Shepherdstown Holiday Rentals

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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec
In four months
23 Jan - 25 Jan

Holiday Rentals in Shepherdstown

❤️ Secluded 1940s Romantic Tiny House on the River
Property grounds

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (61)
"We truly loved this location and definitely will be back!"
The price is HK$315
HK$823 total
includes taxes & fees
12 Oct - 13 Oct
❤️ Secluded 1940s Romantic Tiny House on the River
Welcome to this patch of serenity on the river's edge, to this hideaway.
Dining

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

10.0 out of 10, Exceptional, (64)
"Enjoyed our stay!!"
Welcome to this patch of serenity on the river's edge, to this hideaway.
Private, light filled retreat space... with your own pickleball court!
Smart TV, fireplace

Private, light filled retreat space... with your own pickleball court!

10.0 out of 10, Exceptional, (50)
"Couldn't ask for a nicer place to stay peaceful, quiet with a great view. Wildlife is abundant and beautiful everything that you could need or want to relax Bill and Patty were excellent hosts looking forward to visiting again"
Private, light filled retreat space... with your own pickleball court!
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
Microwave

Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry

9.4 out of 10, Exceptional, (16)
"Small basement apartment had all we needed and wanted. Wonderful location. "
The price is HK$875
HK$1,460 total
includes taxes & fees
14 Oct - 15 Oct
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
Mirror Villas - Modern Retreat with private hot tubs and mountain view
Terrace/patio

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

3.5 star property
10.0 out of 10, Exceptional, (1)
"Great "
The price is HK$4,031
HK$5,642 total
includes taxes & fees
4 Oct - 5 Oct
Mirror Villas - Modern Retreat with private hot tubs and mountain view
Hidden Gem in the woods with hot tub
Property grounds

Hidden Gem in the woods with hot tub

9.6 out of 10, Exceptional, (82)
"Outstanding property was just what the doctor ordered for a rejuvenating time of R&R. Clean and comfortable, all of the amenities—including the hot tub— made for a lovely stay. "
Hidden Gem in the woods with hot tub
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Property grounds

Countryside Cabin with Mountain Views near Surreybrooke Gardens

10.0 out of 10, Exceptional, (121)
"Good location "
Countryside Cabin with Mountain Views near Surreybrooke Gardens
The Oculus - Huge Cabin with a Hot Tub!
Terrace/patio

The Oculus - Huge Cabin with a Hot Tub!

9.6 out of 10, Exceptional, (24)
"The place was big and very roomy and comfortable. Very clean .. very nice. "
The price is HK$778
HK$3,387 total
includes taxes & fees
9 Oct - 10 Oct
The Oculus - Huge Cabin with a Hot Tub!
Enchanting Cottage, walk to Downtown Harpers Ferry
Terrace/patio

Enchanting Cottage, walk to Downtown Harpers Ferry

9.6 out of 10, Exceptional, (41)
"This place was perfect for our one-night stay in Harpers Ferry. Its location is in easy walking distance of the main sites. The house is old but charming. "
The price is HK$1,925
HK$3,041 total
includes taxes & fees
5 Oct - 6 Oct
Enchanting Cottage, walk to Downtown Harpers Ferry
Waterfront Cabin overlooking the Potomac River W/ Hot Tub, firepit, pavilion
2 bedrooms, desk, free WiFi

Waterfront Cabin overlooking the Potomac River W/ Hot Tub, firepit, pavilion

9.8 out of 10, Exceptional, (71)
"It was nice and relaxing. "
The price is HK$1,085
HK$2,152 total
includes taxes & fees
7 Oct - 8 Oct
Waterfront Cabin overlooking the Potomac River W/ Hot Tub, firepit, pavilion
RIVERKEEPER INN, Waterfront Property on the Potomac River
Terrace/patio

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.4 out of 10, Exceptional, (128)
"Beautiful location right on the Potomac River."
RIVERKEEPER INN, Waterfront Property on the Potomac River
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home
Fridge, microwave, oven, stovetop

Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home

9.4 out of 10, Exceptional, (106)
"Great little farm house in a quaint little town "
The price is HK$1,237
HK$2,301 total
includes taxes & fees
9 Oct - 10 Oct
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home
Blue Ridge Getaway - Sunset Views, A.T. Access
Exterior

