Family-friendly holiday rentals in Hagerstown

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Popular amenities for Hagerstown 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!
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.
Guest favourite
Home in Clearville
4.93 out of 5 average rating, 298 reviews

Grouseland's Pondside Vacation Cottage

GinaRating, 5 stars4 weeks 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!
Top Guest favourite
Cabin in Berkeley Springs
4.96 out of 5 average rating, 310 reviews

Wild, Wonderful Five-Bedrm Loghome

GailRating, 5 stars2 weeks ago
Susan's house was exactly what we wanted for our girl's weekend. We take this trip annually, and all we want to do is relax. We eat, drink and play games. Susan's house was perfect. The screened in porch was our favorite place to be. Susan was wonderful - gave detailed instructions ahead of time, left a ton of breakfast choices - eggs in the fridge, and bagels, muffins, etc. in the freezer. The kitchen had everything you could possibly need. The house is surrounded by beautiful trees and rocks. We will definitely return!
Superhost
Cabin in Harpers Ferry
4.81 out of 5 average rating, 438 reviews

Cozy Cabin Hidden Away on a Lake!

JohnRating, 5 stars1 month ago
Excellent stay! Beautiful locale! Would stay again for sure!
Guest favourite
Home in Fairfield
4.93 out of 5 average rating, 243 reviews

Brent Road Retreat

LiamRating, 5 stars3 weeks ago
We had a great golf weekend in the area and really liked the accommodations. It was private, enough to fit 8 golfers, and close to many of the course we played. We will go back again.

Family- and pet-friendly home rentals

Guest favourite
Cabin in Upperville
4.94 out of 5 average rating, 155 reviews

Island cabin

WilliamRating, 5 stars1 month ago
Julia's place is an Idyllic setting - so tranquil, yet close enough to a great tavern for dinner. Amazing - we cannot wait to come back.
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!
Top Guest favourite
Home in Harpers Ferry
4.94 out of 5 average rating, 398 reviews

Gayte House Gay Owned, Liberal Oasis

LeslieRating, 5 stars3 weeks ago
This house was adorable and is in a location that couldn't be beat! We enjoyed our stay - coffee and wine on the decks and easy walks around the sites and shops in the lower town. Beds were comfortable, kitchen was well-stocked and the views from everywhere were amazing! Easy 20-ish minute drive over to Loudon County wine country, if that's your destination. Check-in and check-out was great. Easy with flexible timing, which we greatly appreciated. Dean was VERY helpful, especially when it came to parking - we brought three cars and he made sure we had ample space, even when some of our drivers were unsure of the narrow roads. (Roads are hilly and corners are sharp in the mountains, if you are not used to that.) The house could use a good dust and sweep, but dishes and linens were clean and plentiful. Not a dealbreaker, unless you have allergies - but it is an old house, after all, so some of it is to be expected. We would gladly stay again!
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 stars4 weeks 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 Knoxville
4.91 out of 5 average rating, 348 reviews

Outdoor Basecamp at Tiny Hidden Ridge

DaleaRating, 5 stars1 month ago
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!
Guest favourite
Cottage in Purcellville
4.83 out of 5 average rating, 212 reviews

Stone School House - Minutes from Harper's Ferry

TinaRating, 5 stars3 weeks ago
The house was so uniquely quaint! It was truly a time to unwind from the craziness of this world! No TV other than in the upstairs bedroom and no Wi-Fi, which made it so nice to “unplug”! The sauna was absolutely amazing! The two options of fire pits to relax and have s’mores! The fireplace in the main living room was such an added bonus, to take the chill off in the morning and to just have a nice fire in the evening before bed. The fact that they had food there for us for breakfast was truly amazing! A bottle of wine to share, which was great considering we were there for our anniversary. You can get to so many places within 20 to 40 minutes! We went into Harpers Ferry for dinner at the Rabbit Hole! Harpers Ferry is a must to visit if you are in the area! Tons of trails, white water rafting and things to see and do are all just a short drive away. If you want a place to truly unwind, this is it! 🥰
Superhost
Home in Aspers
4.89 out of 5 average rating, 199 reviews

Bear Mountain Getaway

ChristopherRating, 5 stars1 day ago
When Luann says it's in the woods...she means it. Beautiful wooded lot with a paved driveway. The house was perfect for our stay. If you don't like the woods this place is not for you. Very quiet, very peaceful. The house is well kept and has everything you could need. Although tricky to get to, pay attention to her directions and you'll have no trouble getting there.
Top Guest favourite
Farm stay in Hamilton
4.97 out of 5 average rating, 235 reviews

Ballenger Farm

PhilRating, 5 stars4 weeks ago
Ballenger Farm is perfectly situated right before entering Purcellville, which gives you the perfect balance of feeling like you're away in the country, but with everything you need including gas, restaturants, pharmacy, and grocery stores within a 2 mile square radius. It's perfec for letting the dogs run around leash free and letting the kids explore every nook and cranny of the property. Not having screens in front of their faces was amazing and they just lit up and had so much fun. Exactly what we wanted! From fishing in the pond every day and catching multiple perch, to smores by the firepit, the family had the perfect little Memorial Day weekend! Thank you to our hosts for being super friendly and responsive!

Family-friendly home rentals with a pool

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
Apartment 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 stars3 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 stars1 day 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.
Guest favourite
Home in Berkeley Springs
4.84 out of 5 average rating, 74 reviews

Autumn Wings - wifi, screen porch, pool access

Jennifer And SteveRating, 5 stars7 months ago
Although our stay was short, it was just the change of scenery we needed! The community is so quiet and feels secluded — a great escape from the city! We enjoyed being tucked in the woods with the remnants of fall foliage around us. Yet the property is just a short distance from downtown Berkeley Springs and Cacapon State Park and other things to do. We especially appreciated the great setup for kids. Our rambunctious toddler stayed busy on a rainy day by cooking in the play kitchen and reading books. He also loved riding in the push-car on the deck!

Quick stats about holiday rentals that are family-friendly in Hagerstown

  • Total rentals

    40 properties

  • Nightly prices starting at

    $67 NZD before taxes and fees

  • Total number of reviews

    2K reviews

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 properties include access to Wi-Fi

Destinations to explore