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 bar area, wooden flooring, and blue bar stools.

1. Anchored Inn at Hidden Harbour Marina

Deale

Beverly

Rp3.581.757

Rp4.083.163 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 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.

2. DoubleTree by Hilton Hotel Annapolis

Annapolis

Michele

Rp1.734.496

Rp1.977.324 total

includes taxes & fees

4 Oct - 5 Oct

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 modern hotel lobby with a curved seating area, a bar, and a large bookshelf.

A store with shelves of beverages, a counter with a cash register, and baskets with items.

3. The Westin Annapolis

Annapolis

Bobbi

Rp3.577.622

Rp4.078.489 total

includes taxes & fees

25 Oct - 26 Oct

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 staircase with a wooden handrail, a blue wall, and a ceiling light fixture.

4. Rod 'N' Reel Resort

Chesapeake Beach

Francine

Rp2.588.505

Rp3.469.411 total

includes taxes & fees

7 Oct - 8 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 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

Cynthia

Rp1.969.330

Rp2.245.036 total

includes taxes & fees

4 Oct - 5 Oct

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 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.

6. SpringHill Suites by Marriott Annapolis

Annapolis

Lisa

Rp2.319.162

Rp2.643.844 total

includes taxes & fees

30 Sept - 1 Oct

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

A microwave, a coffee maker, and a refrigerator in a kitchen area.

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.

7. Holiday Inn Express & Suites Annapolis by IHG

Annapolis

Wilma

Rp1.887.690

Rp2.151.966 total

includes taxes & fees

4 Oct - 5 Oct

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

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 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.

8. Graduate by Hilton Annapolis

Annapolis

princess

Rp2.638.811

Rp3.008.245 total

includes taxes & fees

26 Oct - 27 Oct

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.

A marina with multiple boats docked during sunset.

9. Historic Inns of Annapolis

Historic District

Ashley

Rp1.911.691

Rp2.794.175 total

includes taxes & fees

12 Oct - 13 Oct

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

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

A waterfront property with a docked boat, a tall building with balconies, and a church spire in the background.

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

10. Annapolis Waterfront Hotel, Autograph Collection

Historic District

William

Rp4.874.735

Rp5.557.197 total

includes taxes & fees

25 Oct - 26 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 Country Inn & Suites by Radisson building with a brick facade, white columns, and a green roof.

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

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

Annapolis

Leslie

Rp1.711.506

Rp1.951.116 total

includes taxes & fees

20 Oct - 21 Oct

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

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

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

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

12. Hilton Garden Inn Annapolis Downtown

Annapolis

petra

Rp2.343.972

Rp2.672.128 total

includes taxes & fees

25 Oct - 26 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 modern lobby with a reception desk, seating area, and a patterned rug.

A gym with treadmills, weight machines, and dumbbells.

13. Sonesta ES Suites Annapolis

Edgewater

Philip

Rp1.635.998

Rp1.865.038 total

includes taxes & fees

28 Oct - 29 Oct

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

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

14. Comfort Inn Conference Center

Bowie

Titus

Rp1.959.602

Rp2.214.350 total

includes taxes & fees

7 Oct - 8 Oct

A courtyard with a stone fire pit surrounded by wicker furniture and a grassy lawn.

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

Jim

Rp2.032.349

Rp2.316.878 total

includes taxes & fees

5 Oct - 6 Oct

A hot tub in a grassy area with a building in the background.

A cozy room with a brick fireplace, leather armchairs, and a rustic wooden table.

A room with a tufted armchair, a vase with white flowers, and a window with a view of the outdoors.

A luxurious living room with a leather sofa, a vintage trunk, and a fireplace.

16. The Inn at Tacaro Estate

Tracys Landing

James

Rp7.130.614

Rp8.128.932 total

includes taxes & fees

6 Oct - 7 Oct

A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.

A spacious dining area with round tables, high ceilings with ductwork, and a stone fireplace.

A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

17. The Inn at Chesapeake Bay Beach Club

Stevensville

scott

Rp3.438.292

Rp4.273.865 total

includes taxes & fees

19 Oct - 20 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.

18. Hilton Garden Inn Annapolis

Annapolis

Glenn

Rp1.754.293

Rp1.999.894 total

includes taxes & fees

12 Oct - 13 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 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.

19. Courtyard by Marriott Bowie

Bowie

Halima

Rp2.410.850

Rp2.724.261 total

includes taxes & fees

12 Oct - 13 Oct

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

A hotel room with two desks, two chairs, a carpeted floor, and artwork on the wall.

A hotel room with a bed, a desk with a TV, a sofa with a red pillow, and a window with curtains.

A pool table with balls, a pool cue, and three framed pictures on the wall.

