Western Maryland Holiday Rentals

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Our top choices for Western Maryland holiday rentals

Private cabin with two double beds (sleep 4)

Private cabin with two double beds (sleep 4)
Flintstone
10.0 out of 10, Exceptional, (5)
"Cozy, beautiful, pretty new and well-maintained cabins. Very inviting outdoor seating area with fire pit and grill on the grounds. There is a (very small) grocery store within walking distance. Highly recommend the short drive to Zumbrun Overlook to watch the sunset - it's unforgettable! The cabins are located in a quiet and very small town (although you can hear the highway traffic in the distance). Nice drive to Little Orleans (to get on the C&O Canal towpath). The host was super responsive....
United States
W L.
The price is NZ$259
includes taxes & fees
4 Jan - 5 Jan
Private cabin with two double beds (sleep 4)

Primitive Cozy Tiny Cabin with Starlink internet

Primitive Cozy Tiny Cabin with Starlink internet
Great Cacapon
10.0 out of 10, Exceptional, (11)
"Super peaceful and relaxing! We had a great time! Will stay again! Thanks Austin!"
United States
Jason M.
The price is NZ$323
includes taxes & fees
4 Jan - 5 Jan
Primitive Cozy Tiny Cabin with Starlink internet

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

Bring Your Own Boat - Meticulously restored house on the Potomac River
Hedgesville
10.0 out of 10, Exceptional, (9)
"Cute little house that my husband and I enjoyed for the weekend. Great location close to Martinsburg. It had everything we needed for our weekend The host communicated well, we had no issues, and we would definitely stay here again. Thank you!"
United States
Jennifer E.
The price is NZ$278
includes taxes & fees
26 Jan - 27 Jan
Bring Your Own Boat - Meticulously restored house on the Potomac River

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, (110)
"I’ve stayed here and will absolutely stay again."
United States
Katherine M.
The price is NZ$313
includes taxes & fees
5 Jan - 6 Jan
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Rustic Tabor Woods Cabin near Cacapon State Park w/Patio, Grill

Rustic Tabor Woods Cabin near Cacapon State Park w/Patio, Grill
Berkeley Springs
9.0 out of 10, Wonderful, (17)
"Hot tub was nice relaxing cozy cabin"
United States
kristin
The price is NZ$344
includes taxes & fees
4 Jan - 5 Jan
Rustic Tabor Woods Cabin near Cacapon State Park w/Patio, Grill

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (67)
"This trip was to celebrate my 64th birthday and wind down from my busy job It was perfect for both .. very relaxing, and very cozy. We'd love to stay again."
United States
Kaleb C
The price is NZ$182
includes taxes & fees
12 Jan - 13 Jan
❤️ Secluded 1940s Romantic Tiny House on the River

Loft two story with first floor workout room, WIFI, complete cottage to yourself

Loft two story with first floor workout room, WIFI, complete cottage to yourself
Grantsville
9.8 out of 10, Exceptional, (37)
"The clean and comfortable looking cabins "
United States
Torrance
The price is NZ$354
includes taxes & fees
4 Jan - 5 Jan
Loft two story with first floor workout room, WIFI, complete cottage to yourself

Dog-Friendly w Hot Tub, Fire Pit & River Access

Dog-Friendly w Hot Tub, Fire Pit & River Access
Great Cacapon
9.4 out of 10, Exceptional, (3)
"Very fun stay, very clean. Beautiful weather for walking around the place. Would definitely come back!!"
United States
Deepan R.
The price is NZ$500
includes taxes & fees
12 Jan - 13 Jan
Dog-Friendly w Hot Tub, Fire Pit & River Access

Pet-friendly, heart of downtown

Pet-friendly, heart of downtown
Frederick
10.0 out of 10, Exceptional, (8)
"Very convenient to everything. Quick walk to shops, breweries, and restaurants."
United States
JENNIFER
The price is NZ$324
includes taxes & fees
5 Jan - 6 Jan
Pet-friendly, heart of downtown

Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!

Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!
Sharpsburg
10.0 out of 10, Exceptional, (40)
"We had an amazing time - lots of walks and places to see - very historical - winery right next door which was an added bonus - accommodation was everything we needed and more - look out for a friendly cat that paid a few visits - thank you Jordan for a great time and will definitely come back to the area"
United Kingdom
Jo W.
The price is NZ$470
includes taxes & fees
7 Jan - 8 Jan
Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!

