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 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 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.

1. Anchored Inn at Hidden Harbour Marina

Deale

Dale

฿6,597

฿7,520 total

includes taxes & fees

8 Sept - 9 Sept

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 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.

2. SpringHill Suites by Marriott Annapolis

Annapolis

Joshua

฿3,546

฿4,043 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 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.

3. Comfort Inn Conference Center

Bowie

Rachel

฿3,940

฿4,452 total

includes taxes & fees

13 Sept - 14 Sept

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

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

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

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

4. Courtyard by Marriott Bowie

Bowie

Yolanda

฿4,440

฿5,017 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 modern living room with a sofa, armchairs, a coffee table, and a fireplace.

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.

5. DoubleTree by Hilton Hotel Annapolis

Annapolis

Fabiana

฿3,231

฿3,683 total

includes taxes & fees

27 Sept - 28 Sept

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

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

Annapolis

Leslie

฿3,152

฿3,593 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 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.

7. Microtel Inn & Suites by Wyndham Gambrills

Gambrills

William

฿3,265

฿3,722 total

includes taxes & fees

13 Sept - 14 Sept

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

A hotel with a covered entrance, large columns, and a brick facade.

A hotel lobby with a fireplace, seating area, and a television mounted on the wall.

A fitness center with exercise equipment, a wall-mounted TV, and a sign listing rules.

8. Holiday Inn Express & Suites Annapolis by IHG

Annapolis

Frank

฿3,245

฿3,699 total

includes taxes & fees

27 Sept - 28 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.

9. Courtyard by Marriott Annapolis

Annapolis

Phyllis

฿3,179

฿3,624 total

includes taxes & fees

7 Sept - 8 Sept

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.

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

10. Crowne Plaza Annapolis by IHG

Annapolis

Heather

฿3,212

฿3,661 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 spacious lobby with a central dining area, multiple seating options, and a large TV screen on the right wall.

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.

11. Hampton Inn & Suites Glenarden/Washington DC

Lanham

Jeffrey

฿3,502

฿3,958 total

includes taxes & fees

7 Sept - 8 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 Best Western hotel with a modern facade, entrance with glass doors, and a parking area.

A gym with treadmills, elliptical machines, and exercise balls.

12. Best Western Annapolis

Annapolis

George

฿2,653

฿3,024 total

includes taxes & fees

13 Sept - 14 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 hotel entrance with a sign indicating pet-friendly services.

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.

13. Executive Inn And Suites

Upper Marlboro

Will

฿2,816

฿3,182 total

includes taxes & fees

1 Sept - 2 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 hotel room with a sofa, a desk, a television, a chair, a bed, and a fireplace.

A gym with treadmills, weight machines, and dumbbells.

14. Sonesta ES Suites Annapolis

Edgewater

Sophia

฿3,013

฿3,435 total

includes taxes & fees

22 Sept - 23 Sept

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

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

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.

15. The Westin Annapolis

Annapolis

susan greco

฿5,882

฿6,706 total

includes taxes & fees

13 Sept - 14 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 historic brick building with a red roof, multiple windows, and a central staircase.

16. Historic Inns of Annapolis

Historic District

Stephanie

฿3,505

฿5,129 total

includes taxes & fees

27 Sept - 28 Sept

A modern dining area with multiple tables and chairs, a kitchen area with a flat-screen TV, and large windows offering a view of the outdoors.

A reception desk with a "WELCOME THE CRAB" sign, a wooden reception desk, and a "Hilton Honors" sign.

A hotel room with a bed, a desk, a chair, a television, a mirror, and a lamp.

A modern interior with a seating area, a dining area, and a view of the outdoors.

17. Hampton Inn Bowie

Bowie

Sterlin

฿3,231

฿3,651 total

includes taxes & fees

7 Sept - 8 Sept

An outdoor patio with tables, chairs, and a fire feature.

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

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

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

18. Residence Inn By Marriott Annapolis

Annapolis

Caitlin

฿5,265

฿6,002 total

includes taxes & fees

1 Sept - 2 Sept

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

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

19. Fairfield Inn & Suites By Marriott Annapolis

Annapolis

Gary

฿4,602

฿5,247 total

includes taxes & fees

1 Sept - 2 Sept

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 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.

20. Rod 'N' Reel Resort

Chesapeake Beach

Theresa

฿4,787

฿6,417 total

includes taxes & fees

1 Oct - 2 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.

See properties

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

Historic Inns of Annapolis

10/10 Excellent

"Location, cleanliness, price, friendliness of the staff. Love it there. Only place we stay when visiting Annapolis."

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"Super friendly front staff & cleaning ladies, also extremely easy to get everything booked and checked in/out!"

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

8/10 Good

"Hotel was very clean and well maintained. The only negative was loud, obnoxious people who made noise overnight in the hallway walking from elevator to their rooms. Please be advised that the neighborhood the hotel is located in is not the greatest."

