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

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  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

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, (536 reviews)
"I stayed here with my daughter the night before a lacrosse tournament at the Naval Academy. Beautiful property, excellent host. I will definitely stay here again! Thank you!"
United States
Michael
$200 nightly
The price is $228
Nov 19 - Nov 20
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
$361 nightly
The price is $412
Nov 24 - Nov 25
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, (101 reviews)
"Charming and picturesque house steps from all of the best things about Annapolis."
United States
Thomas
$227 nightly
The price is $259
Nov 15 - Nov 16
Total with taxes and fees
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, (139 reviews)
"The staff were great. The breakfast was delicious and the location is perfect for walking into town."
United States
Susan
$230 nightly
The price is $253
Nov 13 - Nov 14
Total with taxes and fees
Parsonage Inn
An outdoor patio with seating, a table, and a blue umbrella.

5. Carib Comfort B and B

Carib Comfort B and B
3.0 star property
Upper Marlboro
$194 nightly
The price is $219
Nov 13 - Nov 14
Total with taxes and fees
Carib Comfort B and B
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
$199 nightly
The price is $219
Nov 12 - Nov 13
Total with taxes and fees
George Brooks House B&B
A residential street with parked cars, a sidewalk, and a tree.

7. 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
$206 nightly
The price is $235
Nov 12 - Nov 13
Total with taxes and fees
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.

8. 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
$489 nightly
The price is $538
Nov 12 - Nov 13
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.

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 traveler
$1,071 nightly
The price is $1,210
Nov 12 - Nov 13
Total with taxes and fees
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.

10. 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.
$827 nightly
The price is $935
Nov 12 - Nov 13
Total with taxes and fees
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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

8/10 Good
"i enjoyed how close the place was to many local shops and resturants."
michel demanche 1-night trip
Posted 1 hour ago
DoubleTree by Hilton Hotel Annapolis

Find out more about Shady Side

Shady Side B&B information

Number of reviews
820
Accommodation
19 B&B
Lowest Price
$219
Highest Price
$1,210

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 $219 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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