𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Shady Side (2026)

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 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.

1. Anchored Inn at Hidden Harbour Marina

Deale

sherman

₹17,523

₹19,976 total

includes taxes & fees

2 Nov - 3 Nov

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 modern hotel with a flat roof and a sign reading "SPRINGHILL SUITES BY MARRIOTT".

2. SpringHill Suites by Marriott Annapolis

Annapolis

Kaiya

₹10,398

₹11,853 total

includes taxes & fees

15 Nov - 16 Nov

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

A restaurant with wooden tables and chairs, a bar area, and a tiled floor.

3. DoubleTree by Hilton Hotel Annapolis

Annapolis

Michele

₹8,631

₹9,839 total

includes taxes & fees

22 Nov - 23 Nov

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.

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

4. The Westin Annapolis

Annapolis

Bobbi

₹16,026

₹18,269 total

includes taxes & fees

22 Nov - 23 Nov

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 breakfast setup with a flat-top griddle, a coffee machine, and a sign directing to the breakfast area.

A modern office setup with two monitors, a keyboard, and two wooden chairs.

5. Holiday Inn Express & Suites Annapolis by IHG

Annapolis

Omer

₹8,724

₹9,945 total

includes taxes & fees

22 Nov - 23 Nov

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

A marina with multiple boats docked during sunset.

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

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

6. Historic Inns of Annapolis

Historic District

Scott

₹8,125

₹12,505 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 bar area with multiple screens displaying sports content, a high ceiling with geometric patterns, and a view of the outside through large windows.

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.

7. Rod 'N' Reel Resort

Chesapeake Beach

Pam

₹10,244

₹11,371 total

includes taxes & fees

12 Nov - 13 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 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.

8. Crowne Plaza Annapolis by IHG

Annapolis

Jose

₹9,767

₹11,134 total

includes taxes & fees

22 Nov - 23 Nov

A spacious living room with a large wooden coffee table, a leather sofa, and a chandelier.

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.

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

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

Annapolis

Catherine

₹7,890

₹8,994 total

includes taxes & fees

23 Nov - 24 Nov

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.

10. Comfort Inn Conference Center

Bowie

Gloria

₹10,297

₹11,636 total

includes taxes & fees

25 Oct - 26 Oct

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

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.

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.

11. Graduate by Hilton Annapolis

Annapolis

Nadine

₹13,141

₹14,981 total

includes taxes & fees

22 Nov - 23 Nov

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 hotel room with a sofa, a desk, a television, a chair, a bed, and a fireplace.

A gym with treadmills, weight machines, and dumbbells.

12. Sonesta ES Suites Annapolis

Edgewater

Ann Christine

₹7,871

₹8,972 total

includes taxes & fees

12 Nov - 13 Nov

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.

13. Courtyard by Marriott Annapolis

Annapolis

Jim

₹9,513

₹10,845 total

includes taxes & fees

9 Nov - 10 Nov

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

A hotel lobby with a dining area, a fireplace, and a view of the outside.

A compact kitchen with a microwave, refrigerator, and granite countertop. There are two chairs, one red and one yellow, and a wooden desk with a lamp.

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

14. Hampton Inn & Suites Annapolis

Annapolis

Christopher

₹8,709

₹9,928 total

includes taxes & fees

22 Nov - 23 Nov

A hotel room with two beds, a desk with a television, a chair, and a balcony with a view of the city.

A multi-story hotel with a modern design, featuring a prominent entrance with arches and a sign for Hilton Garden Inn.

15. Hilton Garden Inn Annapolis Downtown

Annapolis

petra

₹9,986

₹11,384 total

includes taxes & fees

3 Nov - 4 Nov

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 gym with treadmills, elliptical machines, and exercise balls.

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

16. Best Western Annapolis

Annapolis

Silvia

₹6,402

₹7,298 total

includes taxes & fees

23 Nov - 24 Nov

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

17. Courtyard by Marriott Bowie

Bowie

Halima

₹12,716

₹14,369 total

includes taxes & fees

8 Nov - 9 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 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.

18. Fairfield Inn & Suites By Marriott Annapolis

Annapolis

Imola

₹12,043

₹13,729 total

includes taxes & fees

1 Nov - 2 Nov

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

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.

