A river with boats, a marina, and a town with houses and buildings.

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Our top choices for Shady Side bed & breakfast

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.6 out of 10, Exceptional, (18 reviews)
"An amazing breakfast. The home is decorated beautifully"
United States
James
$378 nightly
The price is $431
Jul 30 - Jul 31
Total with taxes and fees
The Inn at Tacaro Estate

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (95 reviews)
"Great spot with easy walking downtown or to the Academy. Very nice sitting rooms downstairs with fresh pastries for breakfast. "
United States
Tyler
$227 nightly
The price is $259
Aug 2 - Aug 3
Total with taxes and fees
Flag House Inn

George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (76 reviews)
"This weekend was an anniversary gift for my daughter and her husband. They had a wonderful time and were highly complimentary of the accommodations, the delicious breakfast and the location."
United States
Erin
$235 nightly
The price is $259
Jul 30 - Jul 31
Total with taxes and fees
George Brooks House B&B

The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (42 reviews)
"Staff, breakfast, and room were all superb!"
United States
Jeffrey
$440 nightly
The price is $484
Aug 4 - Aug 5
Total with taxes and fees
The Oaks Waterfront

Spacious 5BR Retreat Near DC with Private Gym - Perfect for Group Getaway

Spacious 5BR Retreat Near DC with Private Gym - Perfect for Group Getaway
Glenn Dale
9.4 out of 10, Exceptional, (3 reviews)
"Beautiful big house. Two of the light fixtures didn't work but it didn't really affect our experience."
United States
Natalia L.
$740 nightly
The price is $837
Jul 30 - Jul 31
Total with taxes and fees
Spacious 5BR Retreat Near DC with Private Gym - Perfect for Group Getaway

Spacious Luxury 8BR Family Retreat Near DC - Perfect for Groups & Families

Spacious Luxury 8BR Family Retreat Near DC - Perfect for Groups & Families
Glenn Dale
5.6 out of 10, (5 reviews)
"Easy to find, easy to get in, spacious "
United States
Anonymous traveler
$914 nightly
The price is $1,033
Jul 30 - Jul 31
Total with taxes and fees
Spacious Luxury 8BR Family Retreat Near DC - Perfect for Groups & Families
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 Shady Side Hotel Reviews

Find out more about Shady Side

Shady Side B&B information

Number of reviews
76
Accommodation
18 B&B
Lowest Price
$259
Highest Price
$484

Frequently asked questions

What is the nightly rate for a B&B in Shady Side?
Prices for B&Bs in Shady Side often vary, but you can find a great deal from $259 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Shady Side 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 B&B in Shady Side?
The best time to book a B&B in Shady Side is during the vibrant spring months from April to June. This period welcomes travelers who appreciate lush landscapes and moderate weather, making it ideal for outdoor activities such as hiking, kayaking, and exploring the scenic waterfront. The spring blooms create a picturesque backdrop, enhancing the overall experience of this charming area.

April typically sees mild temperatures ranging from the mid-50s to low 70s Fahrenheit, which is superb for leisurely strolls along the shoreline or visiting local parks. As the season progresses into May and June, the warmth invites a lively atmosphere, with various festivals and events that showcase the local culture and community spirit.

For those looking for a more budget-friendly option, consider visiting in December. While the weather is cooler, with temperatures averaging in the low 30s to mid-40s Fahrenheit, the holiday season brings a unique charm to Shady Side. You can enjoy festive decorations, cozy gatherings, and a peaceful ambiance that allows for reflective exploration of the area.
What is the difference between a Shady Side Bed and Breakfast and a hotel?
Every Shady Side 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 Shady Side B&Bs.

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