Vacation rentals with outdoor seating in St. Michaels

Apartment in Saint Michaels

A cozy sleeping area is furnished with a queen-size bed featuring a patterned white and yellow duvet. Two accent pillows add color, and a red throw blanket sits at the foot. A neutral rug is positioned underneath, complementing the wood flooring.

4.92 out of 5 average rating, 203 reviews

Charming Studio in the heart of St. Michael's, MD.

Welcome to Lucky Ducks Studio! Enjoy a fully renovated furnished studio in the heart of St. Michael's, MD. Located on Talbot Street in the historic 1850’s McMillian House, the 2nd floor studio offers couples a cozy "British" style experience that sleeps 4 (queen size bed & sofa that transitions to queen), a full bath with a claw tub and a gorgeous industrial style kitchen. Your steps away from the Miles River, shopping, museums, restaurants, breweries and wineries. Free WIFI and YouTube TV.

5 out of 5 average rating, 191 reviews

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

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.

4.87 out of 5 average rating, 151 reviews

The living area features vaulted ceilings with exposed beams and skylights allowing natural light to fill the space. A combination of orange and blue furnishings, including a spacious sofa and accent chairs, surround a coffee table. Decorative elements and a large area rug add warmth to the room.

Cottage in Neavitt

The Middle Point Cottage at Saint Michaels

Middle Point Cottage is a beautifully updated/fully renovated cottage just minutes outside of the famous Saint Michaels destination getaway. Guests can enjoy all the fine dining/shopping Saint Michales has to offer then escape to the peaceful peninsula life this cozy cottage in Neavitt has to offer. A minute walk to the city park complete with a extensive playground equipment for kids and a beautiful pavilion with numerous picnic tables and just a short drive to the water/community Marina.

4.99 out of 5 average rating, 104 reviews

A spacious open-concept living area features large windows offering unobstructed views of the water and sunset. A comfortable sectional sofa is positioned near the windows, with a dining table visible in the background. Natural light fills the space, enhancing the tranquil setting.

Home in Leonardtown

Water's Edge Cottage | Luxury Retreat

We are thrilled to host guests at the newly renovated Water's Edge Cottage -- a serene oasis offering what may be the best views on the Potomac. The rural charm of St. Mary’s County is among Maryland’s best kept secrets -- 90 minutes but a world away from Washington DC (with no Bay Bridge traffic!). We are near historic Leonardtown, boasting one of Maryland’s few remaining town squares (we affectionately call it “Mayberry”). And be sure to visit our sister property, White Point Cottage!

4.9 out of 5 average rating, 317 reviews

The entrance of the guest cottage is framed by a charming picket fence, featuring a blue door and a welcoming porch. A small table with two chairs and an umbrella is situated on a wooden deck, surrounded by lush greenery.

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.

4.99 out of 5 average rating, 131 reviews

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

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!

4.99 out of 5 average rating, 630 reviews

The exterior entrance of a converted corn crib features natural wood siding and a gabled roof. Large double doors framed by lantern-style lights open into a welcoming space, complemented by potted plants on either side. Lush green trees and a gravel path are visible in the surrounding landscape.

Guesthouse in Easton

Chill in The Crib! Easton, Maryland

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for ONLY TWO INDIVIDUALS (No children under 8 years of age.), and please limit your visit to one vehicle only.

Apartment in Saint Michaels

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.

4.98 out of 5 average rating, 120 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.

Cottage in Saint Michaels

A modern guesthouse features a peaked roof and large windows, set against a vibrant sunset sky. The surrounding landscape includes wild grasses and a paved pathway, suggesting a serene connection to nature.

4.97 out of 5 average rating, 176 reviews

La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

Cottage in Saint Michaels

A serene waterfront scene is framed by a sprawling tree. Boats are moored along the docks, with calm water reflecting the sky. Quaint buildings line the shore, and a bench is positioned on the grass, inviting quiet contemplation of the picturesque surroundings.

4.97 out of 5 average rating, 260 reviews

The Little Anchor Cottage, St. Michaels, MD

Welcome to the Little Anchor cottage in St. Michaels, Maryland! The cottage was built in late 1880s and is located in the charming Historic District, where you can enjoy the convenience of walking one block to the downtown shops and restaurants on S. Talbot street. And for another 5 to 15 minute walk, you can reach more waterfront dining on St. Michaels Harbor with its boat slips, boat ramps, the Chesapeake Bay Maritime Museum, Muskrat Park and Hollis Park.

5 out of 5 average rating, 118 reviews

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

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

4.99 out of 5 average rating, 187 reviews

Home in Saint Michaels

Grace Cottage, Saint Michaels Walk to everything!

Welcome to Grace Street Cottage with a newly renovated kitchen! Located in the heart of Saint Michaels. Walk to shops, restaurants and experience the best of the Eastern Shore. This cottage has all you will need for a perfect getaway. Sit by the fire pit and grill out or take a few steps to Talbot Street where your dining options are endless! Pack your bags and head to the shore! The experience awaits you!

Popular amenities for St. Michaels outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.99 out of 5 average rating, 111 reviews

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

Nautical Luxe Retreat 6 Guests • 3 BDR • 2 Baths

4.93 out of 5 average rating, 168 reviews

A serene waterfront view is presented, featuring a wooden dock extending over still water. Lush green grass fills the foreground, while trees line the opposite bank, creating a natural backdrop under a partly cloudy blue sky.

