Vacation rentals in Shady Side

4.97 out of 5 average rating, 184 reviews

A spacious kitchen area is highlighted by a central island featuring two stools. Natural light floods in from multiple windows, and the ceiling showcases wooden beams that enhance the openness of the space. The adjacent dining area contains a large table, ideal for gatherings.

Home in Edgewater

Annapolis Area Waterside Retreat

This Rhode River home is your perfect getaway to the Annapolis area - whether you’re looking to get away to a unique home overlooking incredible sunsets, a fun weekend with friends along the water, a family trip to the Chesapeake, or a private work retreat away from the bustle of the city, this home has it all. The house is a short drive from DC or Baltimore and unlike any Airbnb this side of the Chesapeake - it is on a 3 acre marina just minutes from Annapolis but private and away from it all!

4.99 out of 5 average rating, 156 reviews

Cottage in Edgewater

Waterfront Chesapeake Bay Sunrises w/Private PIER!

Gorgeous sunrises and bay breezes await at this newly remodeled Chesapeake Bay waterfront cottage! Catch crabs or fish from your private pier, relax on the furnished deck, or explore Selby Bay with our complimentary canoe. Enjoy water views from the kitchen, dining, living room, and enclosed porch. Just 15 minutes from Annapolis & the Naval Academy, and 45 from DC—peaceful, clean, full of charm. Ideal for USNA families! Unplug, unwind, and make memories on the water—year-round relaxation & fun!

5 out of 5 average rating, 168 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silver Water is a serene 5 Star retreat for those who value tranquility over spectacle. Set along the Chesapeake, it offers front-row seats to breathtaking sunsets—where golden light dances across the water. Inside, Nordic-inspired design meets quiet luxury, featuring award-winning mattresses and bedding that promise restorative sleep. Here, time slows, and luxury isn’t just something you see—it’s something you feel. We invite you to read the reviews of so many happy guests.

4.9 out of 5 average rating, 287 reviews

A wooden sign displaying the name 'bean rush café' is mounted on a white fence. The café entrance is visible in the background, along with a flag displayed on the porch. Green foliage surrounds the sign, contributing to a welcoming neighborhood vibe.

Guesthouse in Annapolis

Calico Cottage Guest House, king bed, free parking

Cute-as-a-bugs ear West Annapolis guest cottage just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8. Cottage features: high speed WiFi, EZ free parking, washer & dryer, kitchenette, air conditioning, self check-in and laptop friendly workspace. Park 10 feet from front door. Only 1 step to enter. No stairs to negotiate while carrying luggage! 15 min. walk to Weems Creek with scenic, serene waterviews and a few more minutes walk to popular Bean Rush Cafe.

4.96 out of 5 average rating, 106 reviews

Waterfront w/ Private Pier, 35 Mins to Annapolis

Located 35 minutes from Annapolis and 45 minutes from Washington DC, Shady Side is a quaint town. This waterfront home is perfect for families or small groups looking to enjoy a relaxing getaway on the Chesapeake Bay. Enjoy the large wrap-around screened in porch and private pier with ladder for easy access for swimming. Large yard, and an incredible view of the Bay Bridge. Free public boat ramp 5 min away in Parish Creek. Listed for 8 people max but contact us for approval of 1-2 more.

4.95 out of 5 average rating, 170 reviews

Guesthouse in Galesville

Nautical Charm and relaxing waterview!

Our comfortable and relaxing studio is a quiet retreat with a fantastic view while still in close proximity to Washington DC, Annapolis and Baltimore! Situated in a charming waterfront and sailing community, this separate and private unit has: parking, 1 bath, queen bed, kitchen (limited), TV, high speed WiFi and Bluetooth speaker. Wake up to the cluck cluck of our four resident chickens who are tucked away in their attractive coop. Sit on the porch and take in the view!

4.98 out of 5 average rating, 123 reviews

The kitchen features white cabinetry and stainless steel appliances, including a dishwasher and stove. A spacious countertop offers ample workspace, illuminated by natural light from the nearby window. The adjacent dining area is visible, showcasing a table and chairs.

Home in West River

Cozy waterview home in West River!

