𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Shady Side (2026)

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

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

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.

1. DoubleTree by Hilton Hotel Annapolis

Annapolis

Michele

S$141

includes taxes & fees

13 Oct - 14 Oct

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

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

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

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

2. Crowne Plaza Annapolis by IHG

Annapolis

Cynthia

S$160

includes taxes & fees

13 Oct - 14 Oct

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

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

3. SpringHill Suites by Marriott Annapolis

Annapolis

Lisa

S$173

includes taxes & fees

25 Oct - 26 Oct

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

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.

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

4. Historic Inns of Annapolis

Historic District

Ashley

S$176

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.

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

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

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

5. Comfort Inn Conference Center

Bowie

Titus

S$157

includes taxes & fees

12 Oct - 13 Oct

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

A gym with treadmills, weight machines, and dumbbells.

6. Sonesta ES Suites Annapolis

Edgewater

Philip

S$133

includes taxes & fees

27 Oct - 28 Oct

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

A hotel with a covered entrance, large columns, and a brick facade.

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

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

7. Holiday Inn Express & Suites Annapolis by IHG

Annapolis

Omer

S$160

includes taxes & fees

25 Oct - 26 Oct

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

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

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.

8. Fairfield Inn & Suites By Marriott Annapolis

Annapolis

Imola

S$147

includes taxes & fees

13 Oct - 14 Oct

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

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.

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

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

Annapolis

Leslie

S$139

includes taxes & fees

27 Oct - 28 Oct

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

A conference room with a long table, chairs, water bottles, and a projector.

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

A hotel room with two desks, two chairs, a carpeted floor, and artwork on the wall.

10. Hampton Inn & Suites Annapolis

Annapolis

Courtney

S$142

includes taxes & fees

4 Nov - 5 Nov

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

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

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.

11. Anchored Inn at Hidden Harbour Marina

Deale

Beverly

S$277

includes taxes & fees

29 Oct - 30 Oct

A modern lobby with a reception desk, seating area, and potted plants.

A Hilton Garden Inn with a large building and a smaller entrance building.

A modern bar area with a wooden counter, bar stools, and a wine display.

A hotel dining area with multiple tables and chairs, large windows, and a chandelier.

12. Hilton Garden Inn Annapolis

Annapolis

Glenn

S$147

includes taxes & fees

25 Oct - 26 Oct

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

A modern bar area with a long counter, bar stools, and shelves stocked with various bottles.

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.

13. Hilton Garden Inn Annapolis Downtown

Annapolis

petra

S$166

includes taxes & fees

2 Nov - 3 Nov

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 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.

14. Best Western Annapolis

Annapolis

Silvia

S$117

includes taxes & fees

13 Oct - 14 Oct

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

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

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

15. Courtyard by Marriott Annapolis

Annapolis

Jim

S$153

includes taxes & fees

25 Oct - 26 Oct

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

16. Graduate by Hilton Annapolis

Annapolis

Mark

S$214

includes taxes & fees

26 Oct - 27 Oct

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

An outdoor patio with a brick floor, surrounded by lush greenery and trees.

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

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

17. Candlewood Suites Annapolis by IHG

Annapolis

Darren

S$142

includes taxes & fees

1 Nov - 2 Nov

A marina with boats docked at wooden piers, surrounded by greenery.

A bed with two pillows, one with "HAPPY PLACE" text, and a framed picture above the bed.

A covered patio area with wicker furniture and a view of a building with large windows.

A waterfront property with houses, a dock, and a grassy area.

18. Knapps Narrows Marina & Inn

Sherwood

BARBARA

S$141

includes taxes & fees

1 Nov - 2 Nov

A patio with a barbecue grill, outdoor seating, and a small garden area with yellow flowers.

A modern hotel kitchen with wooden cabinets, a buffet area, and a dining area with wooden tables and chairs.

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

A modern hotel room with a kitchenette, a dining area, a sofa, and a small round table.

