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Holiday Homes in Western Maryland

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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, (54 reviews)
"Great lodging and communicative host"
United States
Peggy D.
The price is NZ$552
includes taxes & fees
19 Oct - 20 Oct
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
A two-story house with a front porch, a chimney, and a small garden with pumpkins.

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (159 reviews)
"Perfect little house in a great historic location."
United States
Donald K.
The price is NZ$455
includes taxes & fees
18 Oct - 19 Oct
Charming "Cream of the Crop" Cape ~❤️of Middletown
A modern kitchen with grey cabinets, a central island, and pendant lighting.

3. 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 NZ$608
includes taxes & fees
4 Nov - 5 Nov
Luxury Condo In Downtown Frederick
A glass-top table with a metal frame, a white cushioned chair, and a vase with sunflowers on a windowsill.

4. 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, (143 reviews)
"Very old but lovely building. Great parking and patio."
United States
Jennifer W.
The price is NZ$544
includes taxes & fees
1 Nov - 2 Nov
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
A square fire pit with a brick base, surrounded by outdoor furniture including a sofa and chairs.

5. 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$588
includes taxes & fees
15 Oct - 16 Oct
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
A bathroom with a towel rack, a mirror, a sink, and a potted plant.

6. 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, (8 reviews)
The price is NZ$393
includes taxes & fees
19 Oct - 20 Oct
Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.
A modern kitchen with white cabinets, a wooden table, a stainless steel refrigerator, and a wooden ceiling.

7. 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, (74 reviews)
"Lovely home. Great location! Host was amazingly helpful!"
United States
Tory D.
The price is NZ$455
includes taxes & fees
18 Oct - 19 Oct
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
A sunroom with a wicker chair, a wooden chest, and a view through large glass doors.

8. 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 NZ$763
includes taxes & fees
19 Oct - 20 Oct
Rural & Historic Detour Escape w/ Horses On-Site!
A bedroom with a bed, a dresser, a ceiling fan, and a window with blinds.

9. Cozy Downtown Cabin - Family Friendly

Cozy Downtown Cabin - Family Friendly
Middletown
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful property. I will definitely stay there again."
United States
Roger
The price is NZ$449
includes taxes & fees
15 Oct - 16 Oct
Cozy Downtown Cabin - Family Friendly
A brick building with a waterfall feature in front.

10. 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 NZ$744
includes taxes & fees
20 Oct - 21 Oct
New townhouse
A modern kitchen with dark cabinets, a large island with stools, a stainless steel refrigerator, and a built-in oven.

11. 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 NZ$877
includes taxes & fees
18 Oct - 19 Oct
Newly constructed 6 bedroom home
A two-story house with a front porch, a staircase, and a mailbox.

12. 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 traveller
The price is NZ$413
includes taxes & fees
18 Oct - 19 Oct
Dog-Friendly | Hiking| Tubing near Harpers Ferry
A hallway with wooden flooring, a staircase, a door with a white frame, a lamp on a small table, and a wall-mounted mirror.

13. 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 NZ$651
includes taxes & fees
22 Oct - 23 Oct
Antietam House Historic Sharpsburg Retreat
A kitchen with wooden cabinets, a stainless steel refrigerator, and a microwave.

14. Charming Shepherdstown Home - Walk to Downtown

Charming Shepherdstown Home - Walk to Downtown
Shepherdstown
The price is NZ$550
includes taxes & fees
18 Oct - 19 Oct
Charming Shepherdstown Home - Walk to Downtown
A cozy room with a dining table set, a sofa, a bed, and a window with curtains.

15. 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 NZ$348
includes taxes & fees
15 Oct - 16 Oct
The Whimsy Loft-Cozy Private Suite in Westminster on 4 acres
A deck with green chairs and a fire pit, surrounded by a house and trees.

16. 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, (32 reviews)
"Great stay, super nice people and wonderful house."
United States
Kenzie S.
The price is NZ$876
includes taxes & fees
18 Oct - 19 Oct
4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry
A garden with a variety of flowers and plants, a wooden structure, and a white fence.

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, (53 reviews)
"Great stay"
United States
Michael R.
The price is NZ$340
includes taxes & fees
15 Oct - 16 Oct
Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi
A residential area with a green house, a covered porch, and a grassy yard with trees.

18. 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, (19 reviews)
"Beautiful house in a bucolic setting. Perfect for a family for the night."
United States
Kate M.
The price is NZ$784
includes taxes & fees
21 Oct - 22 Oct
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
A spacious living room with a wooden ceiling, large windows, a fireplace, and a cozy seating area.

19. Large Family Home: 5 Mi to Dtwn Hagerstown!

Large Family Home: 5 Mi to Dtwn Hagerstown!
Williamsport
8.8 out of 10, Excellent, (21 reviews)
"Property was very nice, plenty of room for our family. We would definitely recommend this house and stay there again."
United States
Charlotte S.
The price is NZ$785
includes taxes & fees
20 Oct - 21 Oct
Large Family Home: 5 Mi to Dtwn Hagerstown!
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, (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 NZ$689
includes taxes & fees
19 Oct - 20 Oct
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

SpringHill Suites by Marriott Frederick

SpringHill Suites by Marriott Frederick

10/10 Excellent
"Nice stay"
Robin 2-night trip
Posted 1 hour ago
SpringHill Suites by Marriott Frederick

Find out more about Western Maryland

Western Maryland Holiday Homes information

Number of reviews
711
Accommodation
1010 Holiday Homes
Lowest Price
NZ$340
Highest Price
NZ$877