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31 Aug - 1 Sept
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1 Sept - 2 Sept
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5 Sept - 7 Sept
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12 Sept - 14 Sept

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Top 10 trending Shady Side hotels

Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (894)
"Wonderful breakfast and lovely outdoor seating next to the water! My favorite place to stay when I visit!!!"
The price is €132
includes taxes & fees
14 Sept - 15 Sept
Holiday Inn Express Annapolis East-Kent Island by IHG
The Wildset
Premium Room

The Wildset

2.5 star property
9.8 out of 10, Exceptional, (364)
"Fantastic place for a couple getaway. "
The price is €244
includes taxes & fees
1 Sept - 2 Sept
The Wildset
The Oaks Waterfront
Front of property

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (37)
"The facility designed was out standing and the staff was very good. "
The price is €389
includes taxes & fees
1 Sept - 2 Sept
The Oaks Waterfront
George Brooks House B&B
Exterior

George Brooks House B&B

3.0 star property
8.8 out of 10, Excellent, (61)
"Gorgeous quaint historic house. Friendly owner, close to town "
The price is €212
includes taxes & fees
1 Sept - 2 Sept
George Brooks House B&B
Comfort Inn Conference Center
American cuisine

Comfort Inn Conference Center

2.5 star property
9.0 out of 10, Wonderful, (1026)
"It was a nice stay "
The price is €96
includes taxes & fees
1 Sept - 2 Sept
Comfort Inn Conference Center
Anchored Inn at Hidden Harbour Marina
Front of property

Anchored Inn at Hidden Harbour Marina

2.5 star property
9.4 out of 10, Exceptional, (447)
"The staff specifically Victoria was impeccable! "
The price is €175
includes taxes & fees
1 Sept - 2 Sept
Anchored Inn at Hidden Harbour Marina
Hampton Inn & Suites Glenarden/Washington DC
Lobby

Hampton Inn & Suites Glenarden/Washington DC

2.5 star property
9.2 out of 10, Wonderful, (1003)
"Nice new hotel in great area "
The price is €106
includes taxes & fees
14 Sept - 15 Sept
Hampton Inn & Suites Glenarden/Washington DC
Wylder Tilghman Island
Seasonal outdoor pool

Wylder Tilghman Island

2.0 star property
8.6 out of 10, Excellent, (66)
"Good service and good options to enjoy the stays. "
The price is €197
includes taxes & fees
18 Sept - 19 Sept
Wylder Tilghman Island
Parsonage Inn
Porch

Parsonage Inn

3.5 star property
9.2 out of 10, Wonderful, (130)
"Beautiful Victorian Cottage Home. Outstanding service and breakfast. Wonderful hosts made us feel right @ home!"
The price is €216
includes taxes & fees
7 Sept - 8 Sept
Parsonage Inn
Hyatt Place Kent Narrows & Marina
Terrace/patio

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (618)
"Great location"
The price is €159
includes taxes & fees
1 Oct - 2 Oct
Hyatt Place Kent Narrows & Marina
Inn at Perry Cabin
Breakfast, lunch, dinner served; sea views

Inn at Perry Cabin

5.0 star property
9.6 out of 10, Exceptional, (361)
"Beautiful place to stay."
The price is €592
includes taxes & fees
17 Sept - 18 Sept
Inn at Perry Cabin
St Michaels Inn
Front of property

St Michaels Inn

2.5 star property
8.2 out of 10, Very good, (1001)
"Great place to stay"
The price is €90
includes taxes & fees
1 Oct - 2 Oct
St Michaels Inn
Quality Inn
Suite, 1 Queen Bed, Non Smoking

Quality Inn

2.5 star property
7.8 out of 10, Good, (817)
"Conveniently located with overall great value."
The price is €93
includes taxes & fees
17 Sept - 18 Sept
Quality Inn
Microtel Inn & Suites by Wyndham Gambrills
Exterior

Microtel Inn & Suites by Wyndham Gambrills

2.0 star property
9.0 out of 10, Wonderful, (1014)
"Great place to stay "
The price is €75
includes taxes & fees
15 Sept - 16 Sept
Microtel Inn & Suites by Wyndham Gambrills
Knapps Narrows Marina & Inn
Exterior

Knapps Narrows Marina & Inn

3.0 star property
9.4 out of 10, Exceptional, (341)
"Our room overlooked the channel at Knapp's Narrows. The staff is friendly and helpful. We will definitely stay here again."
The price is €207
includes taxes & fees
28 Sept - 29 Sept
Knapps Narrows Marina & Inn
The Tilghman Island Inn
Outdoor banquet area

The Tilghman Island Inn

3.5 star property
9.8 out of 10, Exceptional, (104)
"So friendly and professional service!"
The price is €193
includes taxes & fees
14 Sept - 15 Sept
The Tilghman Island Inn
Residence Inn Largo Medical Center Drive
Reception

Residence Inn Largo Medical Center Drive

3.0 star property
9.0 out of 10, Wonderful, (552)
"Very nice hotel l will come back soon "
The price is €122
includes taxes & fees
15 Sept - 16 Sept
Residence Inn Largo Medical Center Drive
Laurel Grove Inn on the South
Outdoor dining

Laurel Grove Inn on the South

3.5 star property
9.0 out of 10, Wonderful, (520)
"Beautiful property and lovely hosts."
Laurel Grove Inn on the South
SpringHill Suites by Marriott Annapolis
Free daily self-service breakfast

SpringHill Suites by Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (1008)
"Clean room, Good breakfast and friendly staff."
The price is €111
includes taxes & fees
15 Sept - 16 Sept
SpringHill Suites by Marriott Annapolis
The Inn at Chesapeake Bay Beach Club
Front of property – evening/night

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (415)
"Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. "
The price is €236
includes taxes & fees
1 Sept - 2 Sept
The Inn at Chesapeake Bay Beach Club
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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Top Shady Side Hotel Reviews

More cheap stays in Shady Side

More cheap stays in Shady Side

Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills

2525 Evergreen Rd., Gambrills, MD
The price is €75 per night from 15 Sept to 16 Sept
€75
15 Sept - 16 Sept
includes taxes & fees

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 Graduate by Hilton Annapolis and Country Inn & Suites by Radisson, Annapolis, MD. 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?

Calloway Drive Retreat | House in Shady Side: This highly rated holiday home rental in Shady Side is located near the beach, and has a patio, a selection of books and air conditioning 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?

Country Inn & Suites by Radisson, Annapolis, MD: Provides buffet, an indoor pool and free self parking. La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway and DoubleTree by Hilton Hotel Largo/Washington DC 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.