Aerial view of Annapolis capital city of Maryland state with expensive waterside properties along the Chesapeake Bay, state capital building and naval academy, dreamy blue sky

Shady Side hotels from HK$792

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
12 Jun - 14 Jun
Next weekend
19 Jun - 21 Jun

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Shady Side hotels

Indoor pool

1. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,000 reviews)
"Good hotel for the price"
United States
Brenda
The price is HK$859
HK$953 total
includes taxes & fees
6 Jul - 7 Jul
Best Western Kent Narrows Inn
In-room safe, iron/ironing board, free WiFi, bed sheets

2. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (917 reviews)
"Room was clean and staff took very good care of us"
United States
Carol
The price is HK$833
HK$924 total
includes taxes & fees
15 Jun - 16 Jun
Quality Inn Grasonville near Kent Island
Exterior

3. Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills
2.0 star property
Gambrills
9.2 out of 10, Wonderful, (1,101 reviews)
"Breakfast was great"
United States
Sean
The price is HK$799
HK$911 total
includes taxes & fees
21 Jun - 22 Jun
Microtel Inn & Suites by Wyndham Gambrills
Outdoor wedding area

4. Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.6 out of 10, Excellent, (1,001 reviews)
"Awesome spot and room, nice walking distance from multiple places"
United States
Travis
The price is HK$1,132
HK$1,492 total
includes taxes & fees
16 Jun - 17 Jun
Rod 'N' Reel Resort
Lobby

5. Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,035 reviews)
"Friendly staff, easy parking, great breakfast"
United States
Theresa
The price is HK$793
HK$904 total
includes taxes & fees
17 Jun - 18 Jun
Country Inn & Suites by Radisson, Annapolis, MD
Front of property

6. St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1,000 reviews)
"Great location, modern rooms compared to area offerings."
United States
Shruti
The price is HK$1,005
HK$1,106 total
includes taxes & fees
17 Jun - 18 Jun
St Michaels Inn
Reception

7. Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.4 out of 10, Exceptional, (143 reviews)
"It was such a lovely quaint resort. I loved everything about staying there. Thank you."
United States
Sue
The price is HK$1,225
HK$1,626 total
includes taxes & fees
23 Jun - 24 Jun
Kent Island Resort
Exterior

8. Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (1,000 reviews)
"Beautiful view!!! Clean hotel and very nice helpful staff. Would stay again."
United States
Michele
The price is HK$1,050
HK$1,166 total
includes taxes & fees
16 Jun - 17 Jun
Holiday Inn Express Annapolis East-Kent Island by IHG
Front of property

9. Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (487 reviews)
"absolutely perfect for this traveler!"
United States
BENNY
The price is HK$1,897
HK$2,163 total
includes taxes & fees
21 Jun - 22 Jun
Anchored Inn at Hidden Harbour Marina
Reception

10. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,015 reviews)
"It was one of the nicest places we've stayed in our travels."
United States
William
The price is HK$871
HK$994 total
includes taxes & fees
21 Jun - 22 Jun
DoubleTree by Hilton Hotel Annapolis
Dining

11. Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1,010 reviews)
"Clean, reasonably priced , great staff and excellent breakfast!"
United States
Brian
The price is HK$721
HK$822 total
includes taxes & fees
14 Jun - 15 Jun
Best Western Annapolis
Meeting facility

12. Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,871 reviews)
"Great hotel..will definitely be back"
United States
Randy
The price is HK$817
HK$1,200 total
includes taxes & fees
15 Jun - 16 Jun
Historic Inns of Annapolis
Exterior

13. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (386 reviews)
"Breakfast is excellent, staff very friendly"
United States
Polina
The price is HK$1,176
HK$1,293 total
includes taxes & fees
11 Jun - 12 Jun
Knapps Narrows Marina & Inn
Desk, iron/ironing board, free WiFi, wheelchair access

14. Executive Inn And Suites

Executive Inn And Suites
2.0 star property
Upper Marlboro
7.2 out of 10, Good, (581 reviews)
"Clean and accommodating staff."
United States
Annette
The price is HK$818
HK$925 total
includes taxes & fees
11 Jun - 12 Jun
Executive Inn And Suites
Terrace/patio

15. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (767 reviews)
"Great Stay!!"
United States
Richard
The price is HK$1,560
HK$1,731 total
includes taxes & fees
30 Jun - 1 Jul
Hyatt Place Kent Narrows & Marina
Lobby

16. Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very good, (1,005 reviews)
"Breakfast was excellent and parking was convenient and safe"
United States
Paul
The price is HK$798
HK$910 total
includes taxes & fees
6 Jul - 7 Jul
Hilton Garden Inn Annapolis
Free daily buffet breakfast

17. Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
3.0 star property
Edgewater
8.8 out of 10, Excellent, (1,013 reviews)
"Lots of room nice arrangement, good outdoor places to be,"
United States
Norma
The price is HK$868
HK$989 total
includes taxes & fees
14 Jun - 15 Jun
Sonesta ES Suites Annapolis
Front of property

18. The Wildset

The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (456 reviews)
"Wonderful stay!"
United States
Rachel
The price is HK$1,795
HK$2,147 total
includes taxes & fees
6 Jul - 7 Jul
The Wildset
Dinner served

19. Comfort Inn Conference Center

Comfort Inn Conference Center
2.5 star property
Bowie
9.2 out of 10, Wonderful, (1,010 reviews)
"Great place and location."
United States
Francis
The price is HK$830
HK$938 total
includes taxes & fees
5 Jul - 6 Jul
Comfort Inn Conference Center
Outdoor banquet area

20. The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.6 out of 10, Exceptional, (134 reviews)
"The inn is very lovely. The views are spectacular. Very easy access to restaurants and shopping. "
United States
Tracey
The price is HK$1,998
HK$2,198 total
includes taxes & fees
30 Jun - 1 Jul
The Tilghman Island Inn
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Stay near popular Shady Side attractions

Shadyside Park

Explore the great outdoors at Shadyside Park, a lovely green space in Shady Side. Stroll along the area's waterfront or simply savour its top-notch restaurants.
See properties

Learn more about Shady Side

Love dining, parks and museums? Get away to Shady Side!

See all hotels in Shady Side
Aerial view of Annapolis capital city of Maryland state with expensive waterside properties along the Chesapeake Bay, state capital building and naval academy, dreamy blue sky

Top Shady Side Hotel Reviews

Comfort Inn Conference Center

Comfort Inn Conference Center

10/10 Excellent
"Great area for this hotel. Close to the highway and 8 minutes away from the mall. Staff was really nice during check in. Really clean inside and outside the hotel. I would stay here again and recommend people to stay here as well."
Kisha 2-night trip
Posted 1 hour ago
Comfort Inn Conference Center

More cheap stays in Shady Side

Country Inn & Suites by Radisson, Washington, D.C. East - Capitol Heights, MD

Country Inn & Suites by Radisson, Washington, D.C. East - Capitol Heights, MD

8850 Hampton Mall Drive North Capitol Heights MD
The price is HK$773 per night from 16 Jun to 17 Jun
HK$773
HK$873 total
16 Jun - 17 Jun
includes taxes & fees
6.4/10 (1,008 reviews)

Frequently asked questions

What's the best place to stay in Shady Side?
Historic Inns of Annapolis, located 9.6 mi (15.4 km) from the heart of Shady Side, is a top choice for your stay, based on our traveller data. Two other choices for your visit to the area are La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway and DoubleTree by Hilton Hotel Largo/Washington DC. See all available top hotels, or vacation rentals in Shady Side.
What are some of the best holiday rentals that Shady Side has to offer?
Lovely bay views with kayaks, bikes, fire pit, crabbing & more: This highly rated holiday home rental in Shady Side offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games. See all vacation rentals in Shady Side.
If I need to cancel my hotel reservation in Shady Side, will I receive a refund?
Yes, the majority of hotel room reservations are fully refundable if you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of check in. If you booked a non-refundable reservation, it might still be possible to cancel it and receive a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Shady Side.
What are some accommodation options with pools in Shady Side?
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway: Hotel located near Northwest Stadium. Provides a snack bar/deli, a seasonal outdoor pool and buffet. DoubleTree by Hilton Hotel Largo/Washington DC and Comfort Inn Largo-Washington DC East are two additional hotels that offer an on-site pool. View all hotels with pools in Shady Side.
What is staying in Shady Side like?
Visitors can enjoy all that Shady Side has to offer, including the shopping, restaurants and parks. Tourists can also enjoy so much more including its museums. In Shady Side, there are 15 hotels and other accommodation options to choose from. Find out more about Shady Side.
What should I see while I'm in Shady Side?
Natural beauty is on display at Shadyside Park, Northern Chesapeake Bay and Chesapeake Bay. A couple of additional sights to add to your itinerary are Captain Avery Museum and Franklin Point State Park. Take a look at what more there is to see and do in Expedia's Shady Side guide.
What's the weather like in Shady Side?
The hottest months are usually July and August, with an average temperature of 24°C, while the coldest months are January and February, with an average of 5°C. Average annual precipitation for Shady Side is 1307 mm.

Explore a world of travel with Expedia