Search Vacation Homes in Shepherdstown

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec
Outdoor dining
Exclusive Wooded Chalet w Magnificent River Views
Exclusive Wooded Chalet w Magnificent River Views
10.0 out of 10, Exceptional, (7)
"This property was super nice and the property managers were super awesome and accommodating! "
United States
Construction V.
The price is HK$2,017
HK$3,730 total
includes taxes & fees
4 Nov - 5 Nov
Exclusive Wooded Chalet w Magnificent River Views
Dining
Downtown Charm: Pets Welcome
Downtown Charm: Pets Welcome
10.0 out of 10, Exceptional, (1)
"House was nice and cozy. And short trip to downtown area. Would definately stay here again."
United States
Ayo P.
The price is HK$1,010
HK$2,619 total
includes taxes & fees
27 Oct - 28 Oct
Downtown Charm: Pets Welcome
Smart TV
*Luxury Condo In Downtown Frederick*
*Luxury Condo In Downtown Frederick*
9.0 out of 10, Wonderful, (68)
"Great time. Everything was perfect and place was just what we needed. "
United States
dominick c.
The price is HK$793
HK$2,035 total
includes taxes & fees
29 Oct - 30 Oct
*Luxury Condo In Downtown Frederick*
Terrace/patio
Charming "Cream of the Crop" Cape ~❤️of Middletown
Charming "Cream of the Crop" Cape ~❤️of Middletown
10.0 out of 10, Exceptional, (137)
"The property is wonderful! Very cozy and convenient to local attractions."
United States
Joanne C.
The price is HK$699
HK$1,870 total
includes taxes & fees
27 Oct - 28 Oct
Charming "Cream of the Crop" Cape ~❤️of Middletown
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
9.4 out of 10, Exceptional, (117)
"Clean and comfortable, quiet and perfectly located, this the perfect place for enjoying downtown "
United States
Carolyn M.
The price is HK$948
HK$2,265 total
includes taxes & fees
2 Nov - 3 Nov
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
9.8 out of 10, Exceptional, (58)
"Very conveniently located for our visit with an amazing bakery and awesome meat market across the street. "
United States
Kathryn B.
The price is HK$699
HK$1,845 total
includes taxes & fees
30 Oct - 31 Oct
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Property grounds
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
9.8 out of 10, Exceptional, (30)
"This place was very clean and had all necessary amenities. The host communicated well. Walkable to town and the park! "
United States
Kyla A.
The price is HK$804
HK$2,006 total
includes taxes & fees
5 Nov - 6 Nov
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Dining tables
Kalia’s Mountain Momma Getaway
Kalia’s Mountain Momma Getaway
10.0 out of 10, Exceptional, (11)
"Location was nice"
United States
michael
The price is HK$847
HK$1,375 total
includes taxes & fees
27 Oct - 28 Oct
Kalia’s Mountain Momma Getaway
Property grounds
Lakefront House w/ Modern Comforts!
Lakefront House w/ Modern Comforts!
8.8 out of 10, Excellent, (3)
"The house is lovely. Very much enjoyed the stay. Looking forward to going back!!"
United States
robert s.
The price is HK$777
HK$2,742 total
includes taxes & fees
26 Oct - 27 Oct
Lakefront House w/ Modern Comforts!
Property grounds
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
9.8 out of 10, Exceptional, (190)
"Property was clean and cozy."
United States
Billie
The price is HK$1,072
HK$1,301 total
includes taxes & fees
27 Oct - 28 Oct
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Fridge, microwave, oven, stovetop
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home
9.4 out of 10, Exceptional, (110)
"Great little farm house in a quaint little town "
United States
Jason A.
The price is HK$1,236
HK$2,298 total
includes taxes & fees
2 Nov - 3 Nov
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home
Exterior
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
10.0 out of 10, Exceptional, (5)
"Great and quiet location with all the amenities. Getting to the parking is a bit tricky but other than that great place to stay with family"
United States
Vinod B.
The price is HK$730
