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

Book Shady Side Bed & Breakfast

Check prices for these dates

Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1
In one month
Nov 13 - Nov 15
In two months
Dec 11 - Dec 13

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, (531 reviews)
"Beautiful property and lovely hosts."
United States
Ruth
$180 nightly
The price is $205
Nov 15 - Nov 16
Total with taxes and fees
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
$377 nightly
The price is $430
Nov 16 - Nov 17
Total with taxes and fees
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
$218 nightly
The price is $248
Oct 18 - Oct 19
Total with taxes and fees
Flag House Inn
A room with a wooden desk, a chair, a fire extinguisher, a map on the wall, and a welcome mat.

4. Carib Comfort B and B

Carib Comfort B and B
3.0 star property
Upper Marlboro
$168 nightly
The price is $190
Oct 21 - Oct 22
Total with taxes and fees
Carib Comfort B and B
Two wooden chairs facing a calm body of water at sunset.

5. 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
$450 nightly
The price is $513
Oct 30 - Oct 31
Total with taxes and fees
Inn at Horn Point
A residential street with parked cars, a sidewalk, and a tree.

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

Charming Living room in beautiful Annapolis with AC discount long stay
Historic District
$303 nightly
The price is $345
Oct 27 - Oct 28
Total with taxes and fees
Charming Living room in beautiful Annapolis with AC discount long stay
A Victorian-style building with a prominent tower, a porch with outdoor seating, and a sign indicating it is a bed and breakfast.

7. Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (138 reviews)
"Nice place"
United States
Paul
$250 nightly
The price is $275
Nov 2 - Nov 3
Total with taxes and fees
Parsonage Inn
A two-story house with a swimming pool, outdoor seating, and a covered patio area.

8. 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
$215 nightly
The price is $237
Nov 2 - Nov 3
Total with taxes and fees
George Brooks House B&B
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, (44 reviews)
"Staff, breakfast, and room were all superb!"
United States
Jeffrey
$489 nightly
The price is $538
Oct 18 - Oct 19
Total with taxes and fees
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 traveler
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, (4 reviews)
"Beautiful big house. Two of the light fixtures didn't work but it didn't really affect our experience."
United States
Natalia L.
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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Top Shady Side Hotel Reviews

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"The staff was awesome. Very professional and helpful. Our room was cleaned and well maintained. The food was great and the spa service was awesome as well."
Lamont 3-night trip
Posted 13 hours ago
The Inn at Chesapeake Bay Beach Club

Find out more about Shady Side

Shady Side B&B information

Number of reviews
840
Accommodation
18 B&B
Lowest Price
$205
Highest Price
$538

Frequently asked questions

What is the nightly rate for a B&B in Shady Side?
Prices for B&Bs in Shady Side often vary, but you can find a great deal from $205 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Shady Side B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a B&B in Shady Side?
The best time to book a B&B in Shady Side is during the vibrant spring months from April to June. This period welcomes travelers who appreciate lush landscapes and moderate weather, making it ideal for outdoor activities such as hiking, kayaking, and exploring the scenic waterfront. The spring blooms create a picturesque backdrop, enhancing the overall experience of this charming area.

April typically sees mild temperatures ranging from the mid-50s to low 70s Fahrenheit, which is superb for leisurely strolls along the shoreline or visiting local parks. As the season progresses into May and June, the warmth invites a lively atmosphere, with various festivals and events that showcase the local culture and community spirit.

For those looking for a more budget-friendly option, consider visiting in December. While the weather is cooler, with temperatures averaging in the low 30s to mid-40s Fahrenheit, the holiday season brings a unique charm to Shady Side. You can enjoy festive decorations, cozy gatherings, and a peaceful ambiance that allows for reflective exploration of the area.
What is the difference between a Shady Side Bed and Breakfast and a hotel?
Every Shady Side B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Shady Side B&Bs.

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