Holiday Homes in Hagerstown

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Check prices for these dates

Our top choices for Hagerstown holiday homes

1. 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, (19 reviews)
"Cute place with a lot of character. Host was very responsive. We enjoyed our sray."
United States
Dawn V.
The price is NZ$541
includes taxes & fees
13 Dec - 14 Dec
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit

2. Foxfire - Secluded Zen Retreat with Spa & Views

Foxfire - Secluded Zen Retreat with Spa & Views
Smithsburg
10.0 out of 10, Exceptional, (33 reviews)
"Beautiful house and property with everything you need for a lovely time away! We were comfortable and made to feel welcome in a variety of ways. Hope to be back soon!"
United States
Sarah Beth R.
The price is NZ$705
includes taxes & fees
15 Nov - 16 Nov
Foxfire - Secluded Zen Retreat with Spa & Views

3. 1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield

1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield
Sharpsburg
10.0 out of 10, Exceptional, (55 reviews)
"The house was in a great location with the winery and battlefield nearby, and the house was very nice and comfortable."
United States
Nancy D.
The price is NZ$678
includes taxes & fees
10 Dec - 11 Dec
1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield

4. Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront

Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
Sharpsburg
8.2 out of 10, Very good, (66 reviews)
"I was surprised to see how dilapidated the decking around the house was. I was concerned we might trip or fall through. The location was ideal for bicycling and fishing . The backyard was beautiful with the most prettiest flowers and trees."
United States
Susie R.
The price is NZ$738
includes taxes & fees
30 Nov - 1 Dec
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront

5. Charming Shepherdstown Home - Walk to Downtown

Charming Shepherdstown Home - Walk to Downtown
Shepherdstown
2.0 out of 10, (1 review)
"The house was not clean. Surfaces were sticky, dishes in the cupboard were dirty, the shower had not been cleaned, the toilet was broken, much of the furniture was unstable, including the beds, one of which had a loose pillar, the other with a headboard that was not attached to anything. The entrance through the carport was dangerous and ill-smelling. There was no functioning key to the front door, so entrance had to be made through the carport every time. In the horse bedroom, there was one...
United States
Sarah E.
The price is NZ$656
includes taxes & fees
23 Nov - 24 Nov
Charming Shepherdstown Home - Walk to Downtown

6. Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
Rohrersville
10.0 out of 10, Exceptional, (22 reviews)
"Our stay was so enjoyable!"
United States
Kimberly C.
The price is NZ$754
includes taxes & fees
19 Nov - 20 Nov
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

7. The Woods Resort w/ Jacuzzi, 2 Decks +Fireplace

The Woods Resort w/ Jacuzzi, 2 Decks +Fireplace
The Woods
The price is NZ$625
includes taxes & fees
17 Nov - 18 Nov
The Woods Resort w/ Jacuzzi, 2 Decks +Fireplace

8. Mountain retreat w/deck, game room & dog-friendly

Mountain retreat w/deck, game room & dog-friendly
The Woods
9.2 out of 10, Wonderful, (7 reviews)
"This property was exactly as advertised and our family had a great time. It was one of the cleanest homes we have stayed at and Tony and his crew responded quickly to any minor needs we had. It is very easy to highly recommend this home."
United States
Roy N.
The price is NZ$1,014
includes taxes & fees
18 Nov - 19 Nov
Mountain retreat w/deck, game room & dog-friendly

9. Modern w/ Hot Tub, Grill, WiFi & Resort Access

Modern w/ Hot Tub, Grill, WiFi & Resort Access
The Woods
The price is NZ$738
includes taxes & fees
16 Nov - 17 Nov
Modern w/ Hot Tub, Grill, WiFi & Resort Access

10. Modern, family-friendly, nature packed getaway

Modern, family-friendly, nature packed getaway
Berkeley Springs
8.8 out of 10, Excellent, (32 reviews)
"It was exactly what we needed for my groomsmen and I the night before my wedding, a clean, open space with private bedrooms and 4 beds. Perfect for a quick stay!"
United States
Ethan L.
The price is NZ$460
includes taxes & fees
15 Nov - 16 Nov
Modern, family-friendly, nature packed getaway

11. Modern Cabin w Hot Tub & Indoor Pool/Gym Access!

Modern Cabin w Hot Tub & Indoor Pool/Gym Access!
The Woods
9.0 out of 10, Wonderful, (14 reviews)
"Great location, everything was great and we would stay again!"
United States
Lauren P.
The price is NZ$681
includes taxes & fees
16 Nov - 17 Nov
Modern Cabin w Hot Tub & Indoor Pool/Gym Access!

