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Compare 61 Cottages in Shepherdstown with updated reviews, rates, and availability.

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Private kitchen

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

10.0 out of 10, Exceptional, (30)
"This is a beautiful, tasteful, updated home. I was surprised at how comfortable the beds were! It's in a great location, and we appreciated the prompt and thoughtful host communication. It's very reasonably priced for all that you get with this stay! Parking was tricky for us as we rented on the night of street sweeping and had to park several blocks away. Other than that, this is an excellent place to stay. "
The price is SAR 529
SAR 1,083 total
includes taxes & fees
7 Jan - 8 January 2025
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Quiet tiny home. Dog-friendly. Private fenced yard
Terrace/patio

Quiet tiny home. Dog-friendly. Private fenced yard

9.6 out of 10, Exceptional, (5)
"I stayed for a few nights over Thanksgiving and this was the perfect place for my dog and I! She loved the backyard and it was walking distance to Jefferson Rock and other trails snd things to see in Harpers Ferry. It was clean and in a very safe and quiet neighborhood. Would definitely come back!"
Quiet tiny home. Dog-friendly. Private fenced yard
Lovettsville Cottage in Heart of Wine Country
Lovettville Vacation Rental | 1BR | 2BA | 2 Stories | 3 Steps Required

Lovettsville Cottage in Heart of Wine Country

9.8 out of 10, Exceptional, (31)
"We stayed here for a few days over the Thanksgiving holiday. It was cozy, comfortable, and had all the great comforts of a home away from home. "
Lovettsville Cottage in Heart of Wine Country
Carrot Top Cottage surrounded by National Park
Exterior

Carrot Top Cottage surrounded by National Park

10.0 out of 10, Exceptional, (30)
"Wonderful "
Carrot Top Cottage surrounded by National Park
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Terrace/patio

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

The price is SAR 939
SAR 1,593 total
includes taxes & fees
5 Jan - 6 January 2025
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Exterior

Amazing dog-friendly cottage. Walk 2 Harpers Ferry

2.0 star property
9.8 out of 10, Exceptional, (8)
"Place was clean ..had all the necessary bath and kitchen items. Very convenient to historic part of Harpers Ferry.. Large fenced backyard for our dog… Would give it 5 stars but winding , circular metal stairway was very tight.Fortunately both of us are slim so was manageable. Plan on staying here again if visiting Harper’s Ferry/Charles Town area.."
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Close to Hiking | Hot Tub | Fire Pit | Pets OK
Our deck is great for relaxing and enjoying the outdoors

Close to Hiking | Hot Tub | Fire Pit | Pets OK

Close to Hiking | Hot Tub | Fire Pit | Pets OK
RIVERKEEPER INN, Waterfront Property on the Potomac River
Private Waterfront Deck with swing goes with rental

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.2 out of 10, Wonderful, (115)
"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!
Property grounds

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
come sit a spell

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
Peaceful Lakefront Cottage with Mountain Views!
Enjoy a soak in the hot tub!

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! "
The price is SAR 928
SAR 2,150 total
includes taxes & fees
26 Jan - 27 January 2025
Peaceful Lakefront Cottage with Mountain Views!
Lake View Retreat - Cottage Near a Peaceful Lake!
This home is just a short walk to Lake Shannondale, and has wintertime views of the lake! Spend your mornings on the front porch, or take a leisurely stroll around the lake.

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 402
SAR 1,353 total
includes taxes & fees
20 Jan - 21 January 2025
Lake View Retreat - Cottage Near a Peaceful Lake!
Entire Mountain Cottage Near Scenic Hiking Trails, Your Getaway Retreat!
Exterior

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

10.0 out of 10, Exceptional, (3)
"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
Private kitchen

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
The Carriage House at Carrot Top Cottage
Terrace/patio

The Carriage House at Carrot Top Cottage

9.8 out of 10, Exceptional, (29)
"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
Cottage w/ Hot Tub and 100-Mile Valley Views!
Outdoor spa tub

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!"
The price is SAR 950
SAR 2,201 total
includes taxes & fees
2 Jan - 3 January 2025
Cottage w/ Hot Tub and 100-Mile Valley Views!
Historic Schoolhouse on Winery Row
Quaint, historic village schoolhouse built 1885.

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!
Exterior

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
Exterior

The Getaway Cottage at Rocky Marsh Farm

10.0 out of 10, Exceptional, (21)
"Modern accommodations with easy access to nearby sights, shopping, restaurants, breweries, etc…disappointed we could not enjoy the outdoor fire pit due to burn ban but maybe next time!"
The Getaway Cottage at Rocky Marsh Farm
Woodsy Retreat with a Hot Tub and Seasonal Views!
Living area

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!
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
Exterior

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (49)
"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
6 Jan - 7 January 2025
❤️ Secluded 1940s Romantic Tiny House on the River
Welcome to this patch of serenity on the river's edge, to this hideaway.
Complete relaxation as you watch the powerful Potomac roll past the window.

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
Property grounds

Plum Lazy on the Potomac

9.2 out of 10, Wonderful, (24)
"Everything was as advertised! We really enjoyed our stay and can't wait to return!"
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 402 and SAR 950 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 61 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?
Expedia is here to help you easily source cheap cottages in Shepherdstown. To lock in your ideal stay in a few quick keystrokes, try out the filter tool to refine your search results by budget, star rating and amenities.