HK$2,515 total
includes taxes & fees
12 Nov - 13 Nov
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
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!
10.0 out of 10, Exceptional, (39)
"The house was very clean, the hot tub felt great, and sitting out on the back deck at night was wonderful. The only negative I had about the house was that it only had one bathroom. Jordan communicated well, he was always available to answer questions. People in town knew him and they all seem to like him. We would definitely recommend this house."
United States
kathy
The price is HK$1,166
HK$2,690 total
includes taxes & fees
4 Nov - 5 Nov
Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!
Outdoor dining
Camp Patowmack - Riverfront, Hot Tub, and Sauna!
Camp Patowmack - Riverfront, Hot Tub, and Sauna!
9.6 out of 10, Exceptional, (4)
"We thoroughly enjoyed this property. It is a beautiful cabin located directly on the Potomac river near Harpers Ferry. We would stay here again. It has everything you could possibly need for a quiet escape! "
United States
Ashley W.
The price is HK$1,018
HK$4,499 total
includes taxes & fees
11 Nov - 12 Nov
Camp Patowmack - Riverfront, Hot Tub, and Sauna!
Exterior detail
Inns of Whitetail #209
Inns of Whitetail #209
10.0 out of 10, Exceptional, (1)
"Love the natural beauty all around."
United States
Krista
The price is HK$1,020
HK$1,905 total
includes taxes & fees
24 Oct - 25 Oct
Inns of Whitetail #209
Outdoor spa tub
Terra Alta - Incredible River Views and Hot Tub!
Terra Alta - Incredible River Views and Hot Tub!
9.6 out of 10, Exceptional, (63)
"We had a great time! The house overlooks the river and we loved the hot tub and fire pit! "
United States
Cherilyn M.
The price is HK$777
HK$3,131 total
includes taxes & fees
6 Nov - 7 Nov
Terra Alta - Incredible River Views and Hot Tub!
Terrace/patio
1939 4BR Rustic Escape by Casino, 1939 4BR Rustic Escape by Casino
1939 4BR Rustic Escape by Casino, 1939 4BR Rustic Escape by Casino
10.0 out of 10, Exceptional, (2)
"Convenient location, close to casino & river tubing. The house was cozy & comfortable for all of us. "
United States
Melissa H.
The price is HK$1,002
HK$2,366 total
includes taxes & fees
27 Oct - 28 Oct
1939 4BR Rustic Escape by Casino, 1939 4BR Rustic Escape by Casino
2 bedrooms, travel cot, WiFi, bed sheets
Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry
Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry
2.0 star property
10.0 out of 10, Exceptional, (11)
"Great place and good location."
United States
Jeffrey S.
The price is HK$1,399
HK$2,398 total
includes taxes & fees
27 Oct - 28 Oct
Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry
Terrace/patio
Private outdoor Spa! Close to Casino, Cozy Pool & Hot Tub Retreat by Casino
Private outdoor Spa! Close to Casino, Cozy Pool & Hot Tub Retreat by Casino
9.0 out of 10, Wonderful, (2)
"Quaint home for a weekend getaway! Exactly as advertised, great communication with host, and the pool & hot tub were clean and in stellar shape. Will definitely schedule another stay in the future!!"
United States
Stephanie W.
The price is HK$1,010
HK$2,396 total
includes taxes & fees
11 Nov - 12 Nov
Private outdoor Spa! Close to Casino, Cozy Pool & Hot Tub Retreat by Casino
Interior
Pleasant 3-bedroom house with AC in Martinsburg
Pleasant 3-bedroom house with AC in Martinsburg
2.0 star property
The price is HK$847
HK$1,824 total
includes taxes & fees
2 Nov - 3 Nov
Pleasant 3-bedroom house with AC in Martinsburg
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Shepherdstown Hotel Reviews

Days Inn by Wyndham Charles Town/Harpers Ferry

Days Inn by Wyndham Charles Town/Harpers Ferry

10/10 Excellent
"Easy - peasy; no problems"
Phyllis 1-night trip
Posted 23 hours ago
Days Inn by Wyndham Charles Town/Harpers Ferry

Find out more about Shepherdstown

Shepherdstown Vacation Homes information

Number of reviews
824
Accommodation
289 Vacation Homes
Lowest Price
HK$1,301
Highest Price
HK$4,499