Search Vacation Homes in Western Maryland

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Our top choices for Western Maryland vacation homes

9.8 out of 10, Exceptional, (33)
"We had a nice relaxing stay at this lovely cottage. It was convenient to downtown and very clean."
United States
Reni J.
The price is ¥18,672
¥29,688 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi
10.0 out of 10, Exceptional, (2)
"We used the property to host our yearly strategic meeting and team building session. The space was perfect for 9 adults to be able to sit comfortably and plan. The games and game room were perfect for team building! "
United States
Amy B.
The price is ¥97,250
¥164,111 total
includes taxes & fees
Dec 22 - Dec 23
Hagrid's Escape Hut & 2 Escape Rooms Sleeps 15+

Vacation Home in Oldtown

Oldtown Guesthouse
10.0 out of 10, Exceptional, (28)
"Absolutely loved this little guesthouse. It was Elian’s yet simple"
United States
Elizabeth
The price is ¥15,560
¥28,204 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Oldtown Guesthouse
9.6 out of 10, Exceptional, (21)
"This stay was perfect for the beginning of our GAP Trail ride! "
United States
Marilyn S.
The price is ¥21,006
¥36,286 total
includes taxes & fees
Dec 27 - Dec 28
Full home near C&O! Perfect for bikers or families!
9.8 out of 10, Exceptional, (58)
"We loved visiting! Wish we could've stayed longer. The accommodations were great; super comfortable and inviting. Everyone enjoyed themselves. Thanks for having us!"
United States
David F.
The price is ¥24,118
¥49,316 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
10.0 out of 10, Exceptional, (21)
"Excellent home in great location and host! Thank you!!"
United States
sharon d.
The price is ¥42,572
¥105,823 total
includes taxes & fees
Dec 21 - Dec 22
Fall Colors! ! Near Wisp! Hot tub & Fire pit! Walk to the lake! Great Location!
9.4 out of 10, Exceptional, (22)
"Beautiful place! Clean and easy check in "
United States
Logan H.
The price is ¥28,008
¥40,079 total
includes taxes & fees
Dec 21 - Dec 22
Renovated Farmhouse located near the C and O Canal

Vacation Home in Frostburg

Knit Inn..
9.6 out of 10, Exceptional, (8)
"We loved our stay! Jennifer was very great and we loved the food and town of Frostburg "
United States
Anonymous traveler
The price is ¥62,240
¥94,178 total
includes taxes & fees
Dec 23 - Dec 24
Knit Inn..
9.4 out of 10, Exceptional, (119)
"We loved being so close to all the action downtown. A perfect getaway for our family to explore the area, visit with family, and eat great food!!! "
United States
Natalie C.
The price is ¥21,784
¥47,502 total
includes taxes & fees
Jan 11 - Jan 12, 2026
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
9.6 out of 10, Exceptional, (5)
"Place was absolutely gorgeous host was very accommodating. Can't say enough good things about it"
United States
Michael M.
The price is ¥42,961
¥89,082 total
includes taxes & fees
Jan 8 - Jan 9, 2026
In the heart of Deep Creek Lake! - "Shamrock Inn"
10.0 out of 10, Exceptional, (139)
"Love the place will book again"
United States
WAYNE M.
The price is ¥24,118
¥49,151 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Charming "Cream of the Crop" Cape ~❤️of Middletown

Vacation Home in Berkeley Springs

Modern, family-friendly, nature packed getaway
9.2 out of 10, Wonderful, (19)
"Great house! We loved the fire pit outside and the beautiful interior. Host was very responsive and helpful! Would def stay here again. "
United States
Erika R.
The price is ¥19,466
¥42,106 total
includes taxes & fees
Dec 23 - Dec 24
Modern, family-friendly, nature packed getaway
9.4 out of 10, Exceptional, (15)
"Over all stay was excellent. House was very nice with floor to ceiling windows. Also there was a hot tub and acade game room. Beautiful location over looking golf course. "
United States
Jeffrey H.
The price is ¥41,919
¥72,245 total
includes taxes & fees
Jan 4 - Jan 5, 2026
King Beds with Hot Tub, Arcade & Golf Course View
2.0 star property
10.0 out of 10, Exceptional, (1)
"Property and location just as advertised. Owner was very good about communicating and letting you know he was available if any issues came up (which they did not). Would stay there again!"
United States
Bruce H.
The price is ¥44,066
¥53,472 total
includes taxes & fees
Dec 25 - Dec 26
Rustic Oasis for the Family - 6 min walk to Downtown
8.6 out of 10, Excellent, (10)
"We had an amazing stay at your cabin! It was just what we were hoping for. The neighborhood is nicely spread out, giving the kids lots of space to roam and explore. The beds were super comfortable, and the kitchen had everything we needed to cook our meals. Communication with the host was excellent, and we really appreciated the guest passes to the sports center. We’d love to return again soon!"
United States
Jamie W.
The price is ¥30,451
¥56,464 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Modern Cabin w Hot Tub & Indoor Pool/Gym Access!

Vacation Home in McHenry

5BR | Fireplace | Deck | Game Room
10.0 out of 10, Exceptional, (12)
"We had a wonderful stay here and will absolutely be back! The house had fun games, the hot tub was clean and functioning and we even had a fire both nights. I would definitely return!"
United States
Suzie M.
The price is ¥49,218
¥116,716 total
includes taxes & fees
Dec 21 - Dec 22
5BR | Fireplace | Deck | Game Room

Vacation Home in Ijamsville

Cozy Peaceful Basement Cabin Vibes
10.0 out of 10, Exceptional, (5)
"Good trip."
United States
Jewell F.
The price is ¥38,900
¥55,913 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Cozy Peaceful Basement Cabin Vibes

Vacation Home in Berkeley Springs

Wooded Nest, Cozy 3BR Chalet Near Spas & Hiking
10.0 out of 10, Exceptional, (2)
"We had a blast! Great place, stocked with everything you need, hot tub was perfect, safe for small kids and close to town! "
United States
Nicole W.
The price is ¥26,468
¥69,638 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Wooded Nest, Cozy 3BR Chalet Near Spas & Hiking
10.0 out of 10, Exceptional, (23)
"Easy, pleasant stay "
United States
Mike H.
The price is ¥30,186
¥68,790 total
includes taxes & fees
Dec 29 - Dec 30
Nice and modern decor, 4BR 3BA, remodeled
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

Western Maryland Vacation Homes information

Number of reviews
522
Accommodation
1024 Vacation Homes
Lowest Price
¥28,204
Highest Price
¥164,111