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Top 10 trending Shady Side hotels

Holiday Inn Express Annapolis East-Kent Island by IHG
Welcome to the Holiday Inn Express, where guests can check in and enjoy a convenient stay.

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (878)
"Great stay beautiful view"
The price is €133
includes taxes & fees
10 Aug - 11 Aug
Holiday Inn Express Annapolis East-Kent Island by IHG
Hyatt Place Kent Narrows & Marina
Relax by the fire pit in this scenic waterfront seating area, overlooking the marina with boats docked.

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (603)
"Great place to stay. "
The price is €148
includes taxes & fees
25 Aug - 26 Aug
Hyatt Place Kent Narrows & Marina
Hilton Garden Inn Kent Island Marina
Relax on the outdoor terrace with a view of the marina, surrounded by wicker furniture and beautiful flowers.

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (975)
"Friendly staff, nice environment"
The price is €148
includes taxes & fees
10 Aug - 11 Aug
Hilton Garden Inn Kent Island Marina
The Westin Annapolis
Experience the grandeur of this classic hotel, featuring a symmetrical facade with a central entrance and evenly spaced windows.

The Westin Annapolis

4.0 star property
8.6 out of 10, Excellent, (1005)
"The Hotel was very clean and convenient to everything that we wanted to do!!!!"
The price is €156
includes taxes & fees
10 Aug - 11 Aug
The Westin Annapolis
Hilton Garden Inn Annapolis
Relax in this stylish room with two beds, a desk, and a flat-screen TV.

Hilton Garden Inn Annapolis

3.0 star property
8.2 out of 10, Very good, (1003)
"Great staff! Super clean."
The price is €94
includes taxes & fees
10 Aug - 11 Aug
Hilton Garden Inn Annapolis
Hampton Inn & Suites Annapolis
Two single beds with white linens, a flat-screen TV, and a desk with a telephone.

Hampton Inn & Suites Annapolis

2.5 star property
8.2 out of 10, Very good, (1005)
"Very nice stay. Front desk staff was friendly and the pool is a great bonus."
The price is €102
includes taxes & fees
14 Aug - 15 Aug
Hampton Inn & Suites Annapolis
Courtyard by Marriott Annapolis
Welcome to the Courtyard by Marriott, featuring a contemporary design and a covered entrance with a walkway leading to the main doors.

Courtyard by Marriott Annapolis

3.0 star property
8.6 out of 10, Excellent, (1006)
"Great place and great staff "
The price is €98
includes taxes & fees
18 Aug - 19 Aug
Courtyard by Marriott Annapolis
Annapolis Waterfront Hotel, Autograph Collection
Relax in this serene room with a large bed, a comfortable armchair, and a floor lamp, offering a view of the nearby water.

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (849)
"We were pleased with the staff, room and the view. We were disappointed that there was no restaurant or bar on the property as the description led us to believe."
The price is €217
includes taxes & fees
10 Aug - 11 Aug
Annapolis Waterfront Hotel, Autograph Collection
The Inn at Chesapeake Bay Beach Club
Welcome to our hotel, featuring a modern entrance with a covered area and lush greenery.

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (404)
"Staff was very polite and friendly. "
The price is €218
includes taxes & fees
24 Aug - 25 Aug
The Inn at Chesapeake Bay Beach Club
Historic Inns of Annapolis
Relax in the serene outdoor patio, surrounded by trees and equipped with comfortable seating and tables.

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1819)
"Loved the hotel-great location "
Historic Inns of Annapolis
Holiday Inn Express & Suites Annapolis by IHG
Indulge in a diverse selection of international cuisine at our buffet, featuring omelets, cheese, and more.

Holiday Inn Express & Suites Annapolis by IHG

2.5 star property
8.2 out of 10, Very good, (1005)
"Bed was very comfortable "
The price is €95
includes taxes & fees
14 Aug - 15 Aug
Holiday Inn Express & Suites Annapolis by IHG
Kent Island Resort
Surrounded by lush greenery and a serene lake, this historic property offers a picturesque setting with a spacious parking area and a circular driveway.

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (107)
"Hotel was great and peaceful. This hotel was water front. Nice surroundings!! I enjoyed to stay here."
The price is €178
includes taxes & fees
3 Sept - 4 Sept
Kent Island Resort
Wylder Tilghman Island
Relax by the serene pool surrounded by comfortable sun loungers and umbrellas, set in an and secure area.

