Hotels in Shady Side
Free cancellation options if plans change
Earn rewards on every night you stay
Save more with Member Prices
Check prices for these dates
Where to stay in Shady Side?

Anchored Inn at Hidden Harbour Marina
Anchored Inn at Hidden Harbour MarinaDeale
9.4 out of 10, Exceptional, (479 reviews)
The price is $152
$173 total
includes taxes & fees
Apr 14 - Apr 15

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

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

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

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

Microtel Inn & Suites by Wyndham Gambrills
Microtel Inn & Suites by Wyndham GambrillsGambrills
9.2 out of 10, Wonderful, (1,067 reviews)
cleanliness Modern lodgings with convenient free parking near Regal Waugh Chapel.
The price is $83
$95 total
includes taxes & fees
Apr 19 - Apr 20

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

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 16 - Apr 17

Candlewood Suites Annapolis by IHG
Candlewood Suites Annapolis by IHGAnnapolis
8.8 out of 10, Excellent, (227 reviews)
cleanliness Boutique lodging near Annapolis Harbor with peaceful environment and hiking trails.
The price is $93
$111 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, (984 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

Rips Country Inn
Rips Country InnBowie
6.6 out of 10, (65 reviews)
cleanliness Gateway to Fort Meade with homestyle dining and cozy accommodations nearby.
The price is $81
$92 total
includes taxes & fees
Apr 12 - Apr 13

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

Comfort Inn Conference Center
Comfort Inn Conference CenterBowie
9.2 out of 10, Wonderful, (1,001 reviews)
cleanliness Convenient Bowie hotel with seasonal pool and cozy dining near Allen Pond Park.
The price is $99
$112 total
includes taxes & fees
Apr 13 - Apr 14

The Inn at Tacaro Estate
The Inn at Tacaro EstateTracys Landing
9.4 out of 10, Exceptional, (13 reviews)
cleanliness Vineyard retreat with seasonal pool and hot tub in tranquil Tracys Landing.
The price is $286
$326 total
includes taxes & fees
Apr 12 - Apr 13

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

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

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

DoubleTree by Hilton Hotel Annapolis
DoubleTree by Hilton Hotel AnnapolisAnnapolis
8.6 out of 10, Excellent, (1,003 reviews)
cleanliness Contemporary hotel near U.S. Naval Academy with fitness center and garden.
The price is $91
$103 total
includes taxes & fees
Apr 12 - Apr 13

Best Western Annapolis
Best Western AnnapolisAnnapolis
7.8 out of 10, Good, (1,000 reviews)
The price is $84
$95 total
includes taxes & fees
Apr 12 - Apr 13

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
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
Pet friendly
Top landmarks in Shady Side
Check out reviews of Shady Side hotels guests love

Hampton Inn & Suites Glenarden/Washington DC
10/10 Excellent




































































