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Family-friendly vacation rentals in Shady Side

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Shady Side

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Sailboats are moored in a serene marina, with soft waves reflecting the sunlight. The docks are lined with wooden posts, guiding the view to a lush green shoreline in the background. A peaceful atmosphere is created by the gentle ripples and warm evening light.

Home in Edgewater

4.96 out of 5 average rating, 196 reviews

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!

A breathtaking sunrise is captured over calm waters, creating a stunning reflection of vibrant hues of orange, pink, and purple. The private pier is visible on the right, complementing the serene landscape of trees on the distant shore and a tranquil island in the background.

Cottage in Edgewater

4.99 out of 5 average rating, 165 reviews

Waterfront Chesapeake Bay Sunrises & 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!

Top guest favorite

The exterior of the cottage is framed by vibrant flowerbeds filled with blooming roses and lush green shrubs. A well-manicured path leads to the entrance, flanked by tall greenery, with glimpses of the sparkling water visible in the background.

Home in Shady Side

5 out of 5 average rating, 184 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. Nestled along the Chesapeake, it offers front-row seats to mesmerizing sunsets, where golden light shimmers across the water. Inside, Nordic-inspired design pairs with quiet luxury, featuring award-winning mattresses and sumptuous bedding for deeply restorative sleep. Here, time slows, and luxury isn’t just seen—it’s felt. Discover why so many guests long to return by reading our reviews.

A waterfront home is depicted with a screened-in porch and a gabled roof. A wooden pier extends from the shore, leading to the water. Lush greenery surrounds the property, and stone embankments partially border the shoreline.

Home in Shady Side

4.95 out of 5 average rating, 111 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.

The exterior of a two-story home is displayed, featuring a light-colored façade, white porch railings, and a chimney. A neatly manicured lawn surrounds the house, complemented by tall trees in the background and a clear blue sky above.

Home in West River

4.96 out of 5 average rating, 139 reviews

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!

Top guest favorite

The exterior of a spacious home is illuminated at dusk, showcasing large windows and warm lighting. The house is surrounded by well-maintained greenery and trees, creating a serene setting. A stone pathway leads to the entrance, inviting guests to explore the welcoming atmosphere.

Home in Harwood

4.95 out of 5 average rating, 142 reviews

Luxury Home, Sleeps 15, Private Pool, Close to DC

Stunning 6 bedroom, 5½ bath home on 34 acres with panoramic woodland views and private salt water pool, perfect for that special gathering. Secluded yet just 35 minutes from Capitol Hill and 20 minutes from Annapolis. The home, with its high ceilings, huge windows and expansive decks comprises over 8000 square feet, so there is plenty of room to stretch out. *** IMPORTANT Please send AN INQUIRY with a little about you PRIOR to requesting a booking.

Top guest favorite

The cottage features a welcoming exterior with a combination of siding and a shingled roof. A well-maintained lawn surrounds the home, and landscaping includes a variety of shrubs. Large windows are visible on the front, providing ample natural light.

4.99 out of 5 average rating, 149 reviews

Hannah’s Hideaway

Cottage style with water view of Rockhold Creek. Water taxi right out front of house to take you to local restaurants. Crabbing excursions or fishing charters available for extra cost. Dog friendly. Local restaurants all within 1 mile from location. Fenced in back yard. Picnic table and fire pit to have own personal crab feasts or cookout. Many local restaurants with outside musicians.Grocery store and gas/liquor stores within 5 minutes from house.

Top guest favorite

A spacious living area features a gray sofa adorned with cushions, positioned in front of a decorative coffee table. A vibrant wall art piece adds color to the room, while potted plants bring a touch of greenery. The open layout connects to the kitchen area, visible in the background.

Home in North Beach

4.97 out of 5 average rating, 161 reviews

Beach Home | King Bds | Firepit | Backyard Dining

Welcome to A Haven Away! Our home has 4 bedrooms (2 king beds + 2 queen beds). 2 mins to the beach, restaurants, and wetlands. We have a private, landscaped backyard perfect for dining and lounging. We provide beach passes, beach gear, games, a Pack & Play, and tips for jet ski rentals and day trips. The shed has a huge Smart TV. Fully-equipped kitchen. Single-story living with 2 bedrooms, accessible shower on the ground floor.

A shaded outdoor area features a glass-top dining table surrounded by six chairs, situated on lush green grass. Nearby, additional loungers invite relaxation, under the canopy of a large tree with vibrant foliage, overlooking a calm waterfront view.

Cottage in Deale

4.83 out of 5 average rating, 184 reviews

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

A view of the sunset over Chesapeake Bay is captured from the deck, with warm hues reflecting on the water. The scene includes a grassy area leading to the shoreline and a subtle silhouette of a dock in the background.