Home in Woolford

Waterfront Getaway with Dock

4.97 out of 5 average rating, 149 reviews

A two-story farmhouse with a light blue exterior features white trim and is complemented by a welcoming front porch. Rocking chairs are positioned on the porch, surrounded by colorful flower beds and lush green grass. Mature trees provide partial shade, enhancing the outdoor setting.

Home in Church Creek

Church Creek Charm (close to Blackwater Refuge)

4.97 out of 5 average rating, 106 reviews

A bright living space is characterized by light blue walls and hardwood flooring. A brown recliner and a wooden coffee table are present, along with a turquoise entertainment unit housing a television. Natural light fills the room through multiple windows, enhancing the inviting atmosphere.

Home in Chestertown

2 Beds, 2.5 Baths - Perfect Downtown Location

4.96 out of 5 average rating, 112 reviews

A single-story home is set amidst a lush, green lawn, surrounded by trees and natural vegetation. The exterior features a light-colored facade with a welcoming front entry and flower beds to the sides, enhancing the serene atmosphere of the wooded location.

Home in Greensboro

Cozy 2 bedroom home on wooded private lane

4.99 out of 5 average rating, 128 reviews

A wooden dock extends over calm waters, leading to a charming home surrounded by trees. The house, featuring large windows, is illuminated as dusk approaches. Adirondack chairs are placed along the shoreline, inviting relaxation in the natural setting.

Home in Stevensville

Kent Island Waterfront Home with Amazing Sunsets

4.98 out of 5 average rating, 215 reviews

The living room features a light-toned couch centered in the space, complemented by a decorative coffee table. A reclined green chair and a lamp beside it provide additional seating. The open kitchen is visible in the background, with light cabinetry and full size appliances.

Home in Shady Side

Canary Pointe-A popular getaway for 2!

4.95 out of 5 average rating, 104 reviews

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

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

Apartment rentals with outdoor seating

Apartment in Upper Marlboro

4.95 out of 5 average rating, 172 reviews

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

Apartment in Union Square

An eclectic studio apartment displays a spacious bed and a patterned throw atop it. Sunlight filters through tall windows, reflecting off decorative wall art. A piano and a book-filled shelving unit add character, while plants bring life to the room's corners.

4.91 out of 5 average rating, 826 reviews

South-Facing Studio Overlooking Union Square Park

4.98 out of 5 average rating, 209 reviews

A serene scene along the Choptank River features a wooden deck leading to a dock, with several boat slips visible in the distance. A sculpture of a heron stands amidst a landscaped area, complemented by a bench nestled under a tree, providing a tranquil waterfront view.

Apartment in Cambridge

Private apt above garage w/ pier and water access

4.9 out of 5 average rating, 146 reviews

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

Little Slice of Cambridge. 2 bedroom, pet friendly

4.96 out of 5 average rating, 285 reviews

A serene view showcases the landscaped yard, featuring blooming pink flower clusters in the foreground. A large tree stands in the center with a backdrop of greenery and a peaceful waterway. The two nearby structures are connected by a deck, reflecting the tranquil surroundings.

Apartment in Essex

A unique place on sue creek

4.91 out of 5 average rating, 620 reviews

A serene waterfront scene is captured at sunset, displaying calm water reflecting soft hues of orange and blue. Silhouettes of trees line the shore, while gentle ripples can be seen across the surface, creating a peaceful atmosphere.

Apartment in Deale

Romantic Wtrfrnt Flat+Solarium@Chesapeake Paradise

4.93 out of 5 average rating, 143 reviews

A close-up view of the sleeping area features a full bed with an earthy-toned quilt and decorative pillows. A soft throw blanket rests at the foot of the bed. Above, a series of wooden wall art pieces adds a touch of warmth, while a 55-inch Smart TV is mounted nearby.

Apartment in Bowie

Just Like Home - Private Entrance Apt in DMV Area

4.96 out of 5 average rating, 199 reviews

A welcoming living space features large arched windows letting in natural light. A plush pink sofa is positioned on a soft area rug, accompanied by a glass-top coffee table. A stylish chandelier hangs above, and plants add a touch of greenery to the room.

Apartment in Lusby

Terrace Suite - Private Flat in Historic Manor.

Condo rentals with outdoor seating

A bright living room features large windows dressed with light curtains, allowing natural light to fill the space. A comfortable sofa and armchair are arranged around a sleek coffee table, with shelves displaying books and decorative items, contributing to a welcoming atmosphere.

4.98 out of 5 average rating, 157 reviews

New Downtown Annapolis Condo With Free Parking

4.96 out of 5 average rating, 51 reviews

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

True Gem: Spacious-Modern-2 King Beds-PRKG-Deck

5 out of 5 average rating, 30 reviews

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

Historic Loft w/ Park View & Spa Access

4.97 out of 5 average rating, 141 reviews

A bright kitchen area features electric appliances, including a microwave and oven, set against vibrant blue cabinetry. A wooden dining table is adorned with a floral centerpiece and a plaid runner, providing a warm gathering space for meals.

Condo in Oxford

Cozy Oxford Getaway

4.98 out of 5 average rating, 103 reviews

Charming Annapolis Waterfront Condo

4.99 out of 5 average rating, 93 reviews

Condo in Mechanicsville

Barnyard Retreat

Superhost

The living area features a comfortable blue sectional sofa paired with a light-colored accent chair. A round metallic coffee table rests on a patterned area rug. Two lamps with white shades provide soft lighting, while large windows offer natural light and views of the outdoors.

4.78 out of 5 average rating, 9 reviews

Waterfront Eastport Condo w Rooftop Pool & Parking

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.