Your family will be close to everything when you stay at this centrally-located place. This home is located just 15 miles to Annapolis, 18 miles to the Naval Academy, and 30 miles to the heart of Washington, DC. Less then 8 miles to Rt 214, providing direct access to beltway, and other major highways. This charming home has as spacious fenced in yard, High Speed Internet, TV (Netflix & Hulu), outdoor seating and a fire pit. Want to get away? Bring the whole family!

4.99 out of 5 average rating, 212 reviews

A dining area is framed by large windows, providing expansive views of the Chesapeake Bay and nearby greenery. A rustic table with weathered wood complements the inviting atmosphere. Natural light fills the space, enhancing the connection to the outdoor scenery.

Home in Tracys Landing

The Little Gypsy BoHome

Welcome to our Little Gypsy BoHome on the bay! The house is situated in Southern Anne Arundel County, MD in the quaint waterfront town of Tracy's Landing. Our home sits directly on The Chesapeake Bay with breathtaking views from every window. We offer a saltwater swimming pool, two corn hole game sets, a basketball hoop, beach access, canoe, 2 Paddle Boards, a gas grill, and a steam shower, an outdoor redwood panoramic barrel sauna and a redwood cold plunge!

4.82 out of 5 average rating, 181 reviews

Cottage in Deale

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Savor our three-bedroom Cottage in this peaceful western shore spot, enjoy two acres of green space, the pier, kayaks, swings, fire pit, shady lawns & sun-drenched loungers, local waterfront dining or eat in, close to Washington, D.C., Annapolis, & Baltimore at this honeymoon-worthy country-like micro-resort. Due to the current COVID-19 situation, we have offered SPECIAL discounts for longer-term rentals

4.96 out of 5 average rating, 160 reviews

A dining area is presented on a wooden deck, featuring a rectangular table surrounded by six chairs, each with cushion padding. The tranquil view of the Chesapeake Bay is visible in the background, with grassy land and a rocky shoreline also noted.

Cottage in Deale

Chesapeake Bay Cottage

Cottage Located directly on the Chesapeake Bay. Includes sandy beach, yard, a screened in porch and deck. Two Kayaks to enjoy. Two bedroom plus den. Two full baths. Fully equipped kitchen.Kurig coffee maker and regular available. Master bedroom -queen size mattress. Second bedroom -a full-size mattress (double) third bedroom -a twin day bed with twin pullout. Both twin size mattresses.

4.99 out of 5 average rating, 167 reviews

A bright kitchen is oriented towards waterfront views, featuring white cabinetry and a spacious island. Two bar stools are positioned at the island, while a seating area with a light-colored couch is visible. Natural light floods the space through sliding glass doors, enhancing the airy atmosphere.

Guesthouse in Annapolis

Coastal Waterfront 1 Bedroom Cottage

This waterfront cottage is located 2 miles from Historic Downtown Annapolis and the United States Naval Academy, making it easy to plan your visit. It is located right on the South River in a quiet neighborhood. There is a full outdoor seating and patio area with a grill and fire pit. It has a full kitchen, 1 bedroom, washer/dryer and can sleep up to 4 with the pull-out sleeper couch.

4.97 out of 5 average rating, 329 reviews

A wooden pier extends into calm waters, with posts lining the edges. The sky displays soft hues of pink and blue, while wispy clouds are scattered above. The tranquil scene invites relaxation and contemplation near the Chesapeake Bay.

Cottage in North Beach

Waterfront Cottage Near Herrington and North Beach

Escape to Osprey Cottage, a renovated oasis overlooking the Chesapeake Bay. Our home is a 1930s bungalow that has been tastefully updated with modern sensibility, while still preserving its original charm. Streamlined decor, gleaming wood floors, and stunning views from the common spaces, deck, and hot tub invite you to simply relax.

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Other great vacation rentals in Shady Side

Apartment in Upper Marlboro

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.

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.

Place to stay in Shady Side

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.

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.

4.98 out of 5 average rating, 57 reviews

Home in Edgewater

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.

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!

5 out of 5 average rating, 14 reviews

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

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.

4.92 out of 5 average rating, 50 reviews

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

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.

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.