19. TownePlace Suites Bowie Town Center

Bowie

Dominick

S$143

includes taxes & fees

27 Oct - 28 Oct

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

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

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

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

20. TownePlace Suites by Marriott Annapolis

Annapolis

Nkusu Lauren

S$172

includes taxes & fees

1 Nov - 2 Nov

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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.

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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

Comfort Inn Largo-Washington DC East

10/10 Excellent

"Very close to getting public transport."

DoubleTree by Hilton Hotel Largo/Washington DC

10/10 Excellent

"my cozy room pet friendly staff"

Microtel Inn & Suites by Wyndham Gambrills/Odenton

10/10 Excellent

"This hotel was clean, well maintained, and conveniently located. The staff was helpful and pleasant. I would recommend a stay at the Microtel in Gambrills to anyone looking for a convenient stay in the area!"

Hilton Garden Inn Annapolis Downtown

10/10 Excellent

"Staff was great, hotel needs real renovation seems like they've done a lot of patch work. Parking should be complimentary for people staying in the hotel or a discounted rate. $35 a day for parking at the hotel you're staying at is crazy. There's very limited parking to begin with."

Best Western Annapolis

8/10 Good

"Friendly and respectful staff, clean premises, well stocked breakfast, rooms need better maintenance."

Sonesta ES Suites Annapolis

10/10 Excellent

"It is an excellent value for the cost!"

Rod 'N' Reel Resort

10/10 Excellent

"The gym was really small. The rooms are very nice"

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

10/10 Excellent

"It’s was a great experience besides the two roaches I found in the bathroom"

St Michaels Inn

10/10 Excellent

"Late night manager was extremely helpful!"

More cheap stays in Shady Side

Best Western Annapolis

2520 Riva Rd Annapolis MD

S$117

13 Oct - 14 Oct

includes taxes & fees

7.8/10 Good! (1,005 reviews)

St Michaels Inn

1228 S Talbot Street St. Michaels MD

S$125

7 Oct - 8 Oct

includes taxes & fees

Microtel Inn & Suites by Wyndham Gambrills/Odenton

2525 Evergreen Rd. Gambrills MD

S$136

1 Nov - 2 Nov

includes taxes & fees

9.2/10 Wonderful! (1,160 reviews)

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

S$153

14 Oct - 15 Oct

includes taxes & fees

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

Comfort Inn Conference Center

4500 Crain Hwy Bowie MD

S$157

12 Oct - 13 Oct

includes taxes & fees

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

S$160

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.

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 S$108

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. DoubleTree by Hilton Hotel Annapolis

2. Crowne Plaza Annapolis by IHG

3. SpringHill Suites by Marriott Annapolis

4. Historic Inns of Annapolis

5. Comfort Inn Conference Center

6. Sonesta ES Suites Annapolis

7. Holiday Inn Express & Suites Annapolis by IHG

8. Fairfield Inn & Suites By Marriott Annapolis

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

10. Hampton Inn & Suites Annapolis

11. Anchored Inn at Hidden Harbour Marina

12. Hilton Garden Inn Annapolis

13. Hilton Garden Inn Annapolis Downtown

14. Best Western Annapolis

15. Courtyard by Marriott Annapolis

16. Graduate by Hilton Annapolis

17. Candlewood Suites Annapolis by IHG

18. Knapps Narrows Marina & Inn

19. TownePlace Suites Bowie Town Center

20. TownePlace 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

Comfort Inn Largo-Washington DC East

DoubleTree by Hilton Hotel Largo/Washington DC

Microtel Inn & Suites by Wyndham Gambrills/Odenton

Hilton Garden Inn Annapolis Downtown

Best Western Annapolis

Sonesta ES Suites Annapolis

Rod 'N' Reel Resort

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

St Michaels Inn

More cheap stays in Shady Side

Best Western Annapolis

St Michaels Inn

Microtel Inn & Suites by Wyndham Gambrills/Odenton

Best Western Kent Narrows Inn

Comfort Inn Conference Center

Holiday Inn Express & Suites Annapolis by IHG

Frequently asked questions

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