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Compare 52 Cottages in Shepherdstown with updated reviews, rates, and availability.

RIVERKEEPER INN, Waterfront Property on the Potomac River
View from property
RIVERKEEPER INN, Waterfront Property on the Potomac River
9.4 out of 10, Exceptional, 104 reviews
"We had a wonderful time, even in the rain! Easy river access and beautiful views of both the water and green spaces."
RIVERKEEPER INN, Waterfront Property on the Potomac River
Cozy Cottage
Exterior
Cozy Cottage
9.2 out of 10, Wonderful, 19 reviews
"Clean, quiet neighborhood, easy walk to downtown"
The price is $94
$216 total
includes taxes & fees
Jul 1 - Jul 2
Cozy Cottage
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Fridge, microwave, oven, stovetop
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
10.0 out of 10, Exceptional, 22 reviews
"Very roomy, comfortable, quiet. Great location"
The price is $200
$360 total
includes taxes & fees
Jul 12 - Jul 13
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Woodsy Retreat with a Hot Tub and Seasonal Views!
Property grounds
Woodsy Retreat with a Hot Tub and Seasonal Views!
10.0 out of 10, Exceptional, 10 reviews
"The cabin was great. Clean, well stocked, and quite. It was just what we needed for a long weekend away from everything. Can't wait to do it again."
Woodsy Retreat with a Hot Tub and Seasonal Views!
Cozy Creek Retreat by Whitetail Resort W/ hot tub
Exterior
Cozy Creek Retreat by Whitetail Resort W/ hot tub
10.0 out of 10, Exceptional, 1 review
"This was an excellent place to stay. Incredibly clean, well kept, and stocked with many helpful home items. I will be looking to book again next time I am in the area."
Cozy Creek Retreat by Whitetail Resort W/ hot tub
Mountain Royal at the Woods Resort
Interior
Mountain Royal at the Woods Resort
9.2 out of 10, Wonderful, 5 reviews
"We love this house and it is so cozy. We had great time w family and enjoyed every moment"
Mountain Royal at the Woods Resort
The Carriage House at Carrot Top Cottage
Aerial view
The Carriage House at Carrot Top Cottage
9.6 out of 10, Exceptional, 18 reviews
"Perfect for a solo getaway. Close to restaurants, shops, and the Appalachian Trail. Squeaky clean, comfy bed, and great communication with owners. Thanks for a great stay!"
The price is $105
$177 total
includes taxes & fees
Jun 27 - Jun 28
The Carriage House at Carrot Top Cottage
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Property grounds
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
10.0 out of 10, Exceptional, 12 reviews
"Very clean! The outdoor space is amazing and better than photos. Host was super responsive to texting. Wish we would have planned an extra day to just enjoy the house and property more!"
The price is $493
$988 total
includes taxes & fees
Jun 20 - Jun 21
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Lock Keepers Cottage on C&O Canal/Potomac River
Lock Keepers Cottage on C&O Canal/Potomac River
10.0 out of 10, Exceptional, 42 reviews
"Our stay was simply amazing! The home was very clean and inviting. You can here the sound of the water as it rolls over the dam from the the front porch. The sounds of the birds chirping right outside is the best sound. We loved this place and will be back. Rorke is especially nice and was very easy to communicate with. 5 Stars easy!"
Lock Keepers Cottage on C&O Canal/Potomac River
Peaceful Lakefront Cottage with Mountain Views!
Fridge, microwave, oven, stovetop
Peaceful Lakefront Cottage with Mountain Views!
10.0 out of 10, Exceptional, 16 reviews
"It was a lovely way to spend our honeymoon I loved it so much will book again with family"
The price is $294
$638 total
includes taxes & fees
Jun 19 - Jun 20
Peaceful Lakefront Cottage with Mountain Views!
Lake View Retreat - Cottage Near a Peaceful Lake!
Property grounds
Lake View Retreat - Cottage Near a Peaceful Lake!
9.6 out of 10, Exceptional, 14 reviews
"This property was a perfect place to stay for our group. While it was a little out of the way, it suited our needs, was clean, and very comfortable. The owners made quick communication with them easy. Definitely recommend!"
