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B&B in Shady Side

Exterior
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
$200 nightly
The price is $220
Nov 27 - Nov 28
Total with taxes and fees
George Brooks House B&B
Fridge, microwave, oven, stovetop
Modern 1BR Near DC – Quiet Comfort, Fast Commute

Modern 1BR Near DC – Quiet Comfort, Fast Commute

District Heights
10.0 out of 10, Exceptional, (4)
"I thoroughly enjoyed my stay. Poo"
United States
Dawn C.
$155 nightly
The price is $175
Nov 28 - Nov 29
Total with taxes and fees
Modern 1BR Near DC – Quiet Comfort, Fast Commute
Porch
Parsonage Inn

Parsonage Inn

3.5 star property
St. Michaels
9.2 out of 10, Wonderful, (130)
"Hosts were wonderful, breakfast was delicious, everything was walkable "
United States
Nathaly
$229 nightly
The price is $252
Nov 27 - Nov 28
Total with taxes and fees
Parsonage Inn
Front of property
Flag House Inn

Flag House Inn

3.5 star property
Historic District
9.4 out of 10, Exceptional, (81)
"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
$191 nightly
The price is $217
Nov 30 - Dec 1
Total with taxes and fees
Flag House Inn
Front of property
The Oaks Waterfront

The Oaks Waterfront

4.0 star property
Easton
10.0 out of 10, Exceptional, (40)
"This was one of the nicest hotels I've stayed at. The property was absolutely beautiful. The public and guest rooms were immaculate and nicely decorated. All staff went out of their way to be helpful and make you feel welcome. We had breakfast and dinner in the restaurant and the food was phenomenal, and the beautiful view of the water was a bonus."
United States
Deborah
$459 nightly
The price is $505
Nov 30 - Dec 1
Total with taxes and fees
The Oaks Waterfront
Horseback riding
The Inn at Tacaro Estate

The Inn at Tacaro Estate

5.0 star property
Tracys Landing
9.2 out of 10, Wonderful, (10)
"Amazing, warm, gracious setting. Can’t wait to return "
United States
Andrea
$280 nightly
The price is $320
Dec 1 - Dec 2
Total with taxes and fees
The Inn at Tacaro Estate
Full-size fridge, blender, toaster oven, waffle maker
Legacy Villa

Legacy Villa

4.0 star property
Upper Marlboro
$283 nightly
The price is $320
Dec 1 - Dec 2
Total with taxes and fees
Legacy Villa
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

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"I have stayed several times over the last month or so totaling at leadt 7 nights and during every stay i have had a great experiene. Particularly with Chrissy who ive seen maonly during the night shift. Cannot understate how helpful and pleasant she has been. Probably the reason i wont stay anywhere else(if theres availability) in and around the Annapolis area. Keep up the amazing customer service!! 5 STARS "
Michael 2-night trip
Posted 1 day ago
Country Inn & Suites by Radisson, Annapolis, MD

Find out more about Shady Side

Shady Side B&B information

Number of reviews
330
Accommodation
10 B&B
Lowest Price
$175
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 $175 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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