Shady Side Hotels from €76 - Fully Refundable Options

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

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Our top choices for Shady Side hotels

A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.

A spacious indoor area with brick walls, multiple tables and chairs, and string lights.

An aerial view of a coastal town with a marina, houses, and a bridge in the background.

A historic brick building with a red roof, multiple windows, and a central staircase.

1. Historic Inns of Annapolis

Historic District

Ashley

€118

includes taxes & fees

20 Oct - 21 Oct

A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.

A spacious lobby with a high ceiling, a central seating area with sofas and tables, and large windows with curtains.

A restaurant with wooden tables and chairs, a bar area, and a tiled floor.

A DoubleTree by Hilton hotel entrance with a brick facade, a gated driveway, and a clear sky.

2. DoubleTree by Hilton Hotel Annapolis

Annapolis

Michele

€108

includes taxes & fees

18 Oct - 19 Oct

A modern hotel room with a large bed, a separate bathroom with a bathtub, a desk, and a microwave.

A buffet with various food items, including omelets and baked goods, in stainless steel containers.

A microwave, a coffee maker, and a refrigerator in a kitchen area.

A coffee station with two coffee machines, a coffee press, and various coffee-related items on a wooden counter.

3. Holiday Inn Express & Suites Annapolis by IHG

Annapolis

Omer

€103

includes taxes & fees

18 Oct - 19 Oct

A modern hotel kitchen with a central island, seating area, and various kitchen appliances.

A hotel room with a large bed, a desk with a laptop, a television, and a door with a curtain.

A hotel lobby with a reception desk, seating area, and dining space.

A Best Western hotel with a modern facade, entrance with glass doors, and a parking area.

4. Best Western Annapolis

Annapolis

€81

includes taxes & fees

20 Oct - 21 Oct

A bar area with multiple seating options, including bar stools and tables, and a variety of bottles and glasses on shelves.

A hotel lobby with a long bar area, seating, and a projection screen.

An outdoor seating area with tables and chairs, blue umbrellas, and a brick building in the background.

A hotel lobby with a reception desk, seating area, and artwork on the walls.

5. Comfort Inn Conference Center

Bowie

Gloria

€110

includes taxes & fees

25 Oct - 26 Oct

An indoor swimming pool with clear glass ceilings, large windows, and lounge chairs.

A multi-story hotel with a brick facade, large windows, and an American flag.

A modern lounge area with two grey armchairs, a round coffee table, a fireplace, and decorative shelves.

A modern hotel lobby with round tables and blue chairs, a bar area with various liquor bottles, and contemporary lighting fixtures.

6. Crowne Plaza Annapolis by IHG

Annapolis

Jose

€107

includes taxes & fees

25 Oct - 26 Oct

A spacious living room with a large wooden coffee table, a leather sofa, and a chandelier.

A spacious dining area with multiple tables and chairs, a central bar area, and large windows providing natural light.

A hotel room with a large bed, a bedside table with a lamp, a phone, a mirror, and a bathroom with a bathtub and toilet.

A Country Inn & Suites by Radisson building with a brick facade, white columns, and a green roof.

7. Country Inn & Suites by Radisson, Annapolis, MD

Annapolis

Catherine

€93

includes taxes & fees

9 Nov - 10 Nov

A modern kitchen with white tiled walls, wooden flooring, and labeled sections for 'CRACKED' and 'BOKED'.

A gym with treadmills, weight machines, and dumbbells.

A hotel room with a sofa, a desk, a television, a chair, a bed, and a fireplace.

A patio area with a stone fire pit, outdoor furniture, and a covered seating area.

8. Sonesta ES Suites Annapolis

Edgewater

Dennis

€96

includes taxes & fees

9 Nov - 10 Nov

A modern lobby with a seating area, a fireplace, and a bookshelf.

A modern hotel room with a flat-screen TV, a sofa, a chair, and a small table.

A restaurant with a yellow cushioned bench, wooden tables, and chairs.

A hotel room with two beds, a desk with a computer, a TV, and a large window with a view of trees.

9. Hilton Garden Inn Annapolis Downtown

Annapolis

petra

€108

includes taxes & fees

25 Oct - 26 Oct

A Hampton Inn & Suites hotel with a modern design, featuring a prominent entrance and a covered outdoor area.

A hotel room with a bed, a desk with a TV, a sofa with a red pillow, and a window with curtains.

A spacious lobby with a fireplace, multiple seating areas, and a view of the upper floor.

A swimming pool with lounge chairs and a brick building in the background.

10. Hampton Inn & Suites Annapolis

Annapolis

Courtney

€99

includes taxes & fees

19 Oct - 20 Oct

A conference room with a large table, chairs, water bottles, and a flat-screen TV on the wall.

A kitchenette with a coffee maker, a microwave, a sink, and a framed picture of a bridge.

An outdoor patio with tables and chairs, a brick floor, and a building with a green roof in the background.

