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Western Maryland Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Western Maryland holiday rentals

A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

1. Modern Condo Right off Market Street

Modern Condo Right off Market Street
Downtown Frederick
9.2 out of 10, Wonderful, (108 reviews)
"Great location"
United States
John
The price is HK$1,539
HK$2,787 total
includes taxes & fees
15 Nov - 16 Nov
Modern Condo Right off Market Street
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, (162 reviews)
"Great little spot!"
United States
Shelby W.
The price is HK$784
HK$2,062 total
includes taxes & fees
15 Nov - 16 Nov
Charming "Cream of the Crop" Cape ~❤️of Middletown
A rustic cabin interior with a wooden ceiling, a fireplace, a dining area, and a kitchen with a refrigerator and hanging pots.

3. Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Middletown
9.6 out of 10, Exceptional, (118 reviews)
"Beautiful property! Owner is very quick to communicate and did a fantastic job making it a very relaxing place to stay!"
United States
Cindy B.
The price is HK$667
HK$1,663 total
includes taxes & fees
15 Nov - 16 Nov
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
A room with a desk, chair, and a couch. There is a framed picture on the wall.

4. Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown

Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown
Frederick
10.0 out of 10, Exceptional, (18 reviews)
"Place was perfect and tbe location great. East in and out town..or to get to down town"
United States
Andrew
The price is HK$587
HK$1,661 total
includes taxes & fees
22 Nov - 23 Nov
Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown
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, (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 HK$1,207
HK$2,444 total
includes taxes & fees
1 Dec - 2 Dec
Luxury Condo In Downtown Frederick
A living room with a dining table, chairs, a sofa, and a television.

6. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (27 reviews)
"Absolutely adorable, perfect location and well appointed. Would absolutely stay here again. Highly recommend and maybe if you’re lucky you’ll meet the little black cat who visited us!!"
United States
Abigail
The price is HK$941
HK$1,654 total
includes taxes & fees
15 Nov - 16 Nov
Quaint Mini Cottage in Shepherdstown - Walking Distance
A two-story brick building with a balcony and a porch decorated with lights and Christmas trees.

7. Cozy Getaway near Harper`s Ferry, C&O & Potomac

Cozy Getaway near Harper`s Ferry, C&O & Potomac
Brunswick
10.0 out of 10, Exceptional, (71 reviews)
"Cute downtown area with multiple spots to grab breakfast and convenience store stuff. Easy access to Harper's Ferry and made for a nice restful spot between hikes in nature and around town."
United States
Robert
The price is HK$776
HK$1,322 total
includes taxes & fees
15 Nov - 16 Nov
Cozy Getaway near Harper`s Ferry, C&O & Potomac
A glass-top table with a metal frame, a white cushioned chair, and a vase with sunflowers on a windowsill.

8. 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 HK$784
HK$1,970 total
includes taxes & fees
12 Nov - 13 Nov
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
A kitchen with a dishwasher, a sink, and a stove. There are pots hanging above the sink and a window with a view of greenery outside.

9. Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (72 reviews)
"The house is very cute and a perfect fit for our needs. We appreciated how clean the house was too! It's conveniently located to some many restaurants and shops. We would gladly stay here again!"
United States
Sara W.
The price is HK$1,124
HK$2,181 total
includes taxes & fees
12 Nov - 13 Nov
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
A rustic cabin with a wooden staircase leading to a porch, surrounded by lush greenery and pink flowers.

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

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.6 out of 10, Exceptional, (88 reviews)
"Great little getaway. Our only issue was the intense heat of 100 every day. The AC was heavenly!"
United States
Dennis C.
The price is HK$360
HK$811 total
includes taxes & fees
18 Nov - 19 Nov
❤️ Secluded 1940s Romantic Tiny House on the River
A room with large windows, wooden floors, and a ceiling fan.

11. Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (101 reviews)
"The cabin was clean, spacious, and"
United States
Daniel
The price is HK$1,765
HK$2,685 total
includes taxes & fees
15 Nov - 16 Nov
Antietam Creek - Quiet 2 Bedroom Cabin
A two-story house with a porch decorated with string lights and garlands.

12. Historic Getaway near C&O Canal, hiking and biking

Historic Getaway near C&O Canal, hiking and biking
Brunswick
9.8 out of 10, Exceptional, (13 reviews)
"We had a very comfortable stay. The apartment was clean, well-equipped, and had everything we needed. The instructions were clear, and the host was responsive and helpful throughout our stay. Parking was a little challenging, but aside from that, everything was great. We would happily stay here again!"
United States
Kamakshi B.
The price is HK$1,035
HK$1,854 total
includes taxes & fees
12 Nov - 13 Nov
Historic Getaway near C&O Canal, hiking and biking
A wooden deck with two Adirondack chairs and a table overlooking a lake with trees and hills in the background.

13. Charming Cabin in the Woods with River Access

Charming Cabin in the Woods with River Access
Shepherdstown
9.6 out of 10, Exceptional, (57 reviews)
"Great property to stay at and would definitely stay there again! Very peaceful!"
United States
Christopher
The price is HK$1,157
HK$2,021 total
includes taxes & fees
24 Nov - 25 Nov
Charming Cabin in the Woods with River Access
A modern kitchen with dark cabinets, a large island with stools, a stainless steel refrigerator, and a built-in oven.

14. 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 HK$1,671
HK$3,699 total
includes taxes & fees
12 Nov - 13 Nov
Newly constructed 6 bedroom home
A modern kitchen with white cabinets, a wooden table, a stainless steel refrigerator, and a wooden ceiling.

15. 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 HK$667
HK$1,805 total
includes taxes & fees
12 Nov - 13 Nov
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
A two-story brick building with a balcony and a porch decorated with lights and Christmas trees.

16. Beautiful, Historic, Hiking, Biking and C&O Canal

Beautiful, Historic, Hiking, Biking and C&O Canal
Brunswick
10.0 out of 10, Exceptional, (29 reviews)
"really nice place"
United States
David R.
The price is HK$906
HK$1,484 total
includes taxes & fees
15 Nov - 16 Nov
Beautiful, Historic, Hiking, Biking and C&O Canal
A rustic building with a sign reading 'The Robin's Nest' and a front door.

17. 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 HK$1,174
HK$2,478 total
includes taxes & fees
15 Nov - 16 Nov
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
A cozy cabin interior with a leather sofa, dining table, and large windows offering a view of the outdoors.

18. 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, (78 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 HK$800
HK$3,200 total
includes taxes & fees
12 Nov - 13 Nov
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
A rustic, cylindrical structure with a thatched roof, a small seating area, and a view of the surrounding forest.

19. Bin There Treehouse - A Grain Bin treehouse!

Bin There Treehouse - A Grain Bin treehouse!
Washington County
9.8 out of 10, Exceptional, (6 reviews)
"Such a neat place! Very peaceful setting."
United States
Abby G.
The price is HK$1,136
HK$1,575 total
includes taxes & fees
12 Nov - 13 Nov
Bin There Treehouse - A Grain Bin treehouse!
A wooden deck with a grill, outdoor seating, and a bottle of wine.

20. 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 HK$1,247
HK$2,871 total
includes taxes & fees
10 Dec - 11 Dec
1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield
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

Country Inn & Suites by Radisson, Hagerstown, MD

Country Inn & Suites by Radisson, Hagerstown, MD

8/10 Good
"The room and hotel were clean but there was an overwhelming smell of disinfectant spray which triggered an asthma scare. The water pressure in the shower was amazing, so massaging. Once again there was a dog in a room near us that was barking quite a lot. I wish there was a separate section for pets. We will be back in January."
Bonnie and Rich 1-night trip
Posted 3 hours ago
Country Inn & Suites by Radisson, Hagerstown, MD

Find out more about Western Maryland

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