Cottage in Deale

4.95 out of 5 average rating, 167 reviews

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.

Top guest favorite

An inviting corner workspace features a wooden table adorned with maps and brochures, alongside a collection of books housed in a wall-mounted cabinet. A bright living area is visible in the background, showcasing a red couch and a decorative round mirror.

Guest suite in Edgewater

4.9 out of 5 average rating, 525 reviews

South River Park Apartment

Located minutes from Annapolis, the in-law apartment offers access to Baltimore and DC in under an hour. The apartment offers its own entrance, full kitchen, one bathroom, one bedroom, tile floors, pullout sofa, Wifi, and parking. The apartment is registered with the Anne Arundel County Dept. of Inspections & Permits, #STR-15, for short term rentals.

The cottage exterior showcases charming blue shingles and a welcoming front porch, furnished with a bench and four chairs. A spacious deck offers outdoor seating and is surrounded by lush greenery and flower beds, enhancing the warm ambiance of the property.

Cottage in Tracys Landing

4.89 out of 5 average rating, 379 reviews

Charming Waterfront on Chesapeake Bay

Perched on a bank overlooking expansive views of the Chesapeake Bay, our shingled cottage is a comfortable country retreat with exposed beams and cathedral ceilings. It is less than an hour to Annapolis and Washington DC. Save on your first Airbnb stay (some restrictions apply): https://abnb.me/e/i9PHYamHUN

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Popular amenities for Shady Side family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A hot tub bubbles gently near a clear blue pool surrounded by greenery. In the background, a hammock is visible, inviting relaxation in a serene outdoor setting. The area is shaded by trees, enhancing a peaceful atmosphere.

Apartment in Upper Marlboro

4.94 out of 5 average rating, 152 reviews

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

Top guest favorite

A tranquil beach scene presents soft sand leading to calm water, framed by an open sky dotted with clouds. A weathered log rests on the shoreline, while distant rocky formations add interest to the horizon.

Cottage in Saint Leonard

4.96 out of 5 average rating, 158 reviews

Block to Private Beach, Screened deck, Hot Tub

Top guest favorite

A charming cottage is visible beside a clear pool, surrounded by well-maintained green lawns. Two shaded umbrellas stand over cushioned lounge chairs by the water's edge, creating a comfortable outdoor space for relaxation. The inviting pool reflects the bright sky, enhancing the serene atmosphere.

Cottage in Easton

5 out of 5 average rating, 114 reviews

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Top guest favorite

A comfortable living area is framed by large windows showcasing a vibrant sunset over the water. Soft furnishings include two chairs with decorative pillows and a coffee table. Plants are positioned thoughtfully, enhancing the serene atmosphere.

Home in North Beach

5 out of 5 average rating, 153 reviews

Waterfront, Dog-friendly, Hot Tub, Peleton

A covered porch is shown with a hanging egg chair and a gray sectional sofa. Soft cushions are placed on the seating area. Beyond the railing, the tranquil waters of Chesapeake Bay can be seen, complemented by lush greenery and nearby homes.

Home in Annapolis

4.87 out of 5 average rating, 182 reviews

Charming Annapolis Water View Home

Top guest favorite

A serene waterfront scene is captured at dusk, featuring a dock illuminated by soft lighting. A swing sits beneath a large tree, providing a peaceful spot to relax while overlooking the calm water.

Home in Grasonville

4.95 out of 5 average rating, 281 reviews

River Front, Private Single Family Home

A serene backyard space features a rectangular pool surrounded by a spacious patio. Lounge chairs are positioned near the water, with a shaded gazebo offering seating nearby. The area is bordered by lush greenery, providing a sense of privacy and tranquility.

Guest suite in Arnold

4.94 out of 5 average rating, 192 reviews

Coastal Comfort Suite Near Annapolis, Hottub, EV

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, 182 reviews

Cattail Landing- Photographer's Waterfront Retreat

Family- and pet-friendly home rentals

A serene swimming pool is featured in a private outdoor area, surrounded by a stone deck. Two white lounge chairs are positioned nearby, with trees providing a shaded atmosphere. The clear water glistens under a partly cloudy sky, inviting relaxation.

Home in Edgewater

4.91 out of 5 average rating, 160 reviews

House in Edgewater Maryland

Top guest favorite

A spacious living area features large windows that allow natural light to fill the space, showcasing views of the surrounding greenery. Comfortable seating is arranged around a low table, with a television mounted on the wall, and decorative shelves filled with various items.

Cottage in Annapolis

4.96 out of 5 average rating, 419 reviews

Relaxing Water Views - Mill Creek Cottage

A wooden pier stretches into the water, flanked by lush greenery. A rainbow arcs above the serene landscape, with gentle waves lapping at the edge of the sandy shore. Trees and homes line the distant banks, completing the tranquil waterfront scene.

