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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, (909 reviews)
"Breakfast menu had a great variety and was fresh. "
United States
Timothy
The price is NZ$201
includes taxes & fees
27 May - 28 May
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, (1,089 reviews)
"Breakfast was great"
United States
Sean
The price is NZ$191
includes taxes & fees
31 May - 1 June
Microtel Inn & Suites by Wyndham Gambrills

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,000 reviews)
"It is a nice Hotel."
United States
Dale
The price is NZ$218
includes taxes & fees
2 June - 3 June
Best Western Kent Narrows Inn

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, (1,000 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 NZ$255
includes taxes & fees
7 June - 8 June
Holiday Inn Express Annapolis East-Kent Island by IHG

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 NZ$454
includes taxes & fees
27 May - 28 May
Anchored Inn at Hidden Harbour Marina

The Wildset

The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (445 reviews)
"Wonderful rooms and many amenities."
United States
Gene
The price is NZ$467
includes taxes & fees
3 June - 4 June
The Wildset

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.6 out of 10, Excellent, (1,001 reviews)
"Nice location "
United States
Duan
The price is NZ$288
includes taxes & fees
25 May - 26 May
Rod 'N' Reel Resort

The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.6 out of 10, Exceptional, (134 reviews)
"The inn is very lovely. The views are spectacular. Very easy access to restaurants and shopping. "
United States
Tracey
The price is NZ$471
includes taxes & fees
25 May - 26 May
The Tilghman Island Inn

Comfort Inn Conference Center

Comfort Inn Conference Center
2.5 star property
Bowie
9.2 out of 10, Wonderful, (1,002 reviews)
"Clean room, wonderful restaurant for dinner with many reasonable options, great staff and perfect location. "
United States
Lanie
The price is NZ$207
includes taxes & fees
15 June - 16 June
Comfort Inn Conference Center

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 NZ$600
includes taxes & fees
23 May - 24 May
George Brooks House B&B

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (763 reviews)
"Great Stay!!"
United States
Richard
The price is NZ$335
includes taxes & fees
16 June - 17 June
Hyatt Place Kent Narrows & Marina

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (138 reviews)
"Very nice room and wonderful stay."
United States
Julie
The price is NZ$352
includes taxes & fees
25 May - 26 May
Kent Island Resort

Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1,000 reviews)
"Older Hotel but clean and staff was great."
United States
Gregory
The price is NZ$173
includes taxes & fees
3 June - 4 June
Best Western Annapolis

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,854 reviews)
"Great location"
United States
Stephanie
The price is NZ$286
includes taxes & fees
1 June - 2 June
Historic Inns of Annapolis

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, (1,007 reviews)
"Great location with good breakfast. 👍"
United States
David
The price is NZ$201
includes taxes & fees
7 June - 8 June
Country Inn & Suites by Radisson, Annapolis, MD

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,001 reviews)
"Awesome "
United States
Nicholas
The price is NZ$294
includes taxes & fees
27 May - 28 May
Hilton Garden Inn Kent Island Marina

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 NZ$825
includes taxes & fees
26 May - 27 May
The Oaks Waterfront

Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (134 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 NZ$468
includes taxes & fees
26 May - 27 May
Parsonage Inn

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,000 reviews)
"We stayed 6 nights and breakfast was good every day."
United States
Daniel Glen Zechenelly
The price is NZ$251
includes taxes & fees
31 May - 1 June
SpringHill Suites by Marriott Annapolis

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1,000 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 NZ$221
includes taxes & fees
3 June - 4 June
St Michaels Inn
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

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Love dining, 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's the best place to stay in Shady Side?
Comfort Inn Largo-Washington DC East, located 18.1 mi (29.2 km) from the heart of Shady Side, is a top choice for your stay, based on our traveller data. Two other choices for your visit to the area are La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway and DoubleTree by Hilton Hotel Annapolis. See all available top hotels, or vacation rentals in Shady Side.
What are some of the best holiday rentals that Shady Side has to offer?
NEW! Charming Farm House in Historic Kent Island: This holiday home rental outside of Shady Side is located on a river, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. See all vacation rentals in Shady Side.
If I need to cancel my hotel reservation in Shady Side, will I receive a refund?
Yes, the majority of hotel room reservations are fully refundable if you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of check in. If you booked a non-refundable reservation, it might still be possible to cancel it and receive a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Shady Side.
What are some accommodation options with pools in Shady Side?
Comfort Inn Largo-Washington DC East: Hotel located near Northwest Stadium. Features buffet, an indoor pool and free self parking. La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway and DoubleTree by Hilton Hotel Largo/Washington DC are two additional hotels that offer an on-site pool. View all hotels with pools in Shady Side.
What is staying in Shady Side like?
Visitors can enjoy all that Shady Side has to offer, including the shopping, restaurants and parks. Tourists can also enjoy so much more including its museums. In Shady Side, there are 15 hotels and other accommodation options to choose from. Find out more about Shady Side.
What should I see while I'm in Shady Side?
Natural beauty is on display at Northern Chesapeake Bay, Chesapeake Bay and Shadyside Park. A couple of additional sights to add to your itinerary are Captain Avery Museum and Franklin Point State Park. Take a look at what more there is to see and do in Expedia's Shady Side guide.
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.

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