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Check prices for these dates

Next weekend
2 May - 4 May
In two weeks
9 May - 11 May
In one month
23 May - 25 May
In two months
20 Jun - 22 Jun

Compare 9 B&B in Shady Side with updated reviews, rates, and availability.

The Oaks Waterfront
Front of property

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (30)
"Beautiful decor, exceptional staff, food was delicious. Serene surroundings. Excellent stay!"
The price is AED 1,517
AED 1,669 total
includes taxes & fees
11 May - 12 May
The Oaks Waterfront
Parsonage Inn
Porch

Parsonage Inn

3.5 star property
9.2 out of 10, Wonderful, (128)
"Beautiful Victorian Cottage Home. Outstanding service and breakfast. Wonderful hosts made us feel right @ home!"
The price is AED 771
AED 848 total
includes taxes & fees
28 Apr - 29 Apr
Parsonage Inn
George Brooks House B&B
Exterior

George Brooks House B&B

3.0 star property
8.6 out of 10, Excellent, (57)
"Very nice property, cozy and clean rooms, excellent service."
The price is AED 845
AED 929 total
includes taxes & fees
28 Apr - 29 Apr
George Brooks House B&B
The Inn at Tacaro Estate
Horseback riding

The Inn at Tacaro Estate

5.0 star property
8.8 out of 10, Excellent, (6)
"Amazing hospitality "
The price is AED 1,162
AED 1,324 total
includes taxes & fees
30 Apr - 1 May
The Inn at Tacaro Estate
Flag House Inn
Chesapeake Suite | Frette Italian sheets, premium bedding, memory foam beds, free minibar

Flag House Inn

3.5 star property
9.6 out of 10, Exceptional, (69)
"Wonderfully friendly staff, great location, and beautiful property "
The price is AED 1,025
AED 1,168 total
includes taxes & fees
27 Apr - 28 Apr
Flag House Inn
Inn at Horn Point
Beach nearby

Inn at Horn Point

3.0 star property
9.4 out of 10, Exceptional, (19)
"This B&B was centrally located, clean,safe and quiet. However, even though I knew there would be no breakfast, I thought that like most B&B’s there would be the possibility of coffee or tea in the morning. There was no one home to welcome us or give information about nearby restaurants, etc. Why take the reservation if you can’t provide the amenities most B&B’s feature?"
The price is AED 1,416
AED 1,614 total
includes taxes & fees
26 Apr - 27 Apr
Inn at Horn Point
Black Walnut Point Inn
Outdoor pool

Black Walnut Point Inn

3.5 star property
9.0 out of 10, Wonderful, (55)
"Unique property in beautiful setting. Home made breakfast. Quiet and peaceful. Lives the cats that live here too."
Black Walnut Point Inn
Laurel Grove Inn on the South
View from property

Laurel Grove Inn on the South

3.5 star property
9.0 out of 10, Wonderful, (513)
"Now I understand why the great ratings! What a wonderful place to stay. Beautiful views, comfortable with all the conveniences of home. Great hosts who go above and beyond to ensure your stay is fabulous. We will definitely return!"
Laurel Grove Inn on the South
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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Other property types in Shady Side

The Cottage
Exterior

The Cottage

10.0 out of 10, Exceptional, (4)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The Cottage
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Miscellaneous

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (212)
"The house was absolutely perfect for our USNA Reunion. About 10 steps to Gate 1 and just a few more to the heart of downtown made it a weekend we will remember. The host was responsive and accommodated our requests and was very kind. I would definitely stay here again."
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Property grounds

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

9.6 out of 10, Exceptional, (75)
"We stayed at the host property for a long weekend in town for a family baby shower nearby. We were totally impressed with the cleanliness of the location, spacious accommodations and responsiveness of the host. There is a weekend farmers market and we wound up getting fresh produce to cook and some great food and desserts to eat. Parking was a breeze and the nearby park was wonderful for our daily walks. Highly recommended! 10 out of 10!!"
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
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.

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. 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 heart of downtown. Enjoy the library and fireplace in the lobby. Flag House Inn: 5 rooms. Located 9.6 mi (15.4 km) from the core of Shady Side. Enjoy the local cuisine 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 explore some things to do in town, Shadyside Park and Captain Avery Museum are some notable sights to visit. You might check out Franklin Point State Park if you have time 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.