
Vacation rentals in Hagerstown
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Top-rated vacation rentals in Hagerstown
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Popular amenities for Hagerstown vacation rentals
Dog friendly vacation rentals in Hagerstown

Harmony Lodge nestled in wooded tranquility!
Harmony Lodge was the perfect getaway to relax with my husband and our dog. The lodging itself is clean, quiet, and well equipped for a vacation weekend . The kitchenette is cozy but has all of the basic utensils and several options to cook food. The bedrooms were spacious. Upstairs the loft is a great spot to unwind. The pool was just as idyllic as it looks in the pictures. But the best part is how ideal her property is set up for dogs. The smartly fenced off areas between the pool, her home, and our entrance was the best experience I have had renting a space while traveling with my pup. Elisa was very respectful of our privacy but also a super friendly host. We enjoyed chatting with her and meeting her pups. We found plenty to do within ~20 minutes of the property: hiking, birding, tasty places to eat and found some good beer. I can't recommend Harmony Lodge enough for anyone looking to unwind with their dog AND enjoy the luxury of a swim!

The Resting Place
This was our second stay at Sherry's it's such cozy place to stay. It's always so clean and welcoming. We were in the area again for a weekend long stockdog clinic and were so grateful that Sherry allows our dog to stay with us.

The Goat Loft - A Private, Peaceful Getaway!
We loved our stay at the Goat Loft! The goats had so much personality and were so interactive. The space was lovely and so well kept. We had everything we needed and felt right at home. We were in town for a wedding but really loved exploring the wineries and local towns. Brian was welcoming and very responsive. Would absolutely stay here again and recommend it to friends and family as a peaceful and unique experience!

Modern Cabin: Hot Tub, Arcade, FirePit, Pets+Pool
We loved our stay! The house is so cute, and the bed was amazingly comfortable. I slept like a rock! We look forward to staying again with our kids in the future.

Cozy Cabin with Creek Access
This cabin is absolutely perfect for a peaceful, quiet get away. The place is gorgeous with an amazing view, wonderful for a break from a hectic life and completely private. Furnishings includes everything you need, kitchen was very well stocked. Not the most difficult place to find but you will need the, very detailed, directions as Google maps just gives up. Will absolutely look to stay here again. Mai-Li was very quick to respond to any messages, and very kindly made sure I got there ok, and sent on a list of local events. Thank you Mai-Li

The Sage Chalet
We had a great stay! Really enjoyed sitting outside on the patio and enjoying the surroundings. Had some great Sunday cookouts and enjoyed sitting outside with the family and enjoying our meal. Lori was very responsive and checked in often during our extended stay. Overall great experience!

Cabin in the Woods - Weekday Specials!
Very peaceful surroundings, enjoyed sitting on the front porch during the rain

Horizon Hill-Log Cabin w/Hot Tub & Views!
Overall excellent experience. High on the hill with a little view. The hot tub was very clean, private and can’t be seen from any neighboring house. The driveway is a tight turn in a full size truck so watch for the ditches. It was rainy and in the high 70s for the 3 days I was there and the wall mounted air conditioner kept up good. Ceiling fans throughout were nice. I will stay here again.
Vacation rentals with pools in Hagerstown

Stoney Spring Overlook
This BnB is in contention for my FAVORITE stay of all time. Family of 6 adults and 1 child had more than enough space, and Jeanne really made our stay effortless. We felt right at home and we didn't have to make that last minute trip to the store you sometimes have to make bc the host skimped on providing toilet paper or dish soap, because she honestly thought of EVERYTHING ❤️ My granddaughter loved the pool and dips in the hot tub after swimsmade the adults happy. The location and view are to die for, and the two pups were ecstatic playing in the large fenced area. We spent a lot of time outside, plenty of furniture, fire pit, just eating dinner on the deck. (Missing NOTHING in the kitchen either!) Our last night we spent sitting and talking on the deck trying to identify the multitude of frog voices from the pond, before we parted ways to our various home states. I am most grateful for memories made and we are definitely considering a repeat! ❤️Thank you!

Bear Pines Retreat ~ Game Room ~ Screened Porch
Lou's place is great! We were 5 people, 3 adults and 2 kids. The house had plenty of space for us to enjoy ourselves. The kids loved the game room and roasting marshmallows in the fire pit. The community was also lovely with two outdoor pools and an indoor pool. we really appreciated the guest passes that allowed us to enjoy the pools for both days we were there. Many thanks, Lou!

Dog-friendly, boutique & chic + fireplace
Teddi and Adam were great hosts and have such a beautiful place that provided some much needed peace and quiet! We really enjoyed our stay!

