Find hotels in Shady Side, MD from 2.023.274 ₫

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Our top choices for Shady Side hotels

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 11.588.273 ₫
12.747.100 ₫ total
includes taxes & fees
14 Apr - 15 Apr
The Oaks Waterfront

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1,002 reviews)
" Great place,great location, was in town for St Michael Chocolate fest "
United States
Katherine
The price is 3.562.321 ₫
3.918.553 ₫ total
includes taxes & fees
20 Apr - 21 Apr
St Michaels Inn

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (380 reviews)
"everything was perfect!"
United States
John
The price is 15.877.593 ₫
17.465.352 ₫ total
includes taxes & fees
16 Apr - 17 Apr
Inn at Perry Cabin

The Wildset

The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (431 reviews)
"Best HOTEL EVER!!!"
United States
Ama
The price is 5.766.489 ₫
6.922.420 ₫ total
includes taxes & fees
29 Apr - 30 Apr
The Wildset

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 4.871.235 ₫
5.358.359 ₫ total
includes taxes & fees
15 Apr - 16 Apr
Parsonage Inn

George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (71 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 4.081.305 ₫
4.489.436 ₫ total
includes taxes & fees
14 Apr - 15 Apr
George Brooks House B&B

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (889 reviews)
"Staff was nice and room was clean "
United States
Lauren
The price is 2.573.065 ₫
2.856.103 ₫ total
includes taxes & fees
15 Apr - 16 Apr
Quality Inn Grasonville near Kent Island

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,003 reviews)
"Beautiful area"
United States
Dan
The price is 3.433.036 ₫
3.810.670 ₫ total
includes taxes & fees
26 Apr - 27 Apr
Hilton Garden Inn Kent Island Marina

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (987 reviews)
"Very nice hotel, good breakfast selection, clean rooms."
United States
Linda
The price is 3.054.396 ₫
3.390.380 ₫ total
includes taxes & fees
20 Apr - 21 Apr
Holiday Inn Express Annapolis East-Kent Island by IHG

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,008 reviews)
"Wonderful staff,Clean rooms and comfortable bed!!"
United States
Evette
The price is 2.615.195 ₫
2.902.867 ₫ total
includes taxes & fees
20 Apr - 21 Apr
Best Western Kent Narrows Inn

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (739 reviews)
"Clean hotel all around. Friendly stafff and comfortable environment."
United States
Jillian
The price is 4.686.918 ₫
5.202.478 ₫ total
includes taxes & fees
14 Apr - 15 Apr
Hyatt Place Kent Narrows & Marina

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (379 reviews)
"Such a marvelous retreat! And the balcony facing the boats and the Bay at sunset is so welcome after exploring St Michael’s (a short 17 mins drive). Extremely friendly staff and good breakfast. Highly recommend to any nature lovers."
United States
Nadia
The price is 3.949.650 ₫
4.344.615 ₫ total
includes taxes & fees
14 Apr - 15 Apr
Knapps Narrows Marina & Inn

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (94 reviews)
"Very relaxing stay."
United States
Anne
The price is 3.222.914 ₫
4.703.769 ₫ total
includes taxes & fees
27 Apr - 28 Apr
Wylder Tilghman Island

The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.6 out of 10, Exceptional, (126 reviews)
"A wonderful property with a fantastic location. Super friendly staff. Couldn't ask for a more pleasant stay anywhere. You should book right now."
United States
Timothy
The price is 6.187.785 ₫
6.806.564 ₫ total
includes taxes & fees
16 Apr - 17 Apr
The Tilghman Island Inn

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (137 reviews)
"Beautiful hotel, nice staff"
United States
Kim
The price is 2.933.197 ₫
4.045.779 ₫ total
includes taxes & fees
15 Apr - 16 Apr
Kent Island Resort

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (447 reviews)
"Very clean room, staff was very nice. "
United States
Byron
The price is 4.891.732 ₫
6.099.683 ₫ total
includes taxes & fees
22 Apr - 23 Apr
The Inn at Chesapeake Bay Beach Club

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.4 out of 10, Very good, (1,004 reviews)
"Great place to stay with lovely views"
United States
David
The price is 4.004.945 ₫
4.972.109 ₫ total
includes taxes & fees
16 Apr - 17 Apr
Rod 'N' Reel Resort

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (917 reviews)
"Great waterfront room with roomy balcony. Gym was nice also. Can't wait for the var and restaurants to open."
United States
Douglas
The price is 7.083.039 ₫
8.074.664 ₫ total
includes taxes & fees
19 Apr - 20 Apr
Annapolis Waterfront Hotel, Autograph Collection

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (93 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 4.912.311 ₫
5.599.813 ₫ total
includes taxes & fees
20 Apr - 21 Apr
Flag House Inn

134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel
2.5 star property
Annapolis
9.8 out of 10, Exceptional, (34 reviews)
"Wonderful place to go, especially during the Annapolis boat show... easy access to everything beautiful property and staff"
United States
Ian
The price is 4.872.762 ₫
5.554.949 ₫ total
includes taxes & fees
15 Apr - 16 Apr
134 Prince - Luxury Boutique Hotel
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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Frequently asked questions

What's the weather like in Shady Side?
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.