12. Scenic Dog-Friendly Mountain Chalet with Panoramic Views & Game Loft Near Berkeley Springs, Hedgesville, WV

Scenic Dog-Friendly Mountain Chalet with Panoramic Views & Game Loft Near Berkeley Springs, Hedgesville, WV
The Woods
The price is NZ$1,347
includes taxes & fees
18 Nov - 19 Nov
Scenic Dog-Friendly Mountain Chalet with Panoramic Views & Game Loft Near Berkeley Springs, Hedgesville, WV

13. Bright Woodland Chalet with Hot Tub & Fireplace Near Berkeley Springs, Hedgesville, WV

Bright Woodland Chalet with Hot Tub & Fireplace Near Berkeley Springs, Hedgesville, WV
The Woods
The price is NZ$861
includes taxes & fees
30 Nov - 1 Dec
Bright Woodland Chalet with Hot Tub & Fireplace Near Berkeley Springs, Hedgesville, WV

14. Gorgeous Vacation Rental with Grill, Fire Pit, Golf Course Views, and Resort Access in Hedgesville, West Virginia

Gorgeous Vacation Rental with Grill, Fire Pit, Golf Course Views, and Resort Access in Hedgesville, West Virginia
The Woods
The price is NZ$1,072
includes taxes & fees
15 Nov - 16 Nov
Gorgeous Vacation Rental with Grill, Fire Pit, Golf Course Views, and Resort Access in Hedgesville, West Virginia

15. Cute Secluded Cabin with Fire Pit in Hedgesville, West Virginia

Cute Secluded Cabin with Fire Pit in Hedgesville, West Virginia
The Woods
The price is NZ$899
includes taxes & fees
23 Nov - 24 Nov
Cute Secluded Cabin with Fire Pit in Hedgesville, West Virginia

16. Renovated Farmhouse located near the C and O Canal

Renovated Farmhouse located near the C and O Canal
Hancock
9.6 out of 10, Exceptional, (39 reviews)
"Beautiful, spacious house."
United States
Gloria
The price is NZ$480
includes taxes & fees
14 Nov - 15 Nov
Renovated Farmhouse located near the C and O Canal

17. 5-Min Walk Downtown +Fireplace + Office

5-Min Walk Downtown +Fireplace + Office
Berkeley Springs
10.0 out of 10, Exceptional, (1 review)
"My friend and I rented this home for a girls out weekend. The home was cozy, clean and well accommodated for our needs. Upon arrival we ran into a small setback with an extra lock on the door keeping us from getting in but Heena responded quickly and walked us through how to get it unlocked. I have a very large SUV that took some maneuvering to get into the driveway but im sure smaller vehicles will not have any issues. Highly recommended if you are looking to stay in Berkley Springs. Thank...
United States
Spyder D.
The price is NZ$531
includes taxes & fees
30 Nov - 1 Dec
5-Min Walk Downtown +Fireplace + Office

18. Charming "Cream of the Crop" Cape ~❤️of Middletown

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (162 reviews)
"Great little spot!"
United States
Shelby W.
The price is NZ$467
includes taxes & fees
15 Nov - 16 Nov
Charming "Cream of the Crop" Cape ~❤️of Middletown

19. Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.

Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.
Highfield-Cascade
10.0 out of 10, Exceptional, (11 reviews)
"I cannot say enough about the wonderful time we had staying at Denise & Mike's lovely cottage. They went above and beyond to make sure our family gathering was perfect...and it truly was. Sitting on the front porch sharing coffee in the a.m. and wine in the evening. Board games, chats and laughter until our bellies ached. Our family spent our much needed reunion sharing long overdue times making more wonderful memories. Upon arrival we found the property even more special than we imagined from...
United States
Julianne L.
The price is NZ$435
includes taxes & fees
24 Nov - 25 Nov
Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.

20. Schilling House

Schilling House
3.0 star property
Bolivar
The price is NZ$560
includes taxes & fees
22 Nov - 23 Nov
Schilling House
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.

Hagerstown and related destinations

Civil War history comes alive at Antietam Battlefield, just a short drive from downtown's revitalised arts district. Explore the Western Maryland Rail Trail by bike, then catch a minor league baseball game at Municipal Stadium where local fans cheer passionately.

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

Top reviews in Hagerstown