Shady Side Hotel & Accommodation Deals 2026 from AU$110 - Compare prices by date

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Shady Side

Pet friendly

Apartment

Family friendly

Condo

Spa pool

Pool

Cottage

Waterpark

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Shady Side hotels

A historic brick building with a corner turret and multiple windows, located on a city street with flags and street lamps.

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.

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

1. Historic Inns of Annapolis

Historic District

Scott

AU$188

includes taxes & fees

9 Nov - 10 Nov

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 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".

2. SpringHill Suites by Marriott Annapolis

Annapolis

Kaiya

AU$178

includes taxes & fees

15 Nov - 16 Nov

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 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.

3. DoubleTree by Hilton Hotel Annapolis

Annapolis

Michele

AU$148

includes taxes & fees

22 Nov - 23 Nov

A modern hotel room with a large bed, a flat-screen TV, a bathroom with a bathtub, and a desk with a chair.

A breakfast buffet area with a display of cinnamon sweet rolls, a sign indicating the roll selection, and a patterned wall in the background.

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.

4. Holiday Inn Express & Suites Annapolis by IHG

Annapolis

Omer

AU$149

includes taxes & fees

22 Nov - 23 Nov

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

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

A gym with treadmills, weight machines, and dumbbells.

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

5. Sonesta ES Suites Annapolis

Edgewater

Ann Christine

AU$135

includes taxes & fees

12 Nov - 13 Nov

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

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.

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

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

Annapolis

Catherine

AU$135

includes taxes & fees

23 Nov - 24 Nov

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

A modern living room with a fireplace, two armchairs, a coffee table, and decorative items.

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

A well-lit snack and beverage kiosk with a variety of snacks and drinks, including bottled water, juices, and snacks.

7. Crowne Plaza Annapolis by IHG

Annapolis

Jose

AU$167

includes taxes & fees

22 Nov - 23 Nov

A Hilton Garden Inn with a prominent entrance, multiple flags, and a well-maintained parking area.

A hotel room with two beds, a desk, a chair, a television, and a large window with curtains.

A modern kitchen with a bar area, bar stools, and a television mounted on the wall.

8. Hilton Garden Inn Annapolis

Annapolis

Walter

AU$151

includes taxes & fees

9 Nov - 10 Nov

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

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

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.

9. Comfort Inn Conference Center

Bowie

Gloria

AU$176

includes taxes & fees

25 Oct - 26 Oct

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 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.

10. Anchored Inn at Hidden Harbour Marina

Deale

sherman

AU$301

includes taxes & fees

26 Oct - 27 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.

11. Courtyard by Marriott Annapolis

Annapolis

Jim

AU$163

includes taxes & fees

9 Nov - 10 Nov

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

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.

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

12. Best Western Annapolis

Annapolis

Silvia

AU$110

includes taxes & fees

23 Nov - 24 Nov

A hotel room with two beds, a desk, a television, and a large window with curtains.

13. Hilton Garden Inn Annapolis Downtown

Annapolis

petra

AU$171

includes taxes & fees

3 Nov - 4 Nov

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

A building with a sign reading "The Inn."

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

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

14. Knapps Narrows Marina & Inn

Sherwood

Jim

AU$204

includes taxes & fees

30 Oct - 31 Oct

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

A gym with treadmills, elliptical machines, a bench, and a rack of dumbbells.

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

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

15. Hampton Inn & Suites Annapolis

Annapolis

Christopher

AU$149

includes taxes & fees

22 Nov - 23 Nov

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

A bar area with a long counter, multiple stools, and a television above.

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

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

16. Fairfield Inn & Suites By Marriott Annapolis

Annapolis

Imola

AU$206

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a large bed, a desk with a flat-screen TV, a chair, a small table with a lamp, and a window with curtains.

A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.

A reception desk with a modern design, a digital display, and a check-in counter.

17. Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

Terry Kyungho

AU$157

includes taxes & fees

22 Nov - 23 Nov

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

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.

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.

18. Graduate by Hilton Annapolis

Annapolis

Nadine

AU$225

includes taxes & fees

22 Nov - 23 Nov

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

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.

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

19. TownePlace Suites by Marriott Annapolis

Annapolis

Nkusu Lauren

AU$192

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

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

A hotel room with a flat-screen TV, a sofa, a chair, a small table, a desk with two chairs, a lamp, and a framed artwork on the wall.

20. TownePlace Suites Bowie Town Center

Bowie

Jennifer

AU$159

includes taxes & fees

8 Nov - 9 Nov

View all properties

Save an average of 15% on thousands of hotels when you're signed in

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

Recent Reviews in Shady Side

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent

"Easy access to downtown, Great waterside restaurants."

The Westin Annapolis

10/10 Excellent

"Great last minute booking. All went smoothly"

Rod 'N' Reel Resort

8/10 Good

"The Hotel was excellent. However, Expedia did not disclose that there was an additional charge for resort fee that was not included in the quoted price from Expedia. There was an additional $33.00 when I checked into the hotel. I could have gone with a different online reservation cheaper."

Best Western Annapolis

8/10 Good

"If you want to get a feel for Annapolis, you should try a hotel closer to the harbor. Since we had seen Annapolis many times and were looking for a quick, efficient stay, this met our needs. A few remarks on the property; - Needs updates -bathroom door did not close fully - mystery eggs were part of breakfast, but coffee was good."

St Michaels Inn

8/10 Good

"older facility but kept clean. a good value for an over night"

Sonesta ES Suites Annapolis

10/10 Excellent

"Very pleasant surprise! Great price for studio apartment- way better than the Marriott I just checked out of!"

Comfort Inn Largo-Washington DC East

8/10 Good

"Convenient location, nice staff, needs updating and better quality lobby coffee"

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent

"It’s a hotel that is a bit worn but the rooms are great and the staff is very polite. I’ll definitely be back."

Comfort Inn Conference Center

10/10 Excellent

"Clean comfortable and quiet. Lots of places to eat nearby. Will book here again!!"