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

1. DoubleTree by Hilton Hotel Annapolis

Annapolis

Michele

Rp1.726.262

Rp1.967.939 total

includes taxes & fees

28 Sept - 29 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 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.

2. Comfort Inn Conference Center

Bowie

Titus

Rp1.942.162

Rp2.194.643 total

includes taxes & fees

7 Oct - 8 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 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.

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

3. Hampton Inn & Suites Glenarden/Washington DC

Lanham

Jeffrey

Rp1.884.788

Rp2.129.810 total

includes taxes & fees

5 Oct - 6 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 hotel room with a sofa, a desk, a television, a chair, a bed, and a fireplace.

4. Sonesta ES Suites Annapolis

Edgewater

Philip

Rp1.726.564

Rp1.968.283 total

includes taxes & fees

7 Oct - 8 Oct

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

5. Microtel Inn & Suites by Wyndham Gambrills/Odenton

Gambrills

Arlaan

Rp1.659.917

Rp1.892.306 total

includes taxes & fees

12 Oct - 13 Oct

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

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

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

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

6. Crowne Plaza Annapolis by IHG

Annapolis

Cynthia

Rp1.959.980

Rp2.234.377 total

includes taxes & fees

4 Oct - 5 Oct

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

7. SpringHill Suites by Marriott Annapolis

Annapolis

FRANK

Rp2.105.197

Rp2.399.925 total

includes taxes & fees

4 Oct - 5 Oct

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

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

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

A coffee station with two coffee machines, a coffee press, and various coffee-related items on a wooden counter.

8. Holiday Inn Express & Suites Annapolis by IHG

Annapolis

Wilma

Rp1.809.516

Rp2.062.848 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 Best Western hotel with a modern facade, entrance with glass doors, and a parking area.

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

9. Best Western Annapolis

Annapolis

Sanaul

Rp1.403.002

Rp1.599.422 total

includes taxes & fees

4 Oct - 5 Oct

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

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

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

10. St Michaels Inn

St. Michaels

Lynn

Rp1.587.584

Rp1.746.342 total

includes taxes & fees

5 Oct - 6 Oct

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 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.

11. Anchored Inn at Hidden Harbour Marina

Deale

Dale

Rp3.672.290

Rp4.186.517 total

includes taxes & fees

30 Sept - 1 Oct

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.

12. Hampton Inn Bowie

Bowie

Michelle

Rp1.738.680

Rp1.964.709 total

includes taxes & fees

8 Oct - 9 Oct

A modern lobby with a reception desk, seating area, and potted plants.

A Hilton Garden Inn with a large building and a smaller entrance building.

A modern bar area with a wooden counter, bar stools, and a wine display.

A modern hotel lobby with a sectional sofa, ottomans, round tables, potted plants, and a large window.

13. Hilton Garden Inn Annapolis

Annapolis

Glenn

Rp1.748.243

Rp1.992.996 total

includes taxes & fees

12 Oct - 13 Oct

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

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

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

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

14. Courtyard by Marriott Bowie

Bowie

Halima

Rp2.402.536

Rp2.714.866 total

includes taxes & fees

12 Oct - 13 Oct

A patio with a barbecue grill, outdoor seating, and a small garden area with yellow flowers.

A modern hotel kitchen with wooden cabinets, a buffet area, and a dining area with wooden tables and chairs.

A hotel room with a flat-screen TV, a sofa, a chair, a small table, a desk with two chairs, a lamp, and a framed artwork on the wall.

A hotel room with a bed, a desk, a chair, a lamp, a heater, and a window with curtains.

15. TownePlace Suites Bowie Town Center

Bowie

Empress Ballalaine

Rp1.952.844

Rp2.206.714 total

includes taxes & fees

12 Oct - 13 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.

16. Historic Inns of Annapolis

Historic District

ian

Rp1.905.097

Rp2.784.538 total

includes taxes & fees

12 Oct - 13 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 living area with a sofa, two armchairs, a coffee table, a flat-screen TV, and built-in shelving.

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

17. Comfort Inn Largo-Washington DC East

Upper Marlboro

Zina

Rp1.562.275

Rp1.765.371 total

includes taxes & fees

18 Oct - 19 Oct

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

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 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.

