Find Winery Hotels in Western Maryland

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Check availability on Western Maryland Winery Hotels

Our top choices for Western Maryland hotels with winery

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Hampton Inn Cumberland

Hampton Inn Cumberland

2.5 star property
Cumberland
9.6 out of 10, Exceptional, (631)
"Big clean room, little pull out drawer shelf from the bathroom was neat."
United States
Soo
The price is SAR 431
SAR 491 total
includes taxes & fees
3 Jan - 4 January 2026
Hampton Inn Cumberland
Property grounds
❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River

Shepherdstown
9.8 out of 10, Exceptional, (65)
"We truly loved this location and definitely will be back!"
United States
Astrid
The price is SAR 149
SAR 393 total
includes taxes & fees
16 Dec - 17 Dec
❤️ Secluded 1940s Romantic Tiny House on the River
Room, 2 Double Beds, Non Smoking | Premium bedding, desk, laptop workspace, free WiFi
Suburban Studios LaVale-Cumberland

Suburban Studios LaVale-Cumberland

2.0 star property
Cumberland
7.0 out of 10, Good, (671)
"Clean room and nice amenities. Good places to stay . "
United States
Alejandro
The price is SAR 236
SAR 269 total
includes taxes & fees
15 Dec - 16 Dec
Suburban Studios LaVale-Cumberland
Terrace/patio
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.

Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.

Berkeley Springs
9.8 out of 10, Exceptional, (294)
"Secluded and peaceful, exactly what we were looking for. Loved this cabin!"
United States
John V.
The price is SAR 330
SAR 1,136 total
includes taxes & fees
23 Dec - 24 Dec
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.
Exterior
Charming Cabin in the Woods with River Access

Charming Cabin in the Woods with River Access

Shepherdstown
9.6 out of 10, Exceptional, (40)
"My family enjoyed our stay at the cabin including having access to the river for morning coffee and playing board games in the evening after a day of tubing. The drive to the cabin was beautiful with lots of deer sightings. "
United States
Leana H.
The price is SAR 469
SAR 944 total
includes taxes & fees
29 Dec - 30 Dec
Charming Cabin in the Woods with River Access
Property grounds
UNIQUE HISTORIC COTTAGE - SPRINGHOUSE 1803

UNIQUE HISTORIC COTTAGE - SPRINGHOUSE 1803

Hagerstown
10.0 out of 10, Exceptional, (123)
"We were very pleased with our stay. We enjoyed the privacy and the house"
United States
Kristine B.
The price is SAR 388
SAR 620 total
includes taxes & fees
10 Dec - 11 Dec
UNIQUE HISTORIC COTTAGE - SPRINGHOUSE 1803
Fridge, microwave, oven, stovetop
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 SAR 432
SAR 976 total
includes taxes & fees
10 Dec - 11 Dec
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Fridge, microwave, oven, stovetop
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)
"Everything was great. Would stay again! Accurate listing."
United States
Marlin S.
The price is SAR 368
SAR 688 total
includes taxes & fees
7 Jan - 8 January 2026
Loft Apt Just off C&O near Harpers Ferry and AT
Fridge, microwave, oven, stovetop
Beautiful, Historic, Hiking, Biking and C&O Canal

Beautiful, Historic, Hiking, Biking and C&O Canal

Brunswick
10.0 out of 10, Exceptional, (21)
"Absolutely loved staying in this historic apartment! The hosts are incredibly friendly and the area is very walkable with local food and shops within a quarter to half mile. Such a great experience here, can’t recommend it enough and can’t wait to stay again!"
United States
Alicia
The price is SAR 394
SAR 696 total
includes taxes & fees
10 Dec - 11 Dec
Beautiful, Historic, Hiking, Biking and C&O Canal
Outdoor spa tub
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, (39)
"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.
Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!
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

Days Inn by Wyndham Westminster

Days Inn by Wyndham Westminster

10/10 Excellent
"Clean wonderful friendly staff and love the free breakfast "
stephanie 1-night trip
Posted 2 days ago
Days Inn by Wyndham Westminster

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