A river with boats, a marina, and a town with houses and buildings.

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Check prices for these dates

Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct
In one month
6 Nov - 8 Nov
In two months
4 Dec - 6 Dec

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
9.2 out of 10, Wonderful, (530 reviews)
"Beautiful property and lovely hosts."
United States
Ruth
The price is HK$1,413
HK$1,610 total
includes taxes & fees
7 Oct - 8 Oct
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, (19 reviews)
"The owners are very friendly and accommodating. Relaxing getaway"
United States
kristine
The price is HK$2,745
HK$3,130 total
includes taxes & fees
1 Nov - 2 Nov
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, (97 reviews)
"Great location. Beautiful room and exemplary service. "
United States
Nathan
The price is HK$1,710
HK$1,949 total
includes taxes & fees
6 Oct - 7 Oct
Flag House Inn
A Victorian-style building with a prominent tower, a porch with outdoor seating, and a sign indicating it is a bed and breakfast.

4. 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 HK$1,962
HK$2,158 total
includes taxes & fees
2 Nov - 3 Nov
Parsonage Inn
A residential street with parked cars, a sidewalk, and a tree.

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

Charming Living room in beautiful Annapolis with AC discount long stay
Historic District
The price is HK$1,452
HK$2,729 total
includes taxes & fees
3 Nov - 4 Nov
Charming Living room in beautiful Annapolis with AC discount long stay
A two-story house with a swimming pool, outdoor seating, and a covered patio area.

6. 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 HK$1,518
HK$1,670 total
includes taxes & fees
2 Nov - 3 Nov
George Brooks House B&B
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.

7. The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (44 reviews)
"Staff, breakfast, and room were all superb!"
United States
Jeffrey
The price is HK$3,454
HK$3,799 total
includes taxes & fees
6 Oct - 7 Oct
The Oaks Waterfront
A spacious living room with a high arched window, a white sofa, a glass coffee table, and a large plant.

8. 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
9.4 out of 10, Exceptional, (3 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 HK$2,715
HK$6,465 total
includes taxes & fees
6 Oct - 7 Oct
Spacious 5BR Retreat Near DC with Private Gym - Perfect for Group Getaway
A staircase with a white and gold design, a living room with a grey sofa, and a decorative console table.

9. 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 HK$4,273
HK$9,546 total
includes taxes & fees
6 Oct - 7 Oct
Spacious Luxury 8BR Family Retreat Near DC - Perfect for Groups & Families
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

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

10/10 Excellent
"Staff was great, hotel needs real renovation seems like they've done a lot of patch work. Parking should be complimentary for people staying in the hotel or a discounted rate. $35 a day for parking at the hotel you're staying at is crazy. There's very limited parking to begin with."
Lauren 2-night trip
Posted less than an hour ago
Hilton Garden Inn Annapolis Downtown

Find out more about Shady Side

Shady Side B&B information

Number of reviews
812
Accommodation
18 B&B
Lowest Price
HK$1,610
Highest Price
HK$9,546

Frequently asked questions

Searching for B&Bs in Shady Side?
If you're interested in something a little quirkier than your standard hotel experience, a bed and breakfast could be the perfect alternative for your holiday. If your ideal holiday to Shady Side includes spending lots of time outside, Shadyside Park is a good spot to enjoy the scenery.
Are you considering an apartment for your stay?
With attentive service, opportunities to meet other guests and top-rated breakfasts, B&Bs provide a truly one-of-a-kind 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 decor and fireplace in reception. George Brooks House B&B: 6 rooms. 15.6 mi (25.1 km) from the city centre. Enjoy the library and fireplace in reception. Laurel Grove Inn on the South: 5 rooms. Situated 9.2 mi (14.8 km) from the heart of Shady Side. Enjoy the snack bar/deli and arcade/games 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 decor.
When should I book my B&B in Shady Side?
When you're dreaming of a stay in Shady Side, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August, with an average temperature of 24°C, while the coldest months are January and February, with an average of 5°C. Average annual precipitation for Shady Side is 1307 mm.
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 should 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. You can also search for flights into College Park, MD (CGS), which is 24.1 mi (38.7 km) away. If you'd like to venture out around the area, consider renting a car to explore more sights.

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