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Oct 10 - Oct 12
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Oct 17 - Oct 19
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Oct 31 - Nov 2
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Nov 28 - Nov 30

B&B in Shady Side

The Oaks Waterfront
Front of property

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (38)
"Loved the Oaks! Fabulous accommodations and excellent staff"
$459 nightly
The price is $505
Oct 2 - Oct 3
Total with taxes and fees
The Oaks Waterfront
Laurel Grove Inn on the South
Outdoor dining

Laurel Grove Inn on the South

3.5 star property
9.0 out of 10, Wonderful, (527)
"Great location with fantastic views. Very friendly owner "
$200 nightly
The price is $228
Oct 6 - Oct 7
Total with taxes and fees
Laurel Grove Inn on the South
George Brooks House B&B
Exterior

George Brooks House B&B

3.0 star property
8.6 out of 10, Excellent, (64)
"Gorgeous quaint historic house. Friendly owner, close to town "
$207 nightly
The price is $228
Oct 1 - Oct 2
Total with taxes and fees
George Brooks House B&B
Flag House Inn
Front of property

Flag House Inn

3.5 star property
9.4 out of 10, Exceptional, (78)
"Lovely B&B close to EVERYTHING! The host were so kind and helpful. The common areas were very nice as well as the front porch!"
$239 nightly
The price is $273
Oct 1 - Oct 2
Total with taxes and fees
Flag House Inn
Parsonage Inn
Porch

Parsonage Inn

3.5 star property
9.2 out of 10, Wonderful, (130)
"Beautiful Victorian Cottage Home. Outstanding service and breakfast. Wonderful hosts made us feel right @ home!"
$229 nightly
The price is $252
Oct 1 - Oct 2
Total with taxes and fees
Parsonage Inn
The Inn at Tacaro Estate
Horseback riding

The Inn at Tacaro Estate

5.0 star property
9.2 out of 10, Wonderful, (9)
"It was perfect!! We had a great stay. Luca was so kind and attentive. The property is astonishing. Perfect weekend retreat! Thank you so much "
$425 nightly
The price is $485
Oct 12 - Oct 13
Total with taxes and fees
The Inn at Tacaro Estate
Inn at Horn Point
Beach nearby

Inn at Horn Point

3.0 star property
9.6 out of 10, Exceptional, (21)
"Family owned with care and pride. Excellent food and recommendations for other restaurants and activities. "
$344 nightly
The price is $392
Oct 1 - Oct 2
Total with taxes and fees
Inn at Horn Point
Legacy Villa
Full-size fridge, blender, toaster oven, waffle maker

Legacy Villa

4.0 star property
$168 nightly
The price is $190
Oct 13 - Oct 14
Total with taxes and fees
Legacy Villa
Black Walnut Point Inn
Outdoor pool

Black Walnut Point Inn

3.5 star property
9.0 out of 10, Wonderful, (56)
"Wife and I stayed 3 days for 41st anniversary. Bob and Tracy are wonderful hosts. "
Black Walnut Point Inn
Modern 1BR Near DC – Quiet Comfort, Fast Commute
Fridge, microwave, oven, stovetop

Modern 1BR Near DC – Quiet Comfort, Fast Commute

10.0 out of 10, Exceptional, (4)
"I thoroughly enjoyed my stay. Poo"
$155 nightly
The price is $175
Oct 7 - Oct 8
Total with taxes and fees
Modern 1BR Near DC – Quiet Comfort, Fast Commute
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"So the entire experience was amazing. There was so much in walking distance. It was kind of weird because there were actually 3 inns and we didn't know which one we were in"
Alison Marie 4-night trip
Posted 1 day ago
Historic Inns of Annapolis

Find out more about Shady Side

Find out more about Shady Side

Shady Side B&B information

Number of reviews
656
Accommodation
11 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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