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Holiday Homes in Western Maryland

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Western Maryland holiday homes

A patio area with a wooden table, chairs, a decorative vase, and a fire pit.

1. Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick

Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Frederick
10.0 out of 10, Exceptional, (52 reviews)
The price is AU$391
includes taxes & fees
29 Sept - 30 Sept
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
A park with a pond, a bridge, and a church in the background.

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, (141 reviews)
"Very old but lovely building. Great parking and patio."
United States
Jennifer W.
The price is AU$411
includes taxes & fees
29 Sept - 30 Sept
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
A modern kitchen with dark cabinets, a large island with stools, a stainless steel refrigerator, and a built-in oven.

3. 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 AU$699
includes taxes & fees
26 Sept - 27 Sept
Newly constructed 6 bedroom home
A two-story house with a front porch, a chimney, and a small garden with pumpkins.

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (156 reviews)
"Great place to stay. Very clean and beautiful. The Host was very nice too and kept us informed. We will definetly stay there again!"
United States
Adair M.
The price is AU$363
includes taxes & fees
27 Sept - 28 Sept
Charming "Cream of the Crop" Cape ~❤️of Middletown
A modern kitchen with grey cabinets, a central island, and pendant lighting.

5. Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (98 reviews)
"Very clean, had everything we needed and close to shopping and restaurants. "
United States
Kathy S.
The price is AU$457
includes taxes & fees
7 Oct - 8 Oct
Luxury Condo In Downtown Frederick
A modern kitchen with white cabinets, a wooden table, a stainless steel refrigerator, and a wooden ceiling.

6. 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, (73 reviews)
"Lovely home. Great location! Host was amazingly helpful!"
United States
Tory D.
The price is AU$363
includes taxes & fees
27 Sept - 28 Sept
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
A kitchen with wooden cabinets, a white stove, a microwave, and a coffee maker.

7. Cozy Downtown Cabin - Family Friendly

Cozy Downtown Cabin - Family Friendly
Middletown
"Cute little cabin. Perfect for our 1 night stay for a concert in the area. Im just sad we left the kids at home cause they would have loved it too!"
United States
Laura K.
The price is AU$359
includes taxes & fees
6 Oct - 7 Oct
Cozy Downtown Cabin - Family Friendly
A brick building with a waterfall feature in front.

8. New townhouse

New townhouse
Frederick
9.6 out of 10, Exceptional, (12 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 AU$606
includes taxes & fees
6 Oct - 7 Oct
New townhouse
A sunroom with a wicker chair, a wooden chest, and a view through large glass doors.

9. 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)
"We had a great time. It is an older house but wonderful. It is in the country with lots of green fields surrounding it. The porch with the rockers was my favorite place to be when we weren’t site seeing, It was so peaceful. I would definitely stay here again."
United States
Charla H.
The price is AU$604
includes taxes & fees
27 Sept - 28 Sept
Rural & Historic Detour Escape w/ Horses On-Site!
A bathroom with a towel rack, a mirror, a sink, and a potted plant.

10. 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, (6 reviews)
The price is AU$326
includes taxes & fees
19 Oct - 20 Oct
Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.
A hallway with wooden flooring, a staircase, a door with a white frame, a lamp on a small table, and a wall-mounted mirror.

11. Antietam House Historic Sharpsburg Retreat

Antietam House Historic Sharpsburg Retreat
Sharpsburg
9.0 out of 10, Wonderful, (4 reviews)
"My friends and I had a wonderful time here for Labor Day! Quiet and a great location for all sorts of activities."
United States
Nick W.
The price is AU$502
includes taxes & fees
19 Oct - 20 Oct
Antietam House Historic Sharpsburg Retreat
A bedroom with a sloped ceiling, floral wallpaper, a bed with a blue quilt, two bedside lamps, and framed floral artwork.

