
Family-friendly holiday rentals in Hagerstown
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Top-rated family-friendly rentals in Hagerstown
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Popular amenities for Hagerstown family-friendly rentals
Family-friendly home rentals with a hot tub

Private Modern Log Cabin w/Hot Tub
We enjoyed our time and the hot tub was great. Truly peace and quiet

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!

Cozy Townhome At The Woods Resort Golf,SPA,Tennis
We had a great time and the check in process was seamless. Keith was proactive and very responsive.

Grouseland's Pondside Vacation Cottage
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!!

Apple Blossom Cottage HT is extra$
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!

Wild, Wonderful Five-Bedrm Loghome
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!

Cozy Cabin Hidden Away on a Lake!
Excellent stay! Beautiful locale! Would stay again for sure!

Brent Road Retreat
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

Island cabin
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.

Shenandoah Siesta
Clean, well-stocked, spacious, and comfy! Town was a five minute walk with some great local shops and restaurants. Enjoyed our stay!

Gayte House Gay Owned, Liberal Oasis
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!

Rustic Cabin on Cacapon River for Private Getaway
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!

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!

Stone School House - Minutes from Harper's Ferry
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! 🥰

Bear Mountain Getaway
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.

Ballenger Farm
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

Deer Crossing at The Woods
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.

Goose Hill
The place was charming, well stocked and very comfortable. The communication was great and we would definitely rent again.

Quiet Antietam Cabin
A very nice area to see fall colors, out of the way but easy to reach a store for anything needed

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

Potomac Overlook Farms: 6 BR, 10 Acre River Estate
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.

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

The McCoy House at the Harpers Ferry KOA
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.

Autumn Wings - wifi, screen porch, pool access
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
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- Cunningham Falls State Park
- Caledonia State Park
- Stone Tower Winery
- The Links at Gettysburg
- Cowans Gap State Park
- Cacapon Resort State Park
- Codorus State Park
- Whiskey Creek Golf Club
- Gambrill State Park
- Whitetail Resort
- Liberty Mountain Resort
- South Mountain State Park
- Field of Screams Maryland
- Pine Grove Furnace State Park
- Creighton Farms
- Shenandoah Valley Golf Club
- Notaviva Vineyards
- Bowling Green Country Club
- Berkeley Springs State Park
- JayDee's Family Fun Center
- River Creek Club
- The Golf Club at Lansdowne
- Herndon Centennial Golf Course
- Dinosaur Land