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Compare 59 Cottages in Shepherdstown with updated reviews, rates, and availability.

The Carriage House at Carrot Top Cottage

9.8 out of 10, Exceptional, (28)
"My wife gave me this trip as a birthday gift (birthday November 7) for my 80th birthday. We walked from the cottage to the town each day which truly proves I am still in shape (lol). We enjoyed our walks, the cleanliness and comfort of the cottage, and the food."
The Carriage House at Carrot Top Cottage

Carrot Top Cottage surrounded by National Park

10.0 out of 10, Exceptional, (26)
"We thoroughly enjoyed our stay here. The home was full of amenities and super clean. We were able to park our car at the cottage and walk to the Appalachian Trail, and on down to the town. We would definitely stay here again."
Carrot Top Cottage surrounded by National Park

Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers

10.0 out of 10, Exceptional, (5)
"This is our 5th stay at this beautiful cottage. We have recommended it to friends as well. The hosts have done everything to insure that your stay will be a wonderful experience. The cottage is immaculate and has everything you need to have a relaxing stay. I highly recommend it! "
The price is SAR 665
SAR 1,604 total
includes taxes & fees
1 Dec - 2 Dec
Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers

Peaceful Lakefront Cottage with Mountain Views!

10.0 out of 10, Exceptional, (22)
"Although short, we had a wonderful stay. Beautiful house with amazing views. Great communication with property host. Cant wait to come back! Thank you for hosting us last minute! "
Peaceful Lakefront Cottage with Mountain Views!

Lake View Retreat - Cottage Near a Peaceful Lake!

9.4 out of 10, Exceptional, (16)
"Beautiful location to relax and enjoy friends. This house was huge. Plenty of room for the 3 of us...could have been 8, lol. "
The price is SAR 886
SAR 2,049 total
includes taxes & fees
26 Dec - 27 Dec
Lake View Retreat - Cottage Near a Peaceful Lake!

Lovettsville Cottage in Heart of Wine Country

10.0 out of 10, Exceptional, (29)
"Family reunion to get 3 sisters together. My Mother-in-Law is 90 and we drove to VA so she can visit with her 88 and 80 year old sisters. We did have an issue wtih the 2 statements below provided in an email on 9Sept2024, which is after the window for cancelation. The homeowner isn't just next door, they are adjoining, which isn't clear in the description. It is also not shown in the pictures. We expected quiet time for morning coffee outdoors, instead we were able to hear the homeowner on...
Lovettsville Cottage in Heart of Wine Country

Quiet tiny home. Dog-friendly. Private fenced yard

9.6 out of 10, Exceptional, (4)
"Such a cute little house! We enjoyed our stay so much we will book again in the future!"
The price is SAR 319
SAR 622 total
includes taxes & fees
26 Dec - 27 Dec
Quiet tiny home. Dog-friendly. Private fenced yard

Spacious Mtn Pet Friendly Home, Hottub, Firepit

Spacious Mtn Pet Friendly Home, Hottub, Firepit

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.4 out of 10, Exceptional, (113)
"Went to Harper’s Ferry for our 25th wedding anniversary and wanted to stay near the water since we usually stay in town. Found this property and it was perfect. Sits on property with owners who we met and their dog Chloe who was an absolute sweetheart. If you are looking for a piece of serenity you will find it at the Riverkeeper Inn. Very nice and quiet neighborhood. The property was tidy and clean and you get to use the gazebo or decks near the water to chill and if it wasn’t too chilly would...
RIVERKEEPER INN, Waterfront Property on the Potomac River

Art Docko - Lakefront Artist Retreat w/ Hot Tub!

10.0 out of 10, Exceptional, (16)
"Check in was seamless. The place was perfect for three couples with all the master suites. "
Art Docko - Lakefront Artist Retreat w/ Hot Tub!

Lock Keepers Cottage on C&O Canal/Potomac River

10.0 out of 10, Exceptional, (48)
"We had a great time. Very comfortable like home. "
Lock Keepers Cottage on C&O Canal/Potomac River

Entire Mountain Cottage Near Scenic Hiking Trails, Your Getaway Retreat!

10.0 out of 10, Exceptional, (2)
"This is a tremendous house. Clean, tons of towels, wash cloths, utensils.. Everything you could need to make it great is there. Just a tremendous job. The owner is fast and helpful with responses. Massive thanks! The inside open space is great!! We had all our group inside for meetings, and it worked awesome! The only things you need to be aware of: 1. You can not use the outside in it's current condition. There is broken glass and trash outside. (Looks like when they renovated...
Entire Mountain Cottage Near Scenic Hiking Trails, Your Getaway Retreat!

