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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
$163 nightly
The price is $186 total per night from Jul 12 to Jul 13
$186 total
Jul 12 - Jul 13
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, ...
"Very nice hotel and convenient location"

Reviewed on Jun 12, 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
$133 nightly
The price is $151 total per night from Jul 1 to Jul 2
$151 total
Jul 1 - Jul 2
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. ...
"First room had non-functional ac in 90+ heat. Went to dinner while it was worked on. Was notified during dinner that it couldn't be repaired and to expect a new room upon return. Eventually got a room but had to wait 10 minutes in heat although they knew we were coming back. The staff member was ..."

Reviewed on Jun 12, 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
$110 nightly
The price is $125 total per night from Jul 5 to Jul 6
$125 total
Jul 5 - Jul 6
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. ...
"The hot tub was out of service. The restaurant was never open when we wanted to dine there. The bathroom in the room had an odor. Otherwise the stay was suitable for the couple of nights my husband and I stayed."

Reviewed on Jun 9, 2026

Opens in a new windowCrowne Plaza Annapolis by IHG
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
$111 nightly
The price is $127 total per night from Jun 14 to Jun 15
$127 total
Jun 14 - Jun 15
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. ...
"Clean room great staff"

Reviewed on Jun 12, 2026

Opens in a new windowDoubleTree by Hilton Hotel 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
$188 nightly
The price is $208 total per night from Jun 21 to Jun 22
$208 total
Jun 21 - Jun 22
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 ...
"It was nice. Under construction so a little challenging but otherwise very nice."

Reviewed on Jun 11, 2026

Opens in a new windowRod 'N' Reel Resort
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
$114 nightly
The price is $129 total per night from Jun 28 to Jun 29
$129 total
Jun 28 - Jun 29
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. ...
"Parking lot was dark , young man that checked me in wasn’t friendly or helpful"

Reviewed on Jun 11, 2026

Opens in a new windowDoubleTree by Hilton Hotel Largo/Washington DC
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
$102 nightly
The price is $115 total per night from Jun 15 to Jun 16
$115 total
Jun 15 - Jun 16
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 ...
"I never stayed there I called to cancel my reservation while traveling on 95 north because we wanted to go father north right after i made it. The phone number on the reservation desk was out of order, the other number to the manager i left a voicemail no one called me back They really don’t care ..."

Reviewed on Jun 11, 2026

Opens in a new windowLa Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
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.
Get rates
Opens in a new windowLovely bay views with kayaks, bikes, fire pit, crabbing & more
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
$84 nightly
The price is $95 total per night from Jul 14 to Jul 15
$95 total
Jul 14 - Jul 15
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 ...
Opens in a new windowComfort Inn Largo-Washington DC East
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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 $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 1,195 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 13 hours ago
Travelocity Verified Review
"First room had non-functional ac in 90+ heat. Went to dinner while it was worked on. Was notified during dinner that it couldn't be repaired and to expect a new room upon return. Eventually got a room but had to wait 10 minutes in heat although they knew we were coming back. The staff member was mediocre at best in soothing the situation. I would have expected a manager to be aware and reach out. Didn't happen."
A verified traveler stayed at Historic Inns of Annapolis
Historic Inns of Annapolis

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