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Vacation rentals with outdoor seating in Talbot County

Find and book unique outdoor seating rentals on Airbnb

Top-rated outdoor seating rentals in Talbot County

Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

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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.

Apartment in Saint Michaels

4.91 out of 5 average rating, 198 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.

Top guest favorite

A modern living area features a light-colored sofa adorned with a teal throw blanket. A round wooden table accompanied by metal chairs is positioned nearby. A decorative mirror and an abstract painting are displayed on the wall, while a stone fireplace adds a subtle touch of warmth.

Apartment in Stevensville

4.98 out of 5 average rating, 293 reviews

Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

A bright living area features a yellow sofa and an oversized ottoman, set against a backdrop of large glass doors overlooking the river. Natural light floods the space, highlighting the modern design and comfortable furnishings. A dining table is also visible, along with a seating area by the window.

Home in Preston

4.93 out of 5 average rating, 107 reviews

River House on the Choptank

Welcome to the River House! Stay in our renovated home on the Choptank River of MD's Eastern Shore, with your own low-tide beach and magnificent sunsets. We offer a peaceful location and thoughtful detail, creating a memorable getaway for a relaxing weekend or remote work location. Enjoy a day on the river with our paddle board or 2 kayaks, and end the day around the firepit. In cool weather, cozy up next to the fireplace. Also, visit nearby towns--St. Michaels, Easton, Oxford, and Chestertown.

A spacious backyard features a circular fire pit surrounded by Adirondack chairs. A picnic table sits to one side, and a hot tub is partially shielded by evergreen trees and a wooden fence, providing a serene outdoor retreat.

Home in Cambridge

4.94 out of 5 average rating, 155 reviews

Peaceful Historic House Near Water, with Hot Tub!

Peaceful 3 bedroom/1.5 bath Victorian house near the water. Located in Historic West End, this 1900 house has been recently renovated to accentuate its historic charm while delivering all the modern comforts. Just a short walk from Long Wharf Park, the Choptank River Lighthouse, and downtown Cambridge with great restaurants and shops. Amenities include air conditioning/heating, a hot tub, WIFI, a back deck and grill, front porch with rocking chairs, and a fire pit with Adirondack chairs.

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!

Top guest favorite

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

4.99 out of 5 average rating, 623 reviews

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.

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.

Top guest favorite

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.

Cottage in Saint Michaels

4.97 out of 5 average rating, 175 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.

Top guest favorite

A two-story house features gray siding with white trim and a balcony accessed by stairs. An umbrella is positioned over the outdoor seating area, providing shade. Large windows illuminate the space, and a comfortable railing surrounds the deck, offering a peaceful setting.

Guest suite in Tilghman Island

4.96 out of 5 average rating, 163 reviews

Black Walnut Cove Retreat, Tilghman Island

Our waterfront studio retreat is a birdwatchers paradise. Located on beautiful Black Walnut Cove at the southern tip of Tilghman Island, you will be in a quiet neighborhood surrounded by water. Enjoy a quiet walk or bike ride along the Chesapeake Bay shoreline. You will have access to our dock and small boat ramp. Crabbing and fishing are a delight. Please note: 1) There is a 3-nt. minimum on holiday weekends. 2) Children between the ages of 1 and 5 are not permitted

Top guest favorite

The image captures a serene evening scene by the pool with a view of the setting sun over the water. Sunlight filters through trees, creating a warm glow. Poolside lounge chairs are visible, along with a clear pool reflecting the colorful sky.

Guesthouse in Stevensville

4.99 out of 5 average rating, 310 reviews

Waterfront Getaway - View of bay from your bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

Top guest favorite

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.

Cottage in Saint Michaels

4.97 out of 5 average rating, 255 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.

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Popular amenities for Talbot County outdoor seating rentals

Free parking on premises

Air conditioning

House rentals with outdoor seating

A serene outdoor area features four white Adirondack chairs arranged around a stone fire pit. A boat is docked nearby, with wooden piers extending into the calm water, surrounded by lush greenery and a clear blue sky.

Home in Newcomb

4.98 out of 5 average rating, 60 reviews

Saint Michaels Waterfront Home

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

A spacious living area features a large sectional sofa with accent pillows, positioned around a glass coffee table. Light enters through multiple windows covered by sheer curtains. A contemporary kitchen is partially visible, with bar stools arranged at a kitchen island.

4.94 out of 5 average rating, 17 reviews

Charming House, Quiet Neighborhood (Entire House)

An aerial view captures a spacious property surrounded by lush greenery. A rectangular pool is positioned in front of a two-story structure, along with multiple lounge chairs and a swing set nearby. The expansive lawn provides an open and inviting outdoor space.

Home in Sherwood

5 out of 5 average rating, 14 reviews

Punch Point boasts a sandy beach w/ pool and pier

Top guest favorite

An aerial view captures a spacious home set on a wooded parcel adjacent to a serene body of water. The exterior features a large swimming pool surrounded by decking, with a manicured lawn and tall trees creating a natural boundary.

Home in Cambridge

4.97 out of 5 average rating, 123 reviews

Come for Water Fowl, Hunting-Big, Beautiful Home!

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, 183 reviews

Charming Annapolis Water View Home

Top guest favorite

A wooden dock extends over the water, featuring two white Adirondack chairs positioned for relaxed seating. The serene water stretches toward the horizon, while the sky is dotted with fluffy clouds, creating a calming outdoor retreat.

