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Check prices for these dates

Next weekend
23 May - 25 May
In two weeks
30 May - 1 Jun
In one month
13 Jun - 15 Jun
In two months
11 Jul - 13 Jul

Compare 78 Cottages in Shepherdstown with updated reviews, rates, and availability.

The Carriage House at Carrot Top Cottage
Aerial view

The Carriage House at Carrot Top Cottage

9.8 out of 10, Exceptional, (36)
"We enjoyed the stay and it was an easy walk to the places we wanted to go!"
The price is AED 386
AED 655 total
includes taxes & fees
21 May - 22 May
The Carriage House at Carrot Top Cottage
Carrot Top Cottage surrounded by National Park
Exterior

Carrot Top Cottage surrounded by National Park

10.0 out of 10, Exceptional, (35)
"This cottage was like a home away from home! It was the perfect location and spotless. We would definitely stay again and recommend to anyone "
Carrot Top Cottage surrounded by National Park
Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond
Fridge, microwave, oven, stovetop

Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond

10.0 out of 10, Exceptional, (1)
"This was a good place to stay for two guys day hiking in the AT. It is clean, quiet, comfortable, and in a very good location. It had everything we needed."
Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Fridge, microwave, oven, stovetop

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

10.0 out of 10, Exceptional, (40)
"Great stay! "
The price is AED 514
AED 1,051 total
includes taxes & fees
13 May - 14 May
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Bring Your Own Boat - Meticulously restored house on the Potomac River
Game room

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

10.0 out of 10, Exceptional, (4)
"Clean, everything you need is there. Peaceful."
The price is AED 364
AED 695 total
includes taxes & fees
13 May - 14 May
Bring Your Own Boat - Meticulously restored house on the Potomac River
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Outdoor dining

Art Docko - Lakefront Artist Retreat w/ Hot Tub!

10.0 out of 10, Exceptional, (16)
"Check in was seamless. The place was perfect for three couples with all the master suites. "
The price is AED 533
AED 1,847 total
includes taxes & fees
14 May - 15 May
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Cottage w/ Hot Tub and 100-Mile Valley Views!
Outdoor spa tub

Cottage w/ Hot Tub and 100-Mile Valley Views!

10.0 out of 10, Exceptional, (17)
"We loved this place! It had everything we needed and everything was very comfortable. The sunset view from the hot tub was a highlight! We would stay here again."
The price is AED 367
AED 1,402 total
includes taxes & fees
14 May - 15 May
Cottage w/ Hot Tub and 100-Mile Valley Views!
Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers
Exterior detail

Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers

9.4 out of 10, Exceptional, (8)
"This is our 5th stay at this beautiful cottage. We have recommended it to friends as well. The hosts have done everything to insure that your stay will be a wonderful experience. The cottage is immaculate and has everything you need to have a relaxing stay. I highly recommend it! "
The price is AED 650
AED 1,550 total
includes taxes & fees
13 May - 14 May
Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers
Lake View Retreat - Cottage Near a Peaceful Lake!
Property grounds

Lake View Retreat - Cottage Near a Peaceful Lake!

9.6 out of 10, Exceptional, (17)
"Was really able to relax and enjoy during our brief stay. Would come again."
The price is AED 367
AED 1,332 total
includes taxes & fees
14 May - 15 May
Lake View Retreat - Cottage Near a Peaceful Lake!
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Exterior

Amazing dog-friendly cottage. Walk 2 Harpers Ferry

2.0 star property
10.0 out of 10, Exceptional, (12)
"We loved our stay. The location was central to everything we did; the car stayed in the driveway for almost our entire trip, and the yard is perfect for dogs. The house itself is exactly as shown in the pcs. Highly recommended "
The price is AED 680
AED 1,211 total
includes taxes & fees
13 May - 14 May
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Cottage at Gray Fox- Many Attraction- Pet Friendly
Aerial view

Cottage at Gray Fox- Many Attraction- Pet Friendly

10.0 out of 10, Exceptional, (21)
"Very peaceful stay in the mountains. Would book again!"
Cottage at Gray Fox- Many Attraction- Pet Friendly
Woodsy Retreat with a Hot Tub and Seasonal Views!
Terrace/patio

Woodsy Retreat with a Hot Tub and Seasonal Views!

