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Our top choices for Western Maryland vacation homes

1. 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 ¥15,872
¥41,724 total
includes taxes & fees
Nov 15 - Nov 16
Charming "Cream of the Crop" Cape ~❤️of Middletown

2. RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Downtown Frederick
9.2 out of 10, Wonderful, (148 reviews)
"Great location. Amenities were perfect for a little bit of an extended stay. Definitely will come back in the future"
United States
Dave T.
The price is ¥15,872
¥40,042 total
includes taxes & fees
Nov 16 - Nov 17
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

3. Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Jefferson
10.0 out of 10, Exceptional, (75 reviews)
"Lovely home. Great location! Host was amazingly helpful!"
United States
Tory D.
The price is ¥15,872
¥39,032 total
includes taxes & fees
Nov 15 - Nov 16
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

4. Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (102 reviews)
"Very convenient location with parking. Prompt communication with owner. However it needs a good deep clean. My towels were used and muddy like the workmen fixing the deck had just showered there. But I would stay there again if necessary."
United States
Jessica
The price is ¥24,713
¥52,105 total
includes taxes & fees
Nov 17 - Nov 18
Luxury Condo In Downtown Frederick

5. Rural & Historic Detour Escape w/ Horses On-Site!

Rural & Historic Detour Escape w/ Horses On-Site!
Detour
9.0 out of 10, Wonderful, (8 reviews)
"Lovely! Our host was gracious and helpful. Property was ideal for our family getaway. i’m"
United States
Mary F.
The price is ¥19,205
¥66,119 total
includes taxes & fees
Nov 14 - Nov 15
Rural & Historic Detour Escape w/ Horses On-Site!

6. Cozy Downtown Cabin - Family Friendly

Cozy Downtown Cabin - Family Friendly
Middletown
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful property. I will definitely stay there again."
United States
Roger
The price is ¥30,157
¥34,827 total
includes taxes & fees
Nov 25 - Nov 26
Cozy Downtown Cabin - Family Friendly

7. 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 ¥18,427
¥39,386 total
includes taxes & fees
Nov 22 - Nov 23
Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.

8. 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 ¥23,751
¥50,483 total
includes taxes & fees
Nov 16 - Nov 17
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit

9. New townhouse

New townhouse
Frederick
9.6 out of 10, Exceptional, (13 reviews)
"We had a great time. It was perfect for us. I would highly recommend it to others and would not hesitate to return there when back in the area. "
United States
Tereasa G.
The price is ¥26,998
¥60,585 total
includes taxes & fees
Nov 16 - Nov 17
New townhouse

10. Newly constructed 6 bedroom home

Newly constructed 6 bedroom home
Frederick
10.0 out of 10, Exceptional, (22 reviews)
"It was a great place to relax, sleep and come home to after busy days in Frederick area. We would definitely stay here again!"
United States
Janice M.
The price is ¥33,807
¥75,541 total
includes taxes & fees
Nov 23 - Nov 24
Newly constructed 6 bedroom home

11. Dog-Friendly | Hiking| Tubing near Harpers Ferry

Dog-Friendly | Hiking| Tubing near Harpers Ferry
Brunswick
2.0 out of 10, (1 review)
"No ac just window units it was soooooo hot"
United States
Anonymous traveler
The price is ¥19,903
¥35,629 total
includes taxes & fees
Nov 17 - Nov 18
Dog-Friendly | Hiking| Tubing near Harpers Ferry

12. Walk to Stores: Home in Historic Shepherdstown!

Walk to Stores: Home in Historic Shepherdstown!
Shepherdstown
9.4 out of 10, Exceptional, (6 reviews)
"Very nice place, the lay out is perfect for multiple adults, we stayed for 10 night for work and it was perfect, we will be back for another long stay soon. "
United States
Brandon K.
The price is ¥13,421
¥58,265 total
includes taxes & fees
Nov 19 - Nov 20
Walk to Stores: Home in Historic Shepherdstown!

13. The Whimsy Loft-Cozy Private Suite in Westminster on 4 acres

The Whimsy Loft-Cozy Private Suite in Westminster on 4 acres
Westminster
The price is ¥19,713
¥29,644 total
includes taxes & fees
Nov 29 - Nov 30
The Whimsy Loft-Cozy Private Suite in Westminster on 4 acres

14. Private Sauna, Fireplace and Country Views

Private Sauna, Fireplace and Country Views
Mount Airy
10.0 out of 10, Exceptional, (6 reviews)
"Wonderful location with a beautiful field where wild animals visited. Hosts really took care of the amenities (great coffee bar). Close to Mt Airy and vineyards."
United States
Richard B.
The price is ¥51,267
¥58,549 total
includes taxes & fees
Nov 16 - Nov 17
Private Sauna, Fireplace and Country Views

15. 4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry

4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry
Knoxville
10.0 out of 10, Exceptional, (37 reviews)
"Great stay, super nice people and wonderful house."
United States
Kenzie S.
The price is ¥25,884
¥77,736 total
includes taxes & fees
Nov 16 - Nov 17
4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry

16. 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 ¥43,648
¥68,475 total
includes taxes & fees
Dec 10 - Dec 11
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

17. Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi

Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi
Cumberland
9.8 out of 10, Exceptional, (57 reviews)
"comfortable cottage. In between most activity areas."
United States
WILSON
The price is ¥19,046
¥29,106 total
includes taxes & fees
Nov 13 - Nov 14
Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi

18. Camp Patowmack - Riverfront, Hot Tub, and Sauna!

Camp Patowmack - Riverfront, Hot Tub, and Sauna!
Harpers Ferry
9.6 out of 10, Exceptional, (11 reviews)
"Great water access"
United States
claire r.
Camp Patowmack - Riverfront, Hot Tub, and Sauna!

19. Oldtown Guesthouse

Oldtown Guesthouse
Oldtown
10.0 out of 10, Exceptional, (37 reviews)
"Wonderful property, comfy and perfect for a getaway. Definitely need to come back."
United States
Stephanie R.
The price is ¥19,840
¥33,649 total
includes taxes & fees
Nov 15 - Nov 16
Oldtown Guesthouse

20. 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 ¥33,384
¥58,162 total
includes taxes & fees
Nov 22 - Nov 23
Charming Shepherdstown Home - Walk to Downtown
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.

Learn more about Western Maryland

Discover the state’s western panhandle to find Civil War monuments, an old-fashioned scenic railroad and cozy towns amid spectacular mountain scenery.

A stone house with a wooden fence and garden.

Top reviews in Western Maryland