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

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Check prices for these dates

Next weekend
28 Aug - 30 Aug
In two weeks
4 Sept - 6 Sept
In one month
18 Sept - 20 Sept
In two months
16 Oct - 18 Oct

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$1,412
HK$1,609 total
includes taxes & fees
23 Aug - 24 Aug
Laurel Grove Inn on the South
Seasonal outdoor pool, pool umbrellas, pool loungers

2. The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.6 out of 10, Exceptional, (18 reviews)
"An amazing breakfast. The home is decorated beautifully"
United States
James
The price is HK$3,110
HK$3,545 total
includes taxes & fees
23 Aug - 24 Aug
The Inn at Tacaro Estate
Lobby lounge

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$1,709
HK$1,948 total
includes taxes & fees
23 Aug - 24 Aug
Flag House Inn
Exterior

4. George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (77 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$1,658
HK$1,824 total
includes taxes & fees
24 Aug - 25 Aug
George Brooks House B&B
Private kitchen

5. 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$3,451
HK$3,796 total
includes taxes & fees
26 Aug - 27 Aug
The Oaks Waterfront
Smart TV

6. 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$2,714
HK$6,541 total
includes taxes & fees
22 Aug - 23 Aug
Spacious 5BR Retreat Near DC with Private Gym - Perfect for Group Getaway
Interior

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

Spacious Luxury 8BR Family Retreat Near DC - Perfect for Groups & Families
Glenn Dale
5.6 out of 10, (5 reviews)
"Easy to find, easy to get in, spacious "
United States
Anonymous traveller
The price is HK$4,913
HK$10,639 total
includes taxes & fees
31 Aug - 1 Sept
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

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Rooms where clean, staff was nice"
Debra 1-night trip
Posted 3 hours ago
Crowne Plaza Annapolis by IHG

Find out more about Shady Side

Shady Side B&B information

Number of reviews
654
Accommodation
18 B&B
Lowest Price
HK$1,609
Highest Price
HK$10,639

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. Situated 15.6 mi (25.1 km) from the heart of Shady Side. Enjoy the library and fireplace in reception. The Inn at Tacaro Estate: 8 rooms. 6 mi (9.7 km) from the city centre. Enjoy the free full breakfast and designer toiletries. 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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