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Check prices for these dates

This weekend
12 June - 14 June
Next weekend
19 June - 21 June

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Our top choices for Shady Side hotels

Indoor pool

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)
"Good hotel for the price"
United States
Brenda
The price is AU$173
includes taxes & fees
28 June - 29 June
Best Western Kent Narrows Inn
Suite, 1 Queen Bed, Non Smoking

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (917 reviews)
"Room was clean and staff took very good care of us"
United States
Carol
The price is AU$167
includes taxes & fees
21 June - 22 June
Quality Inn Grasonville near Kent Island
Exterior

Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills
2.0 star property
Gambrills
9.2 out of 10, Wonderful, (1,100 reviews)
"Breakfast was great"
United States
Sean
The price is AU$165
includes taxes & fees
7 July - 8 July
Microtel Inn & Suites by Wyndham Gambrills
Outdoor wedding area

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.6 out of 10, Excellent, (1,008 reviews)
"Awesome spot and room, nice walking distance from multiple places"
United States
Travis
The price is AU$270
includes taxes & fees
23 June - 24 June
Rod 'N' Reel Resort
Lobby

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, (1,036 reviews)
"Friendly staff, easy parking, great breakfast"
United States
Theresa
The price is AU$168
includes taxes & fees
21 June - 22 June
Country Inn & Suites by Radisson, Annapolis, MD
Front of property

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1,002 reviews)
"Great location, modern rooms compared to area offerings."
United States
Shruti
The price is AU$184
includes taxes & fees
16 June - 17 June
St Michaels Inn
Reception

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (142 reviews)
"We loved the quaintness of the room, complete with a gas fireplace and floor to ceiling drapes. Having a restaurant right on site was incredible. I especially loved the girl dinner deal! We enjoyed the stay and the property was beautiful."
United States
Kiana
The price is AU$290
includes taxes & fees
10 June - 11 June
Kent Island Resort
Exterior

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, (1,001 reviews)
"Beautiful view!!! Clean hotel and very nice helpful staff. Would stay again."
United States
Michele
The price is AU$211
includes taxes & fees
16 June - 17 June
Holiday Inn Express Annapolis East-Kent Island by IHG
Front of property

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (487 reviews)
"absolutely perfect for this traveler!"
United States
BENNY
The price is AU$383
includes taxes & fees
10 June - 11 June
Anchored Inn at Hidden Harbour Marina
Reception

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1,014 reviews)
"It was one of the nicest places we've stayed in our travels."
United States
William
The price is AU$172
includes taxes & fees
10 June - 11 June
DoubleTree by Hilton Hotel Annapolis
Dining

Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1,009 reviews)
"Clean, reasonably priced , great staff and excellent breakfast!"
United States
Brian
The price is AU$134
includes taxes & fees
14 June - 15 June
Best Western Annapolis
Meeting facility

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,868 reviews)
"Great hotel..will definitely be back"
United States
Randy
The price is AU$217
includes taxes & fees
15 June - 16 June
Historic Inns of Annapolis
Exterior

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (386 reviews)
"Breakfast is excellent, staff very friendly"
United States
Polina
Knapps Narrows Marina & Inn
King Jacuzzi Room

Executive Inn And Suites

Executive Inn And Suites
2.0 star property
Upper Marlboro
7.2 out of 10, Good, (581 reviews)
"Clean and accommodating staff."
United States
Annette
The price is AU$149
includes taxes & fees
13 June - 14 June
Executive Inn And Suites
Terrace/patio

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (767 reviews)
"Great Stay!!"
United States
Richard
The price is AU$309
includes taxes & fees
29 June - 30 June
Hyatt Place Kent Narrows & Marina
Lobby

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very good, (1,005 reviews)
"Breakfast was excellent and parking was convenient and safe"
United States
Paul
The price is AU$168
includes taxes & fees
6 July - 7 July
Hilton Garden Inn Annapolis
Free daily buffet breakfast

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
3.0 star property
Edgewater
8.8 out of 10, Excellent, (1,011 reviews)
"Lots of room nice arrangement, good outdoor places to be,"
United States
Norma
The price is AU$192
includes taxes & fees
11 June - 12 June
Sonesta ES Suites Annapolis
Front of property

The Wildset

The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (455 reviews)
"Wonderful stay!"
United States
Rachel
The price is AU$389
includes taxes & fees
6 July - 7 July
The Wildset
Dinner served

Comfort Inn Conference Center

Comfort Inn Conference Center
2.5 star property
Bowie
9.2 out of 10, Wonderful, (1,008 reviews)
"Great place and location."
United States
Francis
The price is AU$170
includes taxes & fees
5 July - 6 July
Comfort Inn Conference Center
Outdoor banquet area

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 AU$398
includes taxes & fees
30 June - 1 July
The Tilghman Island 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

Shadyside Park

Explore the great outdoors at Shadyside Park, a lovely green space in Shady Side. Stroll along the area's waterfront or simply savour its top-notch restaurants.
See properties

Learn more about Shady Side

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

See all hotels in 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

Top Shady Side Hotel Reviews

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Nice hotel with good amenities. It was a mix of updated and outdated, but the outdated wasn’t too big of a deal. Nice staff."
Aaron 1-night trip
Posted 3 hours ago
Country Inn & Suites by Radisson, Annapolis, MD

More cheap accommodation in Shady Side

Country Inn & Suites by Radisson, Washington, D.C. East - Capitol Heights, MD

Country Inn & Suites by Radisson, Washington, D.C. East - Capitol Heights, MD

8850 Hampton Mall Drive North Capitol Heights MD
The price is AU$158 per night from 16 June to 17 June
AU$158
16 June - 17 June
includes taxes & fees
6.4/10 (1,008 reviews)

Frequently asked questions

What's the best place to stay in Shady Side?
Historic Inns of Annapolis, located 9.6 mi (15.4 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 Largo/Washington DC. 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?
Lovely bay views with kayaks, bikes, fire pit, crabbing & more: This highly rated holiday home rental in Shady Side offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable 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. You can relax into your holiday with a garden and a selection of games. 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?
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway: Hotel located near Northwest Stadium. Provides a snack bar/deli, a seasonal outdoor pool and buffet. DoubleTree by Hilton Hotel Largo/Washington DC and Comfort Inn Largo-Washington DC East 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 Shadyside Park, Northern Chesapeake Bay and Chesapeake Bay. 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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