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24 Apr - 25 Apr
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25 Apr - 26 Apr
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24 Apr - 26 Apr
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1 May - 3 May

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Our top choices for Shady Side hotels

Exterior

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 AU$389
includes taxes & fees
27 Apr - 28 Apr
Wylder Tilghman Island
Reception

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 AU$259
includes taxes & fees
27 Apr - 28 Apr
Kent Island Resort
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, (482 reviews)
"absolutely perfect for this traveler!"
United States
BENNY
The price is AU$243
includes taxes & fees
26 Apr - 27 Apr
Anchored Inn at Hidden Harbour Marina
Exterior

Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills
2.0 star property
Gambrills
9.2 out of 10, Wonderful, (1,069 reviews)
"Always great stay "
United States
Damani
The price is AU$149
includes taxes & fees
10 May - 11 May
Microtel Inn & Suites by Wyndham Gambrills
American cuisine

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 AU$149
includes taxes & fees
28 Apr - 29 Apr
Comfort Inn Conference Center
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, (993 reviews)
"Very nice hotel, good breakfast selection, clean rooms."
United States
Linda
The price is AU$171
includes taxes & fees
26 Apr - 27 Apr
Holiday Inn Express Annapolis East-Kent Island by IHG
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, (898 reviews)
"Breakfast menu had a great variety and was fresh. "
United States
Timothy
The price is AU$165
includes taxes & fees
19 May - 20 May
Quality Inn Grasonville near Kent Island
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,002 reviews)
"Wonderful staff,Clean rooms and comfortable bed!!"
United States
Evette
The price is AU$168
includes taxes & fees
5 May - 6 May
Best Western Kent Narrows Inn
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 place,great location, was in town for St Michael Chocolate fest "
United States
Katherine
The price is AU$194
includes taxes & fees
28 Apr - 29 Apr
St Michaels Inn
Exterior

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 AU$230
includes taxes & fees
3 May - 4 May
Knapps Narrows Marina & Inn
Terrace/patio

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)
"Beautiful area"
United States
Dan
The price is AU$232
includes taxes & fees
27 Apr - 28 Apr
Hilton Garden Inn Kent Island Marina
Outdoor wedding area

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 AU$253
includes taxes & fees
6 May - 7 May
Rod 'N' Reel Resort
Lobby lounge

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 AU$290
includes taxes & fees
26 Apr - 27 Apr
Flag House Inn
Front of property

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 AU$384
includes taxes & fees
5 May - 6 May
The Wildset
Porch

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 AU$278
includes taxes & fees
26 Apr - 27 Apr
Parsonage Inn
Lobby

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 AU$174
includes taxes & fees
24 May - 25 May
Candlewood Suites Annapolis by IHG
Seasonal outdoor pool, pool umbrellas, pool loungers

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 AU$392
includes taxes & fees
27 Apr - 28 Apr
The Inn at Tacaro Estate
Dining

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 AU$121
includes taxes & fees
29 Apr - 30 Apr
Best Western Annapolis
Outdoor banquet area

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 AU$361
includes taxes & fees
26 Apr - 27 Apr
The Tilghman Island Inn
Exterior

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 AU$298
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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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

Captain Avery Museum

You can spend time exploring the galleries in Captain Avery Museum during your trip to Shady Side. Stroll along the area's waterfront or simply savour its top-notch restaurants.
See properties

Top Shady Side Hotel Reviews

Recent Reviews in Shady Side

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

10/10 Excellent
"It was a clean and spacious room."
Penny 1-night trip
Posted 1 hour ago
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

More cheap accommodation in Shady Side

WoodSpring Suites Washington DC East Arena Drive

WoodSpring Suites Washington DC East Arena Drive

1603 Brightseat Rd. Hyattsville MD
The price is AU$114 per night from 5 May to 6 May
AU$114
5 May - 6 May
includes taxes & fees
6.2/10 (1,001 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 Comfort Inn Largo-Washington DC East 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?
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. Offers buffet, an indoor pool and free self parking. DoubleTree by Hilton Hotel Largo/Washington DC and La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway 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 14 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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