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Check prices for these dates

Tonight
15 Apr - 16 Apr
Tomorrow
16 Apr - 17 Apr
This weekend
17 Apr - 19 Apr
Next weekend
24 Apr - 26 Apr

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Our top choices for Shady Side hotels

Luxury Cottage, 1 Bedroom, Kitchen, River View | Private kitchen

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 ฿14,079
฿15,487 total
includes taxes & fees
16 Apr - 17 Apr
The Oaks Waterfront
Front of property

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1,000 reviews)
" Great place,great location, was in town for St Michael Chocolate fest "
United States
Katherine
The price is ฿4,140
฿4,554 total
includes taxes & fees
22 Apr - 23 Apr
St Michaels Inn
Breakfast, lunch, dinner served; sea views

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (380 reviews)
"everything was perfect!"
United States
John
The price is ฿19,291
฿21,220 total
includes taxes & fees
5 May - 6 May
Inn at Perry Cabin
Front of property

The Wildset

The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (431 reviews)
"Best HOTEL EVER!!!"
United States
Ama
The price is ฿7,326
฿8,762 total
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)
"Hosts were wonderful, breakfast was delicious, everything was walkable "
United States
Nathaly
The price is ฿5,119
฿5,630 total
includes taxes & fees
19 Apr - 20 Apr
Parsonage Inn
Exterior

George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (72 reviews)
"A beautiful renovated historical house with charm, clean rooms, decorative furnishings and a wonderful hot breakfast. What we enjoyed the most was the warm hospitality of Willard, Valerie, and the other staff. Very close to downtown St. Michael’s, but just far enough away to give a nice feel of natural serenity. Great for a quick getaway from the city. We will be back. "
United States
Charles
The price is ฿4,959
฿5,454 total
includes taxes & fees
16 Apr - 17 Apr
George Brooks House B&B
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (891 reviews)
"Staff was nice and room was clean "
United States
Lauren
The price is ฿3,378
฿3,750 total
includes taxes & fees
16 Apr - 17 Apr
Quality Inn Grasonville near Kent Island
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, (1,000 reviews)
"Beautiful area"
United States
Dan
The price is ฿4,178
฿4,637 total
includes taxes & fees
26 Apr - 27 Apr
Hilton Garden Inn Kent Island Marina
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, (987 reviews)
"Very nice hotel, good breakfast selection, clean rooms."
United States
Linda
The price is ฿3,871
฿4,297 total
includes taxes & fees
22 Apr - 23 Apr
Holiday Inn Express Annapolis East-Kent Island by IHG
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,000 reviews)
"Wonderful staff,Clean rooms and comfortable bed!!"
United States
Evette
The price is ฿3,177
฿3,527 total
includes taxes & fees
27 Apr - 28 Apr
Best Western Kent Narrows Inn
Terrace/patio

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (740 reviews)
"Clean hotel all around. Friendly stafff and comfortable environment."
United States
Jillian
The price is ฿4,863
฿5,398 total
includes taxes & fees
27 Apr - 28 Apr
Hyatt Place Kent Narrows & Marina
Exterior

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (379 reviews)
"Such a marvelous retreat! And the balcony facing the boats and the Bay at sunset is so welcome after exploring St Michael’s (a short 17 mins drive). Extremely friendly staff and good breakfast. Highly recommend to any nature lovers."
United States
Nadia
Knapps Narrows Marina & Inn
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 ฿3,922
฿5,724 total
includes taxes & fees
27 Apr - 28 Apr
Wylder Tilghman Island
Outdoor banquet area

The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.6 out of 10, Exceptional, (126 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 ฿7,518
฿8,270 total
includes taxes & fees
16 Apr - 17 Apr
The Tilghman Island Inn
Reception

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (137 reviews)
"Beautiful hotel, nice staff"
United States
Kim
The price is ฿3,569
฿4,923 total
includes taxes & fees
16 Apr - 17 Apr
Kent Island Resort
Front of property – evening/night

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (448 reviews)
"Very clean room, staff was very nice. "
United States
Byron
The price is ฿5,953
฿7,423 total
includes taxes & fees
22 Apr - 23 Apr
The Inn at Chesapeake Bay Beach Club
Outdoor wedding area

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.6 out of 10, Excellent, (1,000 reviews)
"Great place to stay with lovely views"
United States
David
The price is ฿4,623
฿5,771 total
includes taxes & fees
27 Apr - 28 Apr
Rod 'N' Reel Resort
Premium bedding, down duvets, pillow-top beds, in-room safe

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (917 reviews)
"Great waterfront room with roomy balcony. Gym was nice also. Can't wait for the var and restaurants to open."
United States
Douglas
The price is ฿9,245
฿10,540 total
includes taxes & fees
10 May - 11 May
Annapolis Waterfront Hotel, Autograph Collection
Lobby lounge

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (94 reviews)
"The B&B website and other on-line links claims "...excellent breakfast" and "the best breakfast in Annapolis". What was served were mini grocery store bought pastry, no fresh coffee, no juice, no plates, no one around. In addition, they state that for a large fee you can have valet parking on-site. There was no valet. I requested a refund for the valet parking and used that money to have a decent breakfast elsewhere. "
United States
Linda
The price is ฿5,819
฿6,633 total
includes taxes & fees
20 Apr - 21 Apr
Flag House 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 ฿5,920
฿6,749 total
includes taxes & fees
20 Apr - 21 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.
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Top Shady Side Hotel Reviews

Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills

8/10 Good
"Clean room"
marie 2-night trip
Posted 5 hours ago
Microtel Inn & Suites by Wyndham Gambrills

More cheap stays 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 ฿2,175 per night from 22 Apr to 23 Apr
฿2,175
฿2,458 total
22 Apr - 23 Apr
includes taxes & fees
6.2/10 (1,002 reviews)

Frequently asked questions

What's the best place to stay in Shady Side?
DoubleTree by Hilton Hotel Largo/Washington DC, located 18.8 mi (30.3 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 Graduate by Hilton Annapolis and Historic Inns of Annapolis. See all available top hotels, or 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?
DoubleTree by Hilton Hotel Largo/Washington DC: Hotel located near Northwest Stadium. Features free self parking, an indoor pool and a 24-hour fitness centre. Crowne Plaza Annapolis by IHG 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.