Top 10 Hotels in Shady Side, MD from ￥13,285 - Competitive Prices

A river with boats, a marina, and a town with houses and buildings.

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Waterpark

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Our top choices for Shady Side hotels

1. SpringHill Suites by Marriott Annapolis

Annapolis

Joshua

￥19,423

￥22,142 total

includes taxes & fees

Sep 9 - Sep 10

2. Hampton Inn & Suites Glenarden/Washington DC

Lanham

Jeffrey

￥16,306

￥18,426 total

includes taxes & fees

Sep 20 - Sep 21

3. Comfort Inn Conference Center

Bowie

Rachel

￥18,595

￥21,012 total

includes taxes & fees

Sep 13 - Sep 14

4. Microtel Inn & Suites by Wyndham Gambrills

Gambrills

Mark

￥16,093

￥18,345 total

includes taxes & fees

Sep 13 - Sep 14

5. DoubleTree by Hilton Hotel Annapolis

Annapolis

Chereis

￥12,961

￥14,775 total

includes taxes & fees

Sep 27 - Sep 28

6. Courtyard by Marriott Bowie

Bowie

Yolanda

￥21,365

￥24,142 total

includes taxes & fees

Oct 5 - Oct 6

7. Anchored Inn at Hidden Harbour Marina

Deale

Dale

￥30,711

￥35,010 total

includes taxes & fees

Sep 10 - Sep 11

8. Crowne Plaza Annapolis by IHG

Annapolis

Cynthia

￥16,957

￥19,331 total

includes taxes & fees

Sep 15 - Sep 16

Room, 1 King Bed, Non Smoking, Fireplace

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

Annapolis

Leslie

￥14,675

￥16,730 total

includes taxes & fees

Oct 4 - Oct 5

10. Best Western Annapolis

Annapolis

George

￥11,654

￥13,285 total

includes taxes & fees

Sep 27 - Sep 28

11. St Michaels Inn

St. Michaels

Karen

￥13,693

￥15,062 total

includes taxes & fees

Sep 10 - Sep 11

12. Staybridge Suites Washington DC East - Largo by IHG

Upper Marlboro

Amy

￥20,810

￥23,515 total

includes taxes & fees

Oct 4 - Oct 5

13. Courtyard by Marriott Annapolis

Annapolis

Phyllis

￥15,415

￥17,573 total

includes taxes & fees

Sep 27 - Sep 28

14. Hilton Garden Inn Annapolis Downtown

Annapolis

Jeffrey

￥19,092

￥21,766 total

includes taxes & fees

Sep 27 - Sep 28

15. Hilton Garden Inn Annapolis

Annapolis

Glenn

￥13,927

￥15,876 total

includes taxes & fees

Sep 16 - Sep 17

16. Sonesta ES Suites Annapolis

Edgewater

Philip

￥14,490

￥16,518 total

includes taxes & fees

Sep 30 - Oct 1

17. La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

Capitol Heights

Natasha

￥13,758

￥15,701 total

includes taxes & fees

Sep 10 - Sep 11

Superior Room, 1 King Bed, Accessible, Non Smoking (Roll-In Shower) | Bathroom

18. Red Roof Inn Annapolis

Annapolis

Melissa

￥11,407

￥13,004 total

includes taxes & fees

Sep 21 - Sep 22

19. Historic Inns of Annapolis

Historic District

Kevin

￥16,320

￥23,876 total

includes taxes & fees

Sep 29 - Sep 30

20. Hampton Inn & Suites Annapolis

Annapolis

Meghalee

￥15,042

￥17,148 total

includes taxes & fees

Sep 28 - Sep 29

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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 savor its top-notch restaurants.

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Captain Avery Museum

You can spend time exploring the galleries in Captain Avery Museum in Shady Side. Stroll along the area's waterfront, or simply savor its top-notch restaurants.

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Learn more about Shady Side

Love dining out, parks, and museums? Get away to Shady Side!

See all hotels in Shady Side

Top Shady Side Hotel Reviews

Crowne Plaza Annapolis by IHG

10/10 Excellent

"I only stayed overnight because we were at the Renaissance fair, it was clean, many places to eat within walking distance is a plus."

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"I loved the free shuttle within 5 miles. It was so great to be dropped off at my conference downtown and not have to worry about parking. They picked me up within 10-15 minutes anytime I called. The restaurant was nice and the food was very good. I loved the location."

Sonesta ES Suites Annapolis

10/10 Excellent

"The lawn around the tennis court and pool need cutting/landscaping. Other than that the room was great and felt like a safe location."

St Michaels Inn

10/10 Excellent

"Nice place. Breakfast was great pool needs more chairs."

Comfort Inn Largo-Washington DC East

8/10 Good

"Everything was fine but there’re not enough varieties for breakfast"

Courtyard by Marriott Annapolis

10/10 Excellent

"Helpful staff. We were in town for a USNA reunion, and the lobby café was surprisingly useful. Rendezvouses with classmates. Late evening bulk sessions. Decent coffee and snacks. Walking distance to stadium park n ride."

Rod 'N' Reel Resort

10/10 Excellent

"Felt like we traveled to a southern town while still being in Maryland. Great hotel."

Graduate by Hilton Annapolis

10/10 Excellent

"GREAT location! The room was huge & beautifully decorated. We are excited to come back again! 10/10!"

