Search Shepherdstown Cottage Rentals from CA $104

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May 2 - May 4
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May 9 - May 11
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May 23 - May 25
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Jun 20 - Jun 22

Browse Select Shepherdstown Cottages

The Carriage House at Carrot Top Cottage
1 bedroom, WiFi, bed sheets

The Carriage House at Carrot Top Cottage

9.8 out of 10, Exceptional, (35)
"My girlfriend and I will definitely be coming back to this spot when we visit Harpers Ferry again. Frederick MD is also just 20 mins away for more food options. "
The price is CA $145
CA $247 total
includes taxes & fees
Apr 22 - Apr 23
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)
"The house is adorable inside and out! Pulling up to the house you just know that you are in for a treat! The decor is absolutely perfect. The home is very comfortable and has all that you need for a exceptional stay...and then some. Walking the streets and admiring the beautiful old homes is so relaxing! This Is Our New " Happy Place!""
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, (36)
"Great location in Frederick - convenient to everything. We enjoyed the house, and particularly liked the cozy kitchen. Easy and good communication with the host augmented our experience. "
The price is CA $220
CA $427 total
includes taxes & fees
Apr 28 - Apr 29
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Bring Your Own Boat - Meticulously restored house on the Potomac River
Living area

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

10.0 out of 10, Exceptional, (3)
"Clean, everything you need is there. Peaceful."
The price is CA $104
CA $223 total
includes taxes & fees
Apr 22 - Apr 23
Bring Your Own Boat - Meticulously restored house on the Potomac River
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Property grounds

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 CA $152
CA $626 total
includes taxes & fees
Apr 23 - Apr 24
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, (15)
"The view of this house is amazing! Absolutely beautiful!"
The price is CA $138
CA $525 total
includes taxes & fees
Apr 23 - Apr 24
Cottage w/ Hot Tub and 100-Mile Valley Views!
Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers
Property grounds

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

9.8 out of 10, Exceptional, (7)
"Good place for a nice quite weekend."
The price is CA $245
CA $584 total
includes taxes & fees
Apr 28 - Apr 29
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)
"Beautiful location to relax and enjoy friends. This house was huge. Plenty of room for the 3 of us...could have been 8, lol. "
The price is CA $138
CA $498 total
includes taxes & fees
Apr 24 - Apr 25
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
9.8 out of 10, Exceptional, (9)
"What a lovely, cozy, clean property! The location was in the heart of Harper’s Ferry. Everything advertised was exactly as described, even nicer, inside and out! Cathy, our property manager was communicative and helpful. We will be back!!"
The price is CA $256
CA $451 total
includes taxes & fees
Apr 22 - Apr 23
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Cottage at Gray Fox- Many Attraction- Pet Friendly
Fridge, microwave, oven, stovetop

Cottage at Gray Fox- Many Attraction- Pet Friendly

10.0 out of 10, Exceptional, (21)
"Wonderful property for a girls' getaway! The owners are very responsive to messages and communicated well with us. Clean, comfy beds, had everything we needed. The hot tub was a plus on a snowy weekend."
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)
"This property was everything we hoped for in a weekend getaway home! So clean, beautifully decorated, and decked out with everything we wanted and more. We will definitely be booking with Mountain Mama again. "
The price is CA $186
CA $536 total
includes taxes & fees
May 8 - May 9
Woodsy Retreat with a Hot Tub and Seasonal Views!
Laurel Cottage in the heart of Harpers Ferry
Fridge, microwave, oven, stovetop

Laurel Cottage in the heart of Harpers Ferry

Laurel Cottage in the heart of Harpers Ferry
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Exterior

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 CA $346
CA $587 total
includes taxes & fees
Apr 23 - Apr 24
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 CA $201
CA $331 total
includes taxes & fees
Apr 22 - Apr 23
Firehouse Cottage | Walk to all of downtown HF
RIVERKEEPER INN, Waterfront Property on the Potomac River
Terrace/patio

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.2 out of 10, Wonderful, (118)
"Riverkeeper Inn is located in a peaceful and quiet area of Harpers Ferry, equally perfect in early mornings and late nights. The check-in and check-out process were very easy, and the property itself had everything we could've asked for, and then some."
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)
"It beautiful vacation place. The host is simply the best whatever you need she has your back.You will love the beauty of the place."
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 CA $216
CA $614 total
includes taxes & fees
May 6 - May 7
Peaceful Lakefront Cottage with Mountain Views!
Magical Treehouse in Woods, Close many Wineries & Breweries, Pet Friendly!
Smart TV

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!
Terrace/patio

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

Charming Cabin in the Woods with River Access
Exterior

Charming Cabin in the Woods with River Access

9.8 out of 10, Exceptional, (19)
"Enjoyed the privacy and convenience of Mossy Rock. "
Charming Cabin in the Woods with River Access
❤️ Secluded 1940s Romantic Tiny House on the River
Exterior

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (53)
"The cabin was perfect for a few days of writing and reflecting! Everything was very clean and it was easy communicating with the owner. The house is not "secluded" as there are neighboring houses on two sides and if I hadn't brought an ax/saw to cut my own dry wood enjoying a fire wouldn't have been possible. But overall a lovely stay and I look forward to going again!"
The price is CA $102
CA $198 total
includes taxes & fees
Apr 28 - Apr 29
❤️ Secluded 1940s Romantic Tiny House on the River
Welcome to this patch of serenity on the river's edge, to this hideaway.
Interior

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

9.8 out of 10, Exceptional, (60)
"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.
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.