Vacation rentals in Shady Side

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Popular amenities for Shady Side vacation rentals

Other great vacation rentals in Shady Side

Guest favorite
A shaded cabana area features a comfortable seating arrangement with neutral cushions, positioned beside a swimming pool. Lush greenery surrounds the setting, providing a natural backdrop. A small table holds refreshments, enhancing the space for relaxation and enjoyment.
Apartment in Upper Marlboro
4.95 out of 5 average rating, 131 reviews

DC Oasis- hot tub, pool, theater/game rm, & more

JasonRating, 5 stars4 days ago
This is a great place to stay and tour the DC Metro area - provided you have a car. Most days it would take us 30 minutes to get to and from DC though if we hit rush-hour, it was as long as an hour. The space is tidy and great. My kids love the pool, though it was a little cold for me-they swam there every night. Jennifer is great to communicate if you have any needs she gets stuff done right away. Note that there is only one bathroom, which can be a pain if you have a full house of six people. The washer and dryer are small so it will take you longer if you’re used to a full size. She had all the cooking methods and appliances available. The theater room has Netflix and Amazon prime ready for you to watch a show. There is even a popcorn maker. We did not use the gym, but it was nice - comparable to a small hotel gym. Property is in the owner’s basement, so there is some sound from upstairs as identified in the listing. Host stays out of your way but is there if you need anything.
Guest favorite
A bright living room features large windows with panoramic views of the Chesapeake Bay. A comfortable gray sectional sofa and an armchair are arranged on a vibrant area rug. A wooden desk with a computer is positioned nearby, and a flat-screen TV is mounted on the wall.
Place to stay in Shady Side
5 out of 5 average rating, 41 reviews

Round House -- Panoramic Views -- Chesapeake Bay

JenniferRating, 5 stars20 months ago
Sarah’s place is one of the most beautiful Airbnbs we have ever stayed in. We cherished every minute! The view from the house and deck is unmatched. The peaceful bay and wildlife was heaven for us and we didn’t want to leave when the weekend was over. The home has everything you need to make your stay so comfortable. Highly highly recommend this home.
Top guest favorite
Home in Edgewater
4.98 out of 5 average rating, 57 reviews

Entire Beach House with Pool and Hot Tub

MalindaRating, 5 stars4 days ago
We were very relaxed at our stay. It was quiet and the ocean was just down the street. We would go and sit on the bench and just listen to the waves.
Superhost
A spacious waterfront house is shown surrounded by lush trees, with multiple balconies and large windows. A sandy area extends toward the water's edge, and smooth stones form a barrier along the shore, reflecting the natural beauty of the Chesapeake Bay.
Home in Shady Side
4.88 out of 5 average rating, 181 reviews

Cattail Landing- Photographer's Waterfront Retreat

AshleyRating, 5 stars8 months ago
We had a wonderful time during our visit. The peaceful environment on the water was just what our group needed. Thank you!
Top guest favorite
A dining area is presented with a large wooden table surrounded by four black chairs and a matching bench. Natural light enters through a window, illuminating the space. A small decorative piece sits on the table, while a console table is positioned in the corner.
Barn in Davidsonville
5 out of 5 average rating, 14 reviews

1bd 1 ba detached guest loft

CharlesRating, 5 stars4 days ago
Mary was an excellent host. Any question I had she responded in great time. Mary's place is set up great. Had everything you need. Super peaceful and quiet. Would stayed longer if I could have. Recommend to anyone.
Guest favorite
A sunroom is shown with a large window providing views of the water. Two wicker chairs and a glass table occupy the space. A door with a dark finish is visible, and natural light enhances the serene atmosphere.
Cottage in Edgewater
4.92 out of 5 average rating, 50 reviews

Waterfront Cottage with Private Pier

RafaelRating, 5 stars2 weeks ago
This is now one of my favorite places to stay at MD bayside! Definitely love it. It is just perfect fit to relax, and definitely have fun at the same time.
Guest favorite
A wooden structure labeled 'BOAT HOUSE' is featured in front, with large windows on either side. Colorful banners hang above the entrance. In the foreground, three adirondack chairs in blue and pink are arranged near a fire pit, creating a welcoming outdoor space.
Home in Shady Side
4.96 out of 5 average rating, 55 reviews

The Cottage

DanRating, 5 stars1 month ago
We had a very nice stay. Everything was SO clean! Thank you.
A comfortable gray sectional sofa sits against a light gray wall, accented by plush throw pillows. A stylish coffee table made of white marble-like material is positioned on a geometric area rug. Tall light fixtures provide soft illumination, and a decorative plant adds a touch of greenery.
Cottage in Shady Side
4.9 out of 5 average rating, 41 reviews

Luxe Chesapeake Cabin * River View* Fire Pit*

VanessaRating, 5 stars3 weeks ago
My family and I really loved staying at Jared’s home, not only was it beautiful, but we really liked the fresh air and nature! Jared was very kind, responsive, and was always there to help us with anything we needed. (the best host!!!) We really enjoyed this experience and highly recommend it. Thank you!

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