11. Hilton Garden Inn Annapolis

Annapolis

Glenn

€95

includes taxes & fees

9 Nov - 10 Nov

A multi-story hotel with a central entrance, a landscaped garden with flowers, and a metal sculpture.

A marina with docked boats, a picnic area, and a grassy lawn with a tree.

A marina with boats docked at wooden piers, surrounded by greenery and houses in the background.

A modern kitchen with a bar area, wooden flooring, and blue bar stools.

12. Anchored Inn at Hidden Harbour Marina

Deale

Beverly

€189

includes taxes & fees

18 Oct - 19 Oct

A courtyard with a stone fire pit surrounded by wicker furniture and a grassy lawn.

An indoor swimming pool with clear glass walls, lounge chairs, and a view of the outside.

A section of a hotel with a wall labeled "the market" and two refrigerated display cases filled with beverages and snacks.

13. Courtyard by Marriott Annapolis

Annapolis

Jim

€103

includes taxes & fees

1 Nov - 2 Nov

A modern living room with a large window, a dining area, and a kitchen in the background.

A modern hotel lobby with grey sofas, wooden accents, and a large TV on the wall.

A hotel room with a bed, desk, chair, television, and a window with curtains.

A modern gym with weight racks, benches, and exercise equipment.

14. Candlewood Suites Annapolis by IHG

Annapolis

Darren

€99

includes taxes & fees

25 Oct - 26 Oct

A modern kitchen with grey cabinets, a white countertop, and various kitchen appliances.

A hotel pool area with two pools, chairs, and a sunshade.

A hotel reception area with a reception desk, a television, and seating area.

A modern hotel with a flat roof and a sign reading "SPRINGHILL SUITES BY MARRIOTT".

15. SpringHill Suites by Marriott Annapolis

Annapolis

Lisa

€122

includes taxes & fees

1 Nov - 2 Nov

A circular fire pit surrounded by outdoor seating with a brick wall and a multi-story building in the background.

A reception desk with a 'HELLO' sign and 'Annapolis' text, wooden paneling, and hanging pendant lights.

A compact hotel room with a kitchenette, a desk with two chairs, a sofa, and a bed.

A hotel with a modern design, featuring a mix of brick and siding exteriors, a covered entrance, and a parking area.

16. TownePlace Suites by Marriott Annapolis

Annapolis

Nkusu Lauren

€116

includes taxes & fees

19 Oct - 20 Oct

A large, two-story barn-style building with a covered front porch and a garage.

A bedroom with a large bed, a bench, a dresser, and two windows with curtains.

A large, two-story white house with a porch and multiple windows.

A rectangular swimming pool with a blue interior, surrounded by white fences and shaded by trees.

17. Kent Island Resort

Stevensville

Bethany

€149

includes taxes & fees

28 Oct - 29 Oct

A gazebo with a dome, surrounded by a white fence, near a waterfront with a clear sky.

A modern bar area with a long counter and multiple bar stools.

A modern salon with multiple black salon chairs, a white reception desk, and large windows allowing natural light.

A bar area with multiple screens displaying sports content, a high ceiling with geometric patterns, and a view of the outside through large windows.

18. Rod 'N' Reel Resort

Chesapeake Beach

Kathleen K

€143

includes taxes & fees

20 Oct - 21 Oct

A multi-story Microtel by Wyndham hotel with a parking lot and a landscaped area in front.

A snack and beverage vending area with various snacks and drinks.

A hotel room with a bed, bedside tables, a desk with a chair, a microwave, a refrigerator, and a window with curtains.

A reception area with a modern design, featuring a reception desk, seating area with patterned ottomans, and a wall with a geometric pattern.

19. Microtel Inn & Suites by Wyndham Gambrills/Odenton

Gambrills

paul

€91

includes taxes & fees

3 Nov - 4 Nov

An outdoor patio with tables, chairs, and a fire feature.

A modern dining area with multiple tables and chairs, large windows with a view of greenery, and decorative wall mirrors.

A modern lounge area with a sofa, round tables, and chairs, featuring geometric wall decor and large windows.

A modern living room with a fireplace, a sofa, and a coffee table.

20. Fairfield Inn & Suites By Marriott Annapolis

Annapolis

Imola

€137

includes taxes & fees

28 Oct - 29 Oct

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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

Learn more about Shady Side

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

See all hotels in Shady Side

Top Shady Side Hotel Reviews

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

10/10 Excellent

"Nice place."

St Michaels Inn

10/10 Excellent

"It was extremely helpful to my mobility challenged companion to have a parking space right in front of the room. The lobby area was charming, comfortable with fresh coffee, particularly helpful when we had to wait for a tow truck driver for our disabled car. The staff member Alison provided help in a variety of ways, local auto shop, contact with a driver, fresh coffee, etc."

