Top 10 Hotels in Shady Side, MD from ₩112,604 - Competitive Prices

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

A modern kitchen with a large island, bar stools, and a wine rack.

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

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

1. Anchored Inn at Hidden Harbour Marina

Deale

Beverly

₩247,592

₩282,255 total

includes taxes & fees

Oct 14 - Oct 15

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

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

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

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

₩141,195

₩160,963 total

includes taxes & fees

Oct 18 - Oct 19

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

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

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

A staircase with a wooden handrail, a blue wall, and a ceiling light fixture.

3. Rod 'N' Reel Resort

Chesapeake Beach

Kathleen K

₩192,992

₩214,221 total

includes taxes & fees

Oct 20 - Oct 21

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

A bar area with multiple seating options, including bar stools and round tables, and a well-stocked bar counter.

4. Crowne Plaza Annapolis by IHG

Annapolis

Jose

₩140,154

₩159,776 total

includes taxes & fees

Oct 25 - Oct 26

A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.

A bar area with a circular seating arrangement, a central bar counter, and a hanging plant decoration.

A store with shelves of beverages, a counter with a cash register, and baskets with items.

5. The Westin Annapolis

Annapolis

Bobbi

₩265,625

₩302,813 total

includes taxes & fees

Oct 25 - Oct 26

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

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

A hotel room with a bed, a desk, a chair, a coffee machine, and a tray table.

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

6. SpringHill Suites by Marriott Annapolis

Annapolis

Lisa

₩158,841

₩181,079 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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

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

7. Holiday Inn Express & Suites Annapolis by IHG

Annapolis

Omer

₩134,815

₩153,689 total

includes taxes & fees

Oct 19 - Oct 20

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

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

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

A marina with multiple boats docked during sunset.

8. Historic Inns of Annapolis

Historic District

Ashley

₩114,366

₩176,027 total

includes taxes & fees

Oct 21 - Oct 22

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 reception desk, seating area, and artwork on the walls.

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

A Comfort Inn hotel with a parking lot and a covered entrance.

9. Comfort Inn Conference Center

Bowie

Gloria

₩145,493

₩164,407 total

includes taxes & fees

Oct 14 - Oct 15

A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.

A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.

10. The Inn at Chesapeake Bay Beach Club

Stevensville

scott

₩272,299

₩336,209 total

includes taxes & fees

Nov 2 - Nov 3

A marina with numerous boats docked, a prominent building with a dome in the background, and a clear view of the water.

A hotel lobby with a high ceiling, large windows, and a blue and white color scheme. Tables and chairs are arranged for dining or meetings.

A bar with a brick wall, a mounted shark, and various bottles and glasses on shelves.

A spacious atrium with a high ceiling, skylights, and a patterned floor.

11. Graduate by Hilton Annapolis

Annapolis

Mark

₩195,922

₩223,351 total

includes taxes & fees

Oct 26 - Oct 27

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

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

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 swimming pool with a tiled edge, wooden chairs, and tables around it.

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

Annapolis

Catherine

₩121,734

₩138,777 total

includes taxes & fees

Nov 9 - Nov 10

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

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.

A modern lobby with a reception desk, seating area, and a patterned rug.

13. Sonesta ES Suites Annapolis

Edgewater

Dennis

₩125,471

₩143,038 total

includes taxes & fees

Nov 1 - Nov 2

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 modern Courtyard by Marriott hotel with a well-lit entrance, landscaped garden, and a clear sky.

14. Courtyard by Marriott Annapolis

Annapolis

Jim

₩133,907

₩152,654 total

includes taxes & fees

Nov 1 - Nov 2

15. Hilton Garden Inn Annapolis Downtown

Annapolis

petra

₩141,195

₩160,963 total

includes taxes & fees

Oct 25 - Oct 26

A balcony with a table set for two, overlooking a marina with boats.

A waterfront property with a docked boat, a tall building with balconies, and a church spire in the background.

A hotel room with a large bed, a chair, a small table, and a view of a body of water.

The exterior of the Annapolis Waterfront Hotel with a clear entrance, large windows, and a bench outside.

16. Annapolis Waterfront Hotel, Autograph Collection

Historic District

William

₩297,927

₩339,638 total

includes taxes & fees

Nov 2 - Nov 3

An outdoor patio area with seating arrangements and a fire feature.

A modern bar area with a wooden counter, bar stools, a television screen, and a variety of beverages.

A Courtyard by Marriott hotel with a curved entrance, multiple floors, and a brick facade.

A hotel room with two beds, a desk, a TV, and a bathroom.

17. Courtyard by Marriott Bowie

Bowie

Halima

₩178,997

₩202,266 total

includes taxes & fees

Oct 25 - Oct 26

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

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

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

18. Hilton Garden Inn Annapolis

Annapolis

Glenn

₩123,669

₩140,984 total

includes taxes & fees

Nov 9 - Nov 10

A hot tub in a grassy area with a building in the background.

