Shepherdstown vacation rentals

KAYAK searches hundreds of travel sites at once for vacation home deals in Shepherdstown

Here is why travelers choose KAYAK

Free to useThere are no hidden charges or fees.

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Recommended by KAYAK
Useful Info
Recommended by KAYAK

Best Shepherdstown vacation rentals

Most recommended vacation rentals in Shepherdstown

Show all
Lovely Tiny House Rental for a Romantic Getaway in Shepherdstown, West Virginia - Shepherdstown - Beach
Lovely Tiny House Rental for a Romantic Getaway in Shepherdstown, West Virginia
Shepherdstown, WV
Free Wi-Fi
$167+
Check availability
Downtown Modern 2BR step from dining and shopping - Shepherdstown - Living room
Downtown Modern 2BR step from dining and shopping
Shepherdstown, WV
Free Wi-Fi
$280+
Check availability
Exclusive Wooded Chalet w Magnificent River Views - Shepherdstown - Dining room
Exclusive Wooded Chalet w Magnificent River Views
Shepherdstown, WV
Free Wi-Fi
$806+
Check availability
The Getaway Cottage at Rocky Marsh Farm - Shepherdstown - Building
The Getaway Cottage at Rocky Marsh Farm
Shepherdstown, WV
Free Wi-Fi
$328+
Check availability
Best Location: Historic Shepherdstown Getaway - Shepherdstown - Living room
Best Location: Historic Shepherdstown Getaway
Shepherdstown, WV
Free Wi-Fi
$364+
Check availability
Historic Townhome in Downtown Shepherdstown! - Shepherdstown - Living room
Historic Townhome in Downtown Shepherdstown!
Shepherdstown, WV
10Wonderful(1)
Free Wi-Fi
$386+
Check availability
Explore Shepherdstown from Downtown Modern 1br Apartment - Shepherdstown - Outdoors view
Explore Shepherdstown from Downtown Modern 1br Apartment
Shepherdstown, WV
Free Wi-Fi
$209+
Check availability
Welcome to this patch of serenity on the river's edge, to this hideaway. - Shepherdstown - Dining room
Welcome to this patch of serenity on the river's edge, to this hideaway.
Shepherdstown, WV
Free Wi-Fi
$405+
Check availability
Graycliff Hall: Riverfront Estate w/ Heli Pad, Private Chef, Hot Tub - Shepherdstown - Living room
Graycliff Hall: Riverfront Estate w/ Heli Pad, Private Chef, Hot Tub
Shepherdstown, WV
Free Wi-Fi
$1,543+
Check availability
Stunning custom Shepherdstown waterfront retreat - Shepherdstown - Dining room
Stunning custom Shepherdstown waterfront retreat
Shepherdstown, WV
Free Wi-Fi
$214+
Check availability
Cottage in Shepherdstown - Shepherdstown
Cottage in Shepherdstown
Shepherdstown, WV
Pool
Spa
$160+
Check availability
Secluded On The River, Historic 1815 House, Romantic Shepherdstown - Shepherdstown
Secluded On The River, Historic 1815 House, Romantic Shepherdstown
Shepherdstown, WV
9.3Wonderful(32)
$234+
Check availability
Cozy Guest House With Swedish Sauna & 5 Star Bbq Hot Tub Removed Due To C V - Shepherdstown
Cozy Guest House With Swedish Sauna & 5 Star Bbq Hot Tub Removed Due To C V
Shepherdstown, WV
Pet friendly
Spa
$112+
Check availability
Stay At Large, Historic Home & Enjoy 5 Star Bbq - Shepherdstown
Stay At Large, Historic Home & Enjoy 5 Star Bbq
Shepherdstown, WV
Pet friendly
$128+
Check availability
Dream House on the Potomac River Canyon South Rim - Shepherdstown
Dream House on the Potomac River Canyon South Rim
Shepherdstown, WV
Free Wi-Fi
Pet friendly
$1,206+
Check availability
Shepherdstown cabin in the country new owner - Shepherdstown
Shepherdstown cabin in the country new owner
Shepherdstown, WV
Free Wi-Fi
Pool
$218+
Check availability
Go to map

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by price

$0 - $386$386 - $772$772 - $1,158$1,158 - $1,543$1,543+ per night

Property Types

ApartmentCottageHouse

Search by freebies

Free cancellationFree breakfastFree parkingFree internet
Useful Info

Good to know

Low season

January

High season

March

Average price (weeknight)

$135
Cheapest month to stay with an average 15% drop in price.
Most expensive month to stay with an average 49% rise in price.
Average Sun - Thu price over the last 2 weeks.

KAYAK's top tips for finding Shepherdstown vacation rental deals

  • The best vacation rental properties in Shepherdstown are Best Location: Historic Shepherdstown Getaway (10.0, 25 reviews), Lovely Tiny House Rental for a Romantic Getaway in Shepherdstown, West Virginia (9.7, 26), and Welcome to this patch of serenity on the river's edge, to this hideaway. (9.6, 24), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Shepherdstown, you should consider visiting during the low season. The cheapest vacation homes in Shepherdstown can be found in January and April.
  • The cheapest night for renting a vacation home in Shepherdstown is Thursday. In contrast, the most expensive is Sunday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Shepherdstown for 2 days.

FAQs when booking a vacation home in Shepherdstown

  • What types of vacation rentals are available in Shepherdstown?

    There are loads of different property types that you can make your vacation home in Shepherdstown. You’ll find apartments, cabins, campgrounds, cottages and houses.

  • Are there any pet-friendly vacation rentals in Shepherdstown?

    There are a number of dog and pet-friendly Shepherdstown vacation rentals, with around 14% allowing you to bring your pet along with you.

  • How can I find vacation rentals near me in Shepherdstown?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Shepherdstown?

Our map will help you find the perfect place to stay in Shepherdstown by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Shepherdstown

Shepherdstown vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Shepherdstown. Find cheap vacation homes to rent in Shepherdstown. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Shepherdstown that suits you best.

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.