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Check prices for these dates

Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov

B&B in Shady Side

The Oaks Waterfront
Front of property

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (38)
"Loved the Oaks! Fabulous accommodations and excellent staff"
The price is AED 1,517
AED 1,669 total
includes taxes & fees
30 Sep - 1 Oct
The Oaks Waterfront
Laurel Grove Inn on the South
Outdoor dining

Laurel Grove Inn on the South

3.5 star property
9.0 out of 10, Wonderful, (527)
"Great location with fantastic views. Very friendly owner "
Laurel Grove Inn on the South
George Brooks House B&B
Exterior

George Brooks House B&B

3.0 star property
8.6 out of 10, Excellent, (64)
"Gorgeous quaint historic house. Friendly owner, close to town "
The price is AED 760
AED 836 total
includes taxes & fees
30 Sep - 1 Oct
George Brooks House B&B
Flag House Inn
Front of property

Flag House Inn

3.5 star property
9.4 out of 10, Exceptional, (78)
"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 604
AED 689 total
includes taxes & fees
30 Sep - 1 Oct
Flag House Inn
Parsonage Inn
Porch

Parsonage Inn

3.5 star property
9.2 out of 10, Wonderful, (130)
"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
30 Sep - 1 Oct
Parsonage Inn
The Inn at Tacaro Estate
Horseback riding

The Inn at Tacaro Estate

5.0 star property
9.2 out of 10, Wonderful, (9)
"It was perfect!! We had a great stay. Luca was so kind and attentive. The property is astonishing. Perfect weekend retreat! Thank you so much "
The price is AED 1,490
AED 1,699 total
includes taxes & fees
6 Oct - 7 Oct
The Inn at Tacaro Estate
Inn at Horn Point
Beach nearby

Inn at Horn Point

3.0 star property
9.6 out of 10, Exceptional, (21)
"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
30 Sep - 1 Oct
Inn at Horn Point
Legacy Villa
Full-size fridge, blender, toaster oven, waffle maker

Legacy Villa

4.0 star property
The price is AED 618
AED 698 total
includes taxes & fees
13 Oct - 14 Oct
Legacy Villa
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
Modern 1BR Near DC – Quiet Comfort, Fast Commute
Fridge, microwave, oven, stovetop

Modern 1BR Near DC – Quiet Comfort, Fast Commute

10.0 out of 10, Exceptional, (4)
"I thoroughly enjoyed my stay. Poo"
The price is AED 349
AED 643 total
includes taxes & fees
7 Oct - 8 Oct
Modern 1BR Near DC – Quiet Comfort, Fast Commute
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"So the entire experience was amazing. There was so much in walking distance. It was kind of weird because there were actually 3 inns and we didn't know which one we were in"
Alison Marie 4-night trip
Posted 1 day ago
Historic Inns of Annapolis

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: Laurel Grove Inn on the South: 5 rooms. 9.2 mi (14.8 km) from the heart of Shady Side. Enjoy the deli and arcade game room. 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 local cuisine breakfast and unique décor. Legacy Villa: 2 rooms. Located 14.9 mi (24 km) from the core of Shady Side. Enjoy the in-room pools and massage services.
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.