A luxurious living room with a leather sofa, a vintage trunk, and a fireplace.

A room with a tufted armchair, a vase with white flowers, and a window with a view of the outdoors.

A cozy room with a brick fireplace, leather armchairs, and a rustic wooden table.

19. The Inn at Tacaro Estate

Tracys Landing

kristine

₩466,953

₩532,332 total

includes taxes & fees

Nov 1 - Nov 2

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

A gym with treadmills, elliptical machines, and exercise balls.

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

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

20. Best Western Annapolis

Annapolis

Silvia

₩105,716

₩120,517 total

includes taxes & fees

Oct 20 - Oct 21

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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 savor its top-notch restaurants.

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Captain Avery Museum

You can spend time exploring the galleries in Captain Avery Museum in Shady Side. Stroll along the area's waterfront, or simply savor its top-notch restaurants.

See properties

Learn more about Shady Side

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

See all hotels in Shady Side

Top Shady Side Hotel Reviews

More cheap stays in Shady Side

St Michaels Inn

1228 S Talbot Street St. Michaels MD

₩106,917

₩117,609 total

Nov 1 - Nov 2

includes taxes & fees

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

Best Western Annapolis

2520 Riva Rd Annapolis MD

₩105,716

₩120,517 total

Oct 20 - Oct 21

includes taxes & fees

7.8/10 Good! (1,008 reviews)

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

₩119,972

₩133,170 total

Nov 8 - Nov 9

includes taxes & fees

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

Microtel Inn & Suites by Wyndham Gambrills/Odenton

2525 Evergreen Rd. Gambrills MD

₩119,131

₩135,810 total

Nov 3 - Nov 4

includes taxes & fees

9.2/10 Wonderful! (1,158 reviews)

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

₩134,815

₩153,689 total

Oct 19 - Oct 20

includes taxes & fees

8.4/10 Very Good! (1,003 reviews)

Comfort Inn Conference Center

4500 Crain Hwy Bowie MD

₩145,493

₩164,407 total

Oct 14 - Oct 15

includes taxes & fees

Frequently asked questions

Where is the best place for a 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 traveler data. Two other choices for your trip 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.

If I need to cancel my hotel reservation in Shady Side, will I receive a refund?

Yes, the majority of hotel reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of your scheduled arrival. If you booked a non-refundable reservation, you might be able to cancel it and be given a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Shady Side.

Where can I learn more about changing or cancelling my trip to Shady Side?

To find more details about updating your trip to Shady Side or cancelling it, click here.

Where is the best hotel to stay near Shadyside Park?

Anchored Inn at Hidden Harbour Marina is one of the top choices for your stay based on our traveler data, and this hotel offers an outdoor pool and free parking. It's located 4.8 mi (7.7 km) from Shadyside Park.

What about the best place to stay near Captain Avery Museum?

One of the top choices for your stay is Anchored Inn at Hidden Harbour Marina, located 5 mi (8.1 km) from Captain Avery Museum, and this hotel offers an outdoor pool and free parking.

What are some accommodations 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 onsite pool. View all hotels with pools in Shady Side.

What's the best place to stay near Ronald Reagan Washington National Airport (DCA)?

Hyatt Regency Crystal City is a popular 4-star hotel featuring a restaurant and an outdoor pool. It's located a short 0.6 mi (1 km) from Ronald Reagan Washington National Airport. Other options near the airport are Courtyard by Marriott Arlington Crystal City/Reagan National and Hilton Garden Inn Reagan National Airport.

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 accommodations 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 agenda are Captain Avery Museum and Franklin Point State Park. Check out what more 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 temp of 75°F, while the coldest months are January and February with an average of 40°F. Average annual precipitation for Shady Side is 51 inches.

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Book Hotels in Shady Side on Expedia.com

Find hotels in Shady Side, MD from ₩112,604

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. Anchored Inn at Hidden Harbour Marina

2. DoubleTree by Hilton Hotel Annapolis

3. Rod 'N' Reel Resort

4. Crowne Plaza Annapolis by IHG

5. The Westin Annapolis

6. SpringHill Suites by Marriott Annapolis

7. Holiday Inn Express & Suites Annapolis by IHG

8. Historic Inns of Annapolis

9. Comfort Inn Conference Center

10. The Inn at Chesapeake Bay Beach Club

11. Graduate by Hilton Annapolis

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

13. Sonesta ES Suites Annapolis

14. Courtyard by Marriott Annapolis

15. Hilton Garden Inn Annapolis Downtown

16. Annapolis Waterfront Hotel, Autograph Collection

17. Courtyard by Marriott Bowie

18. Hilton Garden Inn Annapolis

19. The Inn at Tacaro Estate

20. Best Western Annapolis

Stay near popular Shady Side attractions

Shadyside Park

Captain Avery Museum

Learn more about Shady Side

Top Shady Side Hotel Reviews

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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