A river with boats, a marina, and a town with houses and buildings.

Shady Side hotels from RM348

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
10 Jul - 12 Jul
Next weekend
17 Jul - 19 Jul

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Shady Side hotels

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, (930 reviews)
"Room was clean and staff took very good care of us"
United States
Carol
The price is RM407
RM452 total
includes taxes & fees
19 Jul - 20 Jul
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, (1,007 reviews)
"Good hotel for the price"
United States
Brenda
The price is RM510
RM566 total
includes taxes & fees
12 Jul - 13 Jul
Best Western Kent Narrows Inn
Reception

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1,019 reviews)
"The staff was great, nice hotel bar and the location was close to everything!"
United States
Diane
The price is RM453
RM516 total
includes taxes & fees
26 Jul - 27 Jul
DoubleTree by Hilton Hotel Annapolis
Front of property

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1,006 reviews)
"Great location, modern rooms compared to area offerings."
United States
Shruti
The price is RM385
RM423 total
includes taxes & fees
14 Jul - 15 Jul
St Michaels Inn
Reception

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.4 out of 10, Exceptional, (155 reviews)
"It was such a lovely quaint resort. I loved everything about staying there. Thank you."
United States
Sue
The price is RM665
RM876 total
includes taxes & fees
9 Jul - 10 Jul
Kent Island Resort
Outdoor wedding area

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.6 out of 10, Excellent, (1,010 reviews)
"Awesome spot and room, nice walking distance from multiple places"
United States
Travis
The price is RM729
RM945 total
includes taxes & fees
9 Jul - 10 Jul
Rod 'N' Reel Resort
Exterior

Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills
2.0 star property
Gambrills
9.2 out of 10, Wonderful, (1,107 reviews)
"Perfect for a weekend stay while going to the let's go music fest. Our 2nd year staying here"
United States
Erin
The price is RM398
RM454 total
includes taxes & fees
3 Aug - 4 Aug
Microtel Inn & Suites by Wyndham Gambrills
Meeting facility

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,880 reviews)
"Great hotel..will definitely be back"
United States
Randy
The price is RM367
RM558 total
includes taxes & fees
13 Jul - 14 Jul
Historic Inns of Annapolis
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, (491 reviews)
"absolutely perfect for this traveler!"
United States
BENNY
The price is RM986
RM1,124 total
includes taxes & fees
9 Jul - 10 Jul
Anchored Inn at Hidden Harbour 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, (1,004 reviews)
"Beautiful view!!! Clean hotel and very nice helpful staff. Would stay again."
United States
Michele
The price is RM582
RM646 total
includes taxes & fees
13 Jul - 14 Jul
Holiday Inn Express Annapolis East-Kent Island by IHG
Lobby

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very good, (1,006 reviews)
"Breakfast was excellent and parking was convenient and safe"
United States
Paul
The price is RM406
RM463 total
includes taxes & fees
15 Jul - 16 Jul
Hilton Garden Inn Annapolis
Front of property

The Wildset

The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (468 reviews)
"Wonderful stay!"
United States
Rachel
The price is RM1,017
RM1,209 total
includes taxes & fees
28 Jul - 29 Jul
The Wildset
Exterior

George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (75 reviews)
"Mr Will very good Host and breakfast very delicious sure we will come back ā¤ļø"
United States
MENBERE
The price is RM802
RM883 total
includes taxes & fees
8 Jul - 9 Jul
George Brooks House B&B
Interior

Bragg Motel

Bragg Motel
2.0 star property
Upper Marlboro
The price is RM387
RM437 total
includes taxes & fees
6 Aug - 7 Aug
Bragg Motel
Terrace/patio

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (784 reviews)
"Great Stay!!"
United States
Richard
The price is RM725
RM804 total
includes taxes & fees
3 Aug - 4 Aug
Hyatt Place Kent Narrows & Marina
Dinner served

Comfort Inn Conference Center

Comfort Inn Conference Center
2.5 star property
Bowie
9.2 out of 10, Wonderful, (1,006 reviews)
"Great place and location."
United States
Francis
The price is RM446
RM504 total
includes taxes & fees
29 Jul - 30 Jul
Comfort Inn Conference Center
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 RM887
RM1,011 total
includes taxes & fees
7 Jul - 8 Jul
Flag House Inn
Exterior

Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
2.5 star property
Annapolis
8.0 out of 10, Very good, (1,004 reviews)
"Clean, breakfast was great"
United States
Robert Y. Vaughn
The price is RM394
RM449 total
includes taxes & fees
12 Jul - 13 Jul
Hampton Inn & Suites Annapolis
Desk, laptop workspace, blackout curtains, free WiFi

Rips Country Inn

Rips Country Inn
2.5 star property
Bowie
6.6 out of 10, (70 reviews)
"Convenient, quiet, and a restaurant right next door."
United States
Robin
The price is RM330
RM373 total
includes taxes & fees
7 Jul - 8 Jul
Rips Country Inn
Indoor pool

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1,006 reviews)
"Great place to stay for a short visit to Annapolis."
United States
Jeffrey
The price is RM480
RM548 total
includes taxes & fees
9 Jul - 10 Jul
Crowne Plaza Annapolis by IHG
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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
A river with boats, a marina, and a town with houses and buildings.

Top Shady Side Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Very friendly front desk staff Room was nice and clean Port of Call Restaurant buffet was excellent and very fair priced No doubt Iā€™ll choose Double Tree when I visit in the fall"
David 2-night trip
Posted less than an hour ago
DoubleTree by Hilton Hotel Annapolis

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 RM308 per night from 9 Jul to 10 Jul
RM308
RM348 total
9 Jul - 10 Jul
includes taxes & fees
6/10 (1,005 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 DoubleTree by Hilton Hotel Annapolis and La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway. 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?
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. Comfort Inn Largo-Washington DC East and Crowne Plaza Annapolis by IHG 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 16 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 24Ā°C, while the coldest months are January and February, with an average of 5Ā°C. Average annual precipitation for Shady Side is 1307 mm.

Explore a world of travel with Expedia