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Top Shady Side hotels

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

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

Shady Side MD
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.
"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."

Reviewed on Aug 9, 2026

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Opens in a new windowLovely bay views with kayaks, bikes, fire pit, crabbing & more
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $111 total per night from Sep 20 to Sep 21
$111 total
Sep 20 - Sep 21
Total with 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. ...
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Reviewed on Aug 31, 2026

Opens in a new windowDoubleTree by Hilton Hotel Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
$103 nightly
The price is $117 total per night from Sep 30 to Oct 1
$117 total
Sep 30 - Oct 1
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. ...
"Pool is open but not clean and hot tub is under maintenance, which is not stated anywhere until you actually head to the pool area"

Reviewed on Aug 31, 2026

Opens in a new windowCrowne Plaza Annapolis by IHG
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street St. Michaels MD
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $105 total per night from Sep 13 to Sep 14
$105 total
Sep 13 - Sep 14
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of ...
"There were a couple of minor details with the room but not enough to dissuade me from staying here again. Ginny on the front desk was a joy."

Reviewed on Sep 1, 2026

Opens in a new windowSt Michaels Inn
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $168 total per night from Sep 29 to Sep 30
$168 total
Sep 29 - Sep 30
Total with 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. ...
Opens in a new windowHistoric Inns of Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
$153 nightly
The price is $175 total per night from Sep 13 to Sep 14
$175 total
Sep 13 - Sep 14
Total with 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, ...
Opens in a new windowGraduate by Hilton Annapolis
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave Chesapeake Beach MD
Fully refundableReserve now, pay when you stay
$191 nightly
The price is $212 total per night from Oct 1 to Oct 2
$212 total
Oct 1 - Oct 2
Total with taxes and fees
A marina, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. Make the most of the 24-hour gym and seasonal outdoor pool, and relax ...
Opens in a new windowRod 'N' Reel Resort
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

3 out of 5
55 Hampton Park Blvd Capitol Heights MD
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $102 total per night from Sep 7 to Sep 8
$102 total
Sep 7 - Sep 8
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 2 ...
Opens in a new windowLa Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3 out of 5
170 Admiral Cochrane Dr Edgewater MD
Fully refundableReserve now, pay when you stay
$91 nightly
The price is $104 total per night from Sep 22 to Sep 23
$104 total
Sep 22 - Sep 23
Total with 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. ...
Opens in a new windowSonesta ES Suites Annapolis
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See all available properties in Shady Side
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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.

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 $102. 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 1,208 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

St Michaels Inn

St Michaels Inn

5 out of 5
Posted 2 hours ago
Travelocity Verified Review
"There were a couple of minor details with the room but not enough to dissuade me from staying here again. Ginny on the front desk was a joy."
A verified traveler stayed at St Michaels Inn
St Michaels Inn

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