A stone bridge with multiple arches over a calm river, surrounded by trees and greenery.

Hagerstown Holiday Rentals

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Our top choices for Hagerstown holiday rentals

1. ❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.6 out of 10, Exceptional, (86 reviews)
"Enjoyed my stay I appreciate the view and Rich. "
United States
Joseph
The price is NZ$199
includes taxes & fees
8 Oct - 9 Oct
❤️ Secluded 1940s Romantic Tiny House on the River

2. Bright 2-Bed ADA Room|Free Parking

Bright 2-Bed ADA Room|Free Parking
Hagerstown
The price is NZ$128
includes taxes & fees
1 Nov - 2 Nov
Bright 2-Bed ADA Room|Free Parking

3. Luxurious large condo, no steps,amenities galore. Brand new, Secure, Parking,W/D

Luxurious large condo, no steps,amenities galore. Brand new, Secure, Parking,W/D
Hagerstown
10.0 out of 10, Exceptional, (3 reviews)
"Carrie was very responsive and helpful. The location is as advertised. Would stay again for sure."
United States
Mark P.
Luxurious large condo, no steps,amenities galore. Brand new, Secure, Parking,W/D

4. Galloping Getaway on the rolling hills of GemStone Stable

Galloping Getaway on the rolling hills of GemStone Stable
Hagerstown
10.0 out of 10, Exceptional, (31 reviews)
"We loved staying here. Beautiful views, great communication with Tammie, and very clean. Definitely will stay again!"
United States
Haley H.
The price is NZ$336
includes taxes & fees
4 Oct - 5 Oct
Galloping Getaway on the rolling hills of GemStone Stable

5. Peregrine's Perch - Cabin Overlooking the River!

Peregrine's Perch - Cabin Overlooking the River!
Falling Waters
9.6 out of 10, Exceptional, (24 reviews)
"Relaxing, close to all."
United States
Valarie
The price is NZ$629
includes taxes & fees
7 Oct - 8 Oct
Peregrine's Perch - Cabin Overlooking the River!

6. Bring Your Own Boat - Meticulously restored house on the Potomac River

Bring Your Own Boat - Meticulously restored house on the Potomac River
Hedgesville
9.6 out of 10, Exceptional, (14 reviews)
"Great little place to stay."
United States
Shannon W.
The price is NZ$286
includes taxes & fees
4 Oct - 5 Oct
Bring Your Own Boat - Meticulously restored house on the Potomac River

7. Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit

Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
Boonsboro
9.8 out of 10, Exceptional, (18 reviews)
"Extremely cute and a wonderful place to relax."
United States
A D.
The price is NZ$578
includes taxes & fees
4 Oct - 5 Oct
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit

8. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (25 reviews)
"We loved staying here, and walking into town to.explore. The kitchen was well stocked, and the tub was.perfect for soaking after a long day hiking."
United States
Alexandra Z.
The price is NZ$457
includes taxes & fees
18 Oct - 19 Oct
Quaint Mini Cottage in Shepherdstown - Walking Distance

9. Modern 2-Bedroom and 2-Bed Apartment with Private Access Door Minutes from I-81

Modern 2-Bedroom and 2-Bed Apartment with Private Access Door Minutes from I-81
Hedgesville
9.0 out of 10, Wonderful, (8 reviews)
"Nice clean property. It was spacious and comfortable. "
United States
Diane G.
The price is NZ$208
includes taxes & fees
5 Oct - 6 Oct
Modern 2-Bedroom and 2-Bed Apartment with Private Access Door Minutes from I-81

10. Secluded WV Retreat Hot Tub, Fire Pit & Kayaks

Secluded WV Retreat Hot Tub, Fire Pit & Kayaks
Sleepy Hollow
10.0 out of 10, Exceptional, (44 reviews)
"Great place, perfect for a getaway"
United States
Cindy T.
The price is NZ$522
includes taxes & fees
5 Oct - 6 Oct
Secluded WV Retreat Hot Tub, Fire Pit & Kayaks

11. Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (98 reviews)
"We had a great stay! Everything was clean & well organized. The house was well stocked with everything we need. We would definitely stay here again."
United States
Stephen V.
The price is NZ$577
includes taxes & fees
6 Oct - 7 Oct
Antietam Creek - Quiet 2 Bedroom Cabin

12. Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
Keedysville
9.8 out of 10, Exceptional, (75 reviews)
"Beautiful cabin in the forest especially in the evening when the fire flies out and the sun sets."
United States
Jared
The price is NZ$794
includes taxes & fees
28 Oct - 29 Oct
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

13. Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (45 reviews)
"Beautiful property and just as described and shown in the pictures. "
United States
Kent Y.
The price is NZ$684
includes taxes & fees
14 Oct - 15 Oct
Antietam Look Out - Incredible Sunset Views!

