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

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

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".

1. SpringHill Suites by Marriott Annapolis

Annapolis

Joshua

3.265.668 ₫

3.722.862 ₫ total

includes taxes & fees

13 Sept - 14 Sept

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.

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

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

2. Comfort Inn Conference Center

Bowie

Rachel

2.825.062 ₫

3.192.320 ₫ total

includes taxes & fees

7 Oct - 8 Oct

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

3. DoubleTree by Hilton Hotel Annapolis

Annapolis

Chereis

2.149.716 ₫

2.450.676 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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

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

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

A hotel room with a bed, bedside tables, a desk with a chair, a microwave, a refrigerator, and a window with curtains.

4. Microtel Inn & Suites by Wyndham Gambrills

Gambrills

Mark

2.621.606 ₫

2.988.631 ₫ total

includes taxes & fees

12 Oct - 13 Oct

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

An indoor swimming pool with clear water, blue chairs, and a lifebuoy on the right side.

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

5. Hampton Inn & Suites Glenarden/Washington DC

Lanham

Jeffrey

2.743.087 ₫

3.099.688 ₫ total

includes taxes & fees

6 Oct - 7 Oct

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

A bar area with multiple seating options, including bar stools and round tables, and a well-stocked bar counter.

6. Crowne Plaza Annapolis by IHG

Annapolis

Cynthia

2.850.980 ₫

3.250.117 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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 reception area with two wooden reception desks, a stone wall, and a modern ceiling design.

7. Courtyard by Marriott Bowie

Bowie

Yolanda

3.475.604 ₫

3.927.432 ₫ total

includes taxes & fees

12 Oct - 13 Oct

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

A gym with treadmills, weight machines, and dumbbells.

8. Sonesta ES Suites Annapolis

Edgewater

Philip

2.358.538 ₫

2.688.734 ₫ total

includes taxes & fees

1 Oct - 2 Oct

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 gym with treadmills, elliptical machines, and exercise balls.

9. Best Western Annapolis

Annapolis

George

1.959.401 ₫

2.233.717 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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

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.

A breakfast bar with labeled sections for cereal and fruit, a kettle, and condiments.

10. Holiday Inn Express & Suites Annapolis by IHG

Annapolis

Harold

2.617.718 ₫

2.984.199 ₫ 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 room with a bed, a desk with a TV, a sofa with a red pillow, and a window with curtains.

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

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

11. Hampton Inn & Suites Annapolis

Annapolis

Meghalee

2.529.078 ₫

2.883.149 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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 marina with multiple boats docked during sunset.

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

12. Historic Inns of Annapolis

Historic District

Amy

2.584.170 ₫

3.832.350 ₫ total

includes taxes & fees

12 Oct - 13 Oct

A multi-story hotel with a central entrance, a landscaped garden with flowers, and a metal sculpture.

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

A modern kitchen with a large island, bar stools, and a wine rack.

A marina with docked boats, a picnic area, and a grassy lawn with a tree.

13. Anchored Inn at Hidden Harbour Marina

Deale

Dale

5.341.700 ₫

6.089.693 ₫ total

includes taxes & fees

14 Sept - 15 Sept

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

A restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.

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

14. St Michaels Inn

St. Michaels

Karen

2.449.251 ₫

2.694.177 ₫ total

includes taxes & fees

14 Sept - 15 Sept

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

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

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 swimming pool with a tiled edge, wooden chairs, and tables around it.

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

Annapolis

Leslie

2.467.394 ₫

2.812.829 ₫ total

includes taxes & fees

12 Oct - 13 Oct

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 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.

16. Hilton Garden Inn Annapolis

Annapolis

Glenn

2.422.815 ₫

2.762.009 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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

A multi-story hotel with a flat roof, a sign reading 'COURTYARD BY MARRIOTT,' and a parking lot with an American flag.

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

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

17. Courtyard Largo Medical Center Drive

Upper Marlboro

Ashley

2.990.419 ₫

3.379.174 ₫ total

includes taxes & fees

5 Oct - 6 Oct

A room with a pool, two sofas, a table, and a patterned rug.

A hotel reception area with a wooden reception desk, teal chairs, and a patterned rug.

A modern hotel room with a bed, sofa, coffee table, TV, and a minibar.

A modern kitchen with wooden cabinets, a white countertop, and various food items displayed.

18. Comfort Inn Largo-Washington DC East

Upper Marlboro

Pili

2.260.050 ₫

2.553.857 ₫ total

includes taxes & fees

5 Oct - 6 Oct

A lobby with a reception desk, a clock, and a wall-mounted deer head.

A restaurant with a counter, seating area, and a clock on the wall.

An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.

