Hotels in Shady Side
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The Oaks Waterfront
The Oaks WaterfrontEaston
10.0 out of 10, Exceptional, (41 reviews)
cleanliness Serene bayside retreat with sunrise views and garden grounds on the Chesapeake shore.
The price is $489
$538 total
includes taxes & fees
Apr 12 - Apr 13

St Michaels Inn
St Michaels InnSt. Michaels
8.2 out of 10, Very Good, (1,001 reviews)
cleanliness Relax in a peaceful inn near St. Michaels Village with a seasonal outdoor pool.
The price is $135
$149 total
includes taxes & fees
Apr 12 - Apr 13

Inn at Perry Cabin
Inn at Perry CabinDowntown St. Michaels
9.6 out of 10, Exceptional, (379 reviews)
cleanliness Classic Chesapeake Bay escape with marina, spa, and waterfront dining options.
The price is $572
$629 total
includes taxes & fees
Apr 19 - Apr 20

The Wildset
The WildsetDowntown St. Michaels
9.8 out of 10, Exceptional, (431 reviews)
cleanliness Experience downtown St. Michaels with free breakfast, WiFi, and marina views.
The price is $219
$263 total
includes taxes & fees
Apr 12 - Apr 13

Parsonage Inn
Parsonage InnDowntown St. Michaels
9.2 out of 10, Wonderful, (133 reviews)
cleanliness Stay in a charming B&B in St. Michaels, with free breakfast and nearby trails.
The price is $229
$252 total
includes taxes & fees
Apr 10 - Apr 11

George Brooks House B&B
George Brooks House B&BSt. Michaels
8.8 out of 10, Excellent, (70 reviews)
cleanliness Victorian charm just steps from St. Michaels attractions with outdoor pool.
The price is $170
$187 total
includes taxes & fees
Apr 13 - Apr 14

Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent IslandGrasonville
7.8 out of 10, Good, (888 reviews)
cleanliness A peaceful stay near Chesapeake Bay with free breakfast and outdoor pool.
The price is $98
$108 total
includes taxes & fees
Apr 15 - Apr 16

Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island MarinaGrasonville
9.0 out of 10, Wonderful, (1,001 reviews)
cleanliness Waterfront hotel with an indoor pool, where stunning bay views greet you every day.
The price is $130
$145 total
includes taxes & fees
Apr 13 - Apr 14

Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
9.2 out of 10, Wonderful, (983 reviews)
cleanliness Escape to scenic Kent Island where bay views and bike trails await your morning coffee.
The price is $116
$129 total
includes taxes & fees
Apr 20 - Apr 21

Best Western Kent Narrows Inn
Best Western Kent Narrows InnGrasonville
8.0 out of 10, Very Good, (1,001 reviews)
cleanliness Waterfront hotel with stunning sunset views and indoor pool near hiking trails.
The price is $99
$110 total
includes taxes & fees
Apr 19 - Apr 20

Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & MarinaGrasonville
9.6 out of 10, Exceptional, (735 reviews)
cleanliness Unwind along the Eastern Shore with waterfront views and indoor pool access.
The price is $152
$169 total
includes taxes & fees
Apr 15 - Apr 16

Knapps Narrows Marina & Inn
Knapps Narrows Marina & InnSherwood
9.4 out of 10, Exceptional, (378 reviews)
cleanliness Enjoy Chesapeake Bay marina views with kayaking and seasonal outdoor pool.
The price is $150
$165 total
includes taxes & fees
Apr 10 - Apr 11

Wylder Tilghman Island
Wylder Tilghman IslandTilghman
8.8 out of 10, Excellent, (94 reviews)
The price is $122
$179 total
includes taxes & fees
Apr 27 - Apr 28

The Tilghman Island Inn
The Tilghman Island InnTilghman
9.6 out of 10, Exceptional, (126 reviews)
cleanliness Immerse in serenity along Chesapeake Bay with stunning water views and island charm.
The price is $235
$259 total
includes taxes & fees
Apr 12 - Apr 13

Kent Island Resort
Kent Island ResortStevensville
9.2 out of 10, Wonderful, (135 reviews)
The price is $111
$154 total
includes taxes & fees
Apr 12 - Apr 13

The Inn at Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach ClubStevensville
9.4 out of 10, Exceptional, (446 reviews)
cleanliness Experience luxury seaside charm at this boutique spa hotel in Stevensville.
The price is $186
$232 total
includes taxes & fees
Apr 12 - Apr 13

Rod 'N' Reel Resort
Rod 'N' Reel ResortChesapeake Beach
8.4 out of 10, Very Good, (1,000 reviews)
The price is $161
$198 total
includes taxes & fees
Apr 15 - Apr 16

Annapolis Waterfront Hotel, Autograph Collection
Annapolis Waterfront Hotel, Autograph CollectionHistoric District
8.8 out of 10, Excellent, (916 reviews)
cleanliness Savor the harbor views and rooftop terrace in walkable downtown Annapolis.
The price is $237
$270 total
includes taxes & fees
Apr 19 - Apr 20

Flag House Inn
Flag House InnHistoric District
9.2 out of 10, Wonderful, (92 reviews)
cleanliness Experience historic charm in the heart of Annapolis near the U.S. Naval Academy.
The price is $182
$207 total
includes taxes & fees
Apr 14 - Apr 15

134 Prince - Luxury Boutique Hotel
134 Prince - Luxury Boutique HotelAnnapolis
9.8 out of 10, Exceptional, (34 reviews)
cleanliness Experience historic charm in Maryland's capital just steps from the U.S. Naval Academy.
The price is $185
$211 total
includes taxes & fees
Apr 12 - Apr 13
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.
Go beyond your typical stay in Shady Side
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DoubleTree by Hilton Hotel Annapolis
8/10 Good




































































