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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

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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, 193 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, 287 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

4.92 out of 5 average rating, 106 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 kayak, 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.

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

5 out of 5 average rating, 119 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, 617 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

4.94 out of 5 average rating, 104 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, 108 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, 173 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

4.97 out of 5 average rating, 158 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, 299 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

4.98 out of 5 average rating, 249 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.

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

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

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Popular amenities for Talbot County outdoor seating rentals

Free parking on premises

Air conditioning

House rentals with outdoor seating

5 out of 5 average rating, 8 reviews

Ferry Bridge House

A serene seating area is presented, featuring two plush pink chairs positioned on a decorative rug. A stylish chandelier adds soft lighting above. A fireplace mantel is adorned with a floral arrangement, and glass-paneled cabinets are visible in the background.

Home in Cambridge

4.85 out of 5 average rating, 78 reviews

High St. Art Gallery Suite

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, 120 reviews

Gorgeous, waterfront home - Perfect for Families.

The image captures a serene waterfront scene at sunset. A wooden pier extends into the Chesapeake Bay, surrounded by rocky shorelines and lush green grasses. The sky displays soft hues, while the sun descends on the horizon, creating a tranquil ambiance.

Home in Tilghman Island

4.95 out of 5 average rating, 44 reviews

Tilghman Retreat: A house on the Chesapeake Bay.

Top guest favorite

A classic three-story home features a navy blue exterior with white trim. A welcoming front porch is furnished with multiple rocking chairs, offering a comfortable space to relax. Decorative details include a distinctive turquoise front door, complemented by white support columns and a well-maintained lawn.

Home in Cambridge

4.95 out of 5 average rating, 247 reviews

Great Historic Cambridge Home With Parking!

Top guest favorite

A charming white cottage with a steep roof is set amidst lush green trees. A brick walkway leads to the front door, bordered by manicured grass and potted plants. The exterior features large windows that enhance its inviting appearance.

Home in Cambridge

5 out of 5 average rating, 23 reviews

Charming cottage, 1 blk water, historic area

A spacious waterfront home is shown against a backdrop of Chesapeake Bay. The property features well-maintained landscaping with colorful flower beds and lush green lawns. Nearby trees provide shade, and the gleaming water is visible in the distance, enhancing the serene coastal atmosphere.

Home in Stevensville

4.98 out of 5 average rating, 42 reviews

Waterfront Chesapeake mansion - Panoramic Bay view

Lush green grass leads to the waterfront, where the calm water reflects the surroundings. Two white Adirondack chairs sit invitingly under the shade of tall trees, providing a serene spot for relaxation. A wooden dock extends into the water, enhancing the picturesque setting.

Home in Neavitt

4.96 out of 5 average rating, 91 reviews

Waterfront, Dog friendly, St Michaels home

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

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, 12 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, 72 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, 139 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, 69 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, 31 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, 27 reviews

The Place in Cambridge-Sailing into Autumn

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

4.93 out of 5 average rating, 59 reviews

Chesapeake Houseboat Getaway

A serene view is presented through an archway, framing the sunset over a tranquil waterfront. Grassy lawns and trees are visible, alongside a peaceful water garden, enhancing the natural beauty of the landscape.

Home in Queenstown

5 out of 5 average rating, 10 reviews

The Perfect Waterfront Escape!

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, 68 reviews

Cottage on Cabin Creek

An open living and dining area features a high ceiling and abundant natural light. A cozy fireplace is positioned between two seating areas, each adorned with comfortable sofas. A dining table with modern chairs occupies one corner, while large windows overlook the outdoor space.

Home in Saint Michaels

4.86 out of 5 average rating, 7 reviews

Crew's Quarters | an ESVR property

Top guest favorite

Large windows in a cozy corner offer expansive views of a sunset over the water, casting warm hues across the sky. The gentle light reflects on the calm surface, creating a serene atmosphere for relaxation.

Townhouse in Tilghman Island

5 out of 5 average rating, 48 reviews

Tilghman Island Waterfront Home w/Stunning Sunsets

A serene waterfront view captures a sunset over Crab Alley Bay, reflecting warm colors on the water. A private pier extends into the bay, with a boat anchored nearby. Lush green grass leads to the water's edge, framed by trees in the background.

Home in Chester

4.96 out of 5 average rating, 51 reviews

A waterfront Paradise with hot tub

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