Wylder Tilghman Island

2.0 star property
8.6 out of 10, Excellent, (57)
"Good service and good options to enjoy the stays. "
The price is €200
includes taxes & fees
18 Aug - 19 Aug
Wylder Tilghman Island
Country Inn & Suites by Radisson, Annapolis, MD
Two large beds with white linens and dark brown headboards, a desk with a lamp and chair, and a large window with curtains.

Country Inn & Suites by Radisson, Annapolis, MD

3.0 star property
9.0 out of 10, Wonderful, (1006)
"Great location , perfect for my family stay."
The price is €95
includes taxes & fees
10 Aug - 11 Aug
Country Inn & Suites by Radisson, Annapolis, MD
DoubleTree by Hilton Hotel Annapolis
Welcome to DoubleTree by Hilton, featuring a traditional brick facade and a distinctive peaked roof.

DoubleTree by Hilton Hotel Annapolis

4.0 star property
8.6 out of 10, Excellent, (1010)
"Excellent hospitable staff made the stay even better!"
The price is €99
includes taxes & fees
10 Aug - 11 Aug
DoubleTree by Hilton Hotel Annapolis
SpringHill Suites by Marriott Annapolis
Fully equipped kitchen with dark cabinetry, white countertops, and modern appliances.

SpringHill Suites by Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (1006)
"One of the nicest rooms I have ever stayed in at a chain hotel. I will definitely stay here again. "
The price is €100
includes taxes & fees
17 Aug - 18 Aug
SpringHill Suites by Marriott Annapolis
Crowne Plaza Annapolis by IHG
Relax by the pool surrounded by lounge chairs and a skylight.

Crowne Plaza Annapolis by IHG

3.5 star property
8.8 out of 10, Excellent, (1001)
"Very clean and friendly staff. Best mattress and pillows have had in hotel."
The price is €120
includes taxes & fees
7 Aug - 8 Aug
Crowne Plaza Annapolis by IHG
Sonesta ES Suites Annapolis
Relax in a spacious room with a large bed, desk, and sofa, offering a comfortable seating area and a view.

Sonesta ES Suites Annapolis

3.0 star property
8.8 out of 10, Excellent, (848)
"Great room for a great price... Very friendly staff, too."
The price is €104
includes taxes & fees
17 Aug - 18 Aug
Sonesta ES Suites Annapolis
Fairfield Inn & Suites By Marriott Annapolis
Hotel exterior with outdoor seating areas and decorative lighting.

Fairfield Inn & Suites By Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (127)
"The breakfast options were amazing."
The price is €133
includes taxes & fees
24 Aug - 25 Aug
Fairfield Inn & Suites By Marriott Annapolis
The Tilghman Island Inn
Enjoy al fresco dining with a view of the water and a warm fire pit.

The Tilghman Island Inn

3.5 star property
9.8 out of 10, Exceptional, (98)
"Beautiful location on the water. The staff are super nice and helpful. The restaurant is very good. We had an excellent house smoked pulled pork sandwich and a shrimp po boy."
The price is €195
includes taxes & fees
24 Aug - 25 Aug
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.
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Learn more about Shady Side

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

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Top Shady Side Hotel Reviews

Comfort Inn Conference Center

Comfort Inn Conference Center

10/10 Excellent
"Very friendly staff, restaurant on site and clean. I wish the TVs offered streaming channels."
Kashieka 1-night trip
Posted 1 day ago
Comfort Inn Conference Center

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 Comfort Inn Largo-Washington DC East. 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?

Bay views with kayaks, bikes, fire pit, crabbing and 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. Other favourite homes for rent in Shady Side are Calloway Drive Retreat | House in Shady Side and Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side. 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. Offers a snack bar/deli, a seasonal outdoor pool and buffet. Comfort Inn Largo-Washington DC East and Country Inn & Suites by Radisson, Annapolis, MD 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 13 hotels and other accommodation options to choose from. Find out more about Shady Side.

What should I see while I'm in Shady Side?

Favourite places to visit include Shadyside Park, Captain Avery Museum and Franklin Point State Park. You'll also find Smithsonian Environmental Research Center and London Town in the area. 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.