutely fabulous this house is and how great Tamara is as a host- communication was excellent and she was quick to respond to any questions. The house and outdoor areas are beautiful, well maintained & comfortable, and everything you could possibly need is provided. My family was in town over a long Memorial Day weekend for my nephew’s wedding which was held at another of Tamara’s properties (also spectacular!) just 2 miles up the road so this property was so convenient for us. We had an A+++ experience and highly recommend!!
Family-friendly apartment rentals

The Boundary House Apartment
We had an excellent stay on our journey along the C&O canal. The owners were very responsive and accommodating to our larger group. Everything was pristinely clean and the bathroom/shower was luxurious. Very happy with our stay and big thanks to the homeowners!

Downtown Modern 2BR step from dining and shopping
Our stay was great! Beautiful apartment in a great location. More than enough space for myself, my husband and our 8 month old. It was quiet and private even being located in the heart of shepherdstown. Our baby even slept through the train! We’ll definitely be back to Shepherdstown and would love to stay here again!

Stone House Mansion (1757)- Basement Apartment
Donald and Barbara have an amazing house! I am into history and the the reason I came here was because of that history. Both Donald and Barbara were very knowledgeable about the house and the history of the house, including the surrounding area. What a beautiful place to stay and soak up the local history, that includes my ancestors. Antietum, Harpers Ferry, and Gettysburg are all within reach from this central location. We had such an awesome visit, and hopefully we can be back sometime soon.

Top o' the Hill Apt. in historic Harpers Ferry
This was a perfect place to stay in Harper's Ferry. Plenty spacious for me, my husband, and our month old. Clean and had everything we needed. Short walk to park, town, restaurants, shops, etc.

The Nashville
place was very nice looked just the pictures, location was good many things to do around the location. Lesley was very friendly and helpful.

Downtown: Explore Shepherdstown from cozy 1br apar
We love visiting Shepherdstown and especially enjoyed the location of the apartment, which is very central to downtown, the university and the C&O canal. So convenient. The apartment was very clean and quiet. The kitchen is well equipped. We thought the apartment quite comfortable and enjoyed our week long stay. We will certainly try to book the apartment again next time we are in town. Oh - and we highly recommend the little natural/organic grocer/deli virtually next door to the apartment. We were able to find what we needed there and they have wonderful sourdough bread.

Trundle Private Suite Location Lily Garden BnB
Great stay! It was an awesome location and there was lots to do within walking distance. Also appreciated the food that was present for us on arrival. There was a small but very nice backyard where we were able to make a fire one night. Host was very informative and responsive. Would definitely stay again.

Best location! The Pullman Apt @ historic 1799 Inn
The apartment was great for our stay and in an amazing location! Very easy to get to, and Bryan & Cathy were proactive with instructions and local recommendations to make the trip easy to plan.
Family-friendly apartment rentals

SlopeSide
I almost don't want to write a positive review because I'd like this condo to be available only to me. It was perfect! The place is comfortable and had everything we needed for our 2 night stay. Easy ski in/out access, and perfect for a family that has some that stay on the slopes a little longer than others. We just hope this place will be available again when we visit next.

2 Queen & 1 Twin Bed / Mountain & Museum Fun
Very quiet and clean place! Michael was very responsive and I loved the museum room!

Ski🎿 & hike from front steps—Mountainside getaway
I think this is the best slope side ski condo at Whitetail. The slopes are right outside the door and the place is cute, clean, and comfortable. We will be going back!

Memory Lane
This AirBnb hosted by Julie was perfect! The space was just what we needed as a little home base as we explored Harper’s Ferry and the surrounding area. Julie provided great recommendations in terms of places to eat. Would love to go back!

Upscale Walkup Apartment
Nice, clean place. Good location for that area.

Stunning Remodeled 1 BR Condo Steps to Everything.
My husband and I were in Leesburg for a wedding and loved the place. It was just as described and close to everything.

Whitetail Resort Ski-in/Ski-out slope side condo.
This air bnb was perfect for a weekend getaway to Whitetail resort. The unit is steps away from the slopes, and Renee was not only responsive and extremely helpful, but able to accommodate schedule changes to make our trip happen.

Historic District Downtown Winchester
Alison's place is great if you value being walkable to Old Town. We prefer this over staying at the Wyndham Grand because of the separate room for our baby to sleep in. The kitchen is modern and fridge with a water filter is clutch. We didn't try to make any meals. Bed was clean/firm, HVAC was responsive, and lounge chair in the sitting area was comfortable. You can hear the train and street noise (especially cars w/o mufflers) at night, but I assume that's the case if you stay anywhere near Old Town.
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- Great Falls Park
- Cunningham Falls State Park
- Caledonia State Park
- Stone Tower Winery
- The Links at Gettysburg
- Cowans Gap State Park
- Cacapon Resort State Park
- Robert Trent Jones Golf Club
- Congressional Country Club
- Whiskey Creek Golf Club
- Gambrill State Park
- Whitetail Resort
- Liberty Mountain Resort
- South Mountain State Park
- Field of Screams Maryland
- Sly Fox Golf Club
- Shenandoah Valley Golf Club
- Creighton Farms
- Washington Golf & Country Club
- Chevy Chase Club
- Bowling Green Country Club
- Notaviva Vineyards
- Columbia Country Club
- Twin Lakes Golf Course