𝗧𝗢𝗣 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Shady Side from RM352 (2026) - 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 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 modern kitchen with a large island, bar stools, and a wine rack.

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

1. Anchored Inn at Hidden Harbour Marina

Deale

Beverly

RM757

RM863 total

includes taxes & fees

18 Oct - 19 Oct

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

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.

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

2. SpringHill Suites by Marriott Annapolis

Annapolis

Kaiya

RM486

RM554 total

includes taxes & fees

1 Nov - 2 Nov

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

A buffet with labeled trays of turkey sausage and cookies.

A modern office setup with two monitors, a keyboard, and two wooden chairs.

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

3. Holiday Inn Express & Suites Annapolis by IHG

Annapolis

Omer

RM388

RM442 total

includes taxes & fees

15 Nov - 16 Nov

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

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

4. DoubleTree by Hilton Hotel Annapolis

Annapolis

Michele

RM432

RM492 total

includes taxes & fees

18 Oct - 19 Oct

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

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

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.

5. Crowne Plaza Annapolis by IHG

Annapolis

Jose

RM449

RM512 total

includes taxes & fees

15 Nov - 16 Nov

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.

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.

6. Historic Inns of Annapolis

Historic District

Jennifer

RM350

RM538 total

includes taxes & fees

9 Nov - 10 Nov

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

An outdoor patio area with tables and chairs, covered by large orange umbrellas, and a brick building in the background.

A conference room with multiple tables and chairs, arranged in rows, with a carpeted floor and a framed picture on the wall.

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

7. Hampton Inn & Suites Annapolis

Annapolis

Courtney

RM398

RM454 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

Annapolis

Catherine

RM372

RM424 total

includes taxes & fees

9 Nov - 10 Nov

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

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

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.

9. Sonesta ES Suites Annapolis

Edgewater

Dennis

RM388

RM442 total

includes taxes & fees

8 Nov - 9 Nov

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 waterfront area with boats docked, a clear sky, and buildings in the background.

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

10. Annapolis Waterfront Hotel, Autograph Collection

Historic District

William

RM911

RM1,039 total

includes taxes & fees

1 Nov - 2 Nov

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.

11. Best Western Annapolis

Annapolis

Silvia

RM309

RM352 total

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 modern kitchen with a white countertop, stainless steel appliances, and wooden cabinets.

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.

12. TownePlace Suites by Marriott Annapolis

Annapolis

Nkusu Lauren

RM482

RM549 total

includes taxes & fees

1 Nov - 2 Nov

13. Hilton Garden Inn Annapolis Downtown

Annapolis

petra

RM432

RM492 total

includes taxes & fees

1 Nov - 2 Nov

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

RM409

RM467 total

includes taxes & fees

1 Nov - 2 Nov

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

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.

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

15. Comfort Inn Conference Center

Bowie

Gloria

RM445

RM503 total

includes taxes & fees

25 Oct - 26 Oct

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

A modern hotel lobby with a curved seating area, a bar, and a large bookshelf.

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

16. The Westin Annapolis

Annapolis

Bobbi

RM812

RM926 total

includes taxes & fees

29 Oct - 30 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.

17. Hilton Garden Inn Annapolis

Annapolis

Walter

RM378

RM431 total

includes taxes & fees

9 Nov - 10 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 bar area with a long counter, multiple stools, and a television above.

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

18. Fairfield Inn & Suites By Marriott Annapolis

Annapolis

Imola

RM551

RM628 total

includes taxes & fees

8 Nov - 9 Nov

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

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.

A reception area with two wooden reception desks, a stone wall, and a modern ceiling design.

19. Courtyard by Marriott Bowie

Bowie

Halima

RM547

RM619 total

includes taxes & fees

2 Nov - 3 Nov

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

A modern lounge area with a blue sofa, red chairs, and plaid armchairs. A coffee table with books and a vase of flowers is in the center. Large windows offer a view of a brick building with awnings.

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

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.

