Search for Cheap Deals on
Hotels in Shady Side

Check Last Minute Shady Side Hotel Deals

Tonight Mar 13 - Mar 14This weekend Mar 13 - Mar 15

Choose from 1184 Shady Side Hotel Deals

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
  • 22 min drive from Shadyside Park
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and ...
9.4/10 Exceptional! (1,007 reviews)
Central l9cation, easy walk to all sites.

Reviewed on Mar 12, 2026

Graduate by Hilton 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
  • 24 min drive from Shadyside Park
Book a stay at this business-friendly hotel in Upper Marlboro. Enjoy free parking, breakfast (surcharge), and a 24-hour fitness center. Popular attractions Northwest ...
8.2/10 Very Good! (1,003 reviews)
⭐️⭐️⭐️⭐️

Reviewed on Mar 7, 2026

DoubleTree by Hilton Hotel Largo/Washington DC
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
  • 23 min drive from Shadyside Park
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.8/10 Excellent! (1,000 reviews)
Clean, friendly staff and great area

Reviewed on Mar 11, 2026

Crowne Plaza Annapolis by IHG
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
  • 22 min drive from Shadyside Park
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,876 reviews)
The recommendations from staff were wonderful. Valet service met my needs as did the hotel keeping my bags for extra hours. This is an older hotel in a historic area and decor reflecs that. For my stay it was perfect.

Reviewed on Mar 13, 2026

Historic Inns of Annapolis
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
  • 23 min drive from Shadyside Park
Book a stay at this business-friendly hotel in Capitol Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
6/10 (1,992 reviews)
Everything was great, no complaints

Reviewed on Mar 12, 2026

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
Comfort Inn Largo-Washington DC East

Comfort Inn Largo-Washington DC East

3 out of 5
9421 Largo Drive West Upper Marlboro MD
  • 23 min drive from Shadyside Park
Book a stay at this business-friendly hotel in Upper Marlboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
7.8/10 Good! (450 reviews)
Nice overnight stay for an NFL game

Reviewed on Mar 11, 2026

Comfort Inn Largo-Washington DC East
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3 out of 5
174 West Street Annapolis MD
  • 22 min drive from Shadyside Park
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
8.6/10 Excellent! (1,014 reviews)
Yes

Reviewed on Mar 13, 2026

Hilton Garden Inn Annapolis Downtown
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3 out of 5
170 Admiral Cochrane Dr Edgewater MD
  • 21 min drive from Shadyside Park
Book a stay at this business-friendly hotel in Parole. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,008 reviews)
The place was amazing.I will not stay anywhere else when I get to annapolis.I stay there probably five or six times out of the year

Reviewed on Mar 12, 2026

Sonesta ES Suites Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
  • 23 min drive from Shadyside Park
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the ...
8.6/10 Excellent! (1,002 reviews)
Didn’t use anything. Ice machine was broken on our floor.

Reviewed on Mar 12, 2026

DoubleTree by Hilton Hotel Annapolis
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3 out of 5
2600 Housley Road Annapolis MD
  • 23 min drive from Shadyside Park
Book a stay at this business-friendly hotel in Annapolis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (1,000 reviews)
The elevator was broken when we got there and no one had notified us. Had there been someone handicapped with us it would have been a real problem. Staff was very helpful.

Reviewed on Mar 8, 2026

Country Inn & Suites by Radisson, Annapolis, MD
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

3 out of 5
2559 Riva Rd Annapolis MD
  • 22 min drive from Shadyside Park
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
8.6/10 Excellent! (1,000 reviews)
The room was clean and well stocked with towels. I liked being able to walk outside to the patio. On addition, having a restaurantwith good food on-site is great!

Reviewed on Mar 8, 2026

Courtyard by Marriott Annapolis
Comfort Inn Conference Center

Comfort Inn Conference Center

2.5 out of 5
4500 Crain Hwy Bowie MD
  • 21 min drive from Shadyside Park
Book a stay at this business-friendly hotel in Bowie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9.2/10 Wonderful! (1,001 reviews)
Nice location

Reviewed on Mar 12, 2026

Comfort Inn Conference Center
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.

Find cheap hotels in Shady Side

You’re not an average traveler—and Hotwire knows it. Your wanderlust takes you off the beaten path to discover unique adventures and every travel destination’s lesser-known tourist scenes. Hotwire has the hookup! Book your Shady Side hotel with Hotwire to complete your one-of-a-kind travel checklist.

For you, intrepid voyager, Hotwire has a large selection of the best hotels in Shady Side.

Choosing the right hotel in Maryland has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Shady Side’s 1,184 hotels. Choose the one that best catches your trip’s tourist drift.

If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $95. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get great Shady Side hotel deals at the last minute.

While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Shady Side. No matter your reason for visiting Shady Side, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.

Frequently Asked Questions About Shady Side hotels

Where can I find the best last-minute travel deals?

If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can unlock great deals on your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in Shady Side for as low as $95.

How many hotels are there in Shady Side?

With over 1,184 hotels in Shady Side, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $95.

How to find cheap car rentals in Shady Side?

Finding a cheap car rental deal in Shady Side is as easy as scoring cheap hotels in Shady Side. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can unlock great car rental deals if you book a Hotwire Hot Rate at the last minute.