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

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Check prices for these dates

Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27
In one month
Oct 9 - Oct 11
In two months
Nov 6 - Nov 8

Our top choices for Shepherdstown bed & breakfast

A large house with a prominent tower, surrounded by lush greenery and a vast landscape.

1. Antietam Overlook Farm

Antietam Overlook Farm
3.5 star property
Keedysville
9.8 out of 10, Exceptional, (237 reviews)
"The view was amazing."
United States
Carol
$214 nightly
The price is $238
Sep 10 - Sep 11
Total with taxes and fees
Antietam Overlook Farm
A staircase with a stone wall, wooden steps, and a red carpet leading to a room with a wooden table and chairs.

2. Light Horse Inn

Light Horse Inn
2.0 star property
Harpers Ferry
9.4 out of 10, Exceptional, (142 reviews)
"This is a very nice and relaxing inn with very helpful staff"
United States
David
$165 nightly
The price is $177
Oct 6 - Oct 7
Total with taxes and fees
Light Horse Inn
A two-story house with a porch and a staircase leading to the front door.

3. Hollerstown Hill Bed and Breakfast

Hollerstown Hill Bed and Breakfast
3.5 star property
Frederick
9.6 out of 10, Exceptional, (104 reviews)
"VERY welcoming hosts! Great location - walking distance to shops and river area. "
United States
Meredith
$224 nightly
The price is $237
Sep 21 - Sep 22
Total with taxes and fees
Hollerstown Hill Bed and Breakfast
A brick house with a front porch, a small garden, and a set of steps leading to the entrance.

4. Dandelion in the Heart of Boonsboro

Dandelion in the Heart of Boonsboro
Boonsboro
10.0 out of 10, Exceptional, (1 review)
"This is a charming vintage house with modern amenities. I had the best night's sleep in a cozy comfortable bedroom with the softest blanket. The host offered every variety of product in the bathroom that a guest might need or enjoy - very thoughtful touch. "
United States
Susan H.
$133 nightly
The price is $141
Sep 16 - Sep 17
Total with taxes and fees
Dandelion in the Heart of Boonsboro
A sign for Antuta Inn B&B and Art Gallery with a stone wall and purple flowers in the background.

5. Cantuta Inn

Cantuta Inn
3.0 star property
Harpers Ferry
9.0 out of 10, Wonderful, (78 reviews)
"Clean, great location, courteous staff. Could not ask for better."
United States
Anthony
$176 nightly
The price is $197
Sep 13 - Sep 14
Total with taxes and fees
Cantuta Inn
A spacious living room with a wooden floor, a large sofa, a coffee table, and a dining area with a wooden table and chairs.

6. Loudoun Valley Manor

Loudoun Valley Manor
3.0 star property
Waterford
9.6 out of 10, Exceptional, (328 reviews)
"This facility was excellent in every area. Thanks for great custom breakfast omlets."
United States
Michael
$150 nightly
The price is $171
Sep 10 - Sep 11
Total with taxes and fees
Loudoun Valley Manor
A two-story house with a front porch, American flags, and a mailbox.

7. The Carriage Inn B&B

The Carriage Inn B&B
3.5 star property
Charles Town
9.6 out of 10, Exceptional, (454 reviews)
"The location of the property was very good for our purpose. Close to the Casino, downtown Charles Town, and Harper Ferry."
United States
Edward
$155 nightly
The price is $176
Sep 15 - Sep 16
Total with taxes and fees
The Carriage Inn B&B
A building with a staircase leading to a gated entrance, surrounded by a grassy area.

8. Cozy Lakefront 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included

Cozy Lakefront 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included
Purcellville
10.0 out of 10, Exceptional, (2 reviews)
"We only spent one night here because my wife had training in the town of Purcellville. However, we were treated like family. Kenny, the general manager, was very kind, welcoming and attentive. He personally prepared our breakfast. Noé, the caretaker was wonderful and always available to us. Beyond that, this is one of the most beautiful, scenic properties I have ever experienced. You have to see it for yourself. Highly recommended!"
United States
Andrew
$316 nightly
The price is $360
Sep 16 - Sep 17
Total with taxes and fees
Cozy Lakefront 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included
A large two-story house with a stone exterior, a covered porch, and a well-maintained garden.

9. Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event

Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
Lovettsville
10.0 out of 10, Exceptional, (1 review)
"Everyone was so kind, house was beautiful and the food was amazing. Really made us feel like home. Highly recommend."
United States
Lukas D.
$12,952 nightly
The price is $15,340
Sep 14 - Sep 15
Total with taxes and fees
Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
A grand staircase with a chandelier, leading to an open doorway with a view of a garden.

