Shady Side Holiday Rentals, Maryland: Private House Rentals

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 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 reception desk, seating area, and artwork on the walls.

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

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

1. Comfort Inn Conference Center

Bowie

Rachel

3.103.877 ₫

3.507.381 ₫ total

includes taxes & fees

30 Aug - 31 Aug

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 Courtyard by Marriott hotel with a curved entrance, multiple floors, and a brick facade.

A hotel room with two beds, a desk, a TV, and a bathroom.

2. Courtyard by Marriott Bowie

Bowie

Yolanda

3.497.730 ₫

3.952.435 ₫ total

includes taxes & fees

7 Sept - 8 Sept

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

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

3. SpringHill Suites by Marriott Annapolis

Annapolis

Joshua

2.793.489 ₫

3.184.577 ₫ total

includes taxes & fees

13 Sept - 14 Sept

A spacious lobby with a modern design, featuring a seating area with blue and yellow chairs, a large abstract painting on the wall, and a patterned carpet.

A modern hotel lobby with a blue sofa, a yellow chair, a small table, and a kitchen area with coffee machines.

A spacious lobby with a central dining area, multiple seating options, and a large TV screen on the right wall.

A modern hotel with a stone facade, a blue van parked in front, and a clear sky.

4. Hampton Inn & Suites Glenarden/Washington DC

Lanham

Jeffrey

2.759.060 ₫

3.117.739 ₫ total

includes taxes & fees

7 Sept - 8 Sept

A two-story building with a covered entrance and an American flag.

A hotel room with two beds, a chair, and a painting on the wall.

A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.

5. St Michaels Inn

St. Michaels

Karen

2.323.995 ₫

2.556.395 ₫ total

includes taxes & fees

31 Aug - 1 Sept

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.

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

6. Sonesta ES Suites Annapolis

Edgewater

Sophia

2.399.636 ₫

2.735.585 ₫ total

includes taxes & fees

22 Sept - 23 Sept

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

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.

A snack and beverage vending area with various snacks and drinks.

7. Microtel Inn & Suites by Wyndham Gambrills

Gambrills

William

2.616.386 ₫

2.982.680 ₫ total

includes taxes & fees

13 Sept - 14 Sept

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

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

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

A spacious lobby with a high ceiling, a central seating area with sofas and tables, and large windows with curtains.

8. DoubleTree by Hilton Hotel Annapolis

Annapolis

Fabiana

2.545.179 ₫

2.901.505 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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.

9. Anchored Inn at Hidden Harbour Marina

Deale

Dale

5.196.516 ₫

5.923.971 ₫ total

includes taxes & fees

8 Sept - 9 Sept

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

A pool area with a hot tub, lounge chairs, and a no diving sign.

A modern hotel lobby with a sectional sofa, armchairs, a coffee table, and a chandelier.

A gym with multiple treadmills and elliptical machines.

10. Crowne Plaza Annapolis by IHG

Annapolis

Heather

2.530.051 ₫

2.884.258 ₫ total

includes taxes & fees

13 Sept - 14 Sept

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

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

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

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

Annapolis

Leslie

2.483.102 ₫

2.830.736 ₫ total

includes taxes & fees

27 Sept - 28 Sept

Two Adirondack chairs facing a calm body of water with a clear sky above.

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

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

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

Grasonville

Betty

3.208.209 ₫

3.561.113 ₫ total

includes taxes & fees

28 Sept - 29 Sept

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 gym with treadmills, elliptical machines, and exercise balls.

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

13. Best Western Annapolis

Annapolis

George

2.089.509 ₫

2.382.039 ₫ total

includes taxes & fees

13 Sept - 14 Sept

A patio with outdoor seating, overlooking a marina with boats.

A spacious dining area with a large rectangular table, multiple chairs, and a chandelier.

A marina with multiple boats docked, a Hilton Garden Inn hotel, and a parking area.

A waterfront hotel with multiple balconies, a marina with yachts, and a well-lit exterior.

14. Hilton Garden Inn Kent Island Marina

Grasonville

roney

4.388.726 ₫

4.871.485 ₫ total

includes taxes & fees

31 Aug - 1 Sept

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.

15. Courtyard by Marriott Annapolis

Annapolis

Phyllis

2.503.968 ₫

2.854.524 ₫ total

includes taxes & fees

7 Sept - 8 Sept

A hotel patio with outdoor seating, a fire pit, and a brick facade.

A swimming pool with lounge chairs and a view of trees.

A hotel lobby with a reception desk, a refrigerator stocked with beverages, and shelves with snacks and bottled water.

A modern bistro with a bar area, seating, and a menu display.

16. Courtyard Largo Medical Center Drive

Upper Marlboro

Nicole

3.009.457 ₫

3.400.685 ₫ total

includes taxes & fees

7 Sept - 8 Sept

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.

17. Historic Inns of Annapolis

Historic District

Stephanie

2.784.975 ₫

4.066.911 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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

A hotel lobby with multiple dining areas, a fireplace, and a balcony with railings.

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

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

18. Hampton Inn & Suites Annapolis

Annapolis

Meghalee

2.566.567 ₫

2.925.887 ₫ total

includes taxes & fees

21 Sept - 22 Sept

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.

