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Check prices for these dates

Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec
In one month
2 Jan - 4 Jan
In two months
30 Jan - 1 Feb

B&B in Shady Side

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
The price is SAR 716
SAR 816 total
includes taxes & fees
7 Dec - 8 Dec
Flag House Inn
Front of property
The Oaks Waterfront

The Oaks Waterfront

4.0 star property
Easton
10.0 out of 10, Exceptional, (41)
"Loved the Oaks! Fabulous accommodations and excellent staff"
United States
Barbara
The price is SAR 1,550
SAR 1,705 total
includes taxes & fees
11 Dec - 12 Dec
The Oaks Waterfront
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
The price is SAR 638
SAR 702 total
includes taxes & fees
1 Jan - 2 January 2026
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.
The price is SAR 356
SAR 657 total
includes taxes & fees
3 Dec - 4 Dec
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
The price is SAR 750
SAR 825 total
includes taxes & fees
1 Jan - 2 January 2026
Parsonage Inn
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
The Inn at Tacaro Estate
Full-size fridge, blender, toaster oven, waffle maker
Legacy Villa

Legacy Villa

4.0 star property
Upper Marlboro
The price is SAR 1,062
SAR 1,201 total
includes taxes & fees
10 Dec - 11 Dec
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
"Clean room, friendly staff"
Jodi 1-night trip
Posted 2 days ago
Country Inn & Suites by Radisson, Annapolis, MD

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?
Here are some B&Bs in the surrounding area: Flag House Inn: 5 rooms. 9.6 mi (15.4 km) from the heart of Shady Side. Enjoy the local cuisine breakfast and unique décor. 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. Parsonage Inn: 8 rooms. Situated 15.9 mi (25.5 km) from the heart of Shady Side. Enjoy the free full breakfast and unique décor. The Inn at Tacaro Estate: 8 rooms. Located 6 mi (9.7 km) from the core of Shady Side. Enjoy the free full breakfast and designer toiletries.
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.