Five Oaks Cabin at The Woods Resort
We really enjoyed our stay here. The house offered so many things for us to do as a family. We had such a good time playing darts, pingpong, board games, and hanging out around the fire pit. The Woods is our favorite place to go because of all the amenities. Highly recommend!

Starcatcher Chalet, The Woods Resort
Beautiful place in a beautiful area! They had everything we needed

Historic Peace and Plenty Farm: Pool House
Duane and Matt were absolutely wonderful hosts! They helped make our quick weekend getaway truly unforgettable. Every amenity at the property was thoughtfully provided, and our daughters enjoyed every bit of it. Even while traveling internationally, Duane remained incredibly attentive and responsive, going above and beyond to ensure our stay was perfect. One of the highlights for our girls was getting to meet a baby sheep—such a thoughtful and special touch! They were especially taken with little Pinky Pie and are still talking about her. Thank you again, Duane, for sharing your beautiful property and creating such a memorable experience for our family!

Stylish Retreat w Fireplace, Games & Pool Access
It's a beautiful escape from the city, tucked away in the woods. very peaceful and Serene, there wasn't too much around but it's the perfect getaway.

Amazing Summer Holiday and Mountain Retreat
This is an excellent home for staying near the slopes! The beds were super comfortable, the welcome basket, kid friendly amenities, and provided essentials were very much appreciated. We would love to stay here again.
Other great vacation rentals in Hagerstown

The Frame ~ Charming Nature Escape ~ Hot Tub ~ BBQ
Wandas place was immaculate, we enjoyed our two night stay. Wanda communicated throughout, to make sure everything was well. We have no complaints, location was great, kitchen fully stocked. Such a great experience, we will be back!

Monte Vista~Golf~Views~PS5~Sport Court~EV Charger
Breathtaking views…this house did NOT disappoint! We loved every single detail and thought put into this property. We will definitely be going back in the future. If you’re looking for a unique property look no further!

Sleepy Hollow Log Cabin
Very beautiful area, incredibly stocked space. The nearby snowcone shop has lots of activities and trails nearby.

Enchanting PET FREE W/Amazing ViewHot Tub Overlook
Brian was an extremely kind and gracious host. The property was scenic and really beautiful. The yard was lit up with fireflies at night and it was a short walk to the overlook of the river. The only thing we weren’t sure about when we arrived was the hot tub. It wasn’t an issue by any means. I would highly recommend Brian and the tiny home.

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!

❤️ Secluded 1940s Romantic Tiny House on the River
I spent the previous 3 nights camping while cycling the GAP/C&O trail from Pittsburgh to DC.... this cabin was the perfect place to relax and recharge; especially since rain was forecastee overnight. The cabin is in a real beautiful area just through Shepherdstown. if you are on a bike and did a long day, stop and get dinner before you go to the cabin... there are a few hills between downtown and the cabin that might hurt a bit.

Easygoing
Wow. Raymond's cabin in the woods is extraordinary. It is indeed off the beaten track, but well worth it. We felt like we were the only humans for miles (we weren't) and we enjoyed the sounds of the forest. The cabin is comfortable, and well appointed. We both enjoyed the outdoor shower, though I cannot imagine doing that in the winter, but I'm a wimp. :) There are horseshoes, and a porch swing, as well as hammock chairs to enjoy the view. We are already discussing returning to this gem next year for a much longer stay.

The Cottage
Great place to stay! Clean - and Eugene was very helpful.
Quick stats about vacation rentals in Hagerstown
Total rentals
90 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
3.3K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
10 properties have a pool
Frequently Asked Questions
Are there apartment rentals with a dedicated workspace in Hagerstown?
Yes! Work meets play with ease at over 10 apartment rentals in Hagerstown featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in house rentals in Hagerstown?
Experience the best of Hagerstown with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly apartment rentals in Hagerstown?
Four-legged friends are welcome in Hagerstown. Choose from more than 10 apartment rentals for guests traveling with pets.
Are there Hagerstown vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Hagerstown, available on Airbnb. Make a splash and soak up the sun in style!
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- Cunningham Falls State Park
- Caledonia State Park
- Stone Tower Winery
- The Links at Gettysburg
- Cowans Gap State Park
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- Whiskey Creek Golf Club
- Gambrill State Park
- Whitetail Resort
- Liberty Mountain Resort
- South Mountain State Park
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- Shenandoah Valley Golf Club
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- Creighton Farms
- Bowling Green Country Club
- Notaviva Vineyards
- Berkeley Springs State Park
- JayDee's Family Fun Center
- River Creek Club
- The Golf Club at Lansdowne
- Dinosaur Land
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