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

Shepherdstown Vacation Rentals

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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sep - 6 Sep
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Shepherdstown vacation rentals

Exterior

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.6 out of 10, Exceptional, (79 reviews)
"Cozy home, great location, and kind and helpful host. Would like to stay again. "
United States
Matthew S.
The price is AED 248
AED 500 total
includes taxes & fees
22 Jul - 23 Jul
❤️ Secluded 1940s Romantic Tiny House on the River
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
The price is AED 1,508
AED 2,470 total
includes taxes & fees
28 Jul - 29 Jul
Exclusive Wooded Chalet w Magnificent River Views
Property grounds

Luxury Mirror Cabin ~ Sauna/Hot Tub/Mountain Views

Luxury Mirror Cabin ~ Sauna/Hot Tub/Mountain Views
Mercersburg
The price is AED 1,293
AED 2,266 total
includes taxes & fees
12 Jul - 13 Jul
Luxury Mirror Cabin ~ Sauna/Hot Tub/Mountain Views
Outdoor dining

3BR cabin w/ hot tub & game room

3BR cabin w/ hot tub & game room
Harpers Ferry
9.0 out of 10, Wonderful, (65 reviews)
"While there was something left to be desired by the kitchen utensils and cookware, this place is located off the beaten path in a beautiful mountainside area. Definitely worth the price. Just bring your own pot holders and pizza cutter if you plan on having pizza lol. "
United States
Tyrell O.
The price is AED 650
AED 1,254 total
includes taxes & fees
12 Jul - 13 Jul
3BR cabin w/ hot tub & game room
House (3 Bedrooms) | Interior

5 Mi to Harpers Ferry Nhp: Quiet Deck & Garden

5 Mi to Harpers Ferry Nhp: Quiet Deck & Garden
3.0 star property
Harpers Ferry
The price is AED 621
AED 1,372 total
includes taxes & fees
1 Aug - 2 Aug
5 Mi to Harpers Ferry Nhp: Quiet Deck & Garden
Fridge, microwave, oven, stovetop

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (68 reviews)
"Everything was very clean and comfortable. The kitchen was well equipped."
United States
Linda D.
The price is AED 430
AED 954 total
includes taxes & fees
13 Jul - 14 Jul
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
1 bedroom, premium bedding, down comforters, laptop workspace

Mirror Villas - Modern Retreat with private hot tubs and mountain view

Mirror Villas - Modern Retreat with private hot tubs and mountain view
3.5 star property
Mercersburg
9.8 out of 10, Exceptional, (16 reviews)
"It was the perfect getaway with amazing views and relaxation."
United States
Natalie
The price is AED 1,031
AED 1,696 total
includes taxes & fees
16 Jul - 17 Jul
Mirror Villas - Modern Retreat with private hot tubs and mountain view
Fridge, microwave, oven, stovetop

Modern Condo Right off Market Street

Modern Condo Right off Market Street
Downtown Frederick
9.2 out of 10, Wonderful, (98 reviews)
"Lovely, cozy apartment, more spacious than we imagined and the perfect place to retreat to after the bustling shops and restaurants a few blocks away."
United States
Alexandra W.
The price is AED 486
AED 1,103 total
includes taxes & fees
23 Jul - 24 Jul
Modern Condo Right off Market Street
Exterior

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (149 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 606
AED 1,246 total
includes taxes & fees
26 Jul - 27 Jul
Charming "Cream of the Crop" Cape ~❤️of Middletown
Property grounds

Antietam Toll House~ an historic waterfront cabin with fully fenced yard.

Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
Waynesboro
9.8 out of 10, Exceptional, (102 reviews)
"This is a beautiful and peaceful property. I enjoyed my stay and will definitely book again. "
United States
Dianne F.
The price is AED 382
AED 869 total
includes taxes & fees
16 Jul - 17 Jul
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
Dining

Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (96 reviews)
"Excellent location and clean, spacious townhome in the heart of the historic downtown district. "
United States
Kelly M.
The price is AED 529
AED 1,219 total
includes taxes & fees
23 Jul - 24 Jul
Luxury Condo In Downtown Frederick
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 658
AED 1,577 total
includes taxes & fees
16 Jul - 17 Jul
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
Interior

