Hotels in Shady Side

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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.

Anchored Inn at Hidden Harbour Marina

Deale

$229

$261 total

includes taxes & fees

Sep 7 - Sep 8

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

A laundry room with four stacked washing machines and a black shelf.

A hotel reception desk with a modern design, a digital screen, and a beverage refrigerator.

A hotel entrance with a covered walkway, large glass doors, and a brick facade.

Holiday Inn Express & Suites Annapolis by IHG

Annapolis

$101

$115 total

includes taxes & fees

Aug 25 - Aug 26

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 restaurant with a high ceiling, large windows, and a central bar area.

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

Rod 'N' Reel Resort

Chesapeake Beach

$117

$164 total

includes taxes & fees

Sep 3 - Sep 4

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.

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

Courtyard by Marriott Annapolis

Annapolis

$92

$105 total

includes taxes & fees

Aug 30 - Aug 31

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

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

DoubleTree by Hilton Hotel Annapolis

Annapolis

$98

$111 total

includes taxes & fees

Aug 30 - Aug 31

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

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

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

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

Hilton Garden Inn Annapolis

Annapolis

$98

$111 total

includes taxes & fees

Sep 13 - Sep 14

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 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.

Country Inn & Suites by Radisson, Annapolis, MD

Annapolis

$95

$109 total

includes taxes & fees

Sep 13 - Sep 14

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 Best Western hotel with a modern facade, entrance with glass doors, and a parking area.

Best Western Annapolis

Annapolis

$80

$91 total

includes taxes & fees

Aug 30 - Aug 31

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

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

SpringHill Suites by Marriott Annapolis

Annapolis

$129

$147 total

includes taxes & fees

Aug 23 - Aug 24

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

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.

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

Sonesta ES Suites Annapolis

Edgewater

$98

$112 total

includes taxes & fees

Sep 22 - Sep 23

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

A hotel room with a sofa, a small table, a TV, a bed, and a view of greenery.

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

A hotel lobby with a reception desk, a fireplace, and a colorful rug.

Hampton Inn & Suites Annapolis

Annapolis

$98

$112 total

includes taxes & fees

Sep 16 - Sep 17

A large indoor swimming pool with clear blue water, surrounded by lounge chairs and a high ceiling with skylights.

A hotel lobby with a bar area, seating, and a patterned carpet.

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

A modern hotel lobby with a round wooden table, comfortable seating, a fireplace, and a reception desk with computers.

Crowne Plaza Annapolis by IHG

Annapolis

$105

$120 total

includes taxes & fees

Sep 7 - Sep 8

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

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

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

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

Candlewood Suites Annapolis by IHG

Annapolis

$98

$117 total

includes taxes & fees

Aug 30 - Aug 31

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

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

Fairfield Inn & Suites By Marriott Annapolis

Annapolis

$118

$135 total

includes taxes & fees

Aug 26 - Aug 27

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

A restaurant with a yellow cushioned bench, wooden tables, and chairs.

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

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

Hilton Garden Inn Annapolis Downtown

Annapolis

$104

$119 total

includes taxes & fees

Aug 30 - Aug 31

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

A marina with multiple boats docked during sunset.

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.

Historic Inns of Annapolis

Historic District

$110

$159 total

includes taxes & fees

Aug 30 - Aug 31

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.

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

Comfort Inn Conference Center

Bowie

$119

$134 total

includes taxes & fees

Aug 23 - Aug 24

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

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

A modern living room with a fireplace, a sofa, a coffee table, and a TV mounted on the wall.

Residence Inn By Marriott Annapolis

Annapolis

$144

$164 total

includes taxes & fees

Aug 26 - Aug 27

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

A reception desk with a 'HELLO' sign and 'Annapolis' text, wooden paneling, and hanging pendant lights.

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

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

TownePlace Suites by Marriott Annapolis

Annapolis

$118

$135 total

includes taxes & fees

Aug 30 - Aug 31

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

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

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

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

The Westin Annapolis

Annapolis

$169

$193 total

includes taxes & fees

Aug 30 - Aug 31

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Go beyond your typical stay in Shady Side

Pet friendly

Pool

Hot tub

Family friendly

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

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

Check out reviews of Shady Side hotels guests love

Rod 'N' Reel Resort

10/10 Excellent

"Very clean room, staff was very friendly and there are several restaurants right there. Oh, plus the casino!!"

Historic Inns of Annapolis

10/10 Excellent

"Great location nicely appointed room, great paintings"

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"Great staff everywhere on the property."

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent

"A"

Comfort Inn Conference Center

10/10 Excellent

"Exceptional staff and services. They provided every amenity. The included daily breakfast was well prepared and staff stood at the ready to help and insure the area was kept clean and accessible asguests came and went. I would definitely recommend as well as use this location again."

Crowne Plaza Annapolis by IHG

10/10 Excellent

"Rooms where clean, staff was nice"

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent

"Top notch staff from the front desk, housekeeping and valet. My only real complaint was the early AM construction in the hallway. But all the workers were friendly and courteous to me passing by to get to the elevator."

Hyatt Place Kent Narrows & Marina

10/10 Excellent

"Property was well maintained and clean. Room was spacious and with a nice view. Parking is somewhat limited. Location is also central to area,attractions."

Comfort Inn Largo-Washington DC East

10/10 Excellent

"Great stay"

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.

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