Book Hotels in Shady Side, MD

Top Shady Side hotels

Bay views with kayaks, bikes, fire pit, crabbing and more

Shady Side

This vacation home features a garden, laundry facilities, and barbecue grills. There's fun for all ages with a playground and an arcade/game room.

Nice Get Away

"Cute cottage in quiet neighborhood for a get away to the Eastern shore. Description is accurate and Mary was easy to communicate with. We enjoyed our stay."

Reviewed on Jun 22, 2025

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Calloway Drive Retreat | House in Shady Side

Shady Side

This vacation home features a water park and laundry facilities.

Military Bowl

"Wonderful place"

Reviewed on Dec 29, 2024

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Graduate by Hilton Annapolis

126 West St, Annapolis, MD

Fully refundableReserve now, pay when you stay

$155 nightly

$177 total

Aug 17 - Aug 18

Total includes taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference space, ...

"This hotel is great. Good location accommodations are beautiful. The only thing they lack is a coffee maker in the room."

Reviewed on Aug 7, 2025

Country Inn & Suites by Radisson, Annapolis, MD

2600 Housley Road, Annapolis, MD

Fully refundable

$97 nightly

$110 total

Aug 17 - Aug 18

Total includes taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot ...

"You all have some of the best staff ever. I liked the property so much that I’m planning my next trip to stay again already. My grandkids love the idea that we can just go downstairs to get breakfast and make your own waffles. Last but not least, the hot tub and swimming pool is on point."

Reviewed on Aug 7, 2025

Historic Inns of Annapolis

58 State Circle, Annapolis, MD

Fully refundableReserve now, pay when you stay

$143 nightly

$163 total

Aug 17 - Aug 18

Total includes taxes and fees

This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. ...

"Excellent location for downtown and Acadamy access. Really enjoyed the history of the location and the displays. Staff was wonderful!"

Reviewed on Aug 7, 2025

Sonesta ES Suites Annapolis

170 Admiral Cochrane Dr, Edgewater, MD

Fully refundableReserve now, pay when you stay

$95 nightly

$108 total

Sep 2 - Sep 3

Total includes taxes and fees

This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. ...

"Great room for a great price... Very friendly staff, too."

Reviewed on Jul 17, 2025

Crowne Plaza Annapolis by IHG

173 Jennifer Rd, Annapolis, MD

Fully refundable

$116 nightly

$132 total

Aug 28 - Aug 29

Total includes taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. ...

"Nice spot in a convenient but quiet area."

Reviewed on Aug 8, 2025

Comfort Inn Largo-Washington DC East

9421 Largo Drive West, Upper Marlboro, MD

Fully refundableReserve now, pay when you stay

$84 nightly

$95 total

Aug 17 - Aug 18

Total includes taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will ...

"Front desk was great. Charming and friendly ladies. Hotel definitely needs some work its kind of dingey but overall good stay."

Reviewed on Aug 3, 2025

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

55 Hampton Park Blvd, Capitol Heights, MD

Fully refundableReserve now, pay when you stay

$87 nightly

$98 total

Sep 2 - Sep 3

Total includes taxes and fees

This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests ...

"Great property if you are in need of a stay close to the stadium."

Reviewed on Aug 6, 2025

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels in Shady Side with star-rating

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Shady Side Hotel & Travel Guide\n

Shady Side has no Travelocity accommodation options itself. However, we offer at least 17 places to rest an easy drive away.

The closest Travelocity accommodation is the Annapolis Waterfront Hotel, Autograph Collection, Maryland, which can be found 10 miles (15 kilometers) from the downtown precinct of Shady Side. A different close Travelocity-listed option is the Historic Kent Manor Inn, located in Maryland, about 14 miles (22 kilometers) from the heart of Shady Side.

The Loews Annapolis Hotel is about 10 miles (16 kilometers) away from the heart of Shady Side. Another alternative is the The Tilghman Island Inn, which is located 12 miles (20 kilometers) away. Some other hotel and apartment options in the region include the Lazyjack Inn on Dogwood Harbor and the The Westin Annapolis.