19. Hyatt Place Kent Narrows & Marina

Grasonville

Karen

4.355.861 ₫

4.835.006 ₫ total

includes taxes & fees

8 Sept - 9 Sept

A hotel room with a large bed, a bedside table with a phone, a nightstand, a wall-mounted TV, and a bathtub.

A golf course with a pond, a fountain, and a bridge.

A building with a sign reading "The Inn of the Hills" and a staircase leading to the entrance.

A living room with a sofa, a coffee table, a dining table with chairs, a mirror, a window with curtains, a radiator, a magazine rack, and a television.

20. Executive Inn And Suites

Upper Marlboro

Will

2.218.360 ₫

2.506.746 ₫ total

includes taxes & fees

30 Aug - 31 Aug

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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

St Michaels Inn

8/10 Good

"The rooms, though dated, are clean. I did bring to the attention of the manager that the towel bar in my bathroom was coming off. The handrail to walk down the steps into the pool was also loose, which I think is a safety hazard. The manager acknowledged he knew about it, but despite tons of cosmetic work being done outside, which was a bit inconvenient, the hand rail was not tightened Staff was nice, especially Tamia at the front desk and Helena in the breakfast room. The rooms are spacious and the A/C works fine!"

DoubleTree by Hilton Hotel Largo/Washington DC

10/10 Excellent

"for the rooms to be outdated they were well maintained & cleaned!! Staff was friendly breakfast was flavorful and parking was limited but available no issues"

Holiday Inn Express & Suites Annapolis by IHG

10/10 Excellent

"."

Comfort Inn Conference Center

8/10 Good

"The pool was soothing."

Crowne Plaza Annapolis by IHG

10/10 Excellent

"Large room"

Microtel Inn & Suites by Wyndham Gambrills

10/10 Excellent

"Elijah and Channing were so kind and helpful! We enjoyed our stay and would definitely go back."

Rod 'N' Reel Resort

10/10 Excellent

"It look like they did a lot of upgrades very nice. I really appreciate the staff and service. I will be back soon 😉"

Hilton Garden Inn Annapolis Downtown

10/10 Excellent

"Reception staff are very helpful, hassle free check in and out process.Good dining options within walking distance and very close to the marina and downtown area."

Sonesta ES Suites Annapolis

10/10 Excellent

"Spacious rooms, very good breakfast selection, even had tacos for breakfast!"

More cheap stays in Shady Side

WoodSpring Suites Washington DC East Arena Drive

1603 Brightseat Rd. Hyattsville MD

2.060.557 ₫

per night

30 Aug - 31 Aug

St Michaels Inn

1228 S Talbot Street St. Michaels MD

2.323.995 ₫

per night

31 Aug - 1 Sept

8/10 Very good! (1,011 reviews)

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

2.556.134 ₫

per night

27 Sept - 28 Sept

8.4/10 Very good! (1,001 reviews)

Hampton Inn & Suites Annapolis

124 Womack Dr Annapolis MD

2.566.567 ₫

per night

21 Sept - 22 Sept

8.2/10 Very good! (1,001 reviews)

Microtel Inn & Suites by Wyndham Gambrills

2525 Evergreen Rd. Gambrills MD

2.616.386 ₫

per night

13 Sept - 14 Sept

9.2/10 Wonderful! (1,130 reviews)

Comfort Inn Conference Center

4500 Crain Hwy Bowie MD

3.103.877 ₫

per night

30 Aug - 31 Aug

9.2/10 Wonderful! (1,003 reviews)

Hotels in Shady Side with star rating

Frequently asked questions

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.

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Book Hotels in Shady Side on Expedia.com

Find hotels in Shady Side, MD from 2.200.362 ₫

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. Comfort Inn Conference Center

2. Courtyard by Marriott Bowie

3. SpringHill Suites by Marriott Annapolis

4. Hampton Inn & Suites Glenarden/Washington DC

5. St Michaels Inn

6. Sonesta ES Suites Annapolis

7. Microtel Inn & Suites by Wyndham Gambrills

8. DoubleTree by Hilton Hotel Annapolis

9. Anchored Inn at Hidden Harbour Marina

10. Crowne Plaza Annapolis by IHG

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

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

13. Best Western Annapolis

14. Hilton Garden Inn Kent Island Marina

15. Courtyard by Marriott Annapolis

16. Courtyard Largo Medical Center Drive

17. Historic Inns of Annapolis

18. Hampton Inn & Suites Annapolis

19. Hyatt Place Kent Narrows & Marina

20. Executive Inn And Suites

Stay near popular Shady Side attractions

Shadyside Park

Captain Avery Museum

Learn more about Shady Side

Top Shady Side Hotel Reviews

St Michaels Inn

DoubleTree by Hilton Hotel Largo/Washington DC

Holiday Inn Express & Suites Annapolis by IHG

Comfort Inn Conference Center

Crowne Plaza Annapolis by IHG

Microtel Inn & Suites by Wyndham Gambrills

Rod 'N' Reel Resort

Hilton Garden Inn Annapolis Downtown

Sonesta ES Suites Annapolis

More cheap stays in Shady Side

WoodSpring Suites Washington DC East Arena Drive

St Michaels Inn

Holiday Inn Express & Suites Annapolis by IHG

Hampton Inn & Suites Annapolis

Microtel Inn & Suites by Wyndham Gambrills

Comfort Inn Conference Center

Hotels in Shady Side with star rating

Frequently asked questions

Explore a world of travel with Expedia

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