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Our top choices for Shady Side hotels

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 £198
includes taxes & fees
26 Apr - 27 Apr
Wylder Tilghman Island

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 £137
includes taxes & fees
28 Apr - 29 Apr
Kent Island Resort

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (482 reviews)
"absolutely perfect for this traveler!"
United States
BENNY
The price is £129
includes taxes & fees
26 Apr - 27 Apr
Anchored Inn at Hidden Harbour Marina

Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills
2.0 star property
Gambrills
9.2 out of 10, Wonderful, (1,069 reviews)
"Always great stay "
United States
Damani
The price is £78
includes taxes & fees
25 May - 26 May
Microtel Inn & Suites by Wyndham Gambrills

Comfort Inn Conference Center

Comfort Inn Conference Center
2.5 star property
Bowie
9.2 out of 10, Wonderful, (1,001 reviews)
"Had a very nice stay"
United States
Laura
The price is £79
includes taxes & fees
28 Apr - 29 Apr
Comfort Inn Conference Center

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, (993 reviews)
"Very nice hotel, good breakfast selection, clean rooms."
United States
Linda
The price is £106
includes taxes & fees
26 Apr - 27 Apr
Holiday Inn Express Annapolis East-Kent Island by IHG

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (898 reviews)
"Breakfast menu had a great variety and was fresh. "
United States
Timothy
The price is £88
includes taxes & fees
19 May - 20 May
Quality Inn Grasonville near Kent Island

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)
"Wonderful staff,Clean rooms and comfortable bed!!"
United States
Evette
The price is £89
includes taxes & fees
5 May - 6 May
Best Western Kent Narrows Inn

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 £105
includes taxes & fees
26 Apr - 27 Apr
St Michaels Inn

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (380 reviews)
"Parking was easy, could see car from room, coffee and tea offered all day, bike sign out was easy"
United States
Katy
The price is £122
includes taxes & fees
5 May - 6 May
Knapps Narrows Marina & Inn

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 £123
includes taxes & fees
28 Apr - 29 Apr
Hilton Garden Inn Kent Island Marina

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.6 out of 10, Excellent, (1,002 reviews)
"Great place to stay with lovely views"
United States
David
The price is £130
includes taxes & fees
10 May - 11 May
Rod 'N' Reel Resort

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (94 reviews)
"Great location. Beautiful room and exemplary service. "
United States
Nathan
The price is £147
includes taxes & fees
26 Apr - 27 Apr
Flag House Inn

The Wildset

The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (433 reviews)
"Best HOTEL EVER!!!"
United States
Ama
The price is £203
includes taxes & fees
5 May - 6 May
The Wildset

Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (133 reviews)
"We really enjoyed our stay at The Parsonage. The property and room were kept well. The staff were sweet and attentive. Very good location as far as walking distance to shops, restaurants and the waterfront area. I would certainly return and certainly recommend to anyone visiting St. Michael’s. "
United States
Katie
The price is £147
includes taxes & fees
26 Apr - 27 Apr
Parsonage Inn

Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
2.5 star property
Annapolis
8.8 out of 10, Excellent, (230 reviews)
"Hotel was clean staff was friendly"
United States
Kim
The price is £91
includes taxes & fees
28 Apr - 29 Apr
Candlewood Suites Annapolis by IHG

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.4 out of 10, Exceptional, (13 reviews)
"Beautiful place to stay with a breathtaking view of the Chesapeake Bay from a hilltop. Has a speakeasy bar in the basement which takes you back to the 1920’s. Breakfast is very subperb!"
United States
Philip
The price is £218
includes taxes & fees
26 Apr - 27 Apr
The Inn at Tacaro Estate

Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1,002 reviews)
"Clean room, amenities were great. Breakfast very good and parking safe. "
United States
Adriana M
The price is £64
includes taxes & fees
28 Apr - 29 Apr
Best Western Annapolis

The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.6 out of 10, Exceptional, (127 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 £192
includes taxes & fees
30 Apr - 1 May
The Tilghman Island 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 £161
includes taxes & fees
27 Apr - 28 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 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 £60 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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