Western Maryland Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Our top choices for Western Maryland vacation rentals

A rustic cabin interior with a wooden ceiling, a fireplace, a dining area, and a kitchen with a refrigerator and hanging pots.

1. 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 CA $121
CA $301 total
includes taxes & fees
Nov 15 - Nov 16
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
A rustic cabin with a wooden staircase leading to a porch, surrounded by lush greenery and pink flowers.

2. ❤️ 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 CA $66
CA $134 total
includes taxes & fees
Dec 6 - Dec 7
❤️ Secluded 1940s Romantic Tiny House on the River
A compact kitchen with a coffee machine, microwave, and a small cart with kitchen tools.

3. 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 CA $100
CA $297 total
includes taxes & fees
Nov 22 - Nov 23
Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown
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, (162 reviews)
"Great little spot!"
United States
Shelby W.
The price is CA $143
CA $378 total
includes taxes & fees
Nov 15 - Nov 16
Charming "Cream of the Crop" Cape ~❤️of Middletown
A glass-top table with a metal frame, a white cushioned chair, and a vase with sunflowers on a windowsill.

5. 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, (149 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 CA $143
CA $361 total
includes taxes & fees
Nov 15 - Nov 16
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
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 CA $171
CA $299 total
includes taxes & fees
Nov 15 - Nov 16
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 CA $141
CA $245 total
includes taxes & fees
Nov 15 - Nov 16
Cozy Getaway near Harper`s Ferry, C&O & Potomac
A modern kitchen with white cabinets, a wooden table, a stainless steel refrigerator, and a wooden ceiling.

8. 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 CA $143
CA $370 total
includes taxes & fees
Nov 15 - Nov 16
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
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 CA $204
CA $399 total
includes taxes & fees
Nov 15 - Nov 16
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
A modern kitchen with grey cabinets, a central island, and pendant lighting.

10. 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 CA $221
CA $445 total
includes taxes & fees
Dec 1 - Dec 2
Luxury Condo In Downtown Frederick
A wooden deck with two Adirondack chairs and a table overlooking a lake with trees and hills in the background.

11. 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 CA $210
CA $368 total
includes taxes & fees
Nov 24 - Nov 25
Charming Cabin in the Woods with River Access
A two-story brick building with a balcony and a porch decorated with lights and Christmas trees.

12. 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 CA $165
CA $270 total
includes taxes & fees
Nov 15 - Nov 16
Beautiful, Historic, Hiking, Biking and C&O Canal
A rustic, cylindrical structure with a thatched roof, a small seating area, and a view of the surrounding forest.

13. 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 CA $207
CA $274 total
includes taxes & fees
Nov 15 - Nov 16
Bin There Treehouse - A Grain Bin treehouse!
A two-story house with a porch decorated with string lights and garlands.

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)
"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 CA $188
CA $340 total
includes taxes & fees
Nov 15 - Nov 16
Historic Getaway near C&O Canal, hiking and biking
A covered patio area with a wooden pergola, outdoor seating, and a board game setup.

15. 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 CA $213
CA $455 total
includes taxes & fees
Nov 15 - Nov 16
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
A sunroom with a wicker chair, a wooden chest, and a view through large glass doors.

16. Rural & Historic Detour Escape w/ Horses On-site!

Rural & Historic Detour Escape w/ Horses On-site!
3.0 star property
Keymar
The price is CA $232
CA $616 total
includes taxes & fees
Nov 30 - Dec 1
Rural & Historic Detour Escape w/ Horses On-site!
A spacious living area with a large window, a wooden ceiling, and a dining area with a table and chairs.

17. 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 CA $143
CA $631 total
includes taxes & fees
Nov 18 - Nov 19
Peregrine's Perch - Cabin Overlooking the River!
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

18. 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 CA $269
CA $499 total
includes taxes & fees
Nov 15 - Nov 16
Modern Condo Right off Market Street
A cozy cabin interior with a leather sofa, dining table, and large windows offering a view of the outdoors.

19. 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 CA $143
CA $688 total
includes taxes & fees
Nov 17 - Nov 18
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
A spacious living room with a fireplace, a television, and a large window with curtains.

20. 2-Bedroom cabin Hot tub Fireplace PS5

2-Bedroom cabin Hot tub Fireplace PS5
2.0 star property
The Woods
6.4 out of 10, (12 reviews)
"This place was wonderful. When have stayed at 4 different cabins like this and this was our favorite. The place was cozy and clean. The pantry was well stocked. The fire pit even had a wood fire prepared. The owners were really nice and communicated well. The facilities at the woods were included We live very the location and the hot tub Highly recommend"
United States
Christopher
The price is CA $208
CA $377 total
includes taxes & fees
Nov 17 - Nov 18
2-Bedroom cabin Hot tub Fireplace PS5
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.
View all properties

Find vacation rentals that suit your style

cabin image
Cabins
Cabins
Cottage image
Cottages
Cottages

Top Western Maryland Hotel Reviews

An outdoor patio area with a long wooden table and chairs, a red umbrella, and a grill station.
Home2 Suites by Hilton Martinsburg, WV

Home2 Suites by Hilton Martinsburg, WV

Home2 Suites by Hilton Martinsburg, WV
Martinsburg

10/10 Excellent

Amazing hotel and staff. I will definitely return on my next vacation!
Canada
Gary
Reviewed May 9, 2026
Home2 Suites by Hilton Martinsburg, WV

Find out more about Western Maryland

Everything you need to know about Western Maryland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Western Maryland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Western Maryland vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Western Maryland vacation rentals we have selected for you start as low as CA $65 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 vacation 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 vacation.

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.

Explore a world of travel with Expedia