Find hotels in Shady Side, MD from CA $116

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Our top choices for Shady Side hotels

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (906 reviews)
"Breakfast menu had a great variety and was fresh. "
United States
Timothy
The price is CA $140
CA $155 total
includes taxes & fees
May 19 - May 20
Quality Inn Grasonville near Kent Island

Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills
2.0 star property
Gambrills
9.2 out of 10, Wonderful, (1,085 reviews)
"Always great stay "
United States
Damani
The price is CA $127
CA $145 total
includes taxes & fees
May 31 - Jun 1
Microtel Inn & Suites by Wyndham Gambrills

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, (1,002 reviews)
"We were very pleased with our overnight here - it was economical and more than sufficient. It was clean, comfortable and it was nice to have breakfast included (try the cinnamon buns!) "
United States
Susan
The price is CA $180
CA $199 total
includes taxes & fees
Jun 15 - Jun 16
Holiday Inn Express Annapolis East-Kent Island by IHG

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (137 reviews)
"Very nice room and wonderful stay."
United States
Julie
The price is CA $211
CA $281 total
includes taxes & fees
May 17 - May 18
Kent Island Resort

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,002 reviews)
"It is a nice Hotel."
United States
Dale
The price is CA $154
CA $171 total
includes taxes & fees
May 17 - May 18
Best Western Kent Narrows Inn

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,008 reviews)
"Great location with good breakfast. 👍"
United States
David
The price is CA $142
CA $161 total
includes taxes & fees
Jun 8 - Jun 9
Country Inn & Suites by Radisson, Annapolis, MD

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.6 out of 10, Excellent, (1,004 reviews)
"Nice location "
United States
Duan
The price is CA $175
CA $221 total
includes taxes & fees
May 26 - May 27
Rod 'N' Reel Resort

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (486 reviews)
"absolutely perfect for this traveler!"
United States
BENNY
The price is CA $329
CA $375 total
includes taxes & fees
May 18 - May 19
Anchored Inn at Hidden Harbour Marina

The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.6 out of 10, Exceptional, (132 reviews)
"Spotless room! Well kept grounds. Would definitely stay here again."
United States
Bethany
The price is CA $343
CA $377 total
includes taxes & fees
May 19 - May 20
The Tilghman Island Inn

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (759 reviews)
"Great Stay!!"
United States
Richard
The price is CA $257
CA $285 total
includes taxes & fees
Jun 15 - Jun 16
Hyatt Place Kent Narrows & Marina

Comfort Inn Conference Center

Comfort Inn Conference Center
2.5 star property
Bowie
9.2 out of 10, Wonderful, (1,003 reviews)
"Had a very nice stay"
United States
Laura
The price is CA $136
CA $153 total
includes taxes & fees
Jun 7 - Jun 8
Comfort Inn Conference Center

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,001 reviews)
"Very friendly and helpful staff. Room was very comfortable and well laid out. Would definitely stay again! "
United States
Cristi
The price is CA $177
CA $202 total
includes taxes & fees
May 31 - Jun 1
SpringHill Suites by Marriott Annapolis

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,000 reviews)
"Beautiful area"
United States
Dan
The price is CA $213
CA $237 total
includes taxes & fees
May 27 - May 28
Hilton Garden Inn Kent Island Marina

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,846 reviews)
"Great location"
United States
Stephanie
The price is CA $160
CA $229 total
includes taxes & fees
May 31 - Jun 1
Historic Inns of Annapolis

Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1,002 reviews)
"Older Hotel but clean and staff was great."
United States
Gregory
The price is CA $116
CA $132 total
includes taxes & fees
May 24 - May 25
Best Western Annapolis

Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis
3.0 star property
Annapolis
8.8 out of 10, Excellent, (199 reviews)
"Clean, friendly staff, will come back"
United States
Yung
The price is CA $174
CA $199 total
includes taxes & fees
May 24 - May 25
Fairfield Inn & Suites By Marriott Annapolis

Executive Inn And Suites

Executive Inn And Suites
2.0 star property
Upper Marlboro
7.2 out of 10, Good, (574 reviews)
"Clean and accommodating staff."
United States
Annette
The price is CA $130
CA $147 total
includes taxes & fees
May 17 - May 18
Executive Inn And Suites

George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (72 reviews)
"Mr Will very good Host and breakfast very delicious sure we will come back ❤️"
United States
MENBERE
The price is CA $521
CA $573 total
includes taxes & fees
May 22 - May 23
George Brooks House B&B

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1,002 reviews)
"We had a lovely stay and would go back again! Pleasant staff and a short ride to everything."
United States
JoAnn
The price is CA $165
CA $182 total
includes taxes & fees
Jun 1 - Jun 2
St Michaels Inn

Home2 Suites By Hilton Capitol Heights Washington Dc

Home2 Suites By Hilton Capitol Heights Washington Dc
3.0 star property
Capitol Heights
8.8 out of 10, Excellent, (12 reviews)
"Clean room, perfect location close to DC, friendly staff. "
United States
Tiffany
The price is CA $184
CA $208 total
includes taxes & fees
Jun 7 - Jun 8
Home2 Suites By Hilton Capitol Heights Washington Dc
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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Stay near popular Shady Side attractions

Learn more about Shady Side

Love dining out, parks, and museums? Get away to Shady Side!

Aerial view of Annapolis capital city of Maryland state with expensive waterside properties along the Chesapeake Bay, state capital building and naval academy, dreamy blue sky

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Frequently asked questions

What is the best area to stay in Shady Side?
The best area to stay in Shady Side is along the waterfront, particularly near the marinas and public access points to the Chesapeake Bay.

This area offers immediate access to the water, which is a key reason for visiting Shady Side. You'll find properties with direct bay views, private docks, and easy access to water-based activities like fishing and boating. The main roads like Shady Side Road and Deale-Churchton Road run parallel to the water, where you'll find local seafood restaurants and small shops.

Families often find staying near the waterfront ideal due to the abundance of outdoor activities. Many accommodations here cater to those looking for a relaxing holiday by the water, with plenty of space for children to play and direct access to crabbing and swimming spots.

For couples seeking a quiet retreat, the more secluded waterfront properties offer privacy and scenic views. Imagine enjoying a sunset over the bay from your own balcony or taking a peaceful stroll along the shore.
When is the best time to go to Shady Side?
The best time to visit Shady Side is during the shoulder seasons of spring (April to May) and autumn (September to October) when the weather is pleasant and the crowds are smaller.

Spring brings mild temperatures, blooming flowers, and the opportunity to enjoy outdoor activities like fishing, kayaking, and exploring the local parks without the intense heat of summer. It's a great time for couples seeking a peaceful getaway with scenic views.

Autumn offers comfortable temperatures and beautiful fall foliage, particularly along the waterfront. This season is ideal for those who enjoy hiking, cycling, or simply relaxing by the Chesapeake Bay. Families might appreciate the various harvest festivals and pumpkin patches in the wider area during this time.

While summer (June to August) is popular for its warm weather and water sports, it can be quite busy, and accommodation prices might be higher.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Shady Side.
How can I save on a Shady Side hotel booking with Expedia?
Members always get our best prices. Find our best Shady Side hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Shady Side hotel?
Prices for hotels in Shady Side often vary, but you can find a great deal from CA $116 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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