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Vacation rentals with a patio in St. Michaels

Find and book unique patio rentals on Airbnb

Top-rated patio rentals in St. Michaels

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The vintage A-frame home is nestled amongst trees, featuring a deck with a canopy in the foreground. A stone path leads to the entrance, where large windows allow for ample natural light. The surrounding landscape is adorned with greenery and decorative plants.

4.91 out of 5 average rating, 220 reviews

Hideaway on the Bay: Waterfront Vintage A Frame

The Hideaway on the Bay is a waterfront A frame where you can disconnect from the things that can wait so you can connect with the people who matter most. A place where kids fall in love with nature, and where old friends make new memories. The house is a 2 bed 1 bath 1974 flat top A Frame that sits on two acres on the outskirts of Lusby, MD—and a low traffic hour(ish) drive from the DMV. Enjoy the indoor fireplace, outdoor fire pit, swinging chairs, kayaks, canoe, fish, and catch crabs --

A collection of various fossilized shark teeth is displayed on an orange background. The teeth are of different sizes and shapes, showcasing both small and large specimens, with some exhibiting intricate details. The vibrant color of the background contrasts with the dark tones of the teeth.

4.95 out of 5 average rating, 115 reviews

Soul Oasis - home on the Chesapeake Bay

Listen to the waves of the Chesapeake Bay from the trex deck. There are 2 private community beaches in the neighborhood where you can find fossils and sharks teeth. A great place to relax and unwind. You will hear the sounds of all kinds of birds, see lots of very tiny frogs in spring and summer and maybe some deer around the house! You can also expect to see/hear aircraft from Pax River Base fly overhead! Book your stay today and let the magic of the woods and water wash away your cares.

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.

Top guest favorite

A serene outdoor setting features a hot tub surrounded by trees, overlooking the lake. A wooden pathway leads from the hot tub to the pier, where boats can be launched. A fire pit with seating is nearby, inviting relaxation in nature.

4.98 out of 5 average rating, 105 reviews

Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade

Welcome to The Lake House - our freshly updated 3 bedroom, 3 bath cabin on Lake Vista with views of the Patuxent River/Chesapeake Bay from the private pier. Enjoy everything Southern Maryland has to offer all within a 10 minute drive - Calvert Cliffs, Flag Ponds, Solomons Island - hiking, fishing, boating and beaches. Located just 90 minutes outside DC, The Lake House will become your new go-to retreat from the hustle. Come relax and make memories on the water with your family and friends.

Top guest favorite

A modern houseboat is anchored at the dock, featuring a covered deck with two lounge chairs. Large windows offer views of the waterfront and allow natural light into the interior. The structure sits on wooden stilts above calm waters, showcasing a serene boating environment.

Houseboat in Kent Narrows

4.96 out of 5 average rating, 170 reviews

Cass-N-Reel Luxury Houseboat

Kent Narrows Rentals Welcomes you aboard Cass-N-Reel! A 432sqft luxury getaway in the Kent Narrows. With 1 bedroom, 1 bathroom, and a gorgeous covered rear facing deck; this is the ultimate couples retreat! 9 waterfront/waterview bars/restaurants within walking distance! Get a taste of what the eastern shore has to offer. Minutes from the Chesapeake Bay Bridge and a short drive to Annapolis, D.C., St. Michaels, and Ocean City. Come stay and live like a local! NO Fishing/Crabbing on property

Home in Montross

4.98 out of 5 average rating, 118 reviews

3N+ Promo! Waterfront | Beach+Gamerm+Kayak+Firepit

*Ask about our 3+ Night promotions* ☀️ Waterfront 🛶 Kayak/Paddleboard 👨‍🍳 Gas griddle ⛱️ 3 Community Beaches 🔥 Fire pit 🐶 Dogs OK 🎯 Gameroom ⚡️EV Outlet If you're looking to take a break or connect with nature, the Riverside Retreat in Montross, VA offers a peaceful sanctuary that is perfect for families, small groups, & couples Relax - Star Gaze - Kayaks/Paddleboard - Hike - Fish - Swim - Beach & more! Book your getaway today or ❤️ us for next time!

Top guest favorite

The exterior of a two-story house is showcased, featuring light blue siding and white railings. A grassy area is visible in front, with four gray Adirondack chairs arranged around a circular fire pit on a stone patio. The sun casts a warm glow over the scene.

