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

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Check prices for these dates

Next weekend
Sep 25 - Sep 27
In two weeks
Oct 2 - Oct 4
In one month
Oct 16 - Oct 18
In two months
Nov 13 - Nov 15

Our top choices for Shepherdstown bed & breakfast

Exterior

1. Antietam Overlook Farm

Antietam Overlook Farm
3.5 star property
Keedysville
9.8 out of 10, Exceptional, (239 reviews)
"Everything about the Overlook far exceeded my expectations. The ambiance and the staff (Tina and Phoebe) were awesome! I will definitely be back!"
United States
Bryan
$214 nightly
The price is $238
Sep 17 - Sep 18
Total with taxes and fees
Antietam Overlook Farm
Reception

2. Light Horse Inn

Light Horse Inn
2.0 star property
Harpers Ferry
9.4 out of 10, Exceptional, (144 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
Front of property

3. The Carriage Inn B&B

The Carriage Inn B&B
3.5 star property
Charles Town
9.6 out of 10, Exceptional, (455 reviews)
"Amazing place with incredible history!"
United States
Andrea
$155 nightly
The price is $176
Oct 1 - Oct 2
Total with taxes and fees
The Carriage Inn B&B
Exterior detail

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 23 - Sep 24
Total with taxes and fees
Dandelion in the Heart of Boonsboro
Reception

5. Loudoun Valley Manor

Loudoun Valley Manor
3.0 star property
Waterford
9.6 out of 10, Exceptional, (331 reviews)
"This facility was excellent in every area. Thanks for great custom breakfast omlets."
United States
Michael
$150 nightly
The price is $171
Sep 17 - Sep 18
Total with taxes and fees
Loudoun Valley Manor
Front of property

6. 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
$229 nightly
The price is $243
Sep 17 - Sep 18
Total with taxes and fees
Hollerstown Hill Bed and Breakfast
Exterior

7. 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
$318 nightly
The price is $363
Sep 22 - Sep 23
Total with taxes and fees
Cozy Lakefront 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included
Exterior

8. 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.
$12,974 nightly
The price is $15,365
Sep 20 - Sep 21
Total with taxes and fees
Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
Interior entrance

9. 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
$648 nightly
The price is $739
Sep 20 - Sep 21
Total with taxes and fees
The Inn at Grass Roots Hill
Exterior

10. 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
$358 nightly
The price is $408
Sep 22 - Sep 23
Total with taxes and fees
Lakefront Gateway 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included
Exterior

11. 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
$398 nightly
The price is $454
Sep 22 - Sep 23
Total with taxes and fees
Peaceful Lakefront 1BR 1 Full Bath w/ Private Island Access & Breakfast Included
Exterior

12. 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
$437 nightly
The price is $498
Sep 22 - Sep 23
Total with taxes and fees
Lakefront Retreat 1 BR 1 Full Bath w/Private Island Access + Breakfast Included
Front of property

13. 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
$159 nightly
The price is $175
Oct 1 - Oct 2
Total with taxes and fees
Hillbrook Inn
Exterior

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

Lakefront B&B Room w/Private Island Access + Breakfast Included
Purcellville
$468 nightly
The price is $534
Sep 21 - Sep 22
Total with taxes and fees
Lakefront B&B Room w/Private Island Access + Breakfast Included
Exterior

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 23 - Sep 24
Total with taxes and fees
5BR Lakefront Estate w/Private Island Access / Entire House + Breakfast Included
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
"Location is great for my travels. Room clean and comfortable, staff accommodating."
Mary 1-night trip
Posted 18 hours ago
Country Inn & Suites by Radisson, Frederick, MD

Find out more about Shepherdstown

Shepherdstown B&B information

Number of reviews
593
Accommodation
34 B&B
Lowest Price
$141
Highest Price
$15,365

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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