Hotels in Shady Side

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Anchored Inn at Hidden Harbour Marina
Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (479 reviews)
The price is $152
$173 total
includes taxes & fees
Apr 14 - Apr 15
Anchored Inn at Hidden Harbour Marina
Wylder Tilghman Island
Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (94 reviews)
The price is $122
$179 total
includes taxes & fees
Apr 27 - Apr 28
Wylder Tilghman Island
Kent Island Resort
Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (135 reviews)
The price is $111
$154 total
includes taxes & fees
Apr 12 - Apr 13
Kent Island Resort
Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
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
Quality Inn Grasonville near Kent Island
Knapps Narrows Marina & Inn
Knapps Narrows Marina & Inn
3.0 star property
Sherwood
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
Knapps Narrows Marina & Inn
Microtel Inn & Suites by Wyndham Gambrills
Microtel Inn & Suites by Wyndham Gambrills
2.0 star property
Gambrills
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
Microtel Inn & Suites by Wyndham Gambrills
Best Western Kent Narrows Inn
Best Western Kent Narrows Inn
2.5 star property
Grasonville
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
Best Western Kent Narrows Inn
Rod 'N' Reel Resort
Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.4 out of 10, Very Good, (1,000 reviews)
The price is $161
$198 total
includes taxes & fees
Apr 16 - Apr 17
Rod 'N' Reel Resort
Candlewood Suites Annapolis by IHG
Candlewood Suites Annapolis by IHG
2.5 star property
Annapolis
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
Candlewood Suites Annapolis by IHG
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
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
Holiday Inn Express Annapolis East-Kent Island by IHG
Rips Country Inn
Rips Country Inn
2.5 star property
Bowie
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
Rips Country Inn
George Brooks House B&B
George Brooks House B&B
3.0 star property
St. 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
George Brooks House B&B
Comfort Inn Conference Center
Comfort Inn Conference Center
2.5 star property
Bowie
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
Comfort Inn Conference Center
The Inn at Tacaro Estate
The Inn at Tacaro Estate
5.0 star property
Tracys 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
The Inn at Tacaro Estate
Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
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
Hilton Garden Inn Kent Island Marina
St Michaels Inn
St Michaels Inn
2.5 star property
St. 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
St Michaels Inn
Flag House Inn
Flag House Inn
3.5 star property
Historic 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
Flag House Inn
DoubleTree by Hilton Hotel Annapolis
DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
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
DoubleTree by Hilton Hotel Annapolis
Best Western Annapolis
Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1,000 reviews)
The price is $84
$95 total
includes taxes & fees
Apr 12 - Apr 13
Best Western Annapolis
The Wildset
The Wildset
2.5 star property
Downtown 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
The Wildset
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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Frequently asked questions

What hotels do travelers like in Shady Side?
Can I book a refundable hotel in Shady Side?
If you need the flexibility to change your plans to Shady Side, most properties provide refundable* bookable rates. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.
Where can I stay in Shady Side if I want a vacation rental instead of a hotel?
If you want to find a good alternative to a hotel, browse our selection of 11 vacation homes.
What will the weather in Shady Side be like during my vacation?
The warmest months in Shady Side are usually July and August with an average temp of 75°F. January and February are the chilliest months when the average temp is 40°F. The rainiest months are July and August.
Why should I book my Shady Side accommodation with Hotels.com?
There are plenty of reasons to book your Shady Side travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.