Home in Solomons

5 out of 5 average rating, 108 reviews

The Little House on Back Creek

Get away and relax at this peaceful, very private and centrally-located home in the heart of Solomons Island on Back Creek with beautiful water views overlooking Solomons Harbour. The property is shared with Jacqueline Morgan Day Spa and The Blue Shell Gifts and Décor. Just a quick walk to a enjoy a massage, facial, mani/pedi, salon services and shopping! Enjoy fishing, kayaking, bicycling, walk to so many great restaurants nearby and bring your boat! Docking is available during your stay.

A wooden deck area is highlighted with four Adirondack chairs arranged around a central fire table, where flames flicker gently. Beyond the deck, a well-maintained lawn leads to the bay, visible in the distance under a colorful sunset sky.

Home in Stevensville

4.95 out of 5 average rating, 100 reviews

25-50% Off~Private Beach~Hot Tub~Fire Table~

Welcome to our Chesapeake Bay Cottage on Kent Island, Maryland! This unique 3 bed 2 bath home with luxurious amenities is a perfect getaway for families or friends looking to create unforgettable memories and experience all the Bay area offers. Escape the hustle and bustle with an easy commute from Annapolis, Washington and Baltimore. The Naval Academy is right across the Chesapeake Bay Bridge. Adventure and relaxation are within easy reach from any mid-Atlantic and northeastern location.

Top guest favorite

A charming two-story cottage features a light green exterior with white trim. The welcoming front porch is furnished with two white chairs and a small table, while a bright red door serves as the main entrance. A private balcony is visible above, framed by railing.

Home in Saint Michaels

4.99 out of 5 average rating, 124 reviews

Shipwrights Cottage in Town!

Charming historic cottage within walking distance to all St. Michaels has to offer! Relax & enjoy the sights of town from your front porch! Once a working shipwrights cottage, this home is 2 stories with a 1st floor full kitchen, combo living-dining room, den with queensize pullout couch & full bath. The 2nd floor has 2 bedrooms & a full bath. Both bedrooms have vaulted ceilings & ceiling fans. The primary bedroom has a private sitting balcony. Walk to shops, restaurants & waterfront!

The exterior of the farmhouse showcases a large, white structure with multiple windows and a spacious lawn surrounded by trees. The scene is complemented by a clear sky, creating a serene environment. Outdoor seating appears to be arranged on the patio, inviting relaxation.

Home in Chester

4.93 out of 5 average rating, 107 reviews

Waterfront Farmhouse Meets Modern Luxury

Enjoy all that the Eastern Shore has to offer while staying at the neoclassical 19th-century "Osprey's Reach" farmhouse. Osprey's Reach blends the original character of Kent Island with modern comforts of a full house restoration, all while enjoying stunning sunsets over the Chesapeake, from the private dock or poolside. Kent Island is centrally located for short day trips to Annapolis, Easton, St. Michael's or Chestertown, with family-friendly dining and shopping options on-island.

Top guest favorite

A bright yellow building features large blue shutters and a welcoming entrance. A sign is placed outside, and vibrant flowers border the steps. In the background, another structure is visible, along with flags proudly displayed.

Apartment in Saint Michaels

4.97 out of 5 average rating, 113 reviews

Blue Crab Lodge

Welcome to your charming and cozy short-term rental above the heart of St. Michaels' vibrant community! Nestled right above the delightful aroma of freshly brewed coffee, this unique and inviting space offers the perfect blend of comfort and convenience. Stepping outside, you'll find yourself in the heart of St. Michaels' quaint streets. The rental's prime location provides easy access to the town's boutique shops, waterfront promenades, and a diverse array of restaurants.

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

4.93 out of 5 average rating, 196 reviews

Coastal Comfort Suite Near Annapolis, Hottub, EV

Our pool is closed for the season; however, our hot tub is open! Ideal for a couple's retreat, this king suite guest room has a seating area, mounted TV, and coffee bar, microwave, and mini-fridge. An ensuite bathroom provides a luxurious shower and a spacious closet. The pool and hot tub are seasonal. Please don’t hesitate to reach out with any questions, concerns, or expectations so that we can address them prior to your stay.