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

19. Annapolis Waterfront Hotel, Autograph Collection

Historic District

William

₹20,407

₹23,264 total

includes taxes & fees

23 Nov - 24 Nov

A kitchen with a microwave, coffee maker, and a dishwasher.

A hotel room with a large bed, two bedside tables with lamps, a flat-screen TV, and a window with curtains.

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

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

20. Hilton Garden Inn Annapolis

Annapolis

Walter

₹8,786

₹10,016 total

includes taxes & fees

9 Nov - 10 Nov

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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

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent

"Easy access to downtown, Great waterside restaurants."

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"Great place"

The Westin Annapolis

10/10 Excellent

"Great last minute booking. All went smoothly"

Rod 'N' Reel Resort

8/10 Good

"The Hotel was excellent. However, Expedia did not disclose that there was an additional charge for resort fee that was not included in the quoted price from Expedia. There was an additional $33.00 when I checked into the hotel. I could have gone with a different online reservation cheaper."

Best Western Annapolis

8/10 Good

"If you want to get a feel for Annapolis, you should try a hotel closer to the harbor. Since we had seen Annapolis many times and were looking for a quick, efficient stay, this met our needs. A few remarks on the property; - Needs updates -bathroom door did not close fully - mystery eggs were part of breakfast, but coffee was good."

St Michaels Inn

8/10 Good

"older facility but kept clean. a good value for an over night"

Sonesta ES Suites Annapolis

10/10 Excellent

"Very pleasant surprise! Great price for studio apartment- way better than the Marriott I just checked out of!"

Comfort Inn Largo-Washington DC East

8/10 Good

"Convenient location, nice staff, needs updating and better quality lobby coffee"

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent

"It’s a hotel that is a bit worn but the rooms are great and the staff is very polite. I’ll definitely be back."

More cheap stays in Shady Side

Best Western Annapolis

2520 Riva Rd Annapolis MD

₹6,402

₹7,298 total

23 Nov - 24 Nov

includes taxes & fees

7.8/10 Good! (1,002 reviews)

St Michaels Inn

1228 S Talbot Street St. Michaels MD

₹7,292

₹8,021 total

23 Nov - 24 Nov

includes taxes & fees

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

Extended Stay America Suites Washington DC Landover

9401 Largo Dr W Upper Marlboro MD

₹7,509

₹8,485 total

4 Nov - 5 Nov

includes taxes & fees

Hampton Inn & Suites Annapolis

124 Womack Dr Annapolis MD

₹8,709

₹9,928 total

22 Nov - 23 Nov

includes taxes & fees

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

₹8,724

₹9,945 total

22 Nov - 23 Nov

includes taxes & fees

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

Comfort Inn Conference Center

4500 Crain Hwy Bowie MD

₹10,297

₹11,636 total

25 Oct - 26 Oct

includes taxes & fees

9.2/10 Wonderful! (1,007 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. 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

Shady Side Hotels from ₹7,298

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. The Westin Annapolis

5. Holiday Inn Express & Suites Annapolis by IHG

6. Historic Inns of Annapolis

7. Rod 'N' Reel Resort

8. Crowne Plaza Annapolis by IHG

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

10. Comfort Inn Conference Center

11. Graduate by Hilton Annapolis

12. Sonesta ES Suites Annapolis

13. Courtyard by Marriott Annapolis

14. Hampton Inn & Suites Annapolis

15. Hilton Garden Inn Annapolis Downtown

16. Best Western Annapolis

17. Courtyard by Marriott Bowie

18. Fairfield Inn & Suites By Marriott Annapolis

19. Annapolis Waterfront Hotel, Autograph Collection

20. Hilton Garden Inn Annapolis

Stay near popular Shady Side attractions

Shadyside Park

Captain Avery Museum

Learn more about Shady Side

Top Shady Side Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

DoubleTree by Hilton Hotel Annapolis

The Westin Annapolis

Rod 'N' Reel Resort

Best Western Annapolis

St Michaels Inn

Sonesta ES Suites Annapolis

Comfort Inn Largo-Washington DC East

Country Inn & Suites by Radisson, Annapolis, MD

More cheap stays in Shady Side

Best Western Annapolis

St Michaels Inn

Extended Stay America Suites Washington DC Landover

Hampton Inn & Suites Annapolis

Holiday Inn Express & Suites Annapolis by IHG

Comfort Inn Conference Center

Frequently asked questions

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