Cottage at Gray Fox- Many Attraction- Pet Friendly

10.0 out of 10, Exceptional, (20)
"Our family of four enjoyed the weekend away"
Cottage at Gray Fox- Many Attraction- Pet Friendly

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

10.0 out of 10, Exceptional, (29)
"We had a wonderful stay and particularly enjoyed the location and sunny back deck! Ed was a kind and responsive host!"
The price is SAR 529
SAR 1,090 total
includes taxes & fees
2 Dec - 3 Dec
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Cottage w/ Hot Tub and 100-Mile Valley Views!

10.0 out of 10, Exceptional, (14)
"The view of this house is amazing! Absolutely beautiful!"
Cottage w/ Hot Tub and 100-Mile Valley Views!

Historic Schoolhouse on Winery Row

10.0 out of 10, Exceptional, (12)
"This VRBO home could not have been any better! It was clean, cozy, comfortable, and well stocked with everything you can possibly need. The owner, Lynn, answered all of our questions and responded to our text messages quickly. She could not have been more helpful. Location is ideal close to wineries and great restaurants. we enjoyed the grill on the back deck as well as the relaxing creek and chairs around the fire pit We enjoyed our stay here so much. We are looking forward to going back...
Historic Schoolhouse on Winery Row

Charming Home With Yard Near Shenandoah River!

3.0 star property
10.0 out of 10, Exceptional, (3)
"Cozy house nestled in the mountains of West Virginia. Well-maintained, clean, great yard for pets and/or kids! Lovely grilling and fire pit area. We throughly enjoyed our stay!"
Charming Home With Yard Near Shenandoah River!

The Getaway Cottage at Rocky Marsh Farm

10.0 out of 10, Exceptional, (20)
"This was our third time staying at this property. It is perfect for spending a down day of reading, cooking or sitting around the fire pit. It is also a great home base for nearby activities such as hiking, shopping, or getting a massage. Close to so much history. Our favorite place to get away!!!!"
The Getaway Cottage at Rocky Marsh Farm

Woodsy Retreat with a Hot Tub and Seasonal Views!

9.8 out of 10, Exceptional, (17)
"We love it! everything was perfect 🤗 we definitely coming back ❤️"
Woodsy Retreat with a Hot Tub and Seasonal Views!

Magical Treehouse in Woods, Close many Wineries & Breweries, Pet Friendly!

Magical Treehouse in Woods, Close many Wineries & Breweries, Pet Friendly!
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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Other property types in Shepherdstown

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (47)
"Excellent little cabin right on the river and close to DT Sheperdstown which is a great town."
The price is SAR 165
SAR 412 total
includes taxes & fees
3 Dec - 4 Dec
❤️ Secluded 1940s Romantic Tiny House on the River

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

9.8 out of 10, Exceptional, (60)
"Loved everything. Quiet, peaceful….loved the small deck off the upstairs bedroom."
Welcome to this patch of serenity on the river's edge, to this hideaway.

Plum Lazy on the Potomac

9.2 out of 10, Wonderful, (23)
"Quiet and relaxing. Had hoped to get the kayaks out but one girl was just post surgery on her wrist so we had to bypass them this trip. Our favorite part of the weekend was sitting on the porch and looking at the Potomac. So relaxing. The house was cute and clean, just like the pictures. Shopped in Shepersdstown and ate at the Blur Moon. It was fun!! Could not find parking in Harper’s Ferry. We were bummed about that but it didn’t ruin our weekend. We will be back to kayak and swim. "
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.

Frequently asked questions

How much do cottages in Shepherdstown cost?
Cottages in Shepherdstown range between SAR 319 and SAR 886 per night. These properties offer a chance to reconnect with nature — at a price you can afford. These prices were 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?
There are 59 cottages in Shepherdstown. No matter if you’re traveling with the kids or planning a weekend retreat with friends, Expedia will help you find the ideal property to escape the hustle and bustle.
Why book your cottage in Shepherdstown with Expedia?
We think that vacations should be simple, so if you’re looking for cottages in Shepherdstown at an affordable rate, Expedia has you covered. Keep the budget in check and choose a cheap option far from the hustle and bustle, or splurge on an upscale cottage to spoil the ones you love most.
How can I find cheap cottages in Shepherdstown?
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