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Popular amenities for St. Michaels patio rentals

Free parking on premises

Air conditioning

Apartment rentals with a patio

A light-filled living space features a large, plush sectional sofa adorned with decorative pillows. A round coffee table sits at the center, surrounded by a tasteful area rug. A small dining area is visible, with a wooden table and chairs, and greenery is provided by a nearby potted plant.

Apartment in Washington

4.96 out of 5 average rating, 166 reviews

Subway & Easy Parking! Sunny 2 Bdrm w/ King Bed

A modern kitchen features warm wooden cabinetry, a sleek black stove, and a variety of kitchen appliances. A rustic dining table sits in the foreground, adorned with a woven runner and a wooden tray holding fresh fruit. The space is complemented by decorative shelves and natural light.

Apartment in Upper Marlboro

4.94 out of 5 average rating, 158 reviews

Kone Oasis- hot tub, pool, theater/game rm.

A cozy living area features a leather sofa accented with patterned cushions. A black coffee table sits on a textured rug, while a flat-screen TV is mounted on the wall. Natural light enters through a window with blinds, illuminating the warm wooden flooring.

Apartment in Federal Hill - Montgomery

4.82 out of 5 average rating, 174 reviews

Charming Federal Hill! One Bedroom With Vibes

A spacious dock area displays two Adirondack chairs positioned for enjoying the water views. The wooden platform features a vibrant finish, with boats visible in the distance and trees lining the shoreline under a partly cloudy sky.

Apartment in Pasadena

4.97 out of 5 average rating, 32 reviews

Relaxing Waterfront Apartment!

A charming exterior is displayed, featuring a white wooden facade and a welcoming entrance. A brick pathway leads to the door, which is illuminated by a warm light fixture. Decorative greenery frames the doorway, enhancing the home's inviting character.

Apartment in Annapolis

4.94 out of 5 average rating, 104 reviews

Historic Annapolis Rental Minutes from Downtown

Top guest favorite

An aerial view showcases a large grassy area surrounding a heated pool, with several lounge chairs positioned nearby. A fire pit is set with white adirondack chairs. Two properties are visible, featuring balconies and umbrellas enhancing the outdoor space.

Apartment in Stevensville

5 out of 5 average rating, 64 reviews

Heron Roost

A cozy living area features a dark leather sofa and two blue chairs arranged around a round coffee table. Soft lighting is provided by stylish lamps on both ends. Framed artwork lines the walls, and natural light streams through the curtains.

Apartment in Cambridge

4.9 out of 5 average rating, 142 reviews

Little Slice of Cambridge. 2 bedroom, pet friendly

A serene sunset is viewed over calm waters, reflecting warm orange and gold hues. Silhouettes of trees and a boat dock are visible in the foreground, with a few boats gently resting on the still water.

Apartment in Dundalk

4.96 out of 5 average rating, 25 reviews

Waterfront Romantic Studio

House rentals with a patio

Adirondack chairs are positioned on a brick patio, overlooking a serene view of the Miles River. The tranquil water reflects a partly cloudy sky, bordered by trees on the shore, creating a peaceful outdoor setting.

5 out of 5 average rating, 8 reviews

Ferry Bridge House

Top guest favorite

A shaded seating area is arranged under a gazebo, featuring a woven outdoor sofa and chairs in warm orange cushions. A central fire pit table complements the setting, surrounded by a patterned outdoor rug on a paved surface, with a fenced backyard visible in the background.

Home in Annapolis

4.99 out of 5 average rating, 104 reviews

Nautical Luxe Retreat 6 Guests • 3 BDR • 2 Baths

A well-decorated bedroom features a spacious bed with neutral bedding. Nearby, a dresser with multiple drawers provides storage. Dual windows allow natural light, complemented by blinds for privacy. A vibrant area rug adds a pop of color, while a ceiling fan enhances air circulation.

Home in Stevensville

4.92 out of 5 average rating, 247 reviews

Relax on Kent Island in 3 Bedroom Home w/Waterview

Top guest favorite

An aerial view captures the nearby marina and lush greenery surrounding the property. The calm waters of the bay reflect the clear blue sky, while residential buildings and open fields are visible, indicating a tranquil environment close to the coast.

Home in Rock Hall

4.92 out of 5 average rating, 53 reviews

Historic Cottage | 1min DT | Views | W/D | Parking

Top guest favorite

A scenic view of a sunset over the water, with a silhouette of a person kayaking. Adjacent, a cozy seating area is set up around a fire pit, surrounded by trees. In the foreground, a table with wine and glasses is shaded by a red umbrella, beside a hot tub.

