Guest Houses in Shady Side
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A river with boats, a marina, and a town with houses and buildings.

Search Guest Houses in Shady Side from CA $158

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your current months are November, 2026 and December, 2026.

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Our top choices for Shady Side guest houses

A modern kitchen with a stainless steel refrigerator, white cabinetry, a wooden dining table with chairs, and a large window with blinds.

A two-story house with a covered porch and a balcony.

A living room with a sofa, a coffee table, a TV, and a patterned rug.

A covered outdoor seating area with white railings, a bench, and a table with a small plant.

1. West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis

West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis

Homewood

10.0 out of 10, Exceptional, (30 reviews)

10/10

Exceptional

(30 reviews)

"Very clean, nice area and very convenient to where we needed to be "

Jordan B.

The price is CA $158

CA $158

CA $468 total

includes taxes & fees

Nov 10 - Nov 11

West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Love dining out, parks, and museums? Get away to Shady Side!

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Top reviews in Shady Side

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

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.

Historic Inns of Annapolis

Historic District

10/10 Excellent

Great hotel great location. Friendly staff

Kelly

Reviewed April 29, 2026Reviewed April 29, 2026

Historic Inns of Annapolis

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 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.

Anchored Inn at Hidden Harbour Marina

Deale

10/10 Excellent

Valerie

Reviewed July 27, 2026Reviewed July 27, 2026

Anchored Inn at Hidden Harbour Marina

A swimming pool with a clear blue water, surrounded by lounge chairs and a glass wall.

A modern lobby with a sectional sofa, a coffee table, and a blue armchair.

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

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

Crowne Plaza Annapolis by IHG

Annapolis

10/10 Excellent

Nice for family

Tarun

Reviewed September 3, 2024Reviewed September 3, 2024

Crowne Plaza Annapolis by IHG

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 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.

DoubleTree by Hilton Hotel Annapolis

Annapolis

10/10 Excellent

Bon emplacement et aux standards des Doubletree

Jean

Reviewed October 25, 2026Reviewed October 25, 2026

DoubleTree by Hilton Hotel Annapolis

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

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

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

A gym with treadmills, weight machines, and dumbbells.

Sonesta ES Suites Annapolis

Edgewater

10/10 Excellent

Clean. Very nice. Courteous staff.

karen

Reviewed November 11, 2025Reviewed November 11, 2025

Sonesta ES Suites Annapolis

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.

A bar with a brick wall, a mounted shark, and various bottles and glasses on shelves.

Graduate by Hilton Annapolis

Annapolis

10/10 Excellent

Great burger in restaurant

JONATHAN

Reviewed September 15, 2026Reviewed September 15, 2026

Graduate by Hilton Annapolis

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 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

10/10 Excellent

All good great room suite all high end Staff eere the best i have experienced in a longtime

Steven

Reviewed April 18, 2026Reviewed April 18, 2026

TownePlace Suites by Marriott Annapolis

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

A hotel room with a bed, a desk with a chair, a television, a kitchenette, and a shower area.

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

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

TownePlace Suites Bowie Town Center

Bowie

10/10 Excellent

Everything was clean 😁

chantal

Reviewed March 17, 2026Reviewed March 17, 2026

TownePlace Suites Bowie Town Center

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.

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

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

Comfort Inn Conference Center

Bowie

10/10 Excellent

I appreciate the location for my purposea. Comfortable, quiet, pleasant personnel.

Maureen

Reviewed September 10, 2024Reviewed September 10, 2024

Comfort Inn Conference Center

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.

Courtyard by Marriott Annapolis

Annapolis

10/10 Excellent

Okay

Shirley

Reviewed July 16, 2026Reviewed July 16, 2026

Courtyard by Marriott Annapolis

A hotel room with two beds, a desk with a chair, a television, and a large window with a view of greenery.

Hilton Garden Inn Annapolis Downtown

Annapolis

10/10 Excellent

Nice hotel in a very central part of town

Francesco

Reviewed July 8, 2026Reviewed July 8, 2026

Hilton Garden Inn Annapolis Downtown

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

A reception area with a modern design, featuring a reception desk, seating area with patterned ottomans, and a wall with a geometric pattern.

Microtel Inn & Suites by Wyndham Gambrills/Odenton

Gambrills

10/10 Excellent

Super clean

Mario

Reviewed May 12, 2026Reviewed May 12, 2026

Microtel Inn & Suites by Wyndham Gambrills/Odenton

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

A modern bar area with a wooden counter, bar stools, a television screen, and a variety of beverages.

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.

Courtyard by Marriott Bowie

Bowie

10/10 Excellent

Had a pleasant stay. Staff were very friendly.

Darko

Reviewed November 11, 2025Reviewed November 11, 2025

Courtyard by Marriott Bowie

A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.

A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.

An outdoor event area with round tables and a view of the water.

Hyatt Place Kent Narrows & Marina

Grasonville

10/10 Excellent

Good place

Uri

Reviewed July 11, 2026Reviewed July 11, 2026

Hyatt Place Kent Narrows & Marina

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Search Guest Houses in Shady Side from CA $158

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Shady Side guest houses

1. West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis

Learn more about Shady Side

Top reviews in Shady Side

Historic Inns of Annapolis

10/10 Excellent

Explore a world of travel with Expedia