
House holiday rentals in Hagerstown
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Top-rated house rentals in Hagerstown
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Popular amenities for house rentals in Hagerstown
House rentals with a pool

Stoney Spring Overlook
This is our fourth year here and it is always a great experience! Jeanne is super communicate and always helpful! The location and house are beautiful! The amenities are excellent: fire pit with wood, pool, and hot tub. Will be coming here forever.

Barnswallow Ranch, 3 BDR Home w private pool
We had a unforgettable weekend at Kathryn's home with good friends! The pool, the barn, the privacy and the surroundings were spectacular! I already recommended the home to mu family because it does feel like home 🏡

4BR, 4BA, Amazing Indoor Pool, EV charger, ~10 acr
Gorgeous private property, surrounded by nature. Welcoming home with wonderful amenities. Instantly aware a great deal of thought was put into all aspects of this home, providing a seamless transition to vacation mode. Host was very communicative and helpful. Would highly recommend.

Civil War Farm House w/Heated (seasonal) Pool
Extremely beautiful historic farmhouse! Went on a family vacation and felt like we were in an oasis! Extremely clean home and clean and smelling wonderful linens and sheets. Felt like I was staying at my grandmothers house. Tina and Todd were only a text away but we also felt like we had the whole place to ourselves. Gettysburg battlefields and downtown only a 10 minute drive. Really wonderful place and worth every penny. Cows were adorable and while they were vocal on our first night, we did not mind. Ear plugs were provided in case they got too rambunctious! Only regret is not asking to have the pool opened because it got up to 80 one day but next time we stay here we will be sure to bring bathing suits!

Harpers Ferry Farmhouse, Heated Year Round Pool
Perfect location for a women’s wellness retreat! The ladies are already asking when we can come back. Plenty of spaces big and small to facilitate us, both as a group as well as individuals looking to relax and recharge. Having two kitchens was nice for feeding such a big group, and the heated saltwater pool was the cherry on top!

Cedar Creek Wayside Castle
It’s a private place to go and enjoy and famili kids are very happy with the pool and activities

SKI YA LATER Whitetail
Awesome hosts. So responsive and place was sweet. Would recommend to anyone.

Sophia’s victorian
Perfect place for our stay in Germantown. Very cozy and the kitchen was fully stocked with cookware. Plenty of rooms for everyone to have their own space and also the family room was big enough for everyone to hang out together.
Weekly house rentals

Indigo Blue modern open vibe on tree lined street
Our group appreciated our stay in Winchester. The host was very clear on instructions to check in and out of the property. Additionally, they were generously accessible if any questions or issues were to arise. Parking was ample for a small to mid-sized group. The space was very clean and in a quiet residential neighborhood, which led to a relaxing vibe for the weekend stay. The property was also conveniently located near many restaurants, bars, and stores. We recommend this spot for anyone looking for a small getaway with friends.

Country Comfort -wifi, fireplace, golf, rec center
This place was just what I was looking for. Quiet place to relax, good place to hike and fitness center and courts. Cabin was just as advertised cozy and well kept. Everything you need for a weekend stay.

Mtn. View~Cave Hot Tub~50 Ac~ATV Trails~Fishing
It was a peaceful family get away. The house is well stocked with necessities. The animals were an adorable touch. I enjoyed feeding them more than the kids did. The trails are more for able bodied people. My clumsy 2 year old was not able to get very far. My kids and dogs loved playing in the mini beach. The cave hot tub unique but we were not able to use it. The peoperty itself is gorgeous. I would love to come back.

Downtown Retreat - whole house full of amenities
We've been staying at Michele and Kim's homes for a few years now and they are always helpful and communicate well before and during our stay! This home was just a few minutes from downtown Carlisle and it was in a great location!

Groovy Crib in Downtown Frederick/1 lvl/fencedyard
The Groovy Crib is a gem! We felt right at home. The place is spotlessly clean and comfortable—just right! We had easy access to the places we wanted to visit around Frederick. We especially enjoyed having the school nearby and loved watching the kids play outside in the afternoon. My husband started calling it "our school" when we were finding our way back to the house after being out for the day. Nicole was very friendly and quickly responded to our questions. I personally appreciated the Anker cubes scattered throughout the rooms where we could plug in our various devices. Clever! And the night lights in the house made it easy to find our way after dark if we needed to get up for anything. Very helpful in a strange new place after a long day of travel. We had a small issue with the security system one night, but it was quickly resolved. We will stay here again next time we are in the area!

