A street lined with brick buildings, including a bank and a restaurant.

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for Shepherdstown vacation homes

Dining

Exclusive Wooded Chalet w Magnificent River Views

Exclusive Wooded Chalet w Magnificent River Views
Shepherdstown
10.0 out of 10, Exceptional, (19 reviews)
"Fantastic location, amazing views, clean property, responsive host"
United States
Brian
Exclusive Wooded Chalet w Magnificent River Views
A park with a pond, a bridge, and a church in the background.

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Downtown Frederick
9.4 out of 10, Exceptional, (130 reviews)
"Great stay, excellent location and host was always readily available. Highly recommended!"
United States
Zayde C.
The price is AED 408
AED 1,001 total
includes taxes & fees
6 Jul - 7 Jul
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Fridge, microwave, oven, stovetop

Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Jefferson
9.8 out of 10, Exceptional, (66 reviews)
"We had 6 in our group and it was perfect especially for the price. Super clean, great responsive host, good location. Bakery directly across the street and ice cream and sandwich shop just down the road at the light. Will definitely stay here again. "
United States
Anonymous traveler
The price is AED 294
AED 857 total
includes taxes & fees
1 Jul - 2 Jul
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Dining

Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (94 reviews)
"All amenities were top notch "
United States
John M.
The price is AED 536
AED 1,183 total
includes taxes & fees
27 Jul - 28 Jul
Luxury Condo In Downtown Frederick
Exterior

Charming "Cream of the Crop" Cape ~❤️of Middletown

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (147 reviews)
"An absolutely charming getaway spot tucked in a small town with trendy shops and eateries. Our host gave fabulous recommendations and the property was spotless, cozy and well equipped for the perfect weekend getaway."
United States
Jennifer P.
The price is AED 661
AED 1,277 total
includes taxes & fees
22 Jul - 23 Jul
Charming "Cream of the Crop" Cape ~❤️of Middletown
Property grounds

The Blue Jay | New House in the Woods w/ Hot Tub

The Blue Jay | New House in the Woods w/ Hot Tub
Harpers Ferry
10.0 out of 10, Exceptional, (3 reviews)
"Great place. Very well stocked house everything you need Great response from host. Very nice place. Road is a little rough as explained in listing "
United States
Brett D.
The price is AED 367
AED 1,341 total
includes taxes & fees
1 Jul - 2 Jul
The Blue Jay | New House in the Woods w/ Hot Tub
Outdoor dining

Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick

Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Frederick
9.8 out of 10, Exceptional, (45 reviews)
"Great location--easy walk to downtown Frederick. Comfortable beds, pleasant spaces and light."
United States
Alan S.
The price is AED 415
AED 981 total
includes taxes & fees
20 Jul - 21 Jul
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Interior

Bluemont home just minutes to wineries, breweries, hiking and more!

Bluemont home just minutes to wineries, breweries, hiking and more!
Bluemont
The price is AED 808
AED 1,701 total
includes taxes & fees
8 Jul - 9 Jul
Bluemont home just minutes to wineries, breweries, hiking and more!
Exterior

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Sharpsburg
9.8 out of 10, Exceptional, (204 reviews)
"This was an amazing experience to stay in a house that was here during the battle, look forward to may more visits while I see the place I love. "
United States
Dave W.
The price is AED 533
AED 646 total
includes taxes & fees
7 Jul - 8 Jul
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
TV, offices

Riverfront Cabin Getaway with Fire Pit!

Riverfront Cabin Getaway with Fire Pit!
Harpers Ferry
9.6 out of 10, Exceptional, (4 reviews)
"Great stay. House was as advertised and communication with our host was super easy. Would stay again. "
United States
Paul I.
The price is AED 426
AED 2,145 total
includes taxes & fees
6 Jul - 7 Jul
Riverfront Cabin Getaway with Fire Pit!
Outdoor dining

Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets

Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets
Harpers Ferry
10.0 out of 10, Exceptional, (28 reviews)
"Host was helpful and everything was wonderful."
United States
Karen
The price is AED 558
AED 1,494 total
includes taxes & fees
5 Jul - 6 Jul
Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets
Interior

Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront

Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
Sharpsburg
8.4 out of 10, Very Good, (63 reviews)
"Great location, spacious living area, plenty of linens, and excellent fire pit! "
United States
Maria Elena S.
The price is AED 757
AED 1,675 total
includes taxes & fees
1 Jul - 2 Jul
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
Property grounds

4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline

4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline
Harpers Ferry
9.6 out of 10, Exceptional, (5 reviews)
"House was beautiful and fully equipped for our stay. The host was very communicative and we really enjoyed our time here. If in the area again would definitely stay here. "
United States
Maeve K.
The price is AED 367
AED 1,501 total
includes taxes & fees
1 Jul - 2 Jul
4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline
3 bedrooms, desk, iron/ironing board, travel crib

Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV

Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV
Harpers Ferry
10.0 out of 10, Exceptional, (12 reviews)
"Perfect place to spend a few nights with our two dogs. Very clean, great amenities, and beautifully decorated. Highly recommend!! "
United States
Megan L.
The price is AED 558
AED 1,458 total
includes taxes & fees
5 Jul - 6 Jul
Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV
Property grounds

Terra Alta - Incredible River Views and Hot Tub!

Terra Alta - Incredible River Views and Hot Tub!
Charles Town
9.6 out of 10, Exceptional, (71 reviews)
"Nice quiet view, able to sit on deck for hours and talk. Close to restaurants, and stores. Had a great stay."
United States
Paul M.
The price is AED 437
AED 1,575 total
includes taxes & fees
16 Jul - 17 Jul
Terra Alta - Incredible River Views and Hot Tub!
Interior

Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!

Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!
Harpers Ferry
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful home. Very attentive hosts, great location. We enjoyed every minute at this home. "
United States
Katrina
The price is AED 659
AED 1,569 total
includes taxes & fees
1 Jul - 2 Jul
Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!
Fridge, oven, stovetop, dishwasher

Mountain Retreat w/2 Living Spaces, Hot Tub & Deck

Mountain Retreat w/2 Living Spaces, Hot Tub & Deck
Harpers Ferry
The price is AED 591
AED 1,208 total
includes taxes & fees
15 Jul - 16 Jul
Mountain Retreat w/2 Living Spaces, Hot Tub & Deck
Outdoor dining

Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach

Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
Harpers Ferry
9.8 out of 10, Exceptional, (6 reviews)
The price is AED 184
AED 948 total
includes taxes & fees
14 Jul - 15 Jul
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
Exterior

Antietam Dome: Level 2 Charger, 1 level, Walk to C&O Canal at Antietam Aqueduct Relax, Naturally!

Antietam Dome: Level 2 Charger, 1 level, Walk to C&O Canal at Antietam Aqueduct Relax, Naturally!
Sharpsburg
9.2 out of 10, Wonderful, (5 reviews)
"Loved the area. House was very clean and the host were very polite. The water has a very foul odor from the well, but that is not within the host control so everything else was excellent. "
United States
Justin C.
The price is AED 707
AED 1,524 total
includes taxes & fees
7 Jul - 8 Jul
Antietam Dome: Level 2 Charger, 1 level, Walk to C&O Canal at Antietam Aqueduct Relax, Naturally!
Property grounds

Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location

Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location
Harpers Ferry
7.4 out of 10, Good, (28 reviews)
"The inside was well done and clean. Even though the neighbors are close, they were quiet. My husband and I were able to relax in a comfortable setting."
United States
Melissa H.
The price is AED 621
AED 1,236 total
includes taxes & fees
19 Jul - 20 Jul
Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location
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 Shepherdstown Hotel Reviews

Tru By Hilton Martinsburg

Tru By Hilton Martinsburg

10/10 Excellent
"The staff was exceptional! They were all very nice and helpful. It didn't have a pool but we knew that when we booked it. The breakfast was alright. It's a little thing but the "do not disturb" signs would not stay on the door handle. They fell off every time you left or entered the room. Be aware that the rooms don't have a microwave, unless you ask for one. All in all it was a very nice stay. The rooms and grounds were very well kept too. We'd be back for the staff alone! Great stay."
Eric 3-night trip
Posted 9 hours ago
Tru By Hilton Martinsburg

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