Microtel Inn & Suites by Wyndham Gambrills/Odenton

10/10 Excellent

"The hotel is well maintained and looks modern. Our room is clean and spacious. It has all the amenities I need, particularly microwave and refrigerator. It has a complimentary continental breakfast as well, basic and has limited options. What I like most of this hotel is the location! We are so near to a lot of restaurants, grocery store, department stores - I love my Target and Ross, and even movie theater. All in all, a great value hotel! We’ll definitely be staying here again in the future."

Comfort Inn Largo-Washington DC East

8/10 Good

"el servicio del hotel es muy bueno, los desayonos son muy ricos, el unico problema que tubimos ellos lo resolvieron sin ningun incombeniente, gracias por su excelente hospitalidad."

Sonesta ES Suites Annapolis

10/10 Excellent

"Shalinda was the most welcoming front desk staff i have ever encountered."

Crowne Plaza Annapolis by IHG

10/10 Excellent

"Good stay , wish the hot tub worked"

DoubleTree by Hilton Hotel Annapolis

8/10 Good

"Breakfast need to work on, it has nothing to eat then we have to go out buy breakfast. Everythingelse is good."

Rod 'N' Reel Resort

10/10 Excellent

"Beautiful property on the Chesapeake Bay. It was very clean. We went off season highly recommend."

The Inn at Chesapeake Bay Beach Club

10/10 Excellent

"Had an amazing stay here. The room was spotlessly clean from top to bottom. The linens were fresh, the bathroom was pristine, and everything felt completely sanitized. It’s rare to find a property that pays such close attention to detail. Fantastic housekeeping service!"

More cheap stays in Shady Side

St Michaels Inn

1228 S Talbot Street St. Michaels MD

€79

1 Nov - 2 Nov

includes taxes & fees

8/10 Very good! (1,000 reviews)

Best Western Annapolis

2520 Riva Rd Annapolis MD

€81

20 Oct - 21 Oct

includes taxes & fees

7.8/10 Good! (1,007 reviews)

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

€89

8 Nov - 9 Nov

includes taxes & fees

8/10 Very good! (1,005 reviews)

Microtel Inn & Suites by Wyndham Gambrills/Odenton

2525 Evergreen Rd. Gambrills MD

€91

3 Nov - 4 Nov

includes taxes & fees

9.2/10 Wonderful! (1,158 reviews)

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

€103

18 Oct - 19 Oct

includes taxes & fees

8.4/10 Very good! (1,001 reviews)

Comfort Inn Conference Center

4500 Crain Hwy Bowie MD

€110

25 Oct - 26 Oct

includes taxes & fees

Frequently asked questions

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

DoubleTree by Hilton Hotel Annapolis, located 9.8 mi (15.8 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 Crowne Plaza Annapolis by IHG. 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?

Crowne Plaza Annapolis by IHG: Hotel located near U.S. Naval Academy. Features free self parking, an indoor pool and complimentary wireless Internet access. Rod 'N' Reel Resort 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 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 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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Things to do in Maryland

Shady Side Hotels

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Shady Side

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Shady Side hotels

1. Historic Inns of Annapolis

2. DoubleTree by Hilton Hotel Annapolis

3. Holiday Inn Express & Suites Annapolis by IHG

4. Best Western Annapolis

5. Comfort Inn Conference Center

6. Crowne Plaza Annapolis by IHG

7. Country Inn & Suites by Radisson, Annapolis, MD

8. Sonesta ES Suites Annapolis

9. Hilton Garden Inn Annapolis Downtown

10. Hampton Inn & Suites Annapolis

11. Hilton Garden Inn Annapolis

12. Anchored Inn at Hidden Harbour Marina

13. Courtyard by Marriott Annapolis

14. Candlewood Suites Annapolis by IHG

15. SpringHill Suites by Marriott Annapolis

16. TownePlace Suites by Marriott Annapolis

17. Kent Island Resort

18. Rod 'N' Reel Resort

19. Microtel Inn & Suites by Wyndham Gambrills/Odenton

20. Fairfield Inn & Suites By Marriott Annapolis

Stay near popular Shady Side attractions

Shadyside Park

Captain Avery Museum

Learn more about Shady Side

Top Shady Side Hotel Reviews

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

St Michaels Inn

Microtel Inn & Suites by Wyndham Gambrills/Odenton

Comfort Inn Largo-Washington DC East

Sonesta ES Suites Annapolis

Crowne Plaza Annapolis by IHG

DoubleTree by Hilton Hotel Annapolis

Rod 'N' Reel Resort

The Inn at Chesapeake Bay Beach Club

More cheap stays in Shady Side

St Michaels Inn

Best Western Annapolis

Best Western Kent Narrows Inn

Microtel Inn & Suites by Wyndham Gambrills/Odenton

Holiday Inn Express & Suites Annapolis by IHG

Comfort Inn Conference Center

Frequently asked questions

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