20. Graduate by Hilton Annapolis

Annapolis

Mark

RM599

RM683 total

includes taxes & fees

26 Oct - 27 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

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Graduate by Hilton Annapolis

10/10 Excellent

"Clean room, very nice decor and great staff"

Comfort Inn Largo-Washington DC East

8/10 Good

"Upon checking inn we decided we did not want to be looking at the dumpster the whole weekend so asked for the interstate view They were very accommodating easy going and made that happen No complaints about thr stay very comfy basic for a 2day weekend very close to ALOT of attractions"

Rod 'N' Reel Resort

10/10 Excellent

"First time staying at the resort. We stayed two nights to celebrate my wife's birthday. I had ordered flowers that were delivered before our arrival and frontbdesk had them delivered to our room. The views from the waterfront tower build were amazing. The entire resort is very clean and well maintained. Good choice of restaurants/bars on site. Other restaurants are walkable or a short drive. The casino was surprisingly quiet and very clean, relaxing way to pass some time and maybe win some money. Enjoyed walking though the railroad museum that is on site as well. Everyone on this property were friendly and helpful. Will definitely return!"

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"my stay went very well. the room was very clean and pleasant. the staff helped me with a couple of items, and the breakfast staff in the restaurant was extremely friendly and helpful."

The Inn at Chesapeake Bay Beach Club

10/10 Excellent

"The staff was awesome. Very professional and helpful. Our room was cleaned and well maintained. The food was great and the spa service was awesome as well."

Microtel Inn & Suites by Wyndham Gambrills/Odenton

10/10 Excellent

"Clean, we'll maintained. Staffers friendly but professional A great stay"

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent

"Perfect place to stay! Classy. Clean comfortable amazing staff"

Best Western Annapolis

8/10 Good

"Noisy balcony"

More cheap stays in Shady Side

Best Western Annapolis

2520 Riva Rd Annapolis MD

RM309

RM352 total

1 Nov - 2 Nov

includes taxes & fees

St Michaels Inn

1228 S Talbot Street St. Michaels MD

RM327

RM360 total

1 Nov - 2 Nov

includes taxes & fees

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

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

RM367

RM407 total

8 Nov - 9 Nov

includes taxes & fees

Microtel Inn & Suites by Wyndham Gambrills/Odenton

2525 Evergreen Rd. Gambrills MD

RM361

RM411 total

3 Nov - 4 Nov

includes taxes & fees

9.2/10 Wonderful! (1,152 reviews)

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

RM388

RM442 total

15 Nov - 16 Nov

includes taxes & fees

Comfort Inn Conference Center

4500 Crain Hwy Bowie MD

RM445

RM503 total

25 Oct - 26 Oct

includes taxes & fees

9.2/10 Wonderful! (1,005 reviews)

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.

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.

Shady Side hotels from RM352

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. SpringHill Suites by Marriott Annapolis

3. Holiday Inn Express & Suites Annapolis by IHG

4. DoubleTree by Hilton Hotel Annapolis

5. Crowne Plaza Annapolis by IHG

6. Historic Inns of Annapolis

7. Hampton Inn & Suites Annapolis

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

9. Sonesta ES Suites Annapolis

10. Annapolis Waterfront Hotel, Autograph Collection

11. Best Western Annapolis

12. TownePlace Suites by Marriott Annapolis

13. Hilton Garden Inn Annapolis Downtown

14. Courtyard by Marriott Annapolis

15. Comfort Inn Conference Center

16. The Westin Annapolis

17. Hilton Garden Inn Annapolis

18. Fairfield Inn & Suites By Marriott Annapolis

19. Courtyard by Marriott Bowie

20. Graduate by Hilton 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

Graduate by Hilton Annapolis

Comfort Inn Largo-Washington DC East

Rod 'N' Reel Resort

DoubleTree by Hilton Hotel Annapolis

The Inn at Chesapeake Bay Beach Club

Microtel Inn & Suites by Wyndham Gambrills/Odenton

Annapolis Waterfront Hotel, Autograph Collection

Best Western Annapolis

More cheap stays in Shady Side

Best Western Annapolis

St Michaels Inn

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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