Home in Chester

5 out of 5 average rating, 44 reviews

*Waterfront Sunset Bayview* sleeps 6

Top guest favorite

The exterior of a newly built house is depicted, showcasing a grey facade with stone accents. A manicured lawn extends in the foreground, while a porch with white railings and steps leads to the entrance. A tree is positioned near the driveway, with a waterfront view visible in the background.

Home in Stevensville

5 out of 5 average rating, 55 reviews

Away at the Bay: New Home on the Chesapeake Bay!

Apartment rentals with outdoor seating

A private balcony is shown with comfortable seating arrangements, including a wooden table and a light-colored bench. Lush greenery and blooming flowers can be seen beyond the railing, while a clear blue sky complements the peaceful setting.

Apartment in Easton

5 out of 5 average rating, 4 reviews

3Br/1Ba Pondview Langsdale House

Apartment in Saint Michaels

New place to stay

Downtown St. Michaels | Porch + Pet-Friendly

A spacious blue house features multiple large windows and a welcoming porch. Four chairs are arranged on the front porch, inviting relaxation. A tree provides shade, and a small white picket fence borders the property, enhancing the front yard's greenery.

Apartment in Cambridge

5 out of 5 average rating, 13 reviews

SUPER WATER-VIEW 1 BEDROOM APT/CAMBRIDGE MARYLAND

A person is seen kayaking on calm waters, with a lighthouse in the background. The kayak is gray with orange and blue accents. The scene captures a peaceful moment on the water, emphasizing the tranquility of the Chesapeake Bay.

Apartment in Annapolis

4.95 out of 5 average rating, 21 reviews

Crow’s Nest Cottage - Down Under: Chesapeake Bay

A cozy living area displays a flat-screen TV on a rustic wooden console. A round coffee table sits center-stage, surrounded by comfortable seating. Light enters through angled windows, highlighting the warm wood flooring and inviting decor elements.

Apartment in Wye Mills

4.79 out of 5 average rating, 73 reviews

⋘ Lakeside Apartment ⋙| Private+Cozy Setting |

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, 141 reviews

Little Slice of Cambridge. 2 bedroom, pet friendly

Top guest favorite

A vibrant navy sofa decorated with red and white cushions sits in front of a glossy black coffee table. A geometric rug covers the wooden flooring, while a decorative plant and a luminous wall create a welcoming atmosphere. A series of signs indicating local towns provide a charming touch.

Apartment in Saint Michaels

4.97 out of 5 average rating, 74 reviews

Charming Apt. in St. Michaels

A serene waterfront scene is captured at sunset, featuring a calming gradient of pink and orange hues in the sky. The sun setting over the water is reflected on a calm surface, while a weathered pier extends into the bay, framed by lush green grass.

Private room in Cambridge

4.97 out of 5 average rating, 33 reviews

Farm View Room at Happy Campers

Other vacation rentals with outdoor seating

Top guest favorite

A spacious room features a queen bed with a wooden bench at the foot, accompanied by a TV on a dresser. A full kitchenette is present, with a microwave and coffee maker. Natural light enters through large windows, and a decorative rug adds warmth to the space.

Guesthouse in Cambridge

5 out of 5 average rating, 32 reviews

The Place in Cambridge-Sailing into Autumn

Top guest favorite

Home in Cambridge

5 out of 5 average rating, 14 reviews

Waterfront Oasis-SaltwaterPool/HotTub/FirePit/Dock

A serene waterfront scene showcases a private dock extending into the water, framed by grassy areas. The horizon is painted with purple and orange hues from the setting sun, reflecting on the water's surface. Trees line the backdrop, adding to the tranquil atmosphere.

Cottage in Cambridge

4.98 out of 5 average rating, 51 reviews

Cozy Cottage on the Bay

The main living area features a comfortable wicker chair with a blue cushion, complemented by a separate white armchair. Natural light pours in through several large windows with blinds, illuminating the light wood flooring and a cozy throw blanket draped over a nearby chair.

Houseboat in Stevensville

4.89 out of 5 average rating, 61 reviews

Chesapeake Houseboat Getaway

Top guest favorite

A serene view of a serene water landscape is showcased, featuring a double rainbow arching across the sky. Reflections of the rainbow are visible on the water's surface. A private pier extends into the water, surrounded by lush greenery.

Cottage in East New Market

4.96 out of 5 average rating, 71 reviews

Cottage on Cabin Creek

A cozy cottage exterior is presented with a stone patio featuring four white Adirondack chairs surrounding a small table. A flagpole with an American flag stands nearby, while trees and greenery provide a peaceful backdrop.

Cottage in Easton

4.88 out of 5 average rating, 50 reviews

Loon Cottage on Leeds Creek

A scenic view is presented of a grassy area leading to a calm waterway. A sailboat glides across the water, while a dock with boats is visible. Lush trees frame the scene, creating a tranquil atmosphere.

Cottage in Saint Michaels

4.96 out of 5 average rating, 24 reviews

Very cosy and nicely appointed Waterfront Cottage

Top guest favorite

A wooden pier extends over gentle waters, surrounded by rocks. The scene is illuminated by a soft pink and orange sky at sunset, reflecting on the water's surface. Additional pilings can be seen in the distance, enhancing the tranquil setting.

Home in Cambridge

5 out of 5 average rating, 44 reviews

• Peaceful Point • A relaxing waterfront retreat

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