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Accommodations in Shady Side You’ll Love

Affordable, Top-Rated Places to Stay in Shady Side – For Every Budget

Looking for accommodation in Shady Side (Maryland)? Discover a wide range of places to stay starting at just $50.00 per night – from hotels and bed & breakfasts to vacation rentals. Whether you're visiting for business or leisure, you'll find the perfect place that fits your budget and travel needs. Book your ideal Shady Side accommodation today!

We found 12 Accommodations in Shady Side and the surrounding area (within 40 miles)

Anchored Inn at Hidden Harbor in Deale, USA

Anchored Inn at Hidden Harbor

Hotel in Deale near Shady Side, Maryland , 604 Cabana Blvd
Located in Deale, 20 miles from Annapolis Harbor, Anchored Inn at Hidden Harbor provides accommodations with a seasonal outdoor swimming pool, free pr...
  • Parking
  • Pets allowed
  • Bar
  • Swimming pool
  • Swimming Pool

Superb 157 Reviews 9.3

from $169.86 Show details »

Luxe Chesapeake Bay Getaway Less Than 20 Mi to Annapolis! in Shady Side, USA

Luxe Chesapeake Bay Getaway Less Than 20...

Holiday home in Shady Side, Maryland
Luxe Chesapeake Bay Getaway Less Than 20 Mi to Annapolis! offers accommodations in Shady Side, 29 miles from Addison Road-Seat Pleasant.
  • Parking

Exceptional 10 Reviews 10.0

from $342.00 Show details »

Coastal Edgewater Home with Private Hot Tub! in Annapolis, USA

Coastal Edgewater Home with Private Hot...

Holiday home in Annapolis near Shady Side, Maryland
The air-conditioned accommodation is 22 miles from Addison Road-Seat Pleasant.
  • Parking

Fabulous 1 Reviews 9.0

from $398.84 Show details »

Searenity Stays in Edgewater, USA

Searenity Stays

Holiday home in Edgewater near Shady Side, Maryland , 4194 Carroll Drive
A recently renovated vacation home, Searenity Stays offers accommodations in Edgewater.
  • Parking
  • Family rooms

Exceptional 10 Reviews 9.6

from $202.68 Show details »

Calloway Drive Retreat in Deale, USA

Calloway Drive Retreat

Holiday home in Deale near Shady Side, Maryland
Calloway Drive Retreat offers accommodations in Deale, 21 miles from Annapolis Harbor and 29 miles from Addison Road-Seat Pleasant.
  • Parking

Exceptional 9 Reviews 9.6

from $217.41 Show details »

Captain’s Retreat! Newly Renovated - Beach House! in Annapolis, USA

Captain’s Retreat! Newly Renovated - Bea...

Holiday home in Annapolis near Shady Side, Maryland , 3534 Newport Avenue
Captain’s Retreat!
  • Parking
  • Family rooms

Exceptional 1 Reviews 10.0

from $73.00 Show details »

Edgewatermayo Getaway! in Edgewater, USA

Edgewatermayo Getaway!

Holiday home in Edgewater near Shady Side, Maryland , 133 Valley View Avenue
Edgewatermayo Getaway! is located in Edgewater, just 12 miles from Annapolis Harbor and 22 miles from Addison Road-Seat Pleasant.
  • Parking
  • Pets allowed

Good 5 Reviews 7.4

from $327.70 Show details »

Gourmet Kitchen Family & Pet Friendly Residence! in Edgewater, USA

Gourmet Kitchen Family & Pet Friendly Re...

Holiday home in Edgewater near Shady Side, Maryland , 1163 Carrs Wharf Road
Gourmet Kitchen Family & Pet Friendly Residence! is located in Edgewater, just 13 miles from Annapolis Harbor and 23 miles from Addison Road-Seat Plea...
  • Parking
  • Pets allowed

no reviews

from $69.00 Show details »

Waterfront Getaway, Dock Your Boat & Play! in Edgewater, USA

Waterfront Getaway, Dock Your Boat & Pla...

Holiday home in Edgewater near Shady Side, Maryland , 4105 Cadle Creek Road
Waterfront Getaway, Dock Your Boat & Play! is located in Edgewater, just 14 miles from Annapolis Harbor and 24 miles from Addison Road-Seat Pleasant.
  • Parking
  • Pets allowed

Superb 5 Reviews 9.4

from $231.35 Show details »

Grandmas Summer House Beverly Beach in Edgewater, USA

Grandmas Summer House Beverly Beach

Holiday home in Edgewater near Shady Side, Maryland , 206 Linden Avenue
Grandmas Summer House Beverly Beach is located in Edgewater, just a 16-minute walk from Triton Beach and 14 miles from Annapolis Harbor.
  • Parking
  • Pets allowed

Exceptional 1 Reviews 10.0

from $293.92 Show details »

Holly Hill Haven in Edgewater, USA

Holly Hill Haven

Holiday home in Edgewater near Shady Side, Maryland , 401 Holly Road
Holly Hill Haven offers accommodations in Edgewater, 12 miles from Annapolis Harbor and 22 miles from Addison Road-Seat Pleasant.
  • Parking
  • Pets allowed

Exceptional 1 Reviews 10.0

from $307.07 Show details »

Waters Edge with Pier in Shady Side, USA

Waters Edge with Pier

Holiday home in Shady Side, Maryland , 1032 Wiers Road
Waters Edge with Pier is located in Shady Side, just 1.8 miles from Triton Beach and 13 miles from Annapolis Harbor.
  • Parking
  • Pets allowed

Fabulous 1 Reviews 9.0

from $328.21 Show details »

Number of Accommodations in Shady Side 12
Number of guest ratings 11
Average price per night $206.00
Lowest price per night $50,00
Highest price per night $1.834,09

Top 10 Cheapest Accommodations in Shady Side

Discover the Cheapest Accommodations in Shady Side – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Accommodations in Shady Side

Check out the Most Booked Accommodations in Shady Side – Based on Guest Popularity.

Discover Shady Side – Your Guide to the Best Places to Stay

Planning a trip to Shady Side? Choosing the right place to stay is one of the most important parts of making your visit memorable. Whether you are looking for a luxury hotel, a cozy guesthouse, a modern apartment, or a family-friendly vacation rental, Shady Side offers a wide range of lodging options to suit every travel style and budget.

When deciding where to stay in Shady Side, consider key factors like location, amenities, reviews, and proximity to attractions or public transport. Do you prefer being in the heart of the city close to restaurants, shops, and nightlife? Or do you want a quiet neighborhood with a more local feel? With so many types of accommodations in Shady Side, from boutique hotels to spacious homes, you are sure to find something that fits your needs.

Tips for Finding the Perfect Stay in Shady Side

To find the perfect place to stay in Shady Side, consider your budget, preferred location, and the amenities you need. Do you want to stay in a hotel or a vacation rental or do your prefer an apartment or house with more space, privacy, and the opportunity to live like a local? Do you need access to a kitchen, laundry facilities, or a gym? Research online reviews and ratings to get an idea of what past guests have experienced. Also, consider the type of trip you're taking. If you're traveling with family, you may need a larger space or a kid-friendly environment. If you're on a romantic getaway, you may want a more intimate setting.

Accommodation data and pictures provided by Booking.com