Holiday rentals with outdoor seating in Chester County

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

Top-rated Holiday Houses with Outdoor Seating in Chester County

Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

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Guest favourite
A spacious living area features a light-colored sofa paired with decorative pillows. A plush rug adds texture to the hardwood floor, and a small table is positioned beside the sofa. Natural light filters through a window adorned with soft drapes, accompanied by a verdant plant.
Apartment in Paradise
4.92 out of 5 average rating, 179 reviews

Apt. 1 at Witmer Estate, Near Amish Attractions

The apartment is located on the property of the historic Witmer Estate. This 2nd floor apartment (above garage) offers a Smart TV, WIFI, King bed, an suite bath, a spacious living room and kitchen, a small desk area if you plan to work during your stay. The home is located near Amish attractions, Intercourse, Bird in Hand, Strasburg all within a few minutes drive. 20 minutes to Downtown Lancaster. Shopping and the outlets also within 10 minutes drive. Outdoor patio area w picnic table & lights.

Top Guest favourite
A charming cottage exterior is surrounded by lush greenery and well-maintained landscaping. The inviting front porch features two turquoise chairs and a small table, with a pathway leading to the entrance. Large windows offer views of nature and enhance the bright atmosphere.
Cottage in Downingtown
4.94 out of 5 average rating, 244 reviews

Silk Purse Cottage-a private, cozy retreat

Silk Purse Cottage (ca. 1920) is in scenic, historic Chester County, PA 6 miles from the PA turnpike. It is a completely renovated, private cottage on a 6 acre property. Perfect spot for a relaxing vacation. Visitors who are interested in gardening, history and outdoor activities will find many opportunities close by. Hike, fish, go boating or mountain biking one mile away at Marsh Creek State Park. Longwood Gardens, Winterthur, Lancaster and Philadelphia are all a short distance by car.

Top Guest favourite
Guest suite in Downingtown
4.98 out of 5 average rating, 100 reviews

Spacious 2-BR in-law suite in Chester County

Enjoy room to relax in our family friendly, two bed room in-law suite minutes from Chester County sights -27 miles to Subaru Park for World Cup! -Spacious living w/fast Wi-Fi & smart TV—for movie nights -Fully equipped kitchen & laundry available—ideal for longer stays -Quiet bedrooms with hotel-quality linens -We are superhosts with a personal touch Visiting family, sports travel, etc.—our home keeps you close to everything! Ready for a worry-free stay? Tap “Reserve” to secure your dates.

Guest favourite
The outdoor patio area features a spacious pool surrounded by lounge chairs. An outdoor seating arrangement with a fire pit is positioned before the pool, inviting relaxation. The stone farmhouse and trees in the background complete the serene retreat atmosphere.
Villa in Morgantown
4.98 out of 5 average rating, 157 reviews

Mill Road Farmhouse: Restored with Beautiful Pool.

The Mill Road Farmhouse is a destination in and of itself. Immaculately restored inside and out, this home is a true retreat in the middle of Amish Country. We have a feeling you will be spending all of your time relaxing by pool and hot tub during the warmer months (or maybe grilling up a feast in the brand new outdoor kitchen area) and curled up next to one of the four indoor fireplaces during the winter months. And then of course end each day star-gazing while sitting around the campfire.

Top Guest favourite
The front entrance of the home features a well-maintained pathway bordered by lush greenery and flowering plants. An elegant lamp post stands beside the path, illuminating the approach to the entrance where double doors and a decorative American flag are positioned.
Apartment in Chadds Ford
4.99 out of 5 average rating, 248 reviews

Silo Suite

Welcome to our charming suite located in the heart of the historic Brandywine Valley. Nestled within the entrance of a beautifully converted 12,000 square foot barn home, this space offers a truly unique and memorable stay. Our special place is perfectly situated between the renowned Brandywine River Museum and the Chadds Ford Winery, and in just minutes, you can explore the enchanting beauty of Longwood Gardens or dive into the world of history at Winterthur.

Top Guest favourite
A charming cottage with a green, A-frame roof is framed by blossoming dogwood trees. A gravel path leads to the entrance, which is flanked by lush greenery and flowering shrubs, providing a tranquil and inviting approach.
Place to stay in West Chester
4.98 out of 5 average rating, 252 reviews

Private West Chester Cottage close to Longwood

Treat yourself to time away in the heart of Chester County history and horse country. This charming little gem, privately nestled under the evergreens is surrounded by acres of American history dating back to the 1700s. Tucked behind the property's historic stone farmhouse is the newly refurbished cottage which you'll have to yourself. The cottage is tastefully decorated with vintage treasures & has spectacular views of the unique property & gardens.

Top Guest favourite
An a-frame home is showcased, featuring a spacious deck with modern outdoor seating arrangements. A fire pit sits on a stone patio, surrounded by greenery. Large windows reflect the surrounding trees, inviting natural light into the living space. A barbecue grill is positioned nearby.
Chalet in Birdsboro
4.96 out of 5 average rating, 250 reviews

Luxury Chalet with Mountain Views & Hot Tub

Escape to this luxurious A-frame chalet nestled in Birdsboro, Pennsylvania, providing breathtaking mountain vistas. Delight in the warmth of the cozy fireplace, unwind in the hot tub, and utilize the outdoor kitchen for culinary adventures. This chalet is ideal for relaxation and rejuvenation, with convenient access to nearby trails for hiking, opportunities for fishing, and the chance to go canoeing. It's a genuine retreat from the everyday.

Guest favourite
The exterior of a historic home is featured, showcasing a lavender front door with decorative glass accents. A brick facade complements the door, while a wooden side door and window add to the character. Potted flowers adorn the entrance, enhancing the inviting atmosphere.
Home in West Chester
4.94 out of 5 average rating, 187 reviews

Historic Home on Gay Street.

Welcome to historic downtown West Chester, PA. This freshly renovated historic home boasts 2 Queen bedrooms and 2 full baths, sleeping 6. Amenities and accommodation await behind the lavender door. This home is nestled on one of the most desirable blocks in the borough that boasts 260 years of history. Convenience, history, haven, and limitless adventures begin with your stay at 236 W Gay street. Take a look behind the lavender door.

Top Guest favourite
The exterior of a red carriage house showcases large, multiple-pane windows, allowing natural light to fill the space. The building is framed by greenery, including flowering plants and bushes, offering a serene garden setting that complements the architecture.
Guesthouse in Kennett Square
4.97 out of 5 average rating, 462 reviews

Longwood Gardens Carriage House

Two miles from Longwood Gardens and six from Winterthur and Brandywