Family-friendly holiday rentals in Charles Town

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Popular amenities for Charles Town family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Cabin in Berkeley Springs
4.91 out of 5 average rating, 148 reviews

Private Modern Log Cabin w/Hot Tub

RandallRating, 5 stars6 months ago
We enjoyed our time and the hot tub was great. Truly peace and quiet
Guest favourite
Home in Harpers Ferry
4.89 out of 5 average rating, 118 reviews

Hot Tub, Wi-fi, Rural Setting, Smrtv, Convenient

JasonRating, 5 stars1 month ago
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!
Guest favourite
Home in Clearville
4.93 out of 5 average rating, 298 reviews

Grouseland's Pondside Vacation Cottage

GinaRating, 5 stars1 month ago
We loved our short stay at Mason’s place!! We needed a peaceful getaway to just relax and it’s exactly what we needed. The hot tub was amazing, and we hiked all around the property and campgrounds! Had so much fun connecting with nature and relaxing. Also loved how many amenities, spices, oils, pots and pans, etc in the kitchen!!
Top guest favourite
Tiny home in Orrtanna
4.93 out of 5 average rating, 442 reviews

Apple Blossom Cottage HT is extra$

VictoriaRating, 5 stars1 month ago
My father and I stayed at Elizabeth’s place for my brother’s graduation from Gettysburg. We thoroughly enjoyed the peace and quiet of the location. Elizabeth’s place was beautifully styled and I really appreciated her attention to detail. Elizabeth was a great host. She was so responsive and I could tell genuinely cared for our every need. I would recommend her place!
Guest favourite
Home in Chester Gap
4.95 out of 5 average rating, 227 reviews

The Nest

ChristopherRating, 5 stars1 month ago
Really beautiful place with lots of character! So peaceful and amazing views!! We loved it. :). Thanks Julie!
Guest favourite
Chalet in Great Cacapon
4.95 out of 5 average rating, 432 reviews

Fern Haven - Waterfront Chalet w/ WiFi & Hot tub!

ErinRating, 5 stars3 days ago
We had a lovely stay! The outdoor space was beautiful and the hot tub and deck were the perfect place to relax. Inside was comfortable and clean. The beds and furniture could probably be updated a bit but that didn’t make our stay less enjoyable. Peaceful to relax and close to Berkley Springs to enjoy the shops and restaurants.
Guest favourite
Cabin in Lost City
4.95 out of 5 average rating, 419 reviews

Lost River Modern - a Modern Prefab

CarolynRating, 5 stars1 month ago
We love staying here. This was our third time. It’s a great area to explore and the house is super comfy. Lounging on the deck is the best part.
Guest favourite
Cabin in Rileyville
4.96 out of 5 average rating, 216 reviews

"Solitude" Secluded 1 BR Cabin with Hot Tub

BritneeRating, 5 stars1 month ago
This cabin was everything we needed and more. Everything was as described in the details. Our dogs loved it, they felt safe and comfortable.

Family- and pet-friendly home rentals

Guest favourite
Home in Strasburg
4.9 out of 5 average rating, 249 reviews

Shenandoah Siesta

PaulaRating, 5 stars2 weeks ago
Clean, well-stocked, spacious, and comfy! Town was a five minute walk with some great local shops and restaurants. Enjoyed our stay!
Guest favourite
Home in Middleburg
4.98 out of 5 average rating, 182 reviews

Modern Home on Middleburg Equestrian Farm

RozRating, 5 stars1 week ago
We loved the area. The house was very clean and we felt very comfortable. We enjoyed coming back to the house after the horse show and just relaxing. We hope to book it for next year.
Top guest favourite
Cabin in Great Cacapon
4.92 out of 5 average rating, 274 reviews

Rustic Cabin on Cacapon River for Private Getaway

WilsonRating, 5 stars1 month ago
Jonathan's place is wonderful as always. Had an exciting weekend to disconnect and enjoy good company in beautiful scenery. Look forward to coming back!
Guest favourite
Home in Harpers Ferry
4.84 out of 5 average rating, 110 reviews

The Nature at Rivermist Lane (Waterfront)

LaurenRating, 5 stars2 weeks ago
This home was such a beautiful escape! It was the perfect location and Andrew was so accommodating and helpful before and throughout our stay. We will definitely be back!
Top guest favourite
Flat in Front Royal
4.98 out of 5 average rating, 119 reviews

Cozy 1BR for Couples & Solo Travel~No Cleaning Fee

SachiRating, 5 stars1 week ago
Super nice, cozy and well thought out decor. Close to Front Royal downtown and conveniently located close to restaurants and Shenandoah National Park’s North Entrance. Space was just right for me and hubby. The place had private access/stairs up (1 flight or so) to the Apt offering a quiet stay and extra privacy. Would stay here again and def recommend this place!
Guest favourite
Cabin in Lost City
4.95 out of 5 average rating, 387 reviews