Lake View Retreat - Cottage Near a Peaceful Lake!
Lovettsville Cottage in Heart of Wine Country
View from property
Lovettsville Cottage in Heart of Wine Country
10.0 out of 10, Exceptional, 22 reviews
"This property was a great place to relax in a peaceful quiet setting. It was very clean. The kitchen had everything to prepare a meal. Easy access to Harper’s Ferry and Louden County wineries. An enjoyable 3 night stay for each of us."
Lovettsville Cottage in Heart of Wine Country
Entire Mountain Cottage Near Scenic Hiking Trails, Your Getaway Retreat!
View from property
Entire Mountain Cottage Near Scenic Hiking Trails, Your Getaway Retreat!
10.0 out of 10, Exceptional, 1 review
"The house was beautiful and perfect for our needs. We were able to be comfortable and enjoy our friend's wedding."
Entire Mountain Cottage Near Scenic Hiking Trails, Your Getaway Retreat!
Cottage at Gray Fox- Many Attraction- Pet Friendly
Exterior
Cottage at Gray Fox- Many Attraction- Pet Friendly
10.0 out of 10, Exceptional, 16 reviews
"We needed a b&b for an out of town wedding and this home could not have been more perfect! The hot tub and gaming system were a huge hit and the beds were beyond comfortable. The hosts were also very responsive and flexible! Highly recommend"
Cottage at Gray Fox- Many Attraction- Pet Friendly
Cottage w/ Hot Tub and 100-Mile Valley Views!
Pool
Cottage w/ Hot Tub and 100-Mile Valley Views!
10.0 out of 10, Exceptional, 12 reviews
"Great place to stay with our family of 4. The house was clean and had everything we needed. The view is beautiful and the neighborhood is nice and quiet."
The price is $322
$678 total
includes taxes & fees
Jul 14 - Jul 15
Cottage w/ Hot Tub and 100-Mile Valley Views!
Historic Schoolhouse on Winery Row
Outdoor dining
Historic Schoolhouse on Winery Row
10.0 out of 10, Exceptional, 6 reviews
"House and property are great. Just what we needed and had everything easily accessible. We enjoyed our stay."
Historic Schoolhouse on Winery Row
Charming Home With Yard Near Shenandoah River!
Interior
Charming Home With Yard Near Shenandoah River!
3.5 star property
10.0 out of 10, Exceptional, 1 review
Charming Home With Yard Near Shenandoah River!
Quiet tiny home. Dog-friendly. Private fenced yard
Terrace/patio
Quiet tiny home. Dog-friendly. Private fenced yard
10.0 out of 10, Exceptional, 2 reviews
"Spotless, well-appointed small house with fenced off privacy from the main house. Comfortable bed. Location was great for walking into town but also being quiet at night. A great play to stay to enjoy all of the outdoor things to do in Harper's Ferry as well as the history. Thoughtful hosts provided a lot of information about the area."
The price is $85
$166 total
includes taxes & fees
Jun 27 - Jun 28
Quiet tiny home. Dog-friendly. Private fenced yard
The Getaway Cottage at Rocky Marsh Farm
Fridge, microwave, oven, stovetop
The Getaway Cottage at Rocky Marsh Farm
10.0 out of 10, Exceptional, 16 reviews
"Great spot! Spent the weekend with three girlfriends and had a blast. The home was spotless, cozy, modern, and with a very well-equipped kitchen. Beautiful, bright windows, excellent views, and warm, inviting decor. Owners were responsive but not intrusive; we had no issues during our stay. I can't wait to come back!"
The Getaway Cottage at Rocky Marsh Farm
🛶 Huckleberry Hills 🛶 Lake Cottage w/ ✨King Beds✨Hot Tub✨Fast Wifi✨Firepit✨
Outdoor dining
🛶 Huckleberry Hills 🛶 Lake Cottage w/ ✨King Beds✨Hot Tub✨Fast Wifi✨Firepit✨
10.0 out of 10, Exceptional, 20 reviews
"This property was clean and comfortable. It was adequate for our needs. The property manager is very responsive and available if any needs arise. Would definitely stay here again."
The price is $390
$700 total
includes taxes & fees
Jun 19 - Jun 20
🛶 Huckleberry Hills 🛶 Lake Cottage w/ ✨King Beds✨Hot Tub✨Fast Wifi✨Firepit✨
Don't see what you're looking for?
See all available properties in Shepherdstown
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.