Crowne Plaza Annapolis by IHG

8/10 Good

"Took awhile to receive additional towels and washcloths. No microwave in rooms. Plus. - Great location to eateries, mall, and downtown Annapolis"

Sonesta ES Suites Annapolis

8/10 Good

"It is an older hotel, but clean. Breakfast was great! They have a good size pool, volleyball court, and basketball hoop. Rooms were very comfy and big. Great for families."

DoubleTree by Hilton Hotel Largo/Washington DC

10/10 Excellent

"This is my go to hotel when I visit family. Ample parking, friendly staff, amenities, and they fresh bake cookies everyday and provide them to guests."

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!"

Courtyard by Marriott Annapolis

10/10 Excellent

"Clean room and staff was very courteous."

More cheap stays in Shady Side

WoodSpring Suites Washington DC East Arena Drive

1603 Brightseat Rd. Hyattsville MD

฿2,616

฿2,956 total

1 Sept - 2 Sept

includes taxes & fees

St Michaels Inn

1228 S Talbot Street St. Michaels MD

฿3,129

฿3,442 total

1 Sept - 2 Sept

includes taxes & fees

8/10 Very good! (1,013 reviews)

Hampton Inn & Suites Annapolis

124 Womack Dr Annapolis MD

฿3,231

฿3,683 total

9 Sept - 10 Sept

includes taxes & fees

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

฿3,245

฿3,699 total

27 Sept - 28 Sept

includes taxes & fees

8.4/10 Very good! (1,003 reviews)

Microtel Inn & Suites by Wyndham Gambrills

2525 Evergreen Rd. Gambrills MD

฿3,265

฿3,722 total

13 Sept - 14 Sept

includes taxes & fees

Comfort Inn Conference Center

4500 Crain Hwy Bowie MD

฿3,940

฿4,452 total

13 Sept - 14 Sept

includes taxes & fees

Frequently asked questions

What's the best place to stay in Shady Side?

DoubleTree by Hilton Hotel Annapolis, located 9.8 mi (15.8 km) from the heart of Shady Side, is a top choice for your stay, based on our traveller data. Two other choices for your visit to the area are Historic Inns of Annapolis and Crowne Plaza Annapolis by IHG. See all available top hotels, or vacation rentals in Shady Side.

If I need to cancel my hotel reservation in Shady Side, will I receive a refund?

Yes, the majority of hotel room reservations are fully refundable if you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of check in. If you booked a non-refundable reservation, it might still be possible to cancel it and receive a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Shady Side.

What are some accommodation options with pools in Shady Side?

Crowne Plaza Annapolis by IHG: Hotel located near U.S. Naval Academy. Offers free self parking, an indoor pool and complimentary wireless Internet access. Rod 'N' Reel Resort and St Michaels Inn are two additional hotels that offer an on-site pool. View all hotels with pools in Shady Side.

What is staying in Shady Side like?

Visitors can enjoy all that Shady Side has to offer, including the shopping, restaurants and parks. Tourists can also enjoy so much more including its museums. In Shady Side, there are 15 hotels and other accommodation options to choose from. Find out more about Shady Side.

What should I see while I'm in Shady Side?

Natural beauty is on display at Northern Chesapeake Bay, Chesapeake Bay and Shadyside Park. A couple of additional sights to add to your itinerary are Captain Avery Museum and Franklin Point State Park. Take a look at what more there is to see and do in Expedia's Shady Side guide.

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 ฿2,956

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. Anchored Inn at Hidden Harbour Marina

2. SpringHill Suites by Marriott Annapolis

3. Comfort Inn Conference Center

4. Courtyard by Marriott Bowie

5. DoubleTree by Hilton Hotel Annapolis

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

7. Microtel Inn & Suites by Wyndham Gambrills

8. Holiday Inn Express & Suites Annapolis by IHG

9. Courtyard by Marriott Annapolis

10. Crowne Plaza Annapolis by IHG

11. Hampton Inn & Suites Glenarden/Washington DC

12. Best Western Annapolis

13. Executive Inn And Suites

14. Sonesta ES Suites Annapolis

15. The Westin Annapolis

16. Historic Inns of Annapolis

17. Hampton Inn Bowie

18. Residence Inn By Marriott Annapolis

19. Fairfield Inn & Suites By Marriott Annapolis

20. Rod 'N' Reel Resort

Stay near popular Shady Side attractions

Shadyside Park

Captain Avery Museum

Learn more about Shady Side

Top Shady Side Hotel Reviews

Historic Inns of Annapolis

DoubleTree by Hilton Hotel Annapolis

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

Crowne Plaza Annapolis by IHG

Sonesta ES Suites Annapolis

DoubleTree by Hilton Hotel Largo/Washington DC

St Michaels Inn

Courtyard by Marriott Annapolis

More cheap stays in Shady Side

WoodSpring Suites Washington DC East Arena Drive

St Michaels Inn

Hampton Inn & Suites Annapolis

Holiday Inn Express & Suites Annapolis by IHG

Microtel Inn & Suites by Wyndham Gambrills

Comfort Inn Conference Center

Frequently asked questions

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