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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
8.8 out of 10, Excellent, (72 reviews)
"A beautiful renovated historical house with charm, clean rooms, decorative furnishings and a wonderful hot breakfast. What we enjoyed the most was the warm hospitality of Willard, Valerie, and the other staff. Very close to downtown St. Michael’s, but just far enough away to give a nice feel of natural serenity. Great for a quick getaway from the city. We will be back. "
United States
Charles
$155 nightly
The price is $171
Apr 16 - Apr 17
Total with taxes and fees
George Brooks House B&B

Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (133 reviews)
"Hosts were wonderful, breakfast was delicious, everything was walkable "
United States
Nathaly
$169 nightly
The price is $186
Apr 16 - Apr 17
Total with taxes and fees
Parsonage Inn

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (94 reviews)
"The room was over the garage. You couldn’t stand up in half the room as the ceiling was too low. Multiple tripping areas walking into and out of the space. No heat in bathroom. You have to walk to the front of house to enter for coffee in the morning. They have the nerve to charge you to park at the house. "
United States
Richard
$182 nightly
The price is $207
Apr 20 - Apr 21
Total with taxes and fees
Flag House Inn

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.4 out of 10, Exceptional, (13 reviews)
"Wonderful experience Felt like being in good friends home without having to help with the dishes Luxurious stay Recommend *****"
United States
Todd
$286 nightly
The price is $326
Apr 16 - Apr 17
Total with taxes and fees
The Inn at Tacaro Estate

The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (41 reviews)
"Staff, breakfast, and room were all superb!"
United States
Jeffrey
$489 nightly
The price is $538
Apr 16 - Apr 17
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
$577 nightly
The price is $652
Apr 16 - Apr 17
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
8.0 out of 10, Very Good, (2 reviews)
"Easy to find, easy to get in, spacious "
United States
Anonymous traveler
$936 nightly
The price is $1,058
Apr 17 - Apr 18
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
355
Accommodation
16 B&B
Lowest Price
$171
Highest Price
$1,058

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 $171 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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