Find a Bed and Breakfast in Shady Side from CA $193

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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

Our top choices for Shady Side bed & breakfast

Land view from property

1. Laurel Grove Inn on the South

Laurel Grove Inn on the South
3.5 star property
Annapolis
9.4 out of 10, Exceptional, (535 reviews)
"Beautiful property and lovely hosts."
United States
Ruth
The price is CA $252
CA $287 total
includes taxes & fees
Nov 16 - Nov 17
Laurel Grove Inn on the South
A hot tub in a grassy area with a building in the background.

2. The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.6 out of 10, Exceptional, (20 reviews)
"The owners are very friendly and accommodating. Relaxing getaway"
United States
kristine
The price is CA $416
CA $474 total
includes taxes & fees
Nov 8 - Nov 9
The Inn at Tacaro Estate
A room with a dark blue wall, a fireplace with lit candles, a leather armchair, and a bookshelf with decorative items.

3. Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (99 reviews)
"Charming and picturesque house steps from all of the best things about Annapolis."
United States
Thomas
The price is CA $305
CA $348 total
includes taxes & fees
Nov 8 - Nov 9
Flag House Inn
An outdoor patio with seating, a table, and a blue umbrella.

4. Carib Comfort B and B

Carib Comfort B and B
3.0 star property
Upper Marlboro
The price is CA $269
CA $304 total
includes taxes & fees
Nov 10 - Nov 11
Carib Comfort B and B
A Victorian-style building with a prominent tower, a porch with outdoor seating, and a sign indicating it is a bed and breakfast.

5. Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (138 reviews)
"Nice place"
United States
Paul
The price is CA $301
CA $332 total
includes taxes & fees
Nov 8 - Nov 9
Parsonage Inn
A house with a porch, a red umbrella, and a garden with pink flowers.

6. Inn at Horn Point

Inn at Horn Point
3.0 star property
Eastport
9.2 out of 10, Wonderful, (25 reviews)
"Very comfortable"
United Kingdom
JOHN
The price is CA $1,324
CA $1,509 total
includes taxes & fees
Nov 7 - Nov 8
Inn at Horn Point
A two-story house with a swimming pool, outdoor seating, and a covered patio area.

7. George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (78 reviews)
"This weekend was an anniversary gift for my daughter and her husband. They had a wonderful time and were highly complimentary of the accommodations, the delicious breakfast and the location."
United States
Erin
The price is CA $250
CA $275 total
includes taxes & fees
Nov 10 - Nov 11
George Brooks House B&B
A bed with a white quilted mattress, a person lying down, and a TV box labeled 'VIZIO' with a Star Wars Ahsoka poster.

8. Charming Living room in beautiful Annapolis with AC discount long stay

Charming Living room in beautiful Annapolis with AC discount long stay
Historic District
2.0 out of 10, (1 review)
"Place was a bedroom inside the owners townhouse. It is a shared living area. It was messy with stuff thrown around everywhere. It was dirty and musty. Strong unbearable odor. The bedroom for rent was in disarray, stuff on the bed and floors. Owner said previous occupants had left their luggage but there were things all over. Laptop and computer table on the bed, bed in disarray, clothes on the floor. Very dirty space, not suitable for rental. Owner said I didn't have to stay if I...
United States
Lee
The price is CA $193
CA $369 total
includes taxes & fees
Nov 7 - Nov 8
Charming Living room in beautiful Annapolis with AC discount long stay
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.

9. The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (46 reviews)
"Absolutely perfect little 3 day get away. The entire atmosphere was excellent, great complementary breakfast from menu, beautiful modern rooms, perfectly manicured landscaping with lots of seating for relaxing by the water. The entire staff were so friendly and helpful. We made an excellent choice and would definitely go back. 10+ out of 10."
United States
William
The price is CA $615
CA $676 total
includes taxes & fees
Nov 10 - Nov 11
The Oaks Waterfront
A staircase with a white and gold design, a living room with a grey sofa, and a decorative console table.

10. Spacious Luxury 8BR Family Retreat Near DC - Perfect for Groups & Families

Spacious Luxury 8BR Family Retreat Near DC - Perfect for Groups & Families
Glenn Dale
6.4 out of 10, (6 reviews)
"Easy to find, easy to get in, spacious "
United States
Anonymous traveller
The price is CA $577
CA $1,479 total
includes taxes & fees
Nov 10 - Nov 11
Spacious Luxury 8BR Family Retreat Near DC - Perfect for Groups & Families
A spacious living room with a high arched window, a white sofa, a glass coffee table, and a large plant.

11. Spacious 5BR Retreat Near DC with Private Gym - Perfect for Group Getaway

Spacious 5BR Retreat Near DC with Private Gym - Perfect for Group Getaway
Glenn Dale
9.6 out of 10, Exceptional, (5 reviews)
"Beautiful big house. Two of the light fixtures didn't work but it didn't really affect our experience."
United States
Natalia L.
The price is CA $516
CA $1,322 total
includes taxes & fees
Nov 9 - Nov 10
Spacious 5BR Retreat Near DC with Private Gym - Perfect for Group Getaway
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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Learn more about Shady Side

Love dining out, parks, and museums? Get away to Shady Side!

See all hotels in Shady Side
A river with boats, a marina, and a town with houses and buildings.

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 unique décor and fireplace in the lobby. 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. Laurel Grove Inn on the South: 5 rooms. Situated 9.2 mi (14.8 km) from the heart of Shady Side. Enjoy the deli and arcade game room. Parsonage Inn: 8 rooms. Located 15.9 mi (25.5 km) from the core of Shady Side. Enjoy the free full 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 spend some time in the great outdoors, Northern Chesapeake Bay and Chesapeake Bay are some notable spots. You might put Shadyside Park 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.

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