Log Cabin in Lost River w/ Indoor Fireplace

NickRating, 5 stars2 months ago
Our trip was absolutely flawless. Maureen is a gracious host who has an amazing place in a perfect location outfitted with everything you could want or need for getting off the grid for a while. We can’t wait to go back! 100% recommend!!!
Top guest favourite
Cabin in Berkeley Springs
4.85 out of 5 average rating, 208 reviews

Retriever’s Retreat ~ High-Tech Log Cabin Oasis

WarrenRating, 5 stars1 week ago
5 stars – A peaceful escape! The cabin was exactly as described—cozy, clean, and tucked perfectly into the woods for a peaceful, relaxing getaway. Every detail matched the listing, and the setting made it feel like a true escape from the everyday. The owner was incredibly pleasant and easy to communicate with, which made the experience even better. Highly recommend to anyone looking for a quiet retreat in nature!
Guest favourite
Home in Thurmont
4.87 out of 5 average rating, 551 reviews

Cabin in the Woods - Weekday Specials!

EwoudRating, 5 stars2 weeks ago
Very peaceful surroundings, enjoyed sitting on the front porch during the rain

Family-friendly home rentals with a pool

Townhouse in Hedgesville
4.89 out of 5 average rating, 64 reviews

Cozy Townhome At The Woods Resort Golf,SPA,Tennis

RogerRating, 5 stars8 months ago
We had a great time and the check in process was seamless. Keith was proactive and very responsive.
Superhost
Cabin in Hedgesville
4.88 out of 5 average rating, 225 reviews

Deer Crossing at The Woods

LauraRating, 5 stars5 months ago
This was our second stay at Janel's place and it was just as enjoyable as the first time. We loved the fireplace and views from the A frame windows. The hot tub wasn't working unfortunately, but things happen and Janel was communicative about it. Had a great weekend regardless. Also love that Janel is accommodating of dogs. Our fur babies were happy to join us on our getaway.
Top guest favourite
Flat in Hamilton
4.97 out of 5 average rating, 60 reviews

Goose Hill

JesseRating, 5 stars6 months ago
The place was charming, well stocked and very comfortable. The communication was great and we would definitely rent again.
Cabin in Keedysville
4.8 out of 5 average rating, 120 reviews

Quiet Antietam Cabin

TheodoreRating, 5 stars20 months ago
A very nice area to see fall colors, out of the way but easy to reach a store for anything needed
Guest favourite
Cabin in Berkeley Springs
4.89 out of 5 average rating, 76 reviews

Hiking, WiFi, 4 Decks, King Suite, Community Pool

MaryRating, 5 stars4 weeks ago
The location was nice, really quiet and private and right in the woods. There are hiking trails right there, so we could do a 2-3 mile hike in the morning before heading out to activities. It's just a 10 minute drive to Berkeley Springs. The views out of the picture windows in the living room, or on the deck, were great. The house is very spacious and clean, with a well stocked kitchen. Everyone found all the beds to be very comfortable with nice linens, features not always found in rental houses. The living room fireplace was welcome as it was chilly when we were there. I can't think of anything we needed that the house didn't have. One thing to note is that the driveway is graveled and there is a little slope to the door. Having said that our mid-80s parents had no issues; just something to keep in mind if you have someone with mobility issues. We enjoyed our stay and would recommend!
Guest favourite
Home in Leesburg
4.97 out of 5 average rating, 121 reviews

Potomac Overlook Farms: 6 BR, 10 Acre River Estate

MelissaRating, 5 stars1 month ago
We had a wonderful family reunion here with 3 generations. Each family had their own private space but there was tons to do on the property together as well. The hosts were very responsive to our questions and made sure we were comfortable and happy! We appreciated that the kitchen was well stocked, too.
Guest favourite
Guest suite in Purcellville
4.82 out of 5 average rating, 230 reviews

Monet Suite, elegnt lrg 2rm suite/blcny in villa

GwenRating, 5 stars2 weeks ago
My husband and I stayed here right after we hot married and it was the most lovely experience! It was an absolute blast, I wouldn’t have changed a thing except I wish I could’ve stayed longer. Maud was so sweet and I loved having her as a host. Cannot recommend enough!
Top guest favourite
Home in Harpers Ferry
4.92 out of 5 average rating, 168 reviews

The McCoy House at the Harpers Ferry KOA

MalcolmRating, 5 stars3 days ago
The home was big and beautiful. It was much more than I was expecting and the access to the KOA was a plus. My family and I can’t wait for an opportunity to return.

Quick stats about holiday rentals that are family-friendly in Charles Town

  • Total rentals

    20 properties

  • Nightly prices starting at

    ₹4,300 before taxes and fees

  • Total number of reviews

    1.3K reviews

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi and Pool

Destinations to explore