Other property types in Shepherdstown

❤️ Secluded 1940s Romantic Tiny House on the River
Beach
❤️ Secluded 1940s Romantic Tiny House on the River
10.0 out of 10, Exceptional, 41 reviews
"The tiny house is exactly as described. Its small, clean, cozy and comfortable. The location right on the river is fantastic. Being able to have a fire right by the water each night was such a plus. In better weather would be a great put in for canoeing, kataking. Very close many historic sights, unique shops, and outdoor activities. The hosts are very thoughtful, kind and responsive. We will be staying again!!"
The price is $75
$144 total
includes taxes & fees
Jun 23 - Jun 24
❤️ Secluded 1940s Romantic Tiny House on the River
Cozy Cottage
Exterior
Cozy Cottage
9.2 out of 10, Wonderful, 19 reviews
"Clean, quiet neighborhood, easy walk to downtown"
The price is $94
$216 total
includes taxes & fees
Jul 1 - Jul 2
Cozy Cottage
Plum Lazy on the Potomac
Property grounds
Plum Lazy on the Potomac
9.4 out of 10, Exceptional, 20 reviews
"My friends and I loved this house can’t wait to go back."
Plum Lazy on the Potomac
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.

Shepherdstown Cottages information

Number of reviews
357
Accommodation
52 Cottages
Lowest Price
$85
Highest Price
$493

Frequently asked questions

How much do cottages in Shepherdstown cost?
Cottages in Shepherdstown range between $85 and $493 per night. These retreats offer a chance to get reacquainted with nature — at a price you can afford. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Shepherdstown?
Reconnect with nature in one of the 52 cottages waiting for you in Shepherdstown. To help you choose a stay that’s right for you, use our filter tool to search for must-have amenities.
Why book your cottage in Shepherdstown with Expedia?
Expedia has some wonderful cottages in Shepherdstown, so get set for a memorable stay on nature’s doorstep. If you have a certain budget, choose how much you’d like to spend and the preferred star rating of your property. Or, use our filters to search for cottages with a pool or a hot tub. We’ll help you find the perfect pad whatever your plans or style of travel.
How can I find cheap cottages in Shepherdstown?
The easiest way to score cheap cottages in Shepherdstown is with Expedia’s filter tool. Fine-tune your search results by amenities, star rating and budget to land unbeatable prices in just a few clicks.
What is there to do in Shepherdstown near my cottage?
Shepherdstown has enough experiences to keep you on the go for weeks (or months!), starting with Big Cork Vineyards. Bolivar Heights Scenic Overlook, For the Kids, By George Childrens Museum and Crystal Grottoes Caverns are other fantastic attractions. If you’re sticking around a while, Apollo Civic Theatre and Shepherdstown Museum are nice finishing touches to your itinerary.

Recent reviews of Shepherdstown hotels
Expedia verified reviews

Hampton Inn Hagerstown

Hampton Inn Hagerstown

5/5 Excellent
"this property was clean and comfortable. Staff was Welcoming and very attentive. I asked for an extra towel and they brought it to our room within minutes. our room was very comfortable. The only suggestion I have would be to fix the showerhead so that the water dispenses through the entire showerhead rather than the perimeter. Otherwise, a great property!"
A verified traveler stayed at Hampton Inn Hagerstown
Posted 2 days ago
Hampton Inn Hagerstown