𝗧𝗢𝗣 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Shady Side from RM361 (2026) - Fully Refundable Options

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 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.

1. Anchored Inn at Hidden Harbour Marina

Deale

Dale

RM815

RM929 total

includes taxes & fees

15 Sept - 16 Sept

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

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

2. SpringHill Suites by Marriott Annapolis

Annapolis

Joshua

RM522

RM595 total

includes taxes & fees

23 Aug - 24 Aug

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 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

eliana

RM396

RM452 total

includes taxes & fees

30 Aug - 31 Aug

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.

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

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

4. Comfort Inn Conference Center

Bowie

Rachel

RM481

RM544 total

includes taxes & fees

23 Aug - 24 Aug

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

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

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

Annapolis

Leslie

RM386

RM440 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 reception desk with a modern design, a digital screen, and a beverage refrigerator.

A hotel entrance with a covered walkway, large glass doors, and a brick facade.

A laundry room with four stacked washing machines and a black shelf.

6. Holiday Inn Express & Suites Annapolis by IHG

Annapolis

Frank

RM409

RM466 total

includes taxes & fees

24 Aug - 25 Aug

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.

An indoor swimming pool with clear glass walls, lounge chairs, and a view of the outside.

A section of a hotel with a wall labeled "the market" and two refrigerated display cases filled with beverages and snacks.

7. Courtyard by Marriott Annapolis

Annapolis

Phyllis

RM372

RM424 total

includes taxes & fees

31 Aug - 1 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 modern lobby with a reception desk, seating area, and a patterned rug.

8. Sonesta ES Suites Annapolis

Edgewater

John

RM392

RM447 total

includes taxes & fees

31 Aug - 1 Sept

A large indoor swimming pool with clear blue water, surrounded by lounge chairs and a high ceiling with skylights.

A hotel lobby with a bar area, seating, and a patterned carpet.

A modern lobby with a central seating area, a chandelier, and a bookshelf.

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

9. Crowne Plaza Annapolis by IHG

Annapolis

Heather

RM445

RM507 total

includes taxes & fees

1 Sept - 2 Sept

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

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.

A hotel dining area with multiple tables and chairs, large windows, and a chandelier.

10. Hilton Garden Inn Annapolis

Annapolis

Glenn

RM395

RM450 total

includes taxes & fees

13 Sept - 14 Sept

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

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.

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

11. Best Western Annapolis

Annapolis

George

RM324

RM369 total

includes taxes & fees

30 Aug - 31 Aug

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

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

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

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

12. Fairfield Inn & Suites By Marriott Annapolis

Annapolis

Tola

RM477

RM544 total

includes taxes & fees

25 Aug - 26 Aug

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

A reception area with a modern design, featuring a reception desk, seating area with patterned ottomans, and a wall with a geometric pattern.

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

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

13. Microtel Inn & Suites by Wyndham Gambrills

Gambrills

James

RM371

RM423 total

includes taxes & fees

30 Aug - 31 Aug

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.

14. Historic Inns of Annapolis

Historic District

Stephanie

RM375

RM565 total

includes taxes & fees

30 Aug - 31 Aug

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

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

15. Rod 'N' Reel Resort

Chesapeake Beach

Tessa

RM427

RM609 total

includes taxes & fees

3 Sept - 4 Sept

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

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.

16. The Westin Annapolis

Annapolis

Charles Eric

RM684

RM779 total

includes taxes & fees

6 Sept - 7 Sept

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

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

A hotel room with a sofa, a small table, a TV, a bed, and a view of greenery.

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

17. Hampton Inn & Suites Annapolis

Annapolis

Meghalee

RM398

RM454 total

includes taxes & fees

16 Sept - 17 Sept

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

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

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.

18. Hilton Garden Inn Annapolis Downtown

Annapolis

Nelson

RM420

RM478 total

includes taxes & fees

30 Aug - 31 Aug

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

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

19. Residence Inn By Marriott Annapolis

Annapolis

Caitlin

RM582

RM664 total

includes taxes & fees

30 Aug - 31 Aug

A circular fire pit surrounded by outdoor seating with a brick wall and a multi-story building in the background.

A reception desk with a 'HELLO' sign and 'Annapolis' text, wooden paneling, and hanging pendant lights.

