A river with boats, a marina, and a town with houses and buildings.

Find a Bed and Breakfast in Shady Side from CA $326

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Check prices for these dates

Next weekend
Aug 7 - Aug 9
In two weeks
Aug 14 - Aug 16
In one month
Aug 28 - Aug 30
In two months
Sep 25 - Sep 27

Our top choices for Shady Side bed & breakfast

Seasonal outdoor pool, pool umbrellas, sun loungers

1. The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.6 out of 10, Exceptional, (18 reviews)
"An amazing breakfast. The home is decorated beautifully"
United States
James
The price is CA $477
CA $544 total
includes taxes & fees
Aug 3 - Aug 4
The Inn at Tacaro Estate
Lobby lounge

2. Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (95 reviews)
"Great spot with easy walking downtown or to the Academy. Very nice sitting rooms downstairs with fresh pastries for breakfast. "
United States
Tyler
The price is CA $319
CA $363 total
includes taxes & fees
Aug 5 - Aug 6
Flag House Inn
Exterior

3. George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (76 reviews)
"This weekend was an anniversary gift for my daughter and her husband. They had a wonderful time and were highly complimentary of the accommodations, the delicious breakfast and the location."
United States
Erin
The price is CA $297
CA $326 total
includes taxes & fees
Aug 3 - Aug 4
George Brooks House B&B
Luxury Cottage, 1 Bedroom, Kitchen, River View | Private kitchen

4. The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (42 reviews)
"Staff, breakfast, and room were all superb!"
United States
Jeffrey
The price is CA $617
CA $679 total
includes taxes & fees
Aug 4 - Aug 5
The Oaks Waterfront
Smart TV

5. 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 $500
CA $1,170 total
includes taxes & fees
Aug 4 - Aug 5
Spacious 5BR Retreat Near DC with Private Gym - Perfect for Group Getaway
Interior

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

Spacious Luxury 8BR Family Retreat Near DC - Perfect for Groups & Families
Glenn Dale
5.6 out of 10, (5 reviews)
"Easy to find, easy to get in, spacious "
United States
Anonymous traveller
The price is CA $544
CA $1,472 total
includes taxes & fees
Aug 3 - Aug 4
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

Comfort Inn Conference Center

Comfort Inn Conference Center

10/10 Excellent
"It’s was quick get away the room was not as modern as I liked but it was clean. The staff are super nice and the pool area was just what I want. The place all in all 8/10"
Monica 2-night trip
Posted 7 hours ago
Comfort Inn Conference Center

Find out more about Shady Side

Shady Side B&B information

Number of reviews
76
Accommodation
18 B&B
Lowest Price
CA $326
Highest Price
CA $679

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: George Brooks House B&B: 6 rooms. 15.6 mi (25.1 km) from the downtown core. Enjoy the library and fireplace in the lobby. Flag House Inn: 5 rooms. Situated 9.6 mi (15.4 km) from the heart of Shady Side. Enjoy the unique décor 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. Parsonage Inn: 8 rooms. Located 15.9 mi (25.5 km) from the core of Shady Side. Enjoy the free full breakfast and unique décor.
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, Northern Chesapeake Bay and Chesapeake Bay are some notable spots. You might 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. 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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