9.8 out of 10, Exceptional, (20)
"Property was a great location for all we wanted to do during our vacation. The beach area was the perfect retreat for some relaxation after long days of hiking. Area is beautiful, house was comfortable (slept like a baby), and we had a great stay. Would definitely stay again."
The price is AED 367
AED 1,255 total
includes taxes & fees
13 May - 14 May
Woodsy Retreat with a Hot Tub and Seasonal Views!
Laurel Cottage in the heart of Harpers Ferry
Outdoor dining

Laurel Cottage in the heart of Harpers Ferry

10.0 out of 10, Exceptional, (1)
"The property is beautifully decorated, spacious, with all amenities needed for a weekend stay and in walking distance to downtown Harper’s Ferry. "
Laurel Cottage in the heart of Harpers Ferry
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Interior

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

10.0 out of 10, Exceptional, (1)
"We had a a great experience at this cabin getaway. The property was immaculate, cozy and well-equipped. The host was incredibly responsive and thoughtful. We can't wait to come back!"
The price is AED 918
AED 1,533 total
includes taxes & fees
14 May - 15 May
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Firehouse Cottage | Walk to all of downtown HF
1 bedroom, iron/ironing board, travel crib, WiFi

Firehouse Cottage | Walk to all of downtown HF

The price is AED 533
AED 891 total
includes taxes & fees
14 May - 15 May
Firehouse Cottage | Walk to all of downtown HF
RIVERKEEPER INN, Waterfront Property on the Potomac River
View from property

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.2 out of 10, Wonderful, (119)
"The hosts are wonderful. I had a great time in their cozy, clean and beautiful place. Highly recommend for a visit to beautiful and historic WV.I particularly appreciated their fondness for dogs. Mine had a great time too!"
RIVERKEEPER INN, Waterfront Property on the Potomac River
ROMANTIC GETAWAY : Relax In Our Outdoor Spa This Winter !
Property grounds

ROMANTIC GETAWAY : Relax In Our Outdoor Spa This Winter !

10.0 out of 10, Exceptional, (137)
"Very well decorated. The owners were very attentive and kind. Left a candle with wine in the bedrooms. Very well set up and beautiful!!"
ROMANTIC GETAWAY : Relax In Our Outdoor Spa This Winter !
Peaceful Lakefront Cottage with Mountain Views!
Fridge, microwave, oven, stovetop

Peaceful Lakefront Cottage with Mountain Views!

10.0 out of 10, Exceptional, (25)
"Wintertime visit. Very peaceful. "
The price is AED 702
AED 1,827 total
includes taxes & fees
22 May - 23 May
Peaceful Lakefront Cottage with Mountain Views!
Magical Treehouse in Woods, Close many Wineries & Breweries, Pet Friendly!
Property grounds

Magical Treehouse in Woods, Close many Wineries & Breweries, Pet Friendly!

10.0 out of 10, Exceptional, (1)
"This treehouse was so dreamy and private! I hope we get to stay here again some time soon!"
Magical Treehouse in Woods, Close many Wineries & Breweries, Pet Friendly!
Entire Mountain Cottage Near Scenic Hiking Trails, Your Getaway Retreat!
Interior

Entire Mountain Cottage Near Scenic Hiking Trails, Your Getaway Retreat!

10.0 out of 10, Exceptional, (3)
"Cozy remodeled property. Plenty of space for 9 adults and teens to celebrate Christmas. George is a great host. Highly recommend. "
Entire Mountain Cottage Near Scenic Hiking Trails, Your Getaway Retreat!
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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Other property types in Shepherdstown

❤️ Secluded 1940s Romantic Tiny House on the River
Beach

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (53)
"Very nice place and area. We had a really nice stay. Would highly recommend to stay at the tiny house."
The price is AED 272
AED 526 total
includes taxes & fees
19 May - 20 May
❤️ Secluded 1940s Romantic Tiny House on the River
Welcome to this patch of serenity on the river's edge, to this hideaway.
Dining

Welcome to this patch of serenity on the river's edge, to this hideaway.

10.0 out of 10, Exceptional, (62)
"Loved everything. Quiet, peaceful….loved the small deck off the upstairs bedroom."
Welcome to this patch of serenity on the river's edge, to this hideaway.
Graycliff Hall: Riverfront Estate w/ Heli Pad, Private Chef, Hot Tub
Fridge, microwave, oven, stovetop

Graycliff Hall: Riverfront Estate w/ Heli Pad, Private Chef, Hot Tub

9.0 out of 10, Wonderful, (2)
"Our family had an unforgettable New Year's holiday at this incredible rental property! From the moment we arrived, we were amazed by the beautiful house, its spaciousness, and the plethora of facilities available to accommodate everyone in our group. The property was clean, well-organized, and tastefully decorated, making it a warm and inviting space for our celebration.The true gem of our stay was the exceptional hospitality provided by the property's management, especially the remarkable Miss...
Graycliff Hall: Riverfront Estate w/ Heli Pad, Private Chef, 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.