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Check prices for these dates

Next weekend
17 Apr - 19 Apr
In two weeks
24 Apr - 26 Apr
In one month
8 May - 10 May
In two months
5 Jun - 7 Jun

Our top choices for Shady Side bed & breakfast

Exterior

George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (70 reviews)
"A beautiful renovated historical house with charm, clean rooms, decorative furnishings and a wonderful hot breakfast. What we enjoyed the most was the warm hospitality of Willard, Valerie, and the other staff. Very close to downtown St. Michael’s, but just far enough away to give a nice feel of natural serenity. Great for a quick getaway from the city. We will be back. "
United States
Charles
The price is HK$1,332
HK$1,466 total
includes taxes & fees
8 Apr - 9 Apr
George Brooks House B&B
Lobby lounge

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (92 reviews)
"The room was over the garage. You couldn’t stand up in half the room as the ceiling was too low. Multiple tripping areas walking into and out of the space. No heat in bathroom. You have to walk to the front of house to enter for coffee in the morning. They have the nerve to charge you to park at the house. "
United States
Richard
The price is HK$1,365
HK$1,556 total
includes taxes & fees
8 Apr - 9 Apr
Flag House Inn
Seasonal outdoor pool, pool umbrellas, pool loungers

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.4 out of 10, Exceptional, (13 reviews)
"Wonderful experience Felt like being in good friends home without having to help with the dishes Luxurious stay Recommend *****"
United States
Todd
The price is HK$2,020
HK$2,303 total
includes taxes & fees
27 Apr - 28 Apr
The Inn at Tacaro Estate
Porch

Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (133 reviews)
"Hosts were wonderful, breakfast was delicious, everything was walkable "
United States
Nathaly
The price is HK$1,959
HK$2,155 total
includes taxes & fees
8 Apr - 9 Apr
Parsonage Inn
Private kitchen

The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (41 reviews)
"Staff, breakfast, and room were all superb!"
United States
Jeffrey
The price is HK$3,449
HK$3,794 total
includes taxes & fees
8 Apr - 9 Apr
The Oaks Waterfront
Smart TV

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
The price is HK$1,801
HK$5,232 total
includes taxes & fees
8 Apr - 9 Apr
Spacious 5BR Retreat Near DC with Private Gym - Perfect for Group Getaway
Interior

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

Spacious Luxury 8BR Family Retreat Near DC - Perfect for Groups & Families
Glenn Dale
8.0 out of 10, Very good, (2 reviews)
"Easy to find, easy to get in, spacious "
United States
Anonymous traveller
The price is HK$2,750
HK$8,288 total
includes taxes & fees
14 Apr - 15 Apr
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

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"Super spacious and clean. Would stay again"
Quiana 2-night trip
Posted 1 hour ago
Sonesta ES Suites Annapolis

Find out more about Shady Side

Shady Side B&B information

Number of reviews
351
Accommodation
16 B&B
Lowest Price
HK$1,466
Highest Price
HK$8,288

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. Parsonage Inn: 8 rooms. 15.9 mi (25.5 km) from the city centre. Enjoy the free full breakfast and unique decor. George Brooks House B&B: 6 rooms. 15.6 mi (25.1 km) from the city centre. Enjoy the library and fireplace in reception.
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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