14. 2-Bedroom cabin Hot tub Fireplace PS5

2-Bedroom cabin Hot tub Fireplace PS5
2.0 star property
The Woods
6.4 out of 10, (12 reviews)
"This place was wonderful. When have stayed at 4 different cabins like this and this was our favorite. The place was cozy and clean. The pantry was well stocked. The fire pit even had a wood fire prepared. The owners were really nice and communicated well. The facilities at the woods were included We live very the location and the hot tub Highly recommend"
United States
Christopher
The price is NZ$482
includes taxes & fees
11 Oct - 12 Oct
2-Bedroom cabin Hot tub Fireplace PS5

15. Pet-Friendly w Fire Pit, Grill & Resort Access

Pet-Friendly w Fire Pit, Grill & Resort Access
The Woods
The price is NZ$702
includes taxes & fees
5 Oct - 6 Oct
Pet-Friendly w Fire Pit, Grill & Resort Access

16. Glamping Clear Spring Maryland 3-Cabin Campground

Glamping Clear Spring Maryland 3-Cabin Campground
Clear Spring
9.8 out of 10, Exceptional, (17 reviews)
"Welcoming and spacious for all invitees and we did not even have a chance to explore all the areas that were surrounding as it was a work related trip but will get out there at some later point for a completely relaxing stay for sure"
United States
Image M.
The price is NZ$876
includes taxes & fees
4 Oct - 5 Oct
Glamping Clear Spring Maryland 3-Cabin Campground

17. Dog Friendly w/FirePit, Fiber WiFi & Resort Access

Dog Friendly w/FirePit, Fiber WiFi & Resort Access
The Woods
9.4 out of 10, Exceptional, (3 reviews)
"Clean rooms and towels. Comforting but very roomie."
United States
Kerfils b
The price is NZ$616
includes taxes & fees
4 Oct - 5 Oct
Dog Friendly w/FirePit, Fiber WiFi & Resort Access

18. Exclusive Wooded Chalet w Magnificent River Views

Exclusive Wooded Chalet w Magnificent River Views
Shepherdstown
10.0 out of 10, Exceptional, (20 reviews)
"Fantastic location, amazing views, clean property, responsive host"
United States
Brian
The price is NZ$1,266
includes taxes & fees
14 Oct - 15 Oct
Exclusive Wooded Chalet w Magnificent River Views

19. Cozy Cottage w Enclosed Porch, Fireplace & Grill

Cozy Cottage w Enclosed Porch, Fireplace & Grill
The Woods
The price is NZ$589
includes taxes & fees
12 Oct - 13 Oct
Cozy Cottage w Enclosed Porch, Fireplace & Grill

20. Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland

Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland
Boonsboro
The price is NZ$548
includes taxes & fees
5 Oct - 6 Oct
Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Hagerstown Hotel Reviews

Find out more about Hagerstown

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Hagerstown holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Hagerstown. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Hagerstown. Seeing all the best attractions is bound to make you fall in love with Hagerstown. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Hagerstown short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Hagerstown?

Yes, there are holiday rentals in Hagerstown close to Hagerstown Roundhouse Museum, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Hagerstown. Make sure you have time to check out the live music and theatres during your trip.

What are some of the best holiday rentals that Hagerstown has to offer?

The Spy House, Historic 1880s Home, Harpers Ferry: This holiday home rental outside of Hagerstown is located on a river, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals will I find in Hagerstown?

With 18 Expedia holiday rentals, you're guaranteed to find just the right place for your Hagerstown stay.

What’s there to see and do in Hagerstown?

Enjoy the outdoors at Marty Snook County Park and Piper Lane Neighborhood Park, or simply take in cultural attractions like Maryland Theater and Hagerstown Roundhouse Museum. Pennsylvania Dutch Market and Hagerstown Premium Outlets are other places to visit while you're in town.

What’s a holiday rental in Hagerstown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Hagerstown. Holiday rentals offer amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from shared hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for family trips or small group gatherings.