19. Best Western Kent Narrows Inn

Grasonville

Joshua

3.015.041 ₫

3.346.695 ₫ total

includes taxes & fees

28 Sept - 29 Sept

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

A modern food court with a central island, various food stations, and a yogurt display.

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.

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

Grasonville

Emily

3.161.996 ₫

3.509.816 ₫ total

includes taxes & fees

12 Oct - 13 Oct

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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.

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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

10/10 Excellent

"Property about 1.5 miles from the center of town. We knew about the location and we were quite pleased with everything and the eggs in the buffet were excellent for a hotel breakfast.....much better than other hotels"

Rod 'N' Reel Resort

8/10 Good

"Great stay! Very clean and kind staff. The amenities close much too early (8pm), making them difficult to enjoy."

Crowne Plaza Annapolis by IHG

8/10 Good

"Parking is good and restaurant was convenient"

Historic Inns of Annapolis

10/10 Excellent

"Wonderful hotel in a great location."

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good

"The location was great. We were able to walk everywhere. Considering the price of rooms, the $39 parking fee was high."

Graduate by Hilton Annapolis

10/10 Excellent

"Great location"

Sonesta ES Suites Annapolis

8/10 Good

"Our extended family had 7 rooms booked for a 4 day weekend wedding and we were all separated in different buildings. It would have been nice to have them in same area. Because we were there several days we ran out of several things such as towels, paper towels, and coffee packets for our room. I was surprised they didn't replenish any of this without having to get them ourselves. They also do not come and remove garbage or offer new sheets. The rooms were nice and spacious and the staff was friendly."

Microtel Inn & Suites by Wyndham Gambrills

10/10 Excellent

"Nice and easy"

DoubleTree by Hilton Hotel Largo/Washington DC

10/10 Excellent

"Perfect location for attending northwest stadium"

More cheap stays in Shady Side

Best Western Annapolis

2520 Riva Rd Annapolis MD

1.959.401 ₫

2.233.717 ₫ total

27 Sept - 28 Sept

includes taxes & fees

7.8/10 Good! (1,001 reviews)

WoodSpring Suites Washington DC East Arena Drive

1603 Brightseat Rd. Hyattsville MD

2.048.628 ₫

2.314.950 ₫ total

13 Sept - 14 Sept

includes taxes & fees

St Michaels Inn

1228 S Talbot Street St. Michaels MD

2.449.251 ₫

2.694.177 ₫ total

14 Sept - 15 Sept

includes taxes & fees

8/10 Very good! (1,007 reviews)

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

2.617.718 ₫

2.984.199 ₫ total

27 Sept - 28 Sept

includes taxes & fees

Microtel Inn & Suites by Wyndham Gambrills

2525 Evergreen Rd. Gambrills MD

2.621.606 ₫

2.988.631 ₫ total

12 Oct - 13 Oct

includes taxes & fees

9.2/10 Wonderful! (1,143 reviews)

Comfort Inn Conference Center

4500 Crain Hwy Bowie MD

2.825.062 ₫

3.192.320 ₫ total

7 Oct - 8 Oct

includes taxes & fees

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 2.155.979 ₫

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. SpringHill Suites by Marriott Annapolis

2. Comfort Inn Conference Center

3. DoubleTree by Hilton Hotel Annapolis

4. Microtel Inn & Suites by Wyndham Gambrills

5. Hampton Inn & Suites Glenarden/Washington DC

6. Crowne Plaza Annapolis by IHG

7. Courtyard by Marriott Bowie

8. Sonesta ES Suites Annapolis

9. Best Western Annapolis

10. Holiday Inn Express & Suites Annapolis by IHG

11. Hampton Inn & Suites Annapolis

12. Historic Inns of Annapolis

13. Anchored Inn at Hidden Harbour Marina

14. St Michaels Inn

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

16. Hilton Garden Inn Annapolis

17. Courtyard Largo Medical Center Drive

18. Comfort Inn Largo-Washington DC East

19. Best Western Kent Narrows Inn

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

Stay near popular Shady Side attractions

Shadyside Park

Captain Avery Museum

Learn more about Shady Side

Top Shady Side Hotel Reviews

St Michaels Inn

Rod 'N' Reel Resort

Crowne Plaza Annapolis by IHG

Historic Inns of Annapolis

Annapolis Waterfront Hotel, Autograph Collection

Graduate by Hilton Annapolis

Sonesta ES Suites Annapolis

Microtel Inn & Suites by Wyndham Gambrills

DoubleTree by Hilton Hotel Largo/Washington DC

More cheap stays in Shady Side

Best Western Annapolis

WoodSpring Suites Washington DC East Arena Drive

St Michaels Inn

Holiday Inn Express & Suites Annapolis by IHG

Microtel Inn & Suites by Wyndham Gambrills

Comfort Inn Conference Center

Hotels in Shady Side with star rating

Frequently asked questions

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