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

Hotels in Shady Side

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

1. DoubleTree by Hilton Hotel Annapolis

Annapolis

$83

$95 total

includes taxes & fees

Sep 27 - Sep 28

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 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.

2. Sonesta ES Suites Annapolis

Edgewater

$97

$110 total

includes taxes & fees

Sep 23 - Sep 24

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

A modern hotel lobby with a sectional sofa, ottomans, round tables, potted plants, and a large window.

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.

3. Hilton Garden Inn Annapolis

Annapolis

$93

$107 total

includes taxes & fees

Sep 28 - Sep 29

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

A self-service snack and drink kiosk with refrigerated sections, a window with blinds, and a tiled floor.

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

A modern hotel kitchen with a buffet setup, including a waffle maker, coffee station, and various food containers.

4. Hampton Inn & Suites Annapolis

Annapolis

$98

$111 total

includes taxes & fees

Sep 30 - Oct 1

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 bar area, wooden flooring, and blue bar stools.

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

5. Anchored Inn at Hidden Harbour Marina

Deale

$211

$240 total

includes taxes & fees

Oct 6 - Oct 7

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.

6. Best Western Annapolis

Annapolis

$75

$85 total

includes taxes & fees

Sep 27 - Sep 28

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.

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

7. Courtyard by Marriott Annapolis

Annapolis

$100

$114 total

includes taxes & fees

Sep 28 - Sep 29

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

8. Crowne Plaza Annapolis by IHG

Annapolis

$110

$125 total

includes taxes & fees

Sep 27 - Sep 28

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

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

9. Holiday Inn Express & Suites Annapolis by IHG

Annapolis

$101

$115 total

includes taxes & fees

Sep 27 - Sep 28

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

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

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

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

10. Candlewood Suites Annapolis by IHG

Annapolis

$98

$117 total

includes taxes & fees

Oct 4 - Oct 5

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

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

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

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

11. SpringHill Suites by Marriott Annapolis

Annapolis

$129

$147 total

includes taxes & fees

Sep 27 - Sep 28

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

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

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.

12. Rod 'N' Reel Resort

Chesapeake Beach

$161

$212 total

includes taxes & fees

Oct 7 - Oct 8

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 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.

13. Comfort Inn Conference Center

Bowie

$109

$123 total

includes taxes & fees

Oct 7 - Oct 8

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

A marina with multiple boats docked during sunset.

14. Historic Inns of Annapolis

Historic District

$110

$159 total

includes taxes & fees

Oct 12 - Oct 13

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

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

Annapolis

$95

$109 total

includes taxes & fees

Oct 12 - Oct 13

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

16. Hilton Garden Inn Annapolis Downtown

Annapolis

$122

$139 total

includes taxes & fees

Sep 30 - Oct 1

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.

17. Fairfield Inn & Suites By Marriott Annapolis

Annapolis

$135

$154 total

includes taxes & fees

Sep 27 - Sep 28

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

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.

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

18. Knapps Narrows Marina & Inn

Sherwood

$150

$165 total

includes taxes & fees

Sep 23 - Sep 24

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

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.

A modern hotel lobby with a sofa area, a flat-screen TV, and a dining area.

19. Microtel Inn & Suites by Wyndham Gambrills/Odenton

Gambrills

$92

$105 total

includes taxes & fees

Oct 12 - Oct 13

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.

20. TownePlace Suites by Marriott Annapolis

Annapolis

$118

$135 total

includes taxes & fees

Sep 28 - Sep 29

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Go beyond your typical stay in Shady Side

Top landmarks in Shady Side

Shadyside Park

Shadyside Park is 0.4 mi (0.6 km) from central Shady Side, why not stop by during your stay. Our travelers also like this walkable area for its port and restaurants.If you like Shadyside Park, you'll love Maryland Quiet Waters Park and Ellen O. Moyer Nature Park at Back Creek, both just a short drive away.

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Captain Avery Museum

Captain Avery Museum is 0.5 mi (0.8 km) from central Shady Side, why not stop by during your stay. Why not take a stroll along the port and watch the sunset while you're here? If you want to experience more of the culture Shady Side has to offer, head to Shadyside Park, Galesville Heritage Museum, and Triton Beach.

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Learn more about Shady Side

Shady Side is well-known for its attractions such as Northern Chesapeake Bay and Chesapeake Bay.

See all hotels in Shady Side

Check out reviews of Shady Side hotels guests love

Anchored Inn at Hidden Harbour Marina

Deale

10/10 Exceptional

We needed overnight accommodations before heading out for a day of sailing on the bay and Hidden Harbour popped up as the closest venue geographically and we're glad it did. The accommodations are new, with quality and fixtures and bathrooms that you wouldn't mind taking home with you. The price seemed fair and as we watched the full moon rising from our deck we wished that we were spending a week.

Rico

Lillian

Candlewood Suites Annapolis by IHG

Annapolis

10/10 Exceptional

Jordan

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 dining room with a round table set for six, surrounded by wooden chairs. A fireplace with ornate details is visible, and a large mirror hangs above it.

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

Kent Island Resort

Stevensville

10/10 Exceptional

I stayed here for a quick overnight and did not utilize many of the amenities however, the staff was incredibly kind overall and with tips on dinner. This place is historic, which is a nice way of saying old but classic. Don’t expect a huge room, the photos portray the room accurately. Some things were a little rickety, but everything was clean. Overall I recommend this if you’re solo or a couple looking for a place as you enjoy the bay.

John

Microtel Inn & Suites by Wyndham Gambrills/Odenton

Gambrills

10/10 Exceptional

Anonymous traveler

SpringHill Suites by Marriott Annapolis

Annapolis

10/10 Exceptional

Julie

Frequently Asked Questions

What hotels do travelers like in Shady Side?

Guests like DoubleTree by Hilton Hotel Annapolis, Historic Inns of Annapolis and Graduate by Hilton Annapolis.

Can I book a refundable hotel in Shady Side?

If you need the flexibility to change your plans to Shady Side, most properties provide refundable* bookable rates. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.

Where can I stay in Shady Side if I want a vacation rental instead of a hotel?

If you want to find a good alternative to a hotel, browse our selection of 12 vacation homes.

What will the weather in Shady Side be like during my vacation?

The warmest months in Shady Side are usually July and August with an average temp of 75°F. January and February are the chilliest months when the average temp is 40°F. The rainiest months are July and August.

Why should I book my Shady Side accommodation with Hotels.com?

There are plenty of reasons to book your Shady Side travel with us: our free cancellations on selected hotels* gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.