12. 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 AU$277
includes taxes & fees
7 Oct - 8 Oct
The Whimsy Loft-Cozy Private Suite in Westminster on 4 acres
A large, curved metal building with a covered entrance and two chairs outside.

13. Antietam Dome: Level 2 Charger, 1 level, Walk to C&O Canal at Antietam Aqueduct Relax, Naturally!

Antietam Dome: Level 2 Charger, 1 level, Walk to C&O Canal at Antietam Aqueduct Relax, Naturally!
Sharpsburg
9.2 out of 10, Wonderful, (5 reviews)
"We enjoyed the views."
United States
Shena M.
The price is AU$548
includes taxes & fees
29 Sept - 30 Sept
Antietam Dome: Level 2 Charger, 1 level, Walk to C&O Canal at Antietam Aqueduct Relax, Naturally!
A modern kitchen with wooden cabinets, a large island with stools, and a bar area.

14. 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, (17 reviews)
"Beautiful house in a bucolic setting. Perfect for a family for the night."
United States
Kate M.
The price is AU$613
includes taxes & fees
30 Sept - 1 Oct
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
A house with a deck, outdoor seating, and a fire pit.

15. 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 AU$1,005
includes taxes & fees
13 Oct - 14 Oct
Exclusive Wooded Chalet w Magnificent River Views

16. Charming Shepherdstown Home - Walk to Downtown

Charming Shepherdstown Home - Walk to Downtown
Shepherdstown
The price is AU$393
includes taxes & fees
28 Sept - 29 Sept
Charming Shepherdstown Home - Walk to Downtown
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with wooden chairs and a table.

17. Modern, family-friendly, nature packed getaway

Modern, family-friendly, nature packed getaway
Berkeley Springs
9.0 out of 10, Wonderful, (29 reviews)
" Clean very nice property"
United States
Lisa D.
The price is AU$408
includes taxes & fees
8 Oct - 9 Oct
Modern, family-friendly, nature packed getaway

18. 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)
"Lovely place along the c&o. The host was very accommodating and helpful."
United States
Laura D.
The price is AU$621
includes taxes & fees
5 Oct - 6 Oct
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
A modern kitchen with stainless steel appliances, white cabinetry, and a window with a view of the outdoors.

19. Oldtown Guesthouse

Oldtown Guesthouse
Oldtown
10.0 out of 10, Exceptional, (35 reviews)
"Beautiful property and house. Very clean and comfortable."
United States
Don B.
The price is AU$355
includes taxes & fees
1 Oct - 2 Oct
Oldtown Guesthouse
A corner room with a sliding glass door closet, a wooden cabinet with glass doors, and a small rug on the floor.

20. Private Sauna, Fireplace and Country Views

Private Sauna, Fireplace and Country Views
Mount Airy
10.0 out of 10, Exceptional, (4 reviews)
"The property is excellent! Beautiful and peaceful surroundings. It was clean warm and welcoming. It’s pet friendly though we didn’t travel with pets. Outstanding host!"
United States
David M.
The price is AU$542
includes taxes & fees
28 Sept - 29 Sept
Private Sauna, Fireplace and Country Views
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 Western Maryland Hotel Reviews

The Country Inn of Berkeley Springs

The Country Inn of Berkeley Springs

10/10 Excellent
"We have travelled through Berkeley Springs many times each year going to and from Route 17 and on to the shore. Each time we drove through the town we would say, "we need to spend some time here sometime". We finally made that happen and we were not disappointed! The Inn was clean and well-appointed considering its age and history. The food at the Tavern was very tasty and portion sizes were large. The staff were helpful in answering any questions we had about the town and activities during our stay. We plan to make this a yearly stop in our travels."
Lois 3-night trip
Posted 5 hours ago
The Country Inn of Berkeley Springs

Find out more about Western Maryland

Western Maryland Holiday Homes information

Number of reviews
726
Accommodation
1010 Holiday Homes
Lowest Price
AU$326
Highest Price
AU$1,005