Oldtown Guesthouse

Oldtown Guesthouse
Oldtown
10.0 out of 10, Exceptional, (30)
"Absolutely loved this little guesthouse. It was Elian’s yet simple"
United States
Elizabeth
The price is NZ$313
includes taxes & fees
28 Jan - 29 Jan
Oldtown Guesthouse

Birch Cabin at Hunting Creek Hideaway

Birch Cabin at Hunting Creek Hideaway
Thurmont
9.8 out of 10, Exceptional, (19)
"Was wonderful..private and peaceful. Perfect getaway. "
United States
Courtney G.
The price is NZ$245
includes taxes & fees
4 Jan - 5 Jan
Birch Cabin at Hunting Creek Hideaway

Private Home in Garrett County, surrounded by trees, fields and farmland.

Private Home in Garrett County, surrounded by trees, fields and farmland.
Grantsville
10.0 out of 10, Exceptional, (42)
"We had a very nice stay. Very comfortable and inviting a home away from home vibe. "
United States
Carol R.
The price is NZ$491
includes taxes & fees
7 Jan - 8 Jan
Private Home in Garrett County, surrounded by trees, fields and farmland.

~The Nest~

~The Nest~
Berkeley Springs
9.8 out of 10, Exceptional, (12)
"Nice get away for couples. Very close to Berkeley Springs, but tucked away in the woods. Newly renovated, and had fun games to play. The hosts were very nice!"
United States
Kelly S.
The price is NZ$468
includes taxes & fees
5 Jan - 6 Jan
~The Nest~

Galloping Getaway on the rolling hills of GemStone Stable

Galloping Getaway on the rolling hills of GemStone Stable
Hagerstown
10.0 out of 10, Exceptional, (16)
"Perfect for us as we visited family."
United States
Felicia H.
The price is NZ$321
includes taxes & fees
5 Jan - 6 Jan
Galloping Getaway on the rolling hills of GemStone Stable

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (62)
"Always clean and comfortable home. Close to restaurants and shops but in quiet neighborhood to relax. Our second stay in this home. "
United States
Jelinda C.
The price is NZ$449
includes taxes & fees
4 Jan - 5 Jan
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

2-Bedroom cabin Hot tub Fireplace PS5

2-Bedroom cabin Hot tub Fireplace PS5
2.0 star property
The Woods
9.4 out of 10, Exceptional, (3)
"Nice cabin. Could’ve been cleaner outside. Host was nice and surrounding area, beautiful. "
United States
Chris
The price is NZ$482
includes taxes & fees
6 Jan - 7 Jan
2-Bedroom cabin Hot tub Fireplace PS5

Secluded WV Retreat Hot Tub, Fire Pit & Kayaks

Secluded WV Retreat Hot Tub, Fire Pit & Kayaks
Sleepy Hollow
9.8 out of 10, Exceptional, (11)
"Had an amazing stay! The VRBO was cozy, comfortable and clean in an amazing area. We loved the amenities, relaxing on the deck, by the fire pit, and in the hot tub were perfect! The host, Emily, was amazing and gave lots of great info about the area and was very responsive. Would love to stay here again!"
United States
Sarah H.
The price is NZ$443
includes taxes & fees
5 Jan - 6 Jan
Secluded WV Retreat Hot Tub, Fire Pit & Kayaks

Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (26)
"Clean, great location, friendly owner"
United States
Christian M.
The price is NZ$330
includes taxes & fees
4 Jan - 5 Jan
Cozy, dog-friendly, downtown

Peregrine's Perch - Cabin Overlooking the River!

Peregrine's Perch - Cabin Overlooking the River!
Falling Waters
9.6 out of 10, Exceptional, (21)
"Very beautiful place to stay, my family and I enjoyed everything that was offered and very scenic great for pictures and overall a great trip with the family "
United States
Blas G.
The price is NZ$624
includes taxes & fees
5 Jan - 6 Jan
Peregrine's Perch - Cabin Overlooking the River!
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, 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$182 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.