A hotel with a modern design, featuring a mix of brick and siding exteriors, a covered entrance, and a parking area.

A compact hotel room with a kitchenette, a desk with two chairs, a sofa, and a bed.

20. TownePlace Suites by Marriott Annapolis

Annapolis

Jamila

RM445

RM507 total

includes taxes & fees

27 Aug - 28 Aug

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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

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"Great staff everywhere on the property."

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent

"A"

Comfort Inn Conference Center

10/10 Excellent

"Exceptional staff and services. They provided every amenity. The included daily breakfast was well prepared and staff stood at the ready to help and insure the area was kept clean and accessible asguests came and went. I would definitely recommend as well as use this location again."

Holiday Inn Express & Suites Annapolis by IHG

10/10 Excellent

"Perfect for what I needed"

Crowne Plaza Annapolis by IHG

10/10 Excellent

"Rooms where clean, staff was nice"

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent

"Top notch staff from the front desk, housekeeping and valet. My only real complaint was the early AM construction in the hallway. But all the workers were friendly and courteous to me passing by to get to the elevator."

Hyatt Place Kent Narrows & Marina

10/10 Excellent

"Property was well maintained and clean. Room was spacious and with a nice view. Parking is somewhat limited. Location is also central to area,attractions."

Comfort Inn Largo-Washington DC East

10/10 Excellent

"Great stay"

Courtyard by Marriott Annapolis

10/10 Excellent

"Perfectly decent hotel for overnight stay during roadtrip."

More cheap stays in Shady Side

WoodSpring Suites Washington DC East Arena Drive

1603 Brightseat Rd. Hyattsville MD

RM320

per night

23 Aug - 24 Aug

St Michaels Inn

1228 S Talbot Street St. Michaels MD

RM360

per night

31 Aug - 1 Sept

Microtel Inn & Suites by Wyndham Gambrills

2525 Evergreen Rd. Gambrills MD

RM371

per night

30 Aug - 31 Aug

9.2/10 Wonderful! (1,131 reviews)

Hampton Inn & Suites Annapolis

124 Womack Dr Annapolis MD

RM398

per night

16 Sept - 17 Sept

8.2/10 Very good! (1,012 reviews)

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

RM409

per night

24 Aug - 25 Aug

8.4/10 Very good! (1,010 reviews)

Comfort Inn Conference Center

4500 Crain Hwy Bowie MD

RM481

per night

23 Aug - 24 Aug

9.2/10 Wonderful! (1,023 reviews)

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.

Shady Side hotels from RM361

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. DoubleTree by Hilton Hotel Annapolis

4. Comfort Inn Conference Center

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

6. Holiday Inn Express & Suites Annapolis by IHG

7. Courtyard by Marriott Annapolis

8. Sonesta ES Suites Annapolis

9. Crowne Plaza Annapolis by IHG

10. Hilton Garden Inn Annapolis

11. Best Western Annapolis

12. Fairfield Inn & Suites By Marriott Annapolis

13. Microtel Inn & Suites by Wyndham Gambrills

14. Historic Inns of Annapolis

15. Rod 'N' Reel Resort

16. The Westin Annapolis

17. Hampton Inn & Suites Annapolis

18. Hilton Garden Inn Annapolis Downtown

19. Residence Inn By Marriott Annapolis

20. TownePlace Suites by Marriott Annapolis

Stay near popular Shady Side attractions

Shadyside Park

Captain Avery Museum

Learn more about Shady Side

Top Shady Side Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

Country Inn & Suites by Radisson, Annapolis, MD

Comfort Inn Conference Center

Holiday Inn Express & Suites Annapolis by IHG

Crowne Plaza Annapolis by IHG

Annapolis Waterfront Hotel, Autograph Collection

Hyatt Place Kent Narrows & Marina

Comfort Inn Largo-Washington DC East

Courtyard by Marriott Annapolis

More cheap stays in Shady Side

WoodSpring Suites Washington DC East Arena Drive

St Michaels Inn

Microtel Inn & Suites by Wyndham Gambrills

Hampton Inn & Suites Annapolis

Holiday Inn Express & Suites Annapolis by IHG

Comfort Inn Conference Center

Frequently asked questions

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