Search Shady Side hotels

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

Top hotels and accommodation in Shady Side

Our top choices for Shady Side hotels

St Michaels Inn

2.5 star property
8.2 out of 10, Very good, (1000)
"Great place to stay"
The price is AU$149
includes taxes & fees
6 Oct - 7 Oct
St Michaels Inn

Quality Inn

2.5 star property
7.8 out of 10, Good, (822)
"Great place and great staff"
The price is AU$164
includes taxes & fees
17 Sept - 18 Sept
Quality Inn

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (896)
"Wonderful breakfast and lovely outdoor seating next to the water! My favorite place to stay when I visit!!!"
The price is AU$220
includes taxes & fees
14 Sept - 15 Sept
Holiday Inn Express Annapolis East-Kent Island by IHG

Best Western Kent Narrows Inn

2.5 star property
8.0 out of 10, Very good, (1005)
"Excellent location"
The price is AU$183
includes taxes & fees
15 Sept - 16 Sept
Best Western Kent Narrows Inn

Rod 'N' Reel Resort

4.0 star property
8.4 out of 10, Very good, (1000)
"great place "
The price is AU$236
includes taxes & fees
15 Sept - 16 Sept
Rod 'N' Reel Resort

Microtel Inn & Suites by Wyndham Gambrills

2.0 star property
9.0 out of 10, Wonderful, (1010)
"Reasonable priced nice clean hotel, loved the room and the location!"
The price is AU$138
includes taxes & fees
22 Sept - 23 Sept
Microtel Inn & Suites by Wyndham Gambrills

Anchored Inn at Hidden Harbour Marina

2.5 star property
9.4 out of 10, Exceptional, (449)
"The staff specifically Victoria was impeccable! "
The price is AU$310
includes taxes & fees
10 Sept - 11 Sept
Anchored Inn at Hidden Harbour Marina

Comfort Inn Conference Center

2.5 star property
9.2 out of 10, Wonderful, (1006)
"Very clean nd the breakfast was delicious "
The price is AU$170
includes taxes & fees
14 Sept - 15 Sept
Comfort Inn Conference Center

The Wildset

2.5 star property
9.8 out of 10, Exceptional, (369)
"Fantastic place for a couple getaway. "
The price is AU$415
includes taxes & fees
5 Oct - 6 Oct
The Wildset

Laurel Grove Inn on the South

3.5 star property
9.0 out of 10, Wonderful, (523)
"Great location with fantastic views. Very friendly owner "
The price is AU$311
includes taxes & fees
8 Oct - 9 Oct
Laurel Grove Inn on the South

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (417)
"Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. "
The price is AU$417
includes taxes & fees
1 Oct - 2 Oct
The Inn at Chesapeake Bay Beach Club

SpringHill Suites by Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (1005)
"Clean room, Good breakfast and friendly staff."
The price is AU$190
includes taxes & fees
15 Sept - 16 Sept
SpringHill Suites by Marriott Annapolis

Wylder Tilghman Island

2.0 star property
8.8 out of 10, Excellent, (72)
"Relax environment great food drinks and entertainment "
The price is AU$349
includes taxes & fees
18 Sept - 19 Sept
Wylder Tilghman Island

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (113)
"Hotel was great and peaceful. This hotel was water front. Nice surroundings!! I enjoyed to stay here."
The price is AU$342
includes taxes & fees
24 Sept - 25 Sept
Kent Island Resort

The Tilghman Island Inn

3.5 star property
9.6 out of 10, Exceptional, (107)
"Staff is so friendly and helpful. The location is very scenic. Rooms were clean and updated. "
The price is AU$342
includes taxes & fees
17 Sept - 18 Sept
The Tilghman Island Inn

Country Inn & Suites by Radisson, Annapolis, MD

3.0 star property
9.0 out of 10, Wonderful, (1005)
"Great place to stay. The pool and hot tub are great amenities. "
The price is AU$175
includes taxes & fees
16 Sept - 17 Sept
Country Inn & Suites by Radisson, Annapolis, MD

Holiday Inn Express & Suites Annapolis by IHG

2.5 star property
8.2 out of 10, Very good, (1000)
"Great staff….property a bit “tired” but a very friendly staff working hard to make it comfortable. A decent value for location and price!"
The price is AU$175
includes taxes & fees
14 Sept - 15 Sept
Holiday Inn Express & Suites Annapolis by IHG

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (995)
"Hotel was great, beautiful location near the water"
The price is AU$250
includes taxes & fees
14 Sept - 15 Sept
Hilton Garden Inn Kent Island Marina

Red Roof Inn Annapolis

2.0 star property
7.2 out of 10, Good, (385)
"Good"
The price is AU$131
includes taxes & fees
18 Sept - 19 Sept
Red Roof Inn Annapolis

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (38)
"The facility designed was out standing and the staff was very good. "
The price is AU$689
includes taxes & fees
11 Sept - 12 Sept
The Oaks Waterfront
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Shady Side Hotel Reviews

More cheap accommodation in Shady Side

More cheap accommodation in Shady Side

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

What's the best place to stay in Shady Side?

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway, located 18.6 mi (30 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 Historic Inns of Annapolis and Sonesta ES Suites 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?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This holiday home rental outside of Shady Side offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 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?

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway: Hotel located near Northwest Stadium. Features a snack bar/deli, a seasonal outdoor pool and buffet. Sonesta ES Suites Annapolis 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 13 hotels and other accommodation options to choose from. Find out more about Shady Side.

What should I see while I'm in Shady Side?

Favourite places to visit include Shadyside Park, Captain Avery Museum and Franklin Point State Park. You'll also find Smithsonian Environmental Research Center and London Town in the area. 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.