Blue Ridge Getaway - Sunset Views, A.T. Access

10.0 out of 10, Exceptional, (59)
"My girlfriend and I had a wonderful weekend escaping the hustle and bustle of the city. The view was spectacular and the property was perfect!"
The price is HK$778
HK$2,841 total
includes taxes & fees
9 Oct - 10 Oct
Blue Ridge Getaway - Sunset Views, A.T. Access
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Exterior detail

Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

10.0 out of 10, Exceptional, (132)
"Wonderful stay in a historic home within walking distance of so much American history and so many trails. Would definitely stay here again."
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Spacious w/Hot Tub, Fire Pit, Deck, Grill and WiFi
Fridge, microwave, oven, stovetop

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

9.4 out of 10, Exceptional, (21)
"We had a great time exploring the region from Spleepy Hollow. The hot tub after a long hike is always great!"
The price is HK$1,318
HK$2,211 total
includes taxes & fees
26 Oct - 27 Oct
Spacious w/Hot Tub, Fire Pit, Deck, Grill and WiFi
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Fridge, microwave, oven, stovetop

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

9.8 out of 10, Exceptional, (100)
"This home was absolutely fantastic! Very clean, very close to all things. We had a fantastic time."
The price is HK$1,510
HK$4,591 total
includes taxes & fees
20 Oct - 21 Oct
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Antietam Creek - Quiet 2 Bedroom Cabin
Interior

Antietam Creek - Quiet 2 Bedroom Cabin

9.4 out of 10, Exceptional, (85)
"I loved the trip to that cabin, one of the most wonderful things"
The price is HK$1,556
HK$2,582 total
includes taxes & fees
7 Oct - 8 Oct
Antietam Creek - Quiet 2 Bedroom Cabin
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry
Property grounds

Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry

9.2 out of 10, Wonderful, (12)
"Four family members stayed for a four day weekend. The place was spotless when we arrived and all amenities are as described. The location is perfect for visiting Harpers Ferry, Shepherdstown, and Antietam. We had wonderful time."
The price is HK$1,292
HK$3,335 total
includes taxes & fees
6 Oct - 7 Oct
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry
Cozy Mountain Cabin w/ Steam Shower! Family Friendly.
Dining

Cozy Mountain Cabin w/ Steam Shower! Family Friendly.

10.0 out of 10, Exceptional, (74)
"Wonderful view from the sunroom. Peaceful and rejuvenating stay in this welcoming home. "
The price is HK$805
HK$2,161 total
includes taxes & fees
6 Oct - 7 Oct
Cozy Mountain Cabin w/ Steam Shower! Family Friendly.
Luxurious Mountaintop Chalet / Cabin in 'The Woods Golf Resort':Access Amenities
Exterior detail

Luxurious Mountaintop Chalet / Cabin in 'The Woods Golf Resort':Access Amenities

10.0 out of 10, Exceptional, (66)
"We had a great stay at the cabin. We hiked, went to the pools, and enjoyed hanging out around the fire!00"
Luxurious Mountaintop Chalet / Cabin in 'The Woods Golf Resort':Access Amenities
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

Country Inn & Suites by Radisson, Frederick, MD

Country Inn & Suites by Radisson, Frederick, MD

10/10 Excellent
"Just short night but nice"
Susan 1-night trip
Posted 3 days ago
Country Inn & Suites by Radisson, Frederick, MD

Find out more about Shepherdstown

Find out more about Shepherdstown

Search for holiday rentals in Shepherdstown on Expedia! You can easily find your home rentals, villas, holiday apartments in Shepherdstown using one of the methods below:

  • View our selection of featured holiday rentals in Shepherdstown
  • Use the map to find apartments and other holiday homes in the Shepherdstown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Shepherdstown while they last

Look no further and take a look at our great range of rental properties in Shepherdstown!

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Are there holiday rentals in Shepherdstown?

Yes, there are holiday rentals close to the most popular sights in Shepherdstown, or you can select a more secluded option if you're looking for a relaxing 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 are some of the best holiday rentals that Shepherdstown has to offer?

Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!: This holiday home rental outside of Shepherdstown is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of private gardens in this rental home to help you unwind.

How many holiday rentals will I find in Shepherdstown?

Expedia has 9 holiday rentals for your stay in Shepherdstown.

What’s there to see and do in Shepherdstown?

Cultural attractions include Shepherdstown Opera House and Shepherdstown Museum, 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 holiday rental in Shepherdstown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Shepherdstown. Holiday rentals feature extras such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can provide a sense of security away from shared hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for a family trip or a small group gathering.