Search B&B in Shady Side

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

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

George Brooks House B&B
Exterior
George Brooks House B&B
3.0 star property
8.6 out of 10, Excellent, (54)
"Very nice property, cozy and clean rooms, excellent service."
The price is AED 808
AED 889 total
includes taxes & fees
11 Nov - 12 Nov
George Brooks House B&B
The Oaks Waterfront
Front of property
The Oaks Waterfront
4.0 star property
10.0 out of 10, Exceptional, (56)
"delightful and charming! great views and peaceful! We really enjoyed our stay!"
The price is AED 1,319
AED 1,451 total
includes taxes & fees
21 Nov - 22 Nov
The Oaks Waterfront
Parsonage Inn
Balcony
Parsonage Inn
3.5 star property
9.2 out of 10, Wonderful, (123)
"Lovely innkeepers- baked treats in the evening and home cooked hot breakfast! Easy to walk and Close to shops. Dark cozy quiet rooms with comfortable pillows and bed. Forgot to pack our fan and were happily surprised there was one in our closet. "
The price is AED 771
AED 848 total
includes taxes & fees
11 Nov - 12 Nov
Parsonage Inn
Flag House Inn
Dining room
Flag House Inn
3.5 star property
9.8 out of 10, Exceptional, (58)
"Very nice facility. Close to shops and restaurants."
The price is AED 657
AED 749 total
includes taxes & fees
10 Nov - 11 Nov
Flag House Inn
The Inn at Tacaro Estate
Room
The Inn at Tacaro Estate
5.0 star property
8.8 out of 10, Excellent, (6)
"Amazing hospitality "
The price is AED 1,235
AED 1,408 total
includes taxes & fees
1 Dec - 2 Dec
The Inn at Tacaro Estate
Inn at Horn Point
Front of property
Inn at Horn Point
3.0 star property
9.6 out of 10, Exceptional, (18)
"I booked the trip to celebrate an anniversary weekend away with my husband. The property came up through a Yelp review so I checked it out. I was impressed with the location, the detail to cleanliness, and the commitment to the environment. Once I booked the room, the innkeepers were very helpful in offering things to do and places to eat, as well as offering to help make our anniversary stay more memorable. Once we arrived, Cory took the time to greet us as we came in and share some of the...
The price is AED 1,237
AED 1,410 total
includes taxes & fees
20 Nov - 21 Nov
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
Room
Laurel Grove Inn on the South
3.5 star property
9.0 out of 10, Wonderful, (512)
"Lovely hostess. Very accommodating. Charming room. Gorgeous view."
Laurel Grove Inn on the South
The Annapolis Inn
Room
The Annapolis Inn
4.0 star property
9.0 out of 10, Wonderful, (4)
"The Annapolis Inn exceed every expectation! The owners are absolutely fabulous. The property is gorgeous and exceptionally appointed. Alex is a gourmet chef who left us wanting more each breakfast. Joe is a tremendous story teller and you will want to sit for hours listening and conversing. Both are wonderful and kind humans who gave us their undivided attention and complete care. This was my first experience at a bed and breakfast and I am forever spoiled. You won’t find better accommodations...
The Annapolis Inn
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.
Don't see what you're looking for?
See all available properties in Shady Side
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Shady Side

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Miscellaneous
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (20)
"Our group had an amazing time staying on this property. There are many areas inside the house as well as outside the house where you can gather with family and friends. It was very quick and easy to order Ubers/lyfts to the downtow Annapolis area whenever we needed. The house is also convientely located near a small shaping center less than a mile away. We would highly recommend this property!"
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Directly Across from Gate One & Steps from the Waterfront
Private rear courtyard
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (200)
"Incredible location! The process was easy and the house completely suited our needs! We would definitely stay again!"
Directly Across from Gate One & Steps from the Waterfront
Charming Annapolis WaterVIEW Home
3 covered balconies, a ground floor patio, and ceramic and propane grills.
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (48)
"This house was perfect for our group of friends especially with infants. Easy check in, comfortable beds and room for pack and plays. Water view is amazing. Definitely worth the rent and would be interested in coming back!"
Charming Annapolis WaterVIEW Home
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 and Franklin Point State Park are good spots 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'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 Franklin Point State Park are some notable spots. You might check out Captain Avery Museum 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.