Hotels in Shady Side

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The Oaks Waterfront
The Oaks Waterfront
4.0 star property
Easton
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
The Oaks Waterfront
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
Inn at Perry Cabin
Inn at Perry Cabin
5.0 star property
Downtown 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
Inn at Perry Cabin
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
Parsonage Inn
Parsonage Inn
3.5 star property
Downtown 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
Parsonage 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
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
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
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, (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
Holiday Inn Express Annapolis East-Kent Island by IHG
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
Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
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
Hyatt Place Kent Narrows & Marina
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
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
The Tilghman Island Inn
The Tilghman Island Inn
3.5 star property
Tilghman
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
The Tilghman Island Inn
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
The Inn at Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
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
The Inn at Chesapeake Bay Beach Club
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 15 - Apr 16
Rod 'N' Reel Resort
Annapolis Waterfront Hotel, Autograph Collection
Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic 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
Annapolis Waterfront Hotel, Autograph Collection
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
134 Prince - Luxury Boutique Hotel
134 Prince - Luxury Boutique Hotel
2.5 star property
Annapolis
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
134 Prince - Luxury Boutique Hotel
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.