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Our top choices for Shady Side bed & breakfast

George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.6 out of 10, Excellent, (65)
"Gorgeous quaint historic house. Friendly owner, close to town "
United States
Christopher
$153 nightly
The price is $168
Jan 1 - Jan 2, 2026
Total with taxes and fees
George Brooks House B&B

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.4 out of 10, Exceptional, (84)
"The Inn is beautiful and the staff very welcoming. My room was spotless, cozy, and tastefully decorated. The location is directly across the street from the USNA. I skipped breakfast, but the offerings looked lovely. Will definitely stay here again. "
United States
Elizabeth
$183 nightly
The price is $208
Dec 23 - Dec 24
Total with taxes and fees
Flag House Inn

The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (41)
" Beautiful property, wonderful staff, excellent food service."
United States
Seth
$459 nightly
The price is $505
Dec 22 - Dec 23
Total with taxes and fees
The Oaks Waterfront

Modern 1BR Near DC – Quiet Comfort, Fast Commute

Modern 1BR Near DC – Quiet Comfort, Fast Commute
District Heights
9.6 out of 10, Exceptional, (5)
"I thoroughly enjoyed my stay. Poo"
United States
Dawn C.
$156 nightly
The price is $176
Dec 22 - Dec 23
Total with taxes and fees
Modern 1BR Near DC – Quiet Comfort, Fast Commute

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.4 out of 10, Exceptional, (11)
"Wonderful experience Felt like being in good friends home without having to help with the dishes Luxurious stay Recommend *****"
United States
Todd
$180 nightly
The price is $206
Dec 22 - Dec 23
Total with taxes and fees
The Inn at Tacaro Estate

Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (130)
"Hosts were wonderful, breakfast was delicious, everything was walkable "
United States
Nathaly
$200 nightly
The price is $220
Jan 1 - Jan 2, 2026
Total with taxes and fees
Parsonage 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 Shady Side Hotel Reviews

Find out more about Shady Side

Shady Side B&B information

Number of reviews
334
Accommodation
16 B&B
Lowest Price
$168
Highest Price
$505

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 $168 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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