Aerial view of Annapolis capital city of Maryland state with expensive waterside properties along the Chesapeake Bay, state capital building and naval academy, dreamy blue sky

Find a Bed and Breakfast in Shady Side from CA $362

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Check prices for these dates

Next weekend
Jun 26 - Jun 28
In two weeks
Jul 3 - Jul 5
In one month
Jul 17 - Jul 19
In two months
Aug 14 - Aug 16

Our top choices for Shady Side bed & breakfast

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 CA $318
CA $362 total
includes taxes & fees
Jun 21 - Jun 22
Flag House Inn
Luxury Cottage, 1 Bedroom, Kitchen, River View | 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 CA $616
CA $677 total
includes taxes & fees
Jun 21 - Jun 22
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, (75 reviews)
"Mr Will very good Host and breakfast very delicious sure we will come back ❤️"
United States
MENBERE
The price is CA $479
CA $527 total
includes taxes & fees
Jun 26 - Jun 27
George Brooks House B&B
Seasonal outdoor pool, pool umbrellas, sun loungers

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.6 out of 10, Exceptional, (16 reviews)
"An amazing breakfast. The home is decorated beautifully"
United States
James
The price is CA $469
CA $535 total
includes taxes & fees
Jul 13 - Jul 14
The Inn at Tacaro Estate
Smart TV

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
9.4 out of 10, Exceptional, (3 reviews)
"Beautiful big house. Two of the light fixtures didn't work but it didn't really affect our experience."
United States
Natalia L.
The price is CA $444
CA $1,098 total
includes taxes & fees
Jun 21 - Jun 22
Spacious 5BR Retreat Near DC with Private Gym - Perfect for Group Getaway
Interior

Spacious Luxury 8BR Family Retreat Near DC - Perfect for Groups & Families

Spacious Luxury 8BR Family Retreat Near DC - Perfect for Groups & Families
Glenn Dale
6.6 out of 10, (4 reviews)
"Easy to find, easy to get in, spacious "
United States
Anonymous traveller
The price is CA $583
CA $1,496 total
includes taxes & fees
Jun 21 - Jun 22
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

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good
"When we arrived people were still checking out because of the problem with the elevators. So we have to wait for the room to be cleaned. We booked a handicap room but was giving a standard room I called down to the desk and they did move us to a handicap room. The Restaurant was closed for remodeling. One of the two elevators was not working. The hallways were hot. The a/c was working in our room just fine. It could be a nice place to stay. The location is great for someone that wants to shop etc. I felt it was a little pricey."
William 2-night trip
Posted 6 hours ago
Annapolis Waterfront Hotel, Autograph Collection

Find out more about Shady Side

Shady Side B&B information

Number of reviews
233
Accommodation
17 B&B
Lowest Price
CA $362
Highest Price
CA $1,496

Frequently asked questions

Searching for B&Bs in Shady Side?
If you're looking for something a little different than the traditional hotel experience, a bed and breakfast might be the perfect option for your vacation. If your ideal vacation to Shady Side includes spending lots of time outside, Shadyside Park is a good spot to enjoy the scenery.
Are you thinking about B&Bs over traditional hotel rooms?
With attentive service, opportunities to meet guests from other places, and of course a full breakfast to start the day, B&Bs provide a unique environment.
What are the best B&Bs in Shady Side?
Below are some well-liked B&Bs in the surrounding area: Parsonage Inn: 8 rooms. 15.9 mi (25.5 km) from the downtown core. Enjoy the free full breakfast and unique décor. George Brooks House B&B: 6 rooms. Situated 15.6 mi (25.1 km) from the heart of Shady Side. Enjoy the library and fireplace in the lobby. The Inn at Tacaro Estate: 8 rooms. 6 mi (9.7 km) from the heart of downtown. Enjoy the free full breakfast and designer toiletries. Flag House Inn: 5 rooms. Located 9.6 mi (15.4 km) from the core of Shady Side. Enjoy the unique décor and fireplace in the lobby.
What's the best time of year to book my B&B in Shady Side?
When you're dreaming of a getaway to Shady Side, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 75°F, while the coldest months are January and February with an average of 40°F. Average annual precipitation for Shady Side is 51 inches.
What is there to do in Shady Side?
When you want to spend some time in the great outdoors, Shadyside Park and Northern Chesapeake Bay are some notable spots. You might put Chesapeake Bay 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. Otherwise, you can search for flights to College Park, MD (CGS), which is 24.1 mi (38.7 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.

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