Search Shady Side hotels

  • 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

Tonight
5 Apr - 6 Apr
Tomorrow
6 Apr - 7 Apr
Next weekend
10 Apr - 12 Apr
In two weeks
17 Apr - 19 Apr

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Shady Side hotels

Suite, 1 Queen Bed, Non Smoking

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (887 reviews)
"Staff was nice and room was clean "
United States
Lauren
The price is NZ$191
includes taxes & fees
7 Apr - 8 Apr
Quality Inn Grasonville near Kent Island
Terrace/patio

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (733 reviews)
"Clean hotel all around. Friendly stafff and comfortable environment."
United States
Jillian
The price is NZ$291
includes taxes & fees
7 Apr - 8 Apr
Hyatt Place Kent Narrows & Marina
Reception

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (135 reviews)
"Beautiful hotel, nice staff"
United States
Kim
The price is NZ$276
includes taxes & fees
14 Apr - 15 Apr
Kent Island Resort
Exterior

Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills
2.0 star property
Gambrills
9.0 out of 10, Wonderful, (1,058 reviews)
"We stayed here while visiting our kids in the area! Very nice staff and clean hotel. Good place to stay for the money! "
United States
Lonnie
The price is NZ$162
includes taxes & fees
19 Apr - 20 Apr
Microtel Inn & Suites by Wyndham Gambrills
Exterior

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, (978 reviews)
"Very nice hotel, good breakfast selection, clean rooms."
United States
Linda
The price is NZ$226
includes taxes & fees
16 Apr - 17 Apr
Holiday Inn Express Annapolis East-Kent Island by IHG
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,002 reviews)
"Wonderful staff,Clean rooms and comfortable bed!!"
United States
Evette
The price is NZ$194
includes taxes & fees
13 Apr - 14 Apr
Best Western Kent Narrows Inn
Free daily self-service breakfast

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,006 reviews)
"Very nice room and staff"
United States
Tara
The price is NZ$227
includes taxes & fees
3 May - 4 May
SpringHill Suites by Marriott Annapolis
Terrace/patio

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,001 reviews)
"Beautiful area"
United States
Dan
The price is NZ$270
includes taxes & fees
9 Apr - 10 Apr
Hilton Garden Inn Kent Island Marina
Outdoor wedding area

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.4 out of 10, Very good, (1,005 reviews)
"Great place to stay with lovely views"
United States
David
The price is NZ$294
includes taxes & fees
22 Apr - 23 Apr
Rod 'N' Reel Resort
Outdoor banquet area

The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.6 out of 10, Exceptional, (126 reviews)
"A wonderful property with a fantastic location. Super friendly staff. Couldn't ask for a more pleasant stay anywhere. You should book right now."
United States
Timothy
The price is NZ$454
includes taxes & fees
7 Apr - 8 Apr
The Tilghman Island Inn
Lobby

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, (1,006 reviews)
"I had a great stay & everything was great"
United States
Timothy L
The price is NZ$208
includes taxes & fees
8 Apr - 9 Apr
Country Inn & Suites by Radisson, Annapolis, MD
Terrace/patio

Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis
3.0 star property
Annapolis
8.8 out of 10, Excellent, (189 reviews)
"Would stay here again! Everyone and everything including location was excellent!"
United States
Paul
The price is NZ$270
includes taxes & fees
12 Apr - 13 Apr
Fairfield Inn & Suites By Marriott Annapolis
Front of property

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (478 reviews)
"The Anchored Inn at Hidden Harbour Marina is a small gem of a hotel in Deale, Maryland. The staff was incredibly kind and professional. We were there "off season" and enjoyed the quiet. The room was a little small, but the bed was very comfortable. We would stay at the Anchored Inn again in a heartbeat!"
United States
Katey
The price is NZ$305
includes taxes & fees
7 Apr - 8 Apr
Anchored Inn at Hidden Harbour Marina
Lobby

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,004 reviews)
"Great location & service was wonderful."
United States
Krisy
The price is NZ$245
includes taxes & fees
19 Apr - 20 Apr
Hilton Garden Inn Annapolis Downtown
American cuisine

Comfort Inn Conference Center

Comfort Inn Conference Center
2.5 star property
Bowie
9.2 out of 10, Wonderful, (1,004 reviews)
"Had a very nice stay"
United States
Laura
The price is NZ$197
includes taxes & fees
6 Apr - 7 Apr
Comfort Inn Conference Center
Dining

Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1,000 reviews)
"Staff was great and recommended good food spots to try. First room we were in smelt like cigarettes, but we were able to switch to a different room. "
United States
Marischel Vhee
The price is NZ$166
includes taxes & fees
7 Apr - 8 Apr
Best Western Annapolis
Reception

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1,008 reviews)
"Wonderful and clean accommodations "
United States
Emily
The price is NZ$218
includes taxes & fees
6 Apr - 7 Apr
DoubleTree by Hilton Hotel Annapolis
Front of property

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1,001 reviews)
" Great place,great location, was in town for St Michael Chocolate fest "
United States
Katherine
The price is NZ$241
includes taxes & fees
8 Apr - 9 Apr
St Michaels Inn
Exterior

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (377 reviews)
"Such a marvelous retreat! And the balcony facing the boats and the Bay at sunset is so welcome after exploring St Michael’s (a short 17 mins drive). Extremely friendly staff and good breakfast. Highly recommend to any nature lovers."
United States
Nadia
The price is NZ$290
includes taxes & fees
8 Apr - 9 Apr
Knapps Narrows Marina & Inn
Free daily buffet breakfast

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
3.0 star property
Edgewater
8.8 out of 10, Excellent, (1,010 reviews)
"Room was specious and the kitchen was a plus the buffet breakfast was great"
United States
Jesus
The price is NZ$188
includes taxes & fees
19 Apr - 20 Apr
Sonesta ES Suites Annapolis
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

Captain Avery Museum

You can spend time exploring the galleries in Captain Avery Museum during your trip to Shady Side. Stroll along the area's waterfront or simply savour its top-notch restaurants.
See properties

Top Shady Side Hotel Reviews

The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Excellent experience. "
Amber 1-night trip
Posted 3 hours ago
The Westin Annapolis

More cheap accommodation in Shady Side

WoodSpring Suites Washington DC East Arena Drive

WoodSpring Suites Washington DC East Arena Drive

1603 Brightseat Rd. Hyattsville MD
The price is NZ$135 per night from 12 Apr to 13 Apr
NZ$135
12 Apr - 13 Apr
includes taxes & fees
6.2/10 (1,004 reviews)

Frequently asked questions

What's the best place to stay in Shady Side?
DoubleTree by Hilton Hotel Largo/Washington DC, located 18.8 mi (30.3 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 Graduate by Hilton Annapolis and Historic Inns of Annapolis. 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?
Sweet Bamboo Beach Cottage: This holiday home rental outside of Shady Side is located on the beach, and has a patio, a garden and a BBQ to put you at ease 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. 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?
DoubleTree by Hilton Hotel Largo/Washington DC: Hotel located near Northwest Stadium. Features free self parking, an indoor pool and a 24-hour fitness centre. Crowne Plaza Annapolis by IHG and La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway 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 14 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 Northern Chesapeake Bay, Chesapeake Bay and Shadyside Park. 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