Travelmyth Logo
7,258,491 hotelsin 60 categories
Sign In
ParkingFree Wi-FiDog FriendlyPoolAccessibleSmall3 StarGymOutdoor PoolBusinessHoneymoonFamilyAdult OnlySustainability JourneyIndoor PoolEV charging stationsPrivate Pool4 StarLuxuryHeated PoolGolfSpaRooms with FireplaceHistoricRomanticRooms with Jacuzzi / Hot-Tub5 StarNightlifeYogaCheapCasinoHealth & SafetyDogs Stay FreeTennisBoutique-Style
  1. World
  2. >North America
  3. >United States
  4. >Maryland
  5. >Anne Arundel
  6. >Shady Side

Hotels in Shady Side

200+ HOTELS IN AND AROUND SHADY SIDERanking can be influenced by the commissions we receive.
The Bay House main photo
The Bay House
Vacation Home in Shady Side MDUS flag
10
Excellent
$
Info
Categories
Dog Friendly
Free Wi-Fi
Parking
Luxe Chesapeake Bay Getaway Less Than 20 Mi to Annapolis! main photo
Luxe Chesapeake Bay Getaway Less Than 20 Mi to Annapolis!
Vacation Home in Shady Side MDUS flag
10
Excellent
$
Info
Categories
Adult Only
Heron's Hideaway main photo
Heron's Hideaway
Vacation Home in Shady Side MDUS flag
0.0
$
Info
Categories
Free Wi-Fi
Parking
Round House -- Panoramic Views -- Chesapeake Bay main photo
Round House -- Panoramic Views -- Chesapeake Bay
Vacation Home in Shady Side MDUS flag
0.0
$
Info
Categories
Free Wi-Fi
Parking
Luxe Chesapeake Cabin * River View* Fire Pit* main photo
Luxe Chesapeake Cabin * River View* Fire Pit*
Vacation Home in Shady Side MDUS flag
0.0
$
Info
Categories
Dog Friendly
Sanare Estates main photo
Sanare Estates
Vacation Home in Shady Side MDUS flag
0.0
$
Info
Categories
Free Wi-Fi
Parking
Water's Edge with Pier main photo
Water's Edge with Pier
Vacation Home in Shady Side MDUS flag
9.0
Excellent
$
Info
Categories
Dog Friendly
Free Wi-Fi
Parking
The Bay House main photo
The Bay House
Vacation Home in Shady Side MDUS flag
0.0
$
Info
Categories
Dog Friendly
Free Wi-Fi
Parking
12 more hotels nearby!
Steps to Chesapeake Bay! Callaway Drive Retreat main photo
Steps to Chesapeake Bay! Callaway Drive Retreat
0.7 km from Shady Side
Vacation Home in Deale MDUS flag
9.6
Excellent
$
Info
Categories
Parking
EV charging stations
Waterfront Shady Side Home with Chesapeake Bay View! main photo
Waterfront Shady Side Home with Chesapeake Bay View!
1.1 km from Shady Side
Vacation Home in Deale MDUS flag
0.0
$
Info
Categories
Free Wi-Fi
Parking
Bay House main photo
Bay House
1.7 km from Shady Side
Vacation Home in Deale MDUS flag
0.0
$
Info
Categories
Free Wi-Fi
Parking
Chesapeake Paradise House - Waterfront Vacation Rental Home on the Maryland Chesapeake Bay main photo
Chesapeake Paradise House - Waterfront Vacation Rental Home on the Maryland Chesapeake Bay
2.3 km from Shady Side
Vacation Home in Deale MDUS flag
0.0
$
Info
Categories
Dog Friendly
Free Wi-Fi
Parking
The 3 Bedroom Waterfront Cottage at Chesapeake Paradise near Annapolis MD main photo
The 3 Bedroom Waterfront Cottage at Chesapeake Paradise near Annapolis MD
2.3 km from Shady Side
Vacation Home in Deale MDUS flag
0.0
$
Info
Categories
Dog Friendly
Free Wi-Fi
Parking
Renovated Waterfront Estate with Dock and Views! main photo
Renovated Waterfront Estate with Dock and Views!
3.6 km from Shady Side
Vacation Home in Deale MDUS flag
0.0
$
Info
Expansive Beverly Triton Retreat main photo
Expansive Beverly Triton Retreat
3.6 km from Shady Side
Vacation Home in Edgewater MDUS flag
0.0
$
Info
Categories
Dog Friendly
Chesapeake Bay Home Dock, Decks and Fire Pit! main photo
Chesapeake Bay Home Dock, Decks and Fire Pit!
3.6 km from Shady Side
Vacation Home in Deale MDUS flag
10
Excellent
$
Info
Anchored Inn at Hidden Harbor main photo
Anchored Inn at Hidden Harbor
3.7 km from Shady Side
Hotel in Deale MDUS flag
9.2
Excellent
From $227
$
Info
Categories
Dog Friendly
Small
Pool
Outdoor Pool
Grandma's Summer House Beverly Beach main photo
Grandma's Summer House Beverly Beach
3.8 km from Shady Side
Vacation Home in Edgewater MDUS flag
10
Excellent
$
Info
Categories
Dog Friendly
Free Wi-Fi
Parking
Waterfront Getaway, Dock Your Boat & Play! main photo
Waterfront Getaway, Dock Your Boat & Play!
4.2 km from Shady Side
Vacation Home in Edgewater MDUS flag
8.0
Very Good
$
Info
Categories
Dog Friendly
Waterfront Getaway, Dock Your Boat & Play! main photo
Waterfront Getaway, Dock Your Boat & Play!
4.2 km from Shady Side
Vacation Home in Edgewater MDUS flag
9.0
Excellent
$
Info
Categories
Dog Friendly
Parking
*Additional taxes or fees may apply. Please check the final price before completing your booking.Showing 1-20 out of 200+ hotels in and around Shady Side
Save more on the App
Categories
Map
7,258,491
Hotels
60
Categories
49,804
Regions
208,995
Cities