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

Grasonville

Marc

Rp1.845.348

Rp2.048.337 total

includes taxes & fees

25 Oct - 26 Oct

A marina with boats docked at wooden piers, surrounded by greenery.

A waterfront property with houses, a dock, and a grassy area.

A building with a sign reading "The Inn."

A bed with two pillows, one with "HAPPY PLACE" text, and a framed picture above the bed.

19. Knapps Narrows Marina & Inn

Sherwood

BARBARA

Rp2.672.700

Rp2.939.970 total

includes taxes & fees

30 Sept - 1 Oct

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

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

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

Annapolis

Leslie

Rp1.705.603

Rp1.944.387 total

includes taxes & fees

20 Oct - 21 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

St Michaels Inn

8/10 Good

"The St. Michaels Inn is a great location and value! It's an older property, but it was clean, safe, and comfortable. I wouldn't hesitate to book again."

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"I liked the staff!"

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

10/10 Excellent

"it was good for the price."

Comfort Inn Largo-Washington DC East

10/10 Excellent

"Staff and xkean roo."

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good

"The view from our room was incredible. The property is clean and the beds comfortable. For the price, however, the only thing that justifies it is the view and location. There are 2 restaurants- Marmo was disappointing and overpriced. The cantina was great. Unfortunately, they take up all of the waterfront dock area, so there is really nowhere else to gather in the hotel to enjoy the water if you just want to sit and visit or play a game, or some such. (The balconies were too small for anything except a cup of coffee). And since the restaurants are open to the public the area is packed all the time. Otherwise, being an older hotel, there really aren't any special amenities. No spa or pool. nothing else special about it. And those terrible nespresso machines in the room. I just want a regular cup of coffee. Parking is overpriced- we hoofed it to a garage a few blocks away for significantly less per day."

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."

The Westin Annapolis

10/10 Excellent

"Only used the valet parking."

Courtyard by Marriott Annapolis

10/10 Excellent

"I thought breakfast was included but apparently not . There was not even complimentary coffee"

More cheap stays in Shady Side

Best Western Annapolis

2520 Riva Rd Annapolis MD

Rp1.403.002

Rp1.599.422 total

4 Oct - 5 Oct

includes taxes & fees

7.8/10 Good! (1,000 reviews)

St Michaels Inn

1228 S Talbot Street St. Michaels MD

Rp1.587.584

Rp1.746.342 total

5 Oct - 6 Oct

includes taxes & fees

8/10 Very good! (1,004 reviews)

Microtel Inn & Suites by Wyndham Gambrills/Odenton

2525 Evergreen Rd. Gambrills MD

Rp1.659.917

Rp1.892.306 total

12 Oct - 13 Oct

includes taxes & fees

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

Rp1.809.516

Rp2.062.848 total

28 Sept - 29 Sept

includes taxes & fees

8.4/10 Very good! (1,000 reviews)

Comfort Inn Conference Center

4500 Crain Hwy Bowie MD

Rp1.942.162

Rp2.194.643 total

7 Oct - 8 Oct

includes taxes & fees

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

Rp2.267.341

Rp2.516.749 total

6 Oct - 7 Oct

includes taxes & fees

8/10 Very good! (1,002 reviews)

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 Rp1.503.126

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. DoubleTree by Hilton Hotel Annapolis

2. Comfort Inn Conference Center

3. Hampton Inn & Suites Glenarden/Washington DC

4. Sonesta ES Suites Annapolis

5. Microtel Inn & Suites by Wyndham Gambrills/Odenton

6. Crowne Plaza Annapolis by IHG

7. SpringHill Suites by Marriott Annapolis

8. Holiday Inn Express & Suites Annapolis by IHG

9. Best Western Annapolis

10. St Michaels Inn

11. Anchored Inn at Hidden Harbour Marina

12. Hampton Inn Bowie

13. Hilton Garden Inn Annapolis

14. Courtyard by Marriott Bowie

15. TownePlace Suites Bowie Town Center

16. Historic Inns of Annapolis

17. Comfort Inn Largo-Washington DC East

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

19. Knapps Narrows Marina & Inn

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

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 Annapolis

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

Comfort Inn Largo-Washington DC East

Annapolis Waterfront Hotel, Autograph Collection

Best Western Annapolis

The Westin Annapolis

Courtyard by Marriott 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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