Shady Side Hotels

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Top 10 trending Shady Side hotels

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (33)
"Loved the Oaks! Fabulous accommodations and excellent staff"
The price is €390
includes taxes & fees
14 Aug - 15 Aug
The Oaks Waterfront

St Michaels Inn

2.5 star property
8.2 out of 10, Very good, (1005)
"Great spot to be close to town for a modest price. "
The price is €95
includes taxes & fees
1 Sept - 2 Sept
St Michaels Inn

The Wildset

2.5 star property
9.8 out of 10, Exceptional, (355)
"This is where we stay everytime we come to St. Michaels - Top Knotch!"
The price is €205
includes taxes & fees
18 Aug - 19 Aug
The Wildset

Inn at Perry Cabin

5.0 star property
9.6 out of 10, Exceptional, (358)
"Beautiful place to stay."
The price is €594
includes taxes & fees
2 Sept - 3 Sept
Inn at Perry Cabin

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
12 Aug - 13 Aug
Parsonage Inn

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 €221
includes taxes & fees
12 Aug - 13 Aug
George Brooks House B&B

Quality Inn

2.5 star property
7.8 out of 10, Good, (805)
"Conveniently located with overall great value."
The price is €93
includes taxes & fees
12 Aug - 13 Aug
Quality Inn

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (982)
"Great spot with beautiful views. "
The price is €145
includes taxes & fees
1 Sept - 2 Sept
Hilton Garden Inn Kent Island Marina

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (881)
"Great stay beautiful view"
The price is €121
includes taxes & fees
24 Aug - 25 Aug
Holiday Inn Express Annapolis East-Kent Island by IHG

Best Western Kent Narrows Inn

2.5 star property
8.2 out of 10, Very good, (1009)
"I like the location and how easy it is to get to our room."
The price is €91
includes taxes & fees
17 Aug - 18 Aug
Best Western Kent Narrows Inn

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (604)
"Great place to stay. "
The price is €152
includes taxes & fees
21 Aug - 22 Aug
Hyatt Place Kent Narrows & Marina

Knapps Narrows Marina & Inn

3.0 star property
9.4 out of 10, Exceptional, (339)
"Our room overlooked the channel at Knapp's Narrows. The staff is friendly and helpful. We will definitely stay here again."
The price is €208
includes taxes & fees
28 Aug - 29 Aug
Knapps Narrows Marina & Inn

Wylder Tilghman Island

2.0 star property
8.6 out of 10, Excellent, (59)
"Good service and good options to enjoy the stays. "
The price is €199
includes taxes & fees
18 Aug - 19 Aug
Wylder Tilghman Island

The Tilghman Island Inn

3.5 star property
9.8 out of 10, Exceptional, (101)
"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 €194
includes taxes & fees
24 Aug - 25 Aug
The Tilghman Island Inn

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 €194
includes taxes & fees
1 Sept - 2 Sept
Kent Island Resort

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (408)
"Great location and amenities"
The price is €217
includes taxes & fees
24 Aug - 25 Aug
The Inn at Chesapeake Bay Beach Club

Rod 'N' Reel Resort

4.0 star property
8.2 out of 10, Very good, (1004)
"Great place to stay."
The price is €145
includes taxes & fees
12 Aug - 13 Aug
Rod 'N' Reel Resort

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 €337
includes taxes & fees
12 Aug - 13 Aug
Inn at Horn Point

Village Inn

2.0 star property
6.2 out of 10, (491)
"The staff is super friendly and there is a convenient store to buy drinks and snacks within walking distance."
The price is €87
includes taxes & fees
12 Aug - 13 Aug
Village Inn

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (853)
" Very clean, spacious room, friendly staff"
The price is €232
includes taxes & fees
24 Aug - 25 Aug
Annapolis Waterfront Hotel, Autograph Collection
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!

Top Shady Side Hotel 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 Graduate by Hilton Annapolis and La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway. 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. Features 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.