2-Bedroom cabin Hot tub Fireplace PS5

2-Bedroom cabin Hot tub Fireplace PS5
2.0 star property
The Woods
7.0 out of 10, Good, (10 reviews)
"Nice cabin. Could’ve been cleaner outside. Host was nice and surrounding area, beautiful. "
United States
Chris
The price is AED 477
AED 909 total
includes taxes & fees
13 Jul - 14 Jul
2-Bedroom cabin Hot tub Fireplace PS5
Interior

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

Bring Your Own Boat - Meticulously restored house on the Potomac River
Hedgesville
9.8 out of 10, Exceptional, (13 reviews)
"Our stay was amazing and we really enjoyed ourselves. The place was perfect and quiet and peaceful! We will be booking with them again! "
United States
Kyndal B.
The price is AED 364
AED 691 total
includes taxes & fees
13 Jul - 14 Jul
Bring Your Own Boat - Meticulously restored house on the Potomac River
Property grounds

Glamping Clear Spring Maryland 3-Cabin Campground

Glamping Clear Spring Maryland 3-Cabin Campground
Clear Spring
9.8 out of 10, Exceptional, (17 reviews)
"Absolutely amazing stay. Tom and Karen are amazing hosts. Cabins and property were spotless. Plenty of seating. Quiet and private and cant wait to go back again. Already planning next years weekend. Thank you for opening up your property to us all and treating us so well. "
United States
Christopher J.
The price is AED 881
AED 1,684 total
includes taxes & fees
12 Jul - 13 Jul
Glamping Clear Spring Maryland 3-Cabin Campground
Property grounds

Spacious w/Hot Tub, Fire Pit, Deck, Grill and WiFi

Spacious w/Hot Tub, Fire Pit, Deck, Grill and WiFi
Sleepy Hollow
9.0 out of 10, Wonderful, (32 reviews)
"Great stay and host."
United States
Chase S.
The price is AED 533
AED 1,193 total
includes taxes & fees
16 Jul - 17 Jul
Spacious w/Hot Tub, Fire Pit, Deck, Grill and WiFi
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 364
AED 962 total
includes taxes & fees
14 Jul - 15 Jul
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Property grounds

Cabin at the Gap | You Won't Believe the View!

Cabin at the Gap | You Won't Believe the View!
Harpers Ferry
The price is AED 408
AED 1,325 total
includes taxes & fees
16 Jul - 17 Jul
Cabin at the Gap | You Won't Believe the View!
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 1,224 total
includes taxes & fees
12 Jul - 13 Jul
Mountain Retreat w/2 Living Spaces, Hot Tub & Deck
Dining

~Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake.

~Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake.
Harpers Ferry
10.0 out of 10, Exceptional, (93 reviews)
"This is a beautiful, clean, traquil and relaxing home away from home. The beds are comfortable, the living space is open and full of light during the day. The hosts have made great efforts to make this a family and/or couple friendly destination. Our dog was welcomed and enjoyed her stay (being with her people). The views are spectacular."
United States
Deb K.
The price is AED 566
AED 1,275 total
includes taxes & fees
13 Jul - 14 Jul
~Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake.
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

8/10 Good
"Sorry but did not like the aestetics of the pool table's predominant presence in the lobbies of both Tru I stayed atl"
Deborah 1-night trip
Posted 1 hour ago
Tru By Hilton Martinsburg

Frequently asked questions

Are there vacation rentals in Shepherdstown?

Yes, we have vacation rentals near well known local attractions in Shepherdstown, or you can go with a more secluded option if you want a relaxing place to stay. Nature enthusiasts will enjoy the riverfront in Shepherdstown. Make sure you have time to check out the university setting and gardens during your trip.

What's the top vacation rental in Shepherdstown?

Walk to Harpers Ferry! Dog-friendly. Beautiful Views.: This vacation home rental near Shepherdstown offers a patio, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals will I find in Shepherdstown?

Expedia has 10 vacation rentals for your stay in Shepherdstown.

What’s there to see and do in Shepherdstown?

Cultural attractions include Shepherdstown Museum and Shepherdstown Opera House, whereas Morgan's Grove Park is one spot to enjoy nature. While here, Shepherdstown Visitors Center and Shepherdstown Historic District are other places worth a visit.

What’s a vacation rental in Shepherdstown like?

Vacation rentals are private properties you can stay in for a couple of days or more in Shepherdstown. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from shared hotel elevators and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for a small group gathering.