20. Hampton Inn & Suites Annapolis

Annapolis

Courtney

Rp1.888.589

Rp2.152.991 total

includes taxes & fees

28 Oct - 29 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

Comfort Inn Largo-Washington DC East

10/10 Excellent

"Great stay, clean space, good wifi, breakfast a plus"

Crowne Plaza Annapolis by IHG

10/10 Excellent

"convenient"

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent

"Excellent location. Marriott has renovated the bar downstairs; one side is a Mexican restaurant and the other is Italian. Both have great food and service."

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"This was a fabulous hotel. Staff was excellent very helpful. We used the shuttle to go to historic downtown. Very prompt picking us up. The drivers were so helpful and very kind. A perfect hotel to stay at especially having a shuttle not having to park in the busy historic area. The best staff we have seen at hotels."

Courtyard by Marriott Annapolis

10/10 Excellent

"The staff were super friendly."

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

8/10 Good

"Great AC Nice breakfast Clean room"

Sonesta ES Suites Annapolis

10/10 Excellent

"We stayed in the 2 bedroom and there was plenty of room. Loved that each bedroom had a bathroom. It felt more lime staying in an apartment having your own entrance. Not having to worry about breakfast was a plus, really liked that it was included. The staff was very helpful. We did use the exercise room that was small but good enough for a quick workout to start the day. We would most definitely stay again."

Microtel Inn & Suites by Wyndham Gambrills/Odenton

10/10 Excellent

"I stay here when I’m flying home because it’s close enough to the airport, friendly staff, clean rooms, quiet at night and lots of dining choices close by!"

Best Western Annapolis

10/10 Excellent

"The room was clean and well maintained. The lobby was pleasant, and the staff was friendly and attentive. The breakfast was excellent for this price point, with a wide selection of hot and cold items."

More cheap stays in Shady Side

Best Western Annapolis

2520 Riva Rd Annapolis MD

Rp1.407.857

Rp1.604.956 total

4 Oct - 5 Oct

includes taxes & fees

7.8/10 Good! (1,003 reviews)

St Michaels Inn

1228 S Talbot Street St. Michaels MD

Rp1.595.157

Rp1.754.672 total

5 Oct - 6 Oct

includes taxes & fees

Microtel Inn & Suites by Wyndham Gambrills/Odenton

2525 Evergreen Rd. Gambrills MD

Rp1.696.224

Rp1.933.695 total

12 Oct - 13 Oct

includes taxes & fees

9.2/10 Wonderful! (1,159 reviews)

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

Rp1.887.690

Rp2.151.966 total

4 Oct - 5 Oct

includes taxes & fees

Comfort Inn Conference Center

4500 Crain Hwy Bowie MD

Rp1.959.602

Rp2.214.350 total

7 Oct - 8 Oct

includes taxes & fees

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

Rp2.082.656

Rp2.311.747 total

5 Oct - 6 Oct

includes taxes & fees

Hotels in Shady Side with star rating

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.

Explore a world of travel with Expedia

Book Hotels in Shady Side on Expedia.com

Find hotels in Shady Side, MD from Rp1.604.956

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. DoubleTree by Hilton Hotel Annapolis

3. The Westin Annapolis

4. Rod 'N' Reel Resort

5. Crowne Plaza Annapolis by IHG

6. SpringHill Suites by Marriott Annapolis

7. Holiday Inn Express & Suites Annapolis by IHG

8. Graduate by Hilton Annapolis

9. Historic Inns of Annapolis

10. Annapolis Waterfront Hotel, Autograph Collection

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

12. Hilton Garden Inn Annapolis Downtown

13. Sonesta ES Suites Annapolis

14. Comfort Inn Conference Center

15. Courtyard by Marriott Annapolis

16. The Inn at Tacaro Estate

17. The Inn at Chesapeake Bay Beach Club

18. Hilton Garden Inn Annapolis

19. Courtyard by Marriott Bowie

20. Hampton Inn & Suites Annapolis

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

Crowne Plaza Annapolis by IHG

Annapolis Waterfront Hotel, Autograph Collection

DoubleTree by Hilton Hotel Annapolis

Courtyard by Marriott Annapolis

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

Sonesta ES Suites Annapolis

Microtel Inn & Suites by Wyndham Gambrills/Odenton

Best Western Annapolis

More cheap stays in Shady Side

Best Western Annapolis

St Michaels Inn

Microtel Inn & Suites by Wyndham Gambrills/Odenton

Holiday Inn Express & Suites Annapolis by IHG

Comfort Inn Conference Center

Best Western Kent Narrows Inn

Hotels in Shady Side with star rating

Frequently asked questions

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