How about you explore more of the coastal plains and wetlands that are located in Southern Maryland? Opt to spend a few extra nights in some of the other areas of Southern Maryland. Relish the chance to look at regional diverse attractions or have a go at hiking and shore fishing before you check in to a convenient Travelocity-listed hotel or apartment.

Lexington Park is 40 miles (68 kilometers) south of Shady Side and is where you'll find St. Mary's College of Maryland and Patuxent River Naval Air Museum. A few Travelocity-listed Lexington Park hotels and apartments include the Comfort Inn & Suites and Americas Best Value Inn & Suites. 35 miles (55 kilometers) to the south of Shady Side, you will find Hollywood, which boasts the The Victorian Candle and Red Roof Inn California, MD - NAVAIR. The Sotterley Plantation and Greenwell State Park are a couple of the popular sites to explore in Hollywood.

Prior to departing from Western Chesapeake Shore, you should make sure you experience a fast-paced match. Stop by Nationals Park, which you will find to the west of Shady Side. Wise travelers who are interested in booking a bed close to the action, book in the The Jefferson, Washington, DC or Marriott Marquis Washington, DC.

Located 25 miles (40 kilometers) away from downtown Shady Side is Baltimore Washington International Thurgood Marshall Airport. Stay nearby at Residence Inn by Marriott Baltimore BWI Airport or BWI Airport Marriott.

Frequently asked questions

What are the top kid-friendly hotels in Shady Side?

Family getaways are where amazing memories are made, but traveling with young ones can be demanding. These kid-friendly Shady Side hotels come with perks that aim to keep visitors of all ages relaxed and happy: Chesapeake Cabin will help make your trip the most memorable one yet. It offers a range of conveniences geared toward families, such as a playground and beach sun loungers. Round House -- Panoramic Views -- Chesapeake Bay is another great choice. After a long day of sightseeing, come back home to your comfortable room and perks like a nearby beach and a travel crib.

Where can I find cheap hotels in Shady Side?

At Travelocity you'll find really nice hotels in Shady Side at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Shady Side rather than in Shady Side. We may find you even better rates, too.

How do I find the best Shady Side hotel deals?

Simple! On Travelocity, look through the fantastic offers we've already found in Shady Side then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.

How much does it cost to stay in a hotel in Shady Side?

The cheapest hotel in Shady Side is $95. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.

How many hotels are in Shady Side?

There are 1,190 hotels in Shady Side on Travelocity.

What are the best hotels in Shady Side?

Shady Side has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Shady Side for you!

When is the best time to visit Shady Side?

If you want the joy of a fun-filled trip in peak season, visit Shady Side during May, June and July. If you'd prefer the peace of off-season, book a stay during quieter months, such as November, December and January.

When is the cheapest time to stay in Shady Side?

Based on historic data is usually the cheapest month to visit Shady Side. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.

Are there any great family-friendly hotels in Shady Side?

There are multiple hotels in Shady Side that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Shady Side. We have plenty of kid-friendly hotels in Shady Side to choose from on Travelocity!

Why book a hotel in Shady Side through Travelocity?

Because we have the top hotels in Shady Side! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!

How do I cancel my hotel booking in Shady Side on Travelocity?

Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Shady Side hotel reviews by fellow wanderers

Best Western Annapolis

5 out of 5

Posted 2 days ago

Travelocity Verified Review

"Love it "

A verified traveler stayed at Best Western Annapolis

Country Inn & Suites by Radisson, Annapolis, MD

5 out of 5

Posted 2 days ago

Travelocity Verified Review

"You all have some of the best staff ever. I liked the property so much that I’m planning my next trip to stay again already. My grandkids love the idea that we can just go downstairs to get breakfast and make your own waffles. Last but not least, the hot tub and swimming pool is on point."

Members can access discounts and special features

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Top Shady Side hotels

Bay views with kayaks, bikes, fire pit, crabbing and more