10. The Inn at Grass Roots Hill

The Inn at Grass Roots Hill
3.0 star property
Purcellville
9.2 out of 10, Wonderful, (10 reviews)
"Beautiful venue, great service, and very close to the local downtown. Would stay again, highly recommend. "
United States
Robert
$636 nightly
The price is $724
Sep 26 - Sep 27
Total with taxes and fees
The Inn at Grass Roots Hill
A building with a staircase leading to a gated entrance, surrounded by a grassy area.

11. Lakefront Gateway 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included

Lakefront Gateway 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included
Purcellville
$356 nightly
The price is $406
Sep 16 - Sep 17
Total with taxes and fees
Lakefront Gateway 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included
A building with a staircase leading to a gated entrance, surrounded by a grassy area.

12. Peaceful Lakefront 1BR 1 Full Bath w/ Private Island Access & Breakfast Included

Peaceful Lakefront 1BR 1 Full Bath w/ Private Island Access & Breakfast Included
Purcellville
$395 nightly
The price is $450
Sep 15 - Sep 16
Total with taxes and fees
Peaceful Lakefront 1BR 1 Full Bath w/ Private Island Access & Breakfast Included
A building with a staircase leading to a gated entrance, surrounded by a grassy area.

13. Lakefront Retreat 1 BR 1 Full Bath w/Private Island Access + Breakfast Included

Lakefront Retreat 1 BR 1 Full Bath w/Private Island Access + Breakfast Included
Purcellville
$434 nightly
The price is $495
Sep 16 - Sep 17
Total with taxes and fees
Lakefront Retreat 1 BR 1 Full Bath w/Private Island Access + Breakfast Included
A building with a staircase leading to a gated entrance, surrounded by a grassy area.

14. Lakefront B&B Room w/Private Island Access + Breakfast Included

Lakefront B&B Room w/Private Island Access + Breakfast Included
Purcellville
$450 nightly
The price is $513
Sep 14 - Sep 15
Total with taxes and fees
Lakefront B&B Room w/Private Island Access + Breakfast Included
A building with a staircase leading to a gated entrance, surrounded by a grassy area.

15. 5BR Lakefront Estate w/Private Island Access / Entire House + Breakfast Included

5BR Lakefront Estate w/Private Island Access / Entire House + Breakfast Included
Purcellville
$2,507 nightly
The price is $2,858
Sep 16 - Sep 17
Total with taxes and fees
5BR Lakefront Estate w/Private Island Access / Entire House + Breakfast Included
A traditional Tudor-style house with a pond in the foreground, surrounded by well-maintained gardens and trees.

16. Hillbrook Inn

Hillbrook Inn
4.0 star property
Charles Town
8.6 out of 10, Excellent, (691 reviews)
"It was beautiful location. The staff was amazing and the food was excellent highly recommend."
United States
Cecile
$161 nightly
The price is $177
Oct 8 - Oct 9
Total with taxes and fees
Hillbrook Inn
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

Fairfield Inn & Suites by Marriott Hagerstown

Fairfield Inn & Suites by Marriott Hagerstown

10/10 Excellent
"Very nice hotel"
David 4-night trip
Posted 8 hours ago
Fairfield Inn & Suites by Marriott Hagerstown

Find out more about Shepherdstown

Shepherdstown B&B information

Number of reviews
1,137
Accommodation
34 B&B
Lowest Price
$141
Highest Price
$15,340

Frequently asked questions

What is the nightly rate for a Bed & Breakfast in Shepherdstown?
Prices for B&Bs in Shepherdstown often vary, but you can find a great deal from $141 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Shepherdstown B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed and Breakfast in Shepherdstown?
The best time to book a B&B in Shepherdstown is during the vibrant spring months of April and May. This period marks the peak season, as travelers flock to the area to enjoy the blooming gardens and numerous outdoor festivals. With mild temperatures ranging from the mid-50s to low 70s Fahrenheit, it's an ideal time for leisurely strolls along the historic streets or scenic hikes in the nearby Appalachian Trail.

April brings with it a delightful atmosphere, as the town hosts various events like the annual Shepherdstown Music and Dance Festival, creating a lively backdrop for visitors. The combination of pleasant weather and local festivities makes this an appealing choice for those who appreciate a blend of culture and nature.

For those seeking a more budget-friendly experience, consider planning your visit in December. While the weather can be cooler, with temperatures dipping into the low 30s, the charm of Shepherdstown during the holiday season is truly enchanting. Enjoy festive decorations, cozy shops, and the warmth of local hospitality without the crowds.
What is the difference between a Shepherdstown Bed & Breakfast and a hotel?
Every Shepherdstown B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Shepherdstown B&Bs.

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