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Holiday homes in Shady Side You’ll Love

Top-Rated Shady Side Holiday homes for Every Budget and Style!

Looking for a holiday home in Shady Side (Maryland)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $50.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Shady Side.

We found 11 Holiday-homes in Shady Side and the surrounding area (within 40 miles)

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 »

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 »

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 »

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 »

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 »

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 »

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 »

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 »

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 »

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 »

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 »

Number of Holiday homes in Shady Side 11
Number of guest ratings 11
Average price per night $316.00
Lowest price per night $50,00
Highest price per night $1.834,09

Top 10 Cheapest Holiday-homes in Shady Side

Discover the Cheapest Holiday-homes in Shady Side – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in Shady Side

Check out the Most Booked Holiday-homes in Shady Side – Based on Guest Popularity.

Holiday homes in Shady Side (Maryland), comfortable and familiar

Staying in a holiday or vacation home in Shady Side can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Shady Side for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Shady Side should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com