Guesthouse in Glen Burnie

4.93 out of 5 average rating, 358 reviews

The Crab House - a Private, Waterfront Guest House

Top guest favorite

The exterior of a historic townhome is showcased, featuring red brick walls and black shutters. Lush greenery and colorful flowers enhance the garden area. A flag may be seen hanging from the building, set against a clear blue sky.

Townhouse in Annapolis

4.95 out of 5 average rating, 167 reviews

Historic 3 Bedroom Downtown Annapolis Townhome

A charming single-story house is presented with a light gray exterior and a prominent teal door. Symmetrical landscaping frames the entrance, featuring neatly trimmed hedges and colorful plants. A concrete pathway leads to the front steps, inviting guests into a welcoming atmosphere.

Home in Annapolis

4.94 out of 5 average rating, 106 reviews

Charming Annapolis Retreat with Hidden Wine Room

The entrance features double glass doors framed by a wooden deck. Seasonal potted plants, including vibrant flowers and greenery, are arranged on either side, while a small pumpkin adds a festive touch. A decorative light fixture hangs nearby, enhancing the welcoming appearance.

Cottage in Glen Burnie

4.91 out of 5 average rating, 206 reviews

Home away from home

A wooden staircase illuminated by soft lights leads down to a private dock. Reflections of trees and evening sky are seen on the calm water of St. Leonard Creek. A sailboat is moored at the end of the dock, adding to the serene waterside ambiance.

4.9 out of 5 average rating, 282 reviews

Peaceful Waterfront Retreat on The Bay

Top guest favorite

A cozy living area features a brown leather sofa next to a white coffee table. A decorative rug with star patterns lies on the floor. A green potted plant adds a natural touch, complemented by a television on a media unit. Light enters from the window.

Apartment in Chester

4.97 out of 5 average rating, 267 reviews

Cozy Waterfront Apartment Chester, MD

Family-friendly home rentals with a pool

Top guest favorite

An aerial view captures the expansive property, featuring a large home surrounded by lush green lawns and mature trees. A heated in-ground pool is visible in the backyard, adjacent to a serene water body, with an expansive landscape enhancing the tranquil setting.

Cabin in Saint Michaels

4.99 out of 5 average rating, 115 reviews

True St. Michaels 6 Acre Waterfront w/heated pool

Top guest favorite

A charming guesthouse exterior is showcased, featuring multiple entrances with glass doors. A staircase leads to the upper level. Two shaded seating areas adorned with potted plants and a clock are visible in a well-kept outdoor space, enhancing the inviting environment.

Guesthouse in Annapolis

5 out of 5 average rating, 164 reviews

Private Art-Filled Guesthouse near Naval Academy

Top guest favorite

A fenced-in pool area is surrounded by lush greenery, with tall plants and trees creating a natural backdrop. The pool features calm blue waters, and a small paved pathway leads toward it. A black chair is positioned near the entrance of the pool gate.

Guest suite in Catonsville

4.94 out of 5 average rating, 539 reviews

Rollingside: Two-Room Guest Suite

The large in-ground pool is surrounded by a spacious patio, offering multiple lounge chairs for relaxation. A vibrant red umbrella provides shade in one corner, while lush greenery and flowering bushes frame the area, creating a private and serene outdoor atmosphere.

4.87 out of 5 average rating, 180 reviews

Large Home with Pool & 7 bedrooms; sleeps 21

A serene view of the Chesapeake Bay is captured from the backyard, featuring a pool surrounded by green lawn. Towering trees provide shade, while a patterned stone patio is visible in the foreground, enhancing the outdoor atmosphere.

Home in Chester

4.94 out of 5 average rating, 105 reviews

Waterfront Farmhouse Meets Modern Luxury

Top guest favorite

An open concept living area features a combination of seating, including two armchairs and a side table. A dining area with a striking blue rug and wooden chairs is visible in the background, alongside a well-lit kitchen area with modern appliances.

Guesthouse in Owings

4.96 out of 5 average rating, 112 reviews

Patuxent River View

Top guest favorite

A spacious outdoor area features an inviting pool surrounded by lush greenery and vibrant landscaping. Colorful umbrellas provide shade over multiple seating areas, including lounge chairs and a dining table. The serene atmosphere is accentuated by the tranquil water and nearby trees.

Home in Kent Narrows

5 out of 5 average rating, 305 reviews

Chester Riverfront At Kent Narrows

A covered porch features white railings and ceiling fans, offering a view of the spacious saltwater pool surrounded by lush greenery. The outdoor area includes well-maintained landscaping and a barbeque grill, providing an inviting space for relaxation and gatherings.

Home in Stevensville

4.96 out of 5 average rating, 104 reviews

Beautiful Kent Island Getaway with Pool

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