Search B&B in Shady Side

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sep - 7 Sep
In two months
3 Oct - 5 Oct

B&B in Shady Side

Laurel Grove Inn on the South
Outdoor dining

Laurel Grove Inn on the South

3.5 star property
9.0 out of 10, Wonderful, (517)
"Beautiful property and lovely hosts."
Laurel Grove Inn on the South
George Brooks House B&B
Exterior

George Brooks House B&B

3.0 star property
8.8 out of 10, Excellent, (61)
"Gorgeous quaint historic house. Friendly owner, close to town "
The price is AED 893
AED 982 total
includes taxes & fees
6 Aug - 7 Aug
George Brooks House B&B
The Oaks Waterfront
Front of property

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (33)
"Loved the Oaks! Fabulous accommodations and excellent staff"
The price is AED 1,517
AED 1,669 total
includes taxes & fees
6 Aug - 7 Aug
The Oaks Waterfront
Flag House Inn
Front of property

Flag House Inn

3.5 star property
9.6 out of 10, Exceptional, (73)
"Lovely B&B close to EVERYTHING! The host were so kind and helpful. The common areas were very nice as well as the front porch!"
The price is AED 512
AED 584 total
includes taxes & fees
6 Aug - 7 Aug
Flag House Inn
The Inn at Tacaro Estate
Horseback riding

The Inn at Tacaro Estate

5.0 star property
9.2 out of 10, Wonderful, (9)
"1940’s estate is maintained to remind you of those times. There was a “Speak-EZ” in the basement they had open Friday and Saturday evenings. My room was spacious and included a balcony. Huge front lawn with a pool and a view to the Bay. "
The price is AED 1,134
AED 1,293 total
includes taxes & fees
10 Aug - 11 Aug
The Inn at Tacaro Estate
Legacy Villa
Family Room, 3 Bedrooms, Pool View | Private kitchen | Full-size fridge

Legacy Villa

4.0 star property
The price is AED 1,300
AED 1,469 total
includes taxes & fees
6 Aug - 7 Aug
Legacy Villa
Parsonage Inn
Porch

Parsonage Inn

3.5 star property
9.2 out of 10, Wonderful, (129)
"Beautiful Victorian Cottage Home. Outstanding service and breakfast. Wonderful hosts made us feel right @ home!"
The price is AED 841
AED 925 total
includes taxes & fees
6 Aug - 7 Aug
Parsonage Inn
Inn at Horn Point
Beach nearby

Inn at Horn Point

3.0 star property
9.4 out of 10, Exceptional, (19)
"Family owned with care and pride. Excellent food and recommendations for other restaurants and activities. "
The price is AED 1,263
AED 1,440 total
includes taxes & fees
6 Aug - 7 Aug
Inn at Horn Point
Black Walnut Point Inn
Outdoor pool

Black Walnut Point Inn

3.5 star property
9.0 out of 10, Wonderful, (56)
"Wife and I stayed 3 days for 41st anniversary. Bob and Tracy are wonderful hosts. "
Black Walnut Point Inn
14 miles to Nat’l Mall - District Heights Retreat
Fridge, microwave, oven, stovetop

14 miles to Nat’l Mall - District Heights Retreat

10.0 out of 10, Exceptional, (3)
"We stayed for a full week and everyone was so nice and helpful. Super easy to find and access. Looked exactly like the picture. Very cozy!"
14 miles to Nat’l Mall - District Heights Retreat
Charming 4-bedroom bed & breakfast with AC, WiFi in tranquil Upper Marlboro
Interior

Charming 4-bedroom bed & breakfast with AC, WiFi in tranquil Upper Marlboro

Charming 4-bedroom bed & breakfast with AC, WiFi in tranquil Upper Marlboro
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Shady Side Hotel Reviews

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Great visit "
Chris 6-night trip
Posted 12 hours 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?
Below are some well-liked B&Bs in the surrounding area: Laurel Grove Inn on the South: 5 rooms. 9.2 mi (14.8 km) from the downtown core. Enjoy the deli and arcade game room. Flag House Inn: 5 rooms. Situated 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 heart of downtown. Enjoy the library and fireplace in the lobby. 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 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.