Western Maryland Holiday Rentals

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Our top choices for Western Maryland holiday rentals

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (66)
"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 HK$322
HK$831 total
includes taxes & fees
1 Jan - 2 Jan 2026
❤️ Secluded 1940s Romantic Tiny House on the River

Private cabin with two double beds (sleep 4)

Private cabin with two double beds (sleep 4)
Flintstone
10.0 out of 10, Exceptional, (5)
"Only problem was coffee maker"
United States
Donna
The price is HK$887
HK$1,248 total
includes taxes & fees
4 Jan - 5 Jan 2026
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 HK$567
HK$1,454 total
includes taxes & fees
23 Dec - 24 Dec
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 HK$584
HK$1,254 total
includes taxes & fees
21 Dec - 22 Dec
Bring Your Own Boat - Meticulously restored house on the Potomac River

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 HK$727
HK$1,677 total
includes taxes & fees
14 Jan - 15 Jan 2026
Rustic Tabor Woods Cabin near Cacapon State Park w/Patio, Grill

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 HK$739
HK$1,666 total
includes taxes & fees
23 Dec - 24 Dec
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Loft Apt Just off C&O near Harpers Ferry and AT

Loft Apt Just off C&O near Harpers Ferry and AT
Brunswick
10.0 out of 10, Exceptional, (16)
"Our Hosts were wonderful and the space was great. It sits right off of the bike trail and across the street from a great bakery and bike shop. We thoroughly enjoyed our stay."
United States
Mark B.
The price is HK$763
HK$1,427 total
includes taxes & fees
23 Dec - 24 Dec
Loft Apt Just off C&O near Harpers Ferry and AT

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 HK$749
HK$1,165 total
includes taxes & fees
22 Dec - 23 Dec
Birch Cabin at Hunting Creek Hideaway

Pet-friendly, heart of downtown

Pet-friendly, heart of downtown
Frederick
10.0 out of 10, Exceptional, (7)
"Very convenient to everything. Quick walk to shops, breweries, and restaurants."
United States
JENNIFER
The price is HK$514
HK$1,551 total
includes taxes & fees
7 Jan - 8 Jan 2026
Pet-friendly, heart of downtown

Romantic Woodland Retreat with Hot Tub & Private Forest Views

Romantic Woodland Retreat with Hot Tub & Private Forest Views
Berkeley Springs
9.8 out of 10, Exceptional, (296)
"We especially enjoyed the hot tub and the privacy of the cabin. Was what we expected and was very clean. Had a nice relaxing couple of days that we were there!"
United States
Ann W.
The price is HK$685
HK$2,355 total
includes taxes & fees
22 Dec - 23 Dec
Romantic Woodland Retreat with Hot Tub & Private Forest Views

Deer Pass – Luxury Glamping Yurt Near Deep CreekMd

Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
Oakland
10.0 out of 10, Exceptional, (9)
"We had an awesome stay here! The yurt was absolutely beautiful, and the location was perfect. We would 100% stay again"
United States
Tyler S.
The price is HK$856
HK$1,839 total
includes taxes & fees
4 Jan - 5 Jan 2026
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd

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 HK$945
HK$1,579 total
includes taxes & fees
21 Dec - 22 Dec
Loft two story with first floor workout room, WIFI, complete cottage to yourself

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (139)
"Love the place will book again"
United States
WAYNE M.
The price is HK$1,206
HK$2,458 total
includes taxes & fees
4 Jan - 5 Jan 2026
Charming "Cream of the Crop" Cape ~❤️of Middletown

Cozy Pine Tree Nest

Cozy Pine Tree Nest
Frederick
9.4 out of 10, Exceptional, (11)
"Really nice apartment was just what we wanted for a weekend while here to run the JFK 50 miler"
United States
David S.
The price is HK$623
HK$1,321 total
includes taxes & fees
29 Dec - 30 Dec
Cozy Pine Tree Nest

Oldtown Guesthouse

Oldtown Guesthouse
Oldtown
10.0 out of 10, Exceptional, (28)
"Absolutely loved this little guesthouse. It was Elian’s yet simple"
United States
Elizabeth
The price is HK$778
HK$1,410 total
includes taxes & fees
31 Dec - 1 Jan 2026
Oldtown Guesthouse

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 HK$1,146
HK$2,253 total
includes taxes & fees
6 Jan - 7 Jan 2026
Dog-Friendly w Hot Tub, Fire Pit & River Access

~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 HK$1,279
HK$2,532 total
includes taxes & fees
22 Dec - 23 Dec
~The Nest~

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (62)
"We thoroughly enjoyed our stay in Frederick. The cottage was comfortable and an easy walk to shops, parks and restaurants. We would definitely stay here for our next trip to Frederick. "
United States
Karen B.
The price is HK$1,004
HK$2,136 total
includes taxes & fees
8 Jan - 9 Jan 2026
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Modern w/Fire Pit, Deck, Grill & Hot Tub

Modern w/Fire Pit, Deck, Grill & Hot Tub
Sleepy Hollow
9.2 out of 10, Wonderful, (13)
"Great little spot. Location is secluded but there are homes very close by. "
United States
stacey f.
The price is HK$1,052
HK$2,020 total
includes taxes & fees
22 Dec - 23 Dec
Modern w/Fire Pit, Deck, Grill & Hot Tub

Lake Views! HOT TUB! 8 min to WISP ski. Central Location. Walk to Coffee & Eats.

Lake Views! HOT TUB! 8 min to WISP ski. Central Location. Walk to Coffee & Eats.
Oakland
10.0 out of 10, Exceptional, (4)
"The place was so clean and fully stocked. We had a wonderful stay. Five stars!! "
United States
Lori S.
The price is HK$798
HK$2,784 total
includes taxes & fees
21 Dec - 22 Dec
Lake Views! HOT TUB! 8 min to WISP ski. Central Location. Walk to Coffee & Eats.
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

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