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 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 NZ$361
includes taxes & fees
16 Nov - 17 Nov
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)
"Enjoyed my stay I appreciate the view and Rich. "
United States
Joseph
The price is NZ$178
includes taxes & fees
29 Nov - 30 Nov
❤️ 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 NZ$369
includes taxes & fees
22 Nov - 23 Nov
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 NZ$455
includes taxes & fees
19 Nov - 20 Nov
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 NZ$455
includes taxes & fees
16 Nov - 17 Nov
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 NZ$404
includes taxes & fees
16 Nov - 17 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 NZ$311
includes taxes & fees
16 Nov - 17 Nov
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 NZ$435
includes taxes & fees
16 Nov - 17 Nov
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 NZ$530
includes taxes & fees
3 Dec - 4 Dec
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 NZ$564
includes taxes & fees
1 Dec - 2 Dec
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 NZ$466
includes taxes & fees
24 Nov - 25 Nov
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 NZ$342
includes taxes & fees
16 Nov - 17 Nov
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.
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 NZ$428
includes taxes & fees
16 Nov - 17 Nov
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 NZ$574
includes taxes & fees
16 Nov - 17 Nov
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 NZ$782
includes taxes & fees
16 Nov - 17 Nov
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 NZ$781
includes taxes & fees
18 Nov - 19 Nov
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
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 NZ$869
includes taxes & fees
17 Nov - 18 Nov
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 NZ$478
includes taxes & fees
17 Nov - 18 Nov
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.
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Find holiday rentals that suit your style

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Top Western Maryland Hotel Reviews

An indoor swimming pool with clear water, surrounded by lounge chairs and a mural of autumn trees.
Best Western Gettysburg

Best Western Gettysburg

Best Western Gettysburg
Gettysburg Historic District

10/10 Excellent

Great convenient location, close to everything in Gettysburg and nice clean hotel. Would stay here again if visiting the same area.
Australia
Paul
Reviewed March 30, 2026
Best Western Gettysburg

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, 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 NZ$177 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.

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