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Check prices for these dates

Next weekend
29 May - 31 May
In two weeks
5 Jun - 7 Jun
In one month
19 Jun - 21 Jun
In two months
17 Jul - 19 Jul

Our top choices for Shady Side bed & breakfast

Porch

Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (134 reviews)
"We really enjoyed our stay at The Parsonage. The property and room were kept well. The staff were sweet and attentive. Very good location as far as walking distance to shops, restaurants and the waterfront area. I would certainly return and certainly recommend to anyone visiting St. Michael’s. "
United States
Katie
The price is HK$1,410
HK$1,551 total
includes taxes & fees
25 May - 26 May
Parsonage Inn
Seasonal outdoor pool, pool umbrellas, pool loungers

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.6 out of 10, Exceptional, (15 reviews)
"An amazing breakfast. The home is decorated beautifully"
United States
James
The price is HK$2,424
HK$2,764 total
includes taxes & fees
31 May - 1 Jun
The Inn at Tacaro Estate
Lobby lounge

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (94 reviews)
"Great location. Beautiful room and exemplary service. "
United States
Nathan
The price is HK$1,780
HK$2,029 total
includes taxes & fees
25 May - 26 May
Flag House Inn
Private kitchen

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
The price is HK$3,447
HK$3,792 total
includes taxes & fees
31 May - 1 Jun
The Oaks Waterfront
Exterior

George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (72 reviews)
"Mr Will very good Host and breakfast very delicious sure we will come back ❤️"
United States
MENBERE
The price is HK$2,977
HK$3,275 total
includes taxes & fees
19 Jun - 20 Jun
George Brooks House B&B
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
"Beautiful place and staff was great. $50 historical fee and high valet cost but worth it for the area!"
Rebecca 1-night trip
Posted less than an hour ago
Historic Inns of Annapolis

Find out more about Shady Side

Shady Side B&B information

Number of reviews
222
Accommodation
17 B&B
Lowest Price
HK$1,551
Highest Price
HK$3,792

Frequently asked questions

Searching for B&Bs in Shady Side?
If you're interested in something a little quirkier than your standard hotel experience, a bed and breakfast could be the perfect alternative for your holiday. If your ideal holiday to Shady Side includes spending lots of time outside, Shadyside Park is a good spot to enjoy the scenery.
Are you considering an apartment for your stay?
With attentive service, opportunities to meet other guests and top-rated breakfasts, B&Bs provide a truly one-of-a-kind environment.
What are the best B&Bs in Shady Side?
Here are some B&Bs in the surrounding area: Parsonage Inn: 8 rooms. 15.9 mi (25.5 km) from the heart of Shady Side. Enjoy the free full breakfast and unique decor. Flag House Inn: 5 rooms. 9.6 mi (15.4 km) from the city centre. Enjoy the unique decor and fireplace in reception. The Inn at Tacaro Estate: 8 rooms. Situated 6 mi (9.7 km) from the heart of Shady Side. Enjoy the free full breakfast and designer toiletries. George Brooks House B&B: 6 rooms. 15.6 mi (25.1 km) from the city centre. Enjoy the library and fireplace in reception.
When should I book my B&B in Shady Side?
When you're dreaming of a stay in Shady Side, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August, with an average temperature of 24°C, while the coldest months are January and February, with an average of 5°C. Average annual precipitation for Shady Side is 1307 mm.
What is there to do in Shady Side?
When you want to spend some time in the great outdoors, Northern Chesapeake Bay and Chesapeake Bay are some notable spots. You should put Shadyside Park and Captain Avery Museum on your list if you want to see more of the area.
How can I get to and around Shady Side?
Planning your excursions in and around Shady Side is easier with these transportation options. Fly into Fort Meade, MD (FME-Tipton), which is located 21.6 mi (34.8 km) away from the heart of the city. You can also search for flights into College Park, MD (CGS), which is 24.1 mi (38.7 km) away. If you'd like to venture out around the area, consider renting a car to explore more sights.

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