Vacation rentals in Shady Side

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Popular amenities for Shady Side vacation rentals

Other great vacation rentals in Shady Side

Top guest favorite
Guest suite in Bowie
5 out of 5 average rating, 104 reviews

Luxury 1BR/1BA Private Suite Close to DC!

BrendaRating, 5 stars3 days ago
Carl’s place is lovely. He has everything you need to be completely comfortable. We loved the ambiance and felt right at home. Carl was invaluable and responded quickly to all my questions. A plus for me was the stainless steel cookware.
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, 58 reviews

Entire Beach House with Pool and Hot Tub

ParsaRating, 5 stars1 day ago
We had a wonderful experience staying at Peggy’s place. It is as pristine as it looks in the photos and is peaceful and relaxing. We especially loved the pool. We would definitely book again
Home in Shady Side
4.57 out of 5 average rating, 7 reviews

3BR home near the beach w/bikes & W/D

MicheleRating, 5 stars13 months ago
We had the pleasure of meeting of staying for 4 days and everything you need for the stay was available. the kitchen was well kept and stocked. beds are super comfortable and the view was amazing!! I would suggest more towels but other then I'd rate this house 💯
Top guest favorite
A clean and inviting efficiency features a spacious bed covered with a light yellow duvet. A comfortable sofa is situated beside a rustic wooden table. An area rug with intricate patterns lays on the floor, complementing the overall decor. A small nightstand sits next to the bed.
Guesthouse in Edgewater
4.98 out of 5 average rating, 114 reviews

1 large room efficiency in detached garage.

ThomasRating, 5 starstoday
5 stars for sure! The detached garage was even nicer than the photos! The neighborhood was so peaceful and had coffee just a short walk away. Rams Head on Stage was a blast of a concert venue too! Thanks Jocelyn for the awesome stay, pets, and local recommendations :) I would absolutely stay here again and strongly recommend
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, 15 reviews

1bd 1 ba detached guest loft

CharlesRating, 5 stars5 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 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 silhouette of an osprey is perched on its nest as the sun sets in the background, creating a warm glow against the horizon. The nest is supported by a pole, surrounded by a backdrop of trees and a colorful sky.
Bungalow in Deale
4.85 out of 5 average rating, 392 reviews

Cozy waterfront getaway on the Bay

MichaelRating, 5 stars1 month ago
This place is awesome!!! Very quiet and nice neighborhood. This was the place that I chose for our 11 th wedding anniversary and could not ask for a better experience. The kitchen is what I loved the most . Many places to eat near by and the Chesapeake bay is right there.

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