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Holiday Rentals in Western Maryland

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Our top choices for Western Maryland holiday rentals

1. ❤️ 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 €90
includes taxes & fees
15 Nov - 16 Nov
❤️ Secluded 1940s Romantic Tiny House on the River

2. 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 €195
includes taxes & fees
22 Nov - 23 Nov
Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown

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, (117 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 €188
includes taxes & fees
8 Nov - 9 Nov
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (161 reviews)
"Great little spot!"
United States
Shelby W.
The price is €233
includes taxes & fees
8 Nov - 9 Nov
Charming "Cream of the Crop" Cape ~❤️of Middletown

5. 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 €147
includes taxes & fees
8 Nov - 9 Nov
Cozy Getaway near Harper`s Ferry, C&O & Potomac

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 €188
includes taxes & fees
8 Nov - 9 Nov
Quaint Mini Cottage in Shepherdstown - Walking Distance

7. 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, (147 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 €227
includes taxes & fees
12 Nov - 13 Nov
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

8. 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 €170
includes taxes & fees
6 Dec - 7 Dec
Beautiful, Historic, Hiking, Biking and C&O Canal

9. Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (46 reviews)
"The house was as great! Plenty of space for 5 adults. Conveniently located to the areas we wanted to visit. Very quiet location"
United States
Melisa T.
The price is €355
includes taxes & fees
18 Nov - 19 Nov
Antietam Look Out - Incredible Sunset Views!

10. 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, (77 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 €423
includes taxes & fees
19 Nov - 20 Nov
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

11. Modern Condo Right off Market Street

Modern Condo Right off Market Street
Downtown Frederick
9.2 out of 10, Wonderful, (107 reviews)
"Great location"
United States
John
The price is €355
includes taxes & fees
6 Dec - 7 Dec
Modern Condo Right off Market Street

12. Charming Cabin in the Woods with River Access

Charming Cabin in the Woods with River Access
Shepherdstown
9.6 out of 10, Exceptional, (56 reviews)
"Very comfortable and cozy. Our family had a great stay here."
United States
bethany c.
The price is €242
includes taxes & fees
12 Nov - 13 Nov
Charming Cabin in the Woods with River Access

13. Peregrine's Perch - Cabin Overlooking the River!

Peregrine's Perch - Cabin Overlooking the River!
Falling Waters
9.6 out of 10, Exceptional, (24 reviews)
"Relaxing, close to all."
United States
Valarie
The price is €338
includes taxes & fees
9 Nov - 10 Nov
Peregrine's Perch - Cabin Overlooking the River!

14. 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)
"Very friendly host who made communications easy. We left our iPad behind and they called us right away. The apartment was large, beds were comfortable, and the bathroom renovation was beautiful with a great shower. It is about a block from the C&O trail plus free parking on the property."
United States
Kelly
The price is €204
includes taxes & fees
8 Nov - 9 Nov
Historic Getaway near C&O Canal, hiking and biking

15. 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 €197
includes taxes & fees
10 Nov - 11 Nov
Bin There Treehouse - A Grain Bin treehouse!

16. 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 €227
includes taxes & fees
8 Nov - 9 Nov
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

17. Bring Your Own Boat - Meticulously restored house on the Potomac River

Bring Your Own Boat - Meticulously restored house on the Potomac River
Hedgesville
9.6 out of 10, Exceptional, (14 reviews)
"Great little place to stay."
United States
Shannon W.
The price is €138
includes taxes & fees
8 Nov - 9 Nov
Bring Your Own Boat - Meticulously restored house on the Potomac River

18. 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 €250
includes taxes & fees
8 Nov - 9 Nov
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

19. 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 €287
includes taxes & fees
9 Nov - 10 Nov
1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield

20. Secluded WV Retreat Hot Tub, Fire Pit & Kayaks

Secluded WV Retreat Hot Tub, Fire Pit & Kayaks
Sleepy Hollow
10.0 out of 10, Exceptional, (51 reviews)
"Great place, perfect for a getaway"
United States
Cindy T.
The price is €258
includes taxes & fees
18 Nov - 19 Nov
Secluded WV Retreat Hot Tub, Fire Pit & Kayaks
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

Find out more about Western Maryland

Everything you need to know about Western Maryland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Western Maryland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Western Maryland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Western Maryland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Western Maryland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Western Maryland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Western Maryland holiday rentals we have selected for you start as low as €227 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Western Maryland rentals

At Expedia, we put the best Western Maryland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Western Maryland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Western Maryland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Western Maryland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.