Home in Dameron

4.98 out of 5 average rating, 117 reviews

Peace Point - Waterfront, Secluded, Home w/hot tub

A bright and inviting room features two pink armchairs with a small table between them, set against a backdrop of light walls and hardwood flooring. An elegant chandelier hangs from the ceiling, while a vintage-style dresser and a decorative fireplace enhance the space's charm.

Home in Cambridge

4.86 out of 5 average rating, 84 reviews

High St. Art Gallery Suite

Top guest favorite

A cozy living area features two brown leather sofas, a patterned rug, and a soft ottoman. A reading nook is created with a gray chair draped in a yellow blanket. Natural light streams in through a large window, with plants and bookshelves enhancing the space.

Home in Chestertown

4.97 out of 5 average rating, 145 reviews

Cozy 3-bedroom home w/ Hot tub & firepit

Four black Adirondack chairs are arranged on a lush green lawn, facing the calm waters of Chesapeake Bay. Gentle waves reflect the bright blue sky, offering a serene view. Small bushes line the edge of the property, providing a natural border.

4.98 out of 5 average rating, 101 reviews

Waterfront with sweeping bay view & private beach

Condo rentals with a patio

Top guest favorite

An open-concept living area features a spacious layout with natural light illuminating the room. A comfortable dark sofa adorned with decorative pillows faces an inviting dining table. Sleek kitchen cabinets and modern appliances are evident in the background, while a sliding door leads to a private deck.

Condo in Deanwood

4.96 out of 5 average rating, 48 reviews

Modern Spacious Oasis: 2 King Beds-Parking-Deck

Top guest favorite

A modern kitchen space is highlighted by stainless steel appliances and wooden accents. Two dining chairs are positioned around a wooden table beside a window, providing a view of the exterior. A patterned rug adds warmth to the wooden floor.

Condo in Chestertown

5 out of 5 average rating, 27 reviews

Historic Loft w/ Park View & Spa Access

Top guest favorite

A private patio space is equipped with a comfortable curved sofa adorned with vibrant blue and green cushions. A dark umbrella provides shade, while a small table nearby holds drinks. The rustic wooden fence and brick wall add a charming backdrop.

Condo in Brookland

5 out of 5 average rating, 50 reviews

The Azure: Lux modern exec suite w/Patio&Fireplace

Condo in Annapolis

4.98 out of 5 average rating, 101 reviews

Charming Annapolis Waterfront Condo

Top guest favorite

An open living area is showcased, featuring a light-colored sofa against a wall adorned with framed photographs. A large rug anchors the space, complemented by a round dining table and chairs. Natural light floods in from large sliding doors leading to a balcony.

Condo in Annapolis

4.97 out of 5 average rating, 66 reviews

Cozy Annapolis Condo

A modern studio space is presented, featuring a spacious bed with a dark comforter. A large wall-mounted television is positioned across from the bed, with a wooden media console below it. The kitchenette is equipped with white cabinets and stainless steel appliances, adding a functional element to the inviting layout.

Condo in Mount Vernon

4.92 out of 5 average rating, 84 reviews

Modern Mt.Vernon studio in great central location

Top guest favorite

A cozy living area is presented, featuring a large gray sectional sofa with soft cushions and decorative pillows. An ottoman with a tray sits in the center, alongside a lamp that provides warm light. A patterned chair complements the space, while natural light filters in through the window blinds.

Condo in Wilde Lake

5 out of 5 average rating, 78 reviews

Luxury & Comfort, 2BR, 1 BA Columbia, Town Center

Top guest favorite

A welcoming living area features a light-colored sofa and an upholstered armchair, positioned around a central wooden coffee table. A unique area rug with intricate patterns adds warmth. The kitchen area, visible in the background, is equipped with modern appliances and a breakfast bar with stools.

Condo in Annapolis

4.96 out of 5 average rating, 104 reviews

Funky Uptown Apt meets Downtown - Hist District

Quick stats about vacation rentals with a patio in St. Michaels

Total rentals
30 properties
Nightly prices starting at
$200 before taxes and fees
Total number of reviews
2.4K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace

Destinations to explore