Upperville Hunt Country Cottage
The house was perfect for our family Middleburg weekend stay. It was clean, cozy, well stocked, and centrally located. The tavern across the street was so convenient and added a local feel. We would definitely stay here again when we are in the area.

Peaceful Waterfall House is waiting for you.
It was a wonderful stay the kids loved looking at the water and playing outside.

A "Suite" Place to Crash
Our family stayed here for a night during an educational visit. Debbie was very welcoming and helpful. The vibe of the space is more of a youth retreat set up, instead of an apartment type, but that was perfect for our kids and this visit to Gettysburg. We didn’t get to explore the grounds but the area was so peaceful and beautiful. One thing that stood out as exceptional was the tremendous number of blankets, pillows and towels available. There was WELL over the number needed to accommodate people staying. Normally, places have just barely enough, but Debbie’s place far exceeded our expectations in this area. Definitely worth staying here!
Private house rentals

Private 3BDR, Spacious 1LVL Home, Mins to Airport
Daniel’s place was absolutely outstanding! The description and photos were spot-on, and the house itself was impeccably clean. It was such a treat to have a peaceful backyard and a driveway—rare finds in the DC area! The single-level, open floor plan made it easy for our family to relax, share meals, and enjoy games together over the holiday weekend. I highly recommend this home and will definitely stay here again. Thanks, Daniel, for being such a thoughtful and responsive host!

Quiet, Simple Pleasure. Between DC and Shenandoah.
We had eight adults, a toddler, and a dog and there was space for everyone. The house has such a cozy feel. It was decorated for Christmas and we were celebrating a belated Christmas with our adult kids so it was perfect!! We had a chess tournament going all week so the game room was well used. The kitchen was huge and well stocked so perfect for all of the cooking we did. Lovely space outside for the dog and the toddler to play. Had to make a trip or two to the grocery store and that was about a 9 minute drive. We definitely hope to stay in this beautiful home again.

Rines' Country Getaway
I had the pleasure of staying in her house for over 4 months and it was everything I needed and more. If and who return to the area I hope to stay here.

Deer Lick Cabin
A little slice of heaven. Beautiful area. Had a wonderful weekend getaway.

Potomac Mansion Close to Nature, Culture & DC
We had a lovely stay at this gorgeous home. There were thoughtful amenities throughout the property. It’s an easy drive to DC from the mansion too. Beautiful, peaceful surroundings and we would love to come back.

The Villa on Lakeside
Everything about this stay was amazing! Beautiful property, super clean, really comfortable beds and furniture, and wow; the kitchen! Very quiet and walkable neighborhood, yet so close to everything (Metro, One Loudon, and so many great areas to visit). Hosts were absolutely wonderful. We’d love to come back.

Cozy Cottage
After spending our day(s) sight-seeing in the Winchester area; Cozy Cottage was the perfect retreat to come back to and relax. We had a minor issue (which may have been User Error) and Matt & Sarah responded quickly and even came to the cottage to remedy the issue. We would definitely rent this cottage again.

The Country French Cottage at High Meadows Estate
Cute cottage! Had everything we needed and it was very peaceful. The only thing to note is that showering is pretty difficult. The tub is nice and there is a shower hose, but you have to hold it up yourself. This might be an obstacle for some people. The host was very nice easy to communicate with. Didnt see any animals on the property unfortunately!
Quick stats about house rentals in Hagerstown
Total rentals
40 properties
Nightly prices starting at
ÂŁ30 before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Whitetail Resort
- Liberty Mountain Resort
- Caledonia State Park
- Cacapon Resort State Park
- Stone Tower Winery
- Gambrill State Park
- Cunningham Falls State Park
- The Links at Gettysburg
- Codorus State Park
- Cowans Gap State Park
- South Mountain State Park
- Notaviva Vineyards
- Shenandoah Valley Golf Club
- Whiskey Creek Golf Club
- JayDee's Family Fun Center
- Berkeley Springs State Park
- River Creek Club
- Pine Grove Furnace State Park
- Creighton Farms
- Bowling Green Country Club
- Dinosaur Land
- The Golf Club at Lansdowne
- Herndon Centennial Golf Course
- Field of Screams Maryland