Lovely bay views with kayaks, bikes, fire pit, crabbing & more

10/10 Excellent

"This property was in a central location to lots of places. I did think there was going to be a larger beach that you could go to within the community, however it was a very enjoyable stay. The hostess was sweet and the house is adorable."

More cheap stays in Shady Side

Best Western Annapolis

2520 Riva Rd Annapolis MD

￥11,654

￥13,285 total

Sep 27 - Sep 28

includes taxes & fees

7.8/10 Good! (1,003 reviews)

WoodSpring Suites Washington DC East Arena Drive

1603 Brightseat Rd. Hyattsville MD

￥12,178

￥13,762 total

Sep 9 - Sep 10

includes taxes & fees

St Michaels Inn

1228 S Talbot Street St. Michaels MD

￥13,693

￥15,062 total

Sep 10 - Sep 11

includes taxes & fees

8/10 Very Good! (1,000 reviews)

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

￥15,782

￥17,992 total

Sep 13 - Sep 14

includes taxes & fees

8.4/10 Very Good! (1,003 reviews)

Microtel Inn & Suites by Wyndham Gambrills

2525 Evergreen Rd. Gambrills MD

￥16,093

￥18,345 total

Sep 13 - Sep 14

includes taxes & fees

Comfort Inn Conference Center

4500 Crain Hwy Bowie MD

￥18,595

￥21,012 total

Sep 13 - Sep 14

includes taxes & fees

Frequently asked questions

Where is the best place for a 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 traveler data. Two other choices for your trip to the area are Crowne Plaza Annapolis by IHG and Graduate by Hilton Annapolis. See all available top hotels, or vacation rentals in Shady Side.

What are some of the best vacation rentals that Shady Side has to offer?

Lovely bay views with kayaks, bikes, fire pit, crabbing & more: This Shady Side vacation home rental offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games. See all 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 reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of your scheduled arrival. If you booked a non-refundable reservation, you might be able to cancel it and be given a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Shady Side.

Where can I learn more about changing or cancelling my trip to Shady Side?

To find more details about updating your trip to Shady Side or cancelling it, click here.

Where is the best hotel to stay near Shadyside Park?

Anchored Inn at Hidden Harbour Marina is one of the top choices for your stay based on our traveler data, and this hotel offers an outdoor pool and free parking. It's located 4.8 mi (7.7 km) from Shadyside Park.

What about the best place to stay near Captain Avery Museum?

One of the top choices for your stay is Anchored Inn at Hidden Harbour Marina, located 5 mi (8.1 km) from Captain Avery Museum, and this hotel offers an outdoor pool and free parking.

What are some accommodations with pools in Shady Side?

Crowne Plaza Annapolis by IHG: Hotel located near U.S. Naval Academy. Provides free self parking, an indoor pool, and complimentary wireless internet access. Rod 'N' Reel Resort and Sonesta ES Suites Annapolis are two additional hotels that offer an onsite pool. View all hotels with pools in Shady Side.

What's the best place to stay near Ronald Reagan Washington National Airport (DCA)?

Hyatt Regency Crystal City is a popular 4-star hotel featuring a restaurant and an outdoor pool. It's located a short 0.6 mi (1 km) from Ronald Reagan Washington National Airport. Other options near the airport are Courtyard by Marriott Arlington Crystal City/Reagan National and Hilton Garden Inn Reagan National Airport.

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 accommodations 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 agenda are Captain Avery Museum and Franklin Point State Park. Check out what more 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 temp of 75°F, while the coldest months are January and February with an average of 40°F. Average annual precipitation for Shady Side is 51 inches.

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Find hotels in Shady Side, MD from ￥13,285

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Shady Side

Check prices for these dates

Filter by

Property class

Guest rating

Our top choices for Shady Side hotels

1. SpringHill Suites by Marriott Annapolis

2. Hampton Inn & Suites Glenarden/Washington DC

3. Comfort Inn Conference Center

4. Microtel Inn & Suites by Wyndham Gambrills

5. DoubleTree by Hilton Hotel Annapolis

6. Courtyard by Marriott Bowie

7. Anchored Inn at Hidden Harbour Marina

8. Crowne Plaza Annapolis by IHG

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

10. Best Western Annapolis

11. St Michaels Inn

12. Staybridge Suites Washington DC East - Largo by IHG

13. Courtyard by Marriott Annapolis

14. Hilton Garden Inn Annapolis Downtown

15. Hilton Garden Inn Annapolis

16. Sonesta ES Suites Annapolis

17. La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

18. Red Roof Inn Annapolis

19. Historic Inns of Annapolis

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

Crowne Plaza Annapolis by IHG

DoubleTree by Hilton Hotel Annapolis

Sonesta ES Suites Annapolis

St Michaels Inn

Comfort Inn Largo-Washington DC East

Courtyard by Marriott Annapolis

Rod 'N' Reel Resort

Graduate by Hilton Annapolis

Lovely bay views with kayaks, bikes, fire pit, crabbing & more

More cheap stays in Shady Side

Best Western Annapolis

WoodSpring Suites Washington DC East Arena Drive

St Michaels Inn

Holiday Inn Express & Suites Annapolis by IHG

Microtel Inn & Suites by Wyndham Gambrills

Comfort Inn Conference Center

Frequently asked questions

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