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

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

A hotel room with a bed, a desk, a chair, a coffee machine, and a tray table.

1. SpringHill Suites by Marriott Annapolis

Annapolis

Lisa

฿4,003

฿4,564 total

includes taxes & fees

1 Nov - 2 Nov

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

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.

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

2. Anchored Inn at Hidden Harbour Marina

Deale

฿6,240

฿7,113 total

includes taxes & fees

11 Oct - 12 Oct

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.

3. DoubleTree by Hilton Hotel Annapolis

Annapolis

Michele

฿3,558

฿4,057 total

includes taxes & fees

11 Oct - 12 Oct

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

A buffet with various food items, including omelets and baked goods, in stainless steel containers.

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.

4. Holiday Inn Express & Suites Annapolis by IHG

Annapolis

฿3,196

฿3,643 total

includes taxes & fees

9 Nov - 10 Nov

An indoor swimming pool with clear glass ceilings, large windows, and lounge chairs.

A modern hotel lobby with round tables and blue chairs, a bar area with various liquor bottles, and contemporary lighting fixtures.

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

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

5. Crowne Plaza Annapolis by IHG

Annapolis

Jose

฿3,902

฿4,449 total

includes taxes & fees

18 Oct - 19 Oct

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.

6. The Westin Annapolis

Annapolis

Bobbi

฿6,694

฿7,632 total

includes taxes & fees

11 Oct - 12 Oct

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

A historic brick building with a red roof, multiple windows, and a central staircase.

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

An aerial view of a coastal town with a marina, houses, and a bridge in the background.

7. Historic Inns of Annapolis

Historic District

Ashley

฿2,882

฿4,436 total

includes taxes & fees

9 Nov - 10 Nov

A gazebo with a dome, surrounded by a white fence, near a waterfront with a clear sky.

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

A modern salon with multiple black salon chairs, a white reception desk, and large windows allowing natural light.

A bar area with multiple screens displaying sports content, a high ceiling with geometric patterns, and a view of the outside through large windows.

8. Rod 'N' Reel Resort

Chesapeake Beach

฿4,864

฿5,399 total

includes taxes & fees

20 Oct - 21 Oct

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

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.

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

Annapolis

Catherine

฿3,068

฿3,497 total

includes taxes & fees

1 Nov - 2 Nov

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.

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

A Comfort Inn hotel with a parking lot and a covered entrance.

10. Comfort Inn Conference Center

Bowie

Christa

฿3,667

฿4,143 total

includes taxes & fees

13 Oct - 14 Oct

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

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

A gym with treadmills, weight machines, and dumbbells.

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

11. Sonesta ES Suites Annapolis

Edgewater

Philip

฿3,061

฿3,490 total

includes taxes & fees

28 Oct - 29 Oct

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.

12. Courtyard by Marriott Annapolis

Annapolis

฿3,375

฿3,847 total

includes taxes & fees

1 Nov - 2 Nov

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

A modern hotel room with a flat-screen TV, a sofa, a chair, and a small table.

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

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

13. Hilton Garden Inn Annapolis Downtown

Annapolis

petra

฿3,558

฿4,057 total

includes taxes & fees

1 Nov - 2 Nov

A marina with numerous boats docked, a prominent building with a dome in the background, and a clear view of the water.

A spacious atrium with a high ceiling, skylights, and a patterned floor.

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

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.

14. Graduate by Hilton Annapolis

Annapolis

Mark

฿4,938

฿5,630 total

includes taxes & fees

26 Oct - 27 Oct

A balcony with a table set for two, overlooking a marina with boats.

The exterior of the Annapolis Waterfront Hotel with a clear entrance, large windows, and a bench outside.

A hotel room with a large bed, a chair, a small table, and a view of a body of water.

A waterfront area with boats docked, a clear sky, and buildings in the background.

15. Annapolis Waterfront Hotel, Autograph Collection

Historic District

฿7,508

฿8,560 total

includes taxes & fees

1 Nov - 2 Nov

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

A swimming pool with lounge chairs and a brick building in the background.

16. Hampton Inn & Suites Annapolis

Annapolis

Courtney

฿3,283

฿3,742 total

includes taxes & fees

18 Oct - 19 Oct

A modern hotel kitchen with a central island, seating area, and various kitchen appliances.

A hotel lobby with a reception desk, seating area, and dining space.

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.

17. Best Western Annapolis

Annapolis

฿2,664

฿3,037 total

includes taxes & fees

13 Oct - 14 Oct

18. Hilton Garden Inn Annapolis

Annapolis

Glenn

฿3,117

฿3,553 total

includes taxes & fees

9 Nov - 10 Nov

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

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.

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

19. Fairfield Inn & Suites By Marriott Annapolis

Annapolis

Imola

฿2,826

฿3,221 total

includes taxes & fees

13 Oct - 14 Oct

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

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.

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

20. Courtyard by Marriott Bowie

Bowie

฿4,511

฿5,098 total

includes taxes & fees

27 Oct - 28 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.

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

Comfort Inn Largo-Washington DC East

8/10 Good

"Clean room."

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

10/10 Excellent

"The elevator was scary.That was the only thing that I had a problem with"

Historic Inns of Annapolis

10/10 Excellent

"Nice"

Microtel Inn & Suites by Wyndham Gambrills/Odenton

10/10 Excellent

"Elijah is a rock star!"

Rod 'N' Reel Resort

10/10 Excellent

"Great local getaway on the water."

DoubleTree by Hilton Hotel Largo/Washington DC

10/10 Excellent

"my cozy room pet friendly staff"

St Michaels Inn

10/10 Excellent

"Late night manager was extremely helpful!"

More cheap stays in Shady Side

Best Western Annapolis

2520 Riva Rd Annapolis MD

฿2,664

฿3,037 total

13 Oct - 14 Oct

includes taxes & fees

St Michaels Inn

1228 S Talbot Street St. Michaels MD

฿2,997

฿3,297 total

11 Oct - 12 Oct

includes taxes & fees

8/10 Very good! (1,001 reviews)

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

฿3,024

฿3,356 total

8 Nov - 9 Nov

includes taxes & fees

8/10 Very good! (1,001 reviews)

Microtel Inn & Suites by Wyndham Gambrills/Odenton

2525 Evergreen Rd. Gambrills MD

฿3,145

฿3,586 total

1 Nov - 2 Nov

includes taxes & fees

9.2/10 Wonderful! (1,154 reviews)

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

฿3,196

฿3,643 total

9 Nov - 10 Nov

includes taxes & fees

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

Comfort Inn Conference Center

4500 Crain Hwy Bowie MD

฿3,667

฿4,143 total

13 Oct - 14 Oct

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. Features free self parking, an indoor pool and complimentary wireless Internet access. Rod 'N' Reel Resort and Comfort Inn Largo-Washington DC East 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 ฿3,037

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. Anchored Inn at Hidden Harbour Marina

3. DoubleTree by Hilton Hotel Annapolis

4. Holiday Inn Express & Suites Annapolis by IHG

5. Crowne Plaza Annapolis by IHG

6. The Westin Annapolis

7. Historic Inns of Annapolis

8. Rod 'N' Reel Resort

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

10. Comfort Inn Conference Center

11. Sonesta ES Suites Annapolis

12. Courtyard by Marriott Annapolis

13. Hilton Garden Inn Annapolis Downtown

14. Graduate by Hilton Annapolis

15. Annapolis Waterfront Hotel, Autograph Collection

16. Hampton Inn & Suites Annapolis

17. Best Western Annapolis

18. Hilton Garden Inn Annapolis

19. Fairfield Inn & Suites By Marriott Annapolis

20. Courtyard by Marriott Bowie

Stay near popular Shady Side attractions

Shadyside Park

Captain Avery Museum

Learn more about Shady Side

Top Shady Side Hotel Reviews

Comfort Inn Largo-Washington DC East

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

Historic Inns of Annapolis

Microtel Inn & Suites by Wyndham Gambrills/Odenton

Rod 'N' Reel Resort

DoubleTree by Hilton Hotel Largo/Washington DC

St Michaels Inn

More cheap stays in Shady Side

Best Western Annapolis

St Michaels Inn

Best Western Kent Narrows Inn

Microtel Inn & Suites by Wyndham Gambrills/Odenton

Holiday Inn Express & Suites Annapolis by IHG

Comfort Inn Conference Center

Frequently asked questions

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