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Most frequently booked 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
1.09 km from city centre
Get rates
Book a stay at this family-friendly vacation home in Shady Side. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Shadyside Park and Captain Avery Museum are located nearby.
Kitchen
Washer
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
15.18 km from city centre
The price is CA $209 per night
CA $209
CA $238 total
Oct 26 - Oct 27
includes taxes & fees
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 the helpful staff in our reviews. Popular attractions Annapolis City Dock and Annapolis Civil Rights Plaque are located nearby.
Pet-friendly
Free WiFi
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
Free cancellation
Reserve now, pay when you stay
30.04 km from city centre
The price is CA $120 per night
CA $120
CA $137 total
Oct 8 - Oct 9
includes taxes & fees
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. Popular attraction Northwest Stadium is located nearby.
Breakfast included
Pet-friendly
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
Free cancellation
Reserve now, pay when you stay
15.84 km from city centre
The price is CA $138 per night
CA $138
CA $157 total
Oct 12 - Oct 13
includes taxes & fees
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 helpful staff in our reviews. Popular attractions Annapolis City Dock and Annapolis Harbor Center Shopping Center are located nearby.
Pet-friendly
Parking included
Comfort Inn Largo-Washington DC East

Comfort Inn Largo-Washington DC East

3 out of 5
9421 Largo Drive West Upper Marlboro MD
Free cancellation
29.17 km from city centre
The price is CA $96 per night
CA $96
CA $108 total
Nov 2 - Nov 3
includes taxes & fees
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 clean rooms in our reviews. Popular attractions Northwest Stadium and Prince George's Sports and Learning Complex are located nearby.
Pool
Breakfast included
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave Chesapeake Beach MD
Free cancellation
Reserve now, pay when you stay
16.96 km from city centre
The price is CA $190 per night
CA $190
CA $210 total
Oct 26 - Oct 27
includes taxes & fees
Book a stay at this business-friendly hotel in Chesapeake Beach. Enjoy an outdoor pool, 2 restaurants, and a marina. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chesapeake Beach Railway Museum and Rod n Reel Charter Fishing are located nearby.
Pool
Spa
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
Free cancellation
16.31 km from city centre
The price is CA $158 per night
CA $158
CA $180 total
Nov 3 - Nov 4
includes taxes & fees
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 clean rooms in our reviews. Popular attractions Annapolis City Dock and Westfield Annapolis Mall are located nearby.
Pool
Parking included
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
Free cancellation
Reserve now, pay when you stay
15.39 km from city centre
The price is CA $122 per night
CA $122
CA $188 total
Nov 1 - Nov 2
includes taxes & fees
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 rooms in our reviews. Popular attractions Annapolis City Dock and The Colonial Players are located nearby.
Pet-friendly
Free WiFi
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street St. Michaels MD
Free cancellation
Reserve now, pay when you stay
27.65 km from city centre
The price is CA $127 per night
CA $127
CA $140 total
Oct 6 - Oct 7
includes taxes & fees
Book a stay at this business-friendly hotel in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Saint Michaels Village and Classic Motor Museum are located nearby.
Pool
Breakfast included
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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.

Top hotels in Shady Side for Extended Stay

Top Location | Free Breakfast + Fitness Center

Top Location | Free Breakfast + Fitness Center

Lanham MD
The price is CA $204 per night from Oct 7 to Oct 8
CA $204
CA $264 total
Oct 7 - Oct 8
includes taxes & fees
10/10 Exceptional! (2 reviews)
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 hotels essential information

Accommodation
1,220 hotels
Lowest Price
CA $108
Highest Price
CA $471
Popular hotels
Lovely bay views with kayaks, bikes, fire pit, crabbing & more, Graduate by Hilton Annapolis, La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway, DoubleTree by Hilton Hotel Annapolis, Comfort Inn Largo-Washington DC East, Rod 'N' Reel Resort, Crowne Plaza Annapolis by IHG, Historic Inns of Annapolis, St Michaels Inn

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 CA $108 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 1,220 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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
Posted 5 hours ago
Travelocity Verified Review
"Staff was nice. Location was great. But hotel is in desperate need of remodeling. I think it’s been about 30 years since they had one."
A verified traveller stayed at DoubleTree by Hilton Hotel Annapolis
DoubleTree by Hilton Hotel Annapolis