Book Hotels in Shady Side, MD

Cabins, apartments, houseboats! We offer comfortable & private vacation rentals

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Filter by

Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Neighborhood
Neighborhood
Traveler experience
Traveler experience
Popular locations
Popular locations
Meal plans available
Meal plans available
Property amenities
Property amenities
Accessibility
Accessibility

Top Shady Side hotels

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
$161 nightly
The price is $183 total per night from May 3 to May 4
$183 total
May 3 - May 4
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, ...
Outstanding

Reviewed on Apr 11, 2026

Opens in a new windowGraduate by Hilton Annapolis
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
$199 nightly
The price is $227 total per night from Apr 19 to Apr 20
$227 total
Apr 19 - Apr 20
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. ...
Warm shower and noisy heating/ cooling system. Very disappointing after reading the earlier reviews.

Reviewed on Apr 16, 2026

Opens in a new windowHistoric Inns of Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
Fully refundable
$118 nightly
The price is $135 total per night from Apr 19 to Apr 20
$135 total
Apr 19 - Apr 20
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. ...
We stayed in a spacious junior suite, which we really enjoyed. However, the room wasn’t well soundproofed, and we could hear highway noise at night. Overall, the room was clean, though the coffee machine could have been better maintained. The pool area was nice, but unfortunately the jacuzzi was ...

Reviewed on Apr 15, 2026

Opens in a new windowCrowne Plaza Annapolis by IHG
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
$98 nightly
The price is $112 total per night from Apr 26 to Apr 27
$112 total
Apr 26 - Apr 27
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. ...
Breakfast was very good…

Reviewed on Apr 14, 2026

Opens in a new windowSonesta ES Suites Annapolis
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3 out of 5
174 West Street Annapolis MD
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $130 total per night from May 3 to May 4
$130 total
May 3 - May 4
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, free WiFi in public areas, and ...
Friendly, excellent service, very clean, and great location (very close to downtown.

Reviewed on Apr 14, 2026

Opens in a new windowHilton Garden Inn Annapolis Downtown
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
$114 nightly
The price is $130 total per night from Apr 20 to Apr 21
$130 total
Apr 20 - Apr 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. ...
The staff were so kind, funny and helpful during our stay! I love the fresh warm cookies they always had available for us at any hour :-)

Reviewed on Apr 15, 2026

Opens in a new windowDoubleTree by Hilton Hotel Annapolis
DoubleTree by Hilton Hotel Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC

4 out of 5
9100 Basil Court Upper Marlboro MD
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $120 total per night from May 17 to May 18
$120 total
May 17 - May 18
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and WiFi in public areas. ...
Had a great stay at this hotel… very nice location and area feels safe

Reviewed on Apr 16, 2026

Opens in a new windowDoubleTree by Hilton Hotel Largo/Washington DC
Comfort Inn Largo-Washington DC East

Comfort Inn Largo-Washington DC East

3 out of 5
9421 Largo Drive West Upper Marlboro MD
Fully refundable
$93 nightly
The price is $105 total per night from May 6 to May 7
$105 total
May 6 - May 7
Total with 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 ...
Comfort Inn never fails to live up to its name. Clean, comfy beds and pillows. Nice breakfast. However there were no blackout curtains.

Reviewed on Apr 15, 2026

Opens in a new windowComfort Inn Largo-Washington DC East
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 Apr 19 to Apr 20
$102 total
Apr 19 - Apr 20
Total with 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 ...
The hotel in general isn’t clean the hallways smelled like cigarettes. The first room I got was so dirty the bathroom tub was peeling and it wasn’t clean at all. The second room was a little better but still not clean and there was mold on the bathroom walls. All in all this hotel needs a good cleaning ...

Reviewed on Apr 13, 2026

Opens in a new windowLa Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
Don't see what you're looking for?
See all available properties in Shady Side
View all properties
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 1,185 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

Historic Inns of Annapolis

Historic Inns of Annapolis

3 out of 5
Posted 9 hours ago
Travelocity Verified Review
"Warm shower and noisy heating/ cooling system. Very disappointing after reading the earlier reviews."
A verified traveler stayed at Historic Inns of Annapolis
Historic Inns of Annapolis

Explore More Ways to Travel with Travelocity