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25 Jul - 26 Jul
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26 Jul - 27 Jul
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25 Jul - 27 Jul
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Top hotels and accommodation in Shady Side

The Oaks Waterfront
Front of property

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (32)
" Beautiful property, wonderful staff, excellent food service."
The price is NZ$752
includes taxes & fees
27 July - 28 July
The Oaks Waterfront
St Michaels Inn
Front of property

St Michaels Inn

2.5 star property
8.2 out of 10, Very good, (1001)
"Great spot to be close to town for a modest price. "
The price is NZ$204
includes taxes & fees
27 July - 28 July
St Michaels Inn
The Wildset
Premium Room

The Wildset

2.5 star property
9.8 out of 10, Exceptional, (342)
"At check in we were notified our room was upgraded for our anniversary. The room was beautiful, right within walking distance to restaurants, shopping and even the water. The included breakfast was great, staff was sweet, and property was just amazing! We would love to return! "
The price is NZ$396
includes taxes & fees
11 Aug - 12 Aug
The Wildset
Inn at Perry Cabin
Breakfast, lunch, dinner served; sea views

Inn at Perry Cabin

5.0 star property
9.6 out of 10, Exceptional, (355)
"Beautiful place to stay."
The price is NZ$1,270
includes taxes & fees
7 Aug - 8 Aug
Inn at Perry Cabin
Parsonage Inn
Porch

Parsonage Inn

3.5 star property
9.2 out of 10, Wonderful, (128)
"Beautiful Victorian Cottage Home. Outstanding service and breakfast. Wonderful hosts made us feel right @ home!"
The price is NZ$417
includes taxes & fees
31 July - 1 Aug
Parsonage Inn
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 NZ$442
includes taxes & fees
5 Aug - 6 Aug
George Brooks House B&B
Quality Inn
Suite, 1 Queen Bed, Non Smoking

Quality Inn

2.5 star property
7.8 out of 10, Good, (793)
"The place was clean and quiet, staff was great, not much nearby to see and do. It’s a fishing town. "
The price is NZ$180
includes taxes & fees
24 Aug - 25 Aug
Quality Inn
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, (874)
"Great place"
The price is NZ$234
includes taxes & fees
31 July - 1 Aug
Holiday Inn Express Annapolis East-Kent Island by IHG
Best Western Kent Narrows Inn
In-room safe, individually decorated, individually furnished, desk

Best Western Kent Narrows Inn

2.5 star property
8.2 out of 10, Very good, (1006)
"Second time staying, it’s priced right, great staff, and amazing restaurants right across the street, quiet area right by the bay bridge. "
The price is NZ$232
includes taxes & fees
10 Aug - 11 Aug
Best Western Kent Narrows Inn
Hyatt Place Kent Narrows & Marina
Terrace/patio

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (595)
"Great place to stay. "
The price is NZ$311
includes taxes & fees
28 July - 29 July
Hyatt Place Kent Narrows & Marina
Knapps Narrows Marina & Inn
Exterior

Knapps Narrows Marina & Inn

3.0 star property
9.4 out of 10, Exceptional, (336)
"This is a wonderful place "
The price is NZ$255
includes taxes & fees
28 July - 29 July
Knapps Narrows Marina & Inn
Wylder Tilghman Island
Seasonal outdoor pool

Wylder Tilghman Island

2.0 star property
8.6 out of 10, Excellent, (56)
"Good service and good options to enjoy the stays. "
The price is NZ$385
includes taxes & fees
18 Aug - 19 Aug
Wylder Tilghman Island
The Tilghman Island Inn
Outdoor banquet area

The Tilghman Island Inn

3.5 star property
9.8 out of 10, Exceptional, (97)
"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 NZ$410
includes taxes & fees
28 July - 29 July
The Tilghman Island Inn
Kent Island Resort
Aerial view

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (105)
"Welcoming and well-staffed property, in a lovely and tranquil setting. Staff was friendly and helpful. Restaurant/bar service and food were outstanding. Great quiet getaway weekend spot. "
The price is NZ$429
includes taxes & fees
27 July - 28 July
Kent Island Resort
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, (403)
"Staff was very polite and friendly. "
The price is NZ$419
includes taxes & fees
24 Aug - 25 Aug
The Inn at Chesapeake Bay Beach Club
Rod 'N' Reel Resort
Superior Studio Suite | Balcony

Rod 'N' Reel Resort

4.0 star property
8.2 out of 10, Very good, (1007)
"Great place to stay."
The price is NZ$312
includes taxes & fees
27 July - 28 July
Rod 'N' Reel Resort
Inn at Horn Point
Beach nearby

Inn at Horn Point

3.0 star property
9.4 out of 10, Exceptional, (19)
"Family owned with care and pride. Excellent food and recommendations for other restaurants and activities. "
The price is NZ$648
includes taxes & fees
30 July - 31 July
Inn at Horn Point
Village Inn
TV

Village Inn

2.0 star property
6.2 out of 10, (488)
"The staff is super friendly and there is a convenient store to buy drinks and snacks within walking distance."
The price is NZ$168
includes taxes & fees
27 July - 28 July
Village Inn
Annapolis Waterfront Hotel, Autograph Collection
Room, 2 Queen Beds, Non Smoking, Balcony

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (843)
"Front desk staff was very friendly and helpful."
The price is NZ$416
includes taxes & fees
17 Aug - 18 Aug
Annapolis Waterfront Hotel, Autograph Collection
Flag House Inn
Front of property

Flag House Inn

3.5 star property
9.6 out of 10, Exceptional, (72)
"Lovely B&B close to EVERYTHING! The host were so kind and helpful. The common areas were very nice as well as the front porch!"
The price is NZ$329
includes taxes & fees
27 July - 28 July
Flag House 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!

See all hotels in Shady Side

Top Shady Side Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"This property is perfectly located within short walking distance of the USNA, downtown shopping/dining and the State House. It could not be in a better location. The property is historic, beautiful and well maintained. The room was spacious, clean and did not feel tired or in need of a refresh. We were absolutely thrilled with the property and will stay here every time we are back in town."
Darren 1-night trip
Posted 2 days ago
Historic Inns of Annapolis

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?

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! : This holiday home rental outside of Shady Side is located in the city centre, and has a fireplace, a patio 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. You and your friends and family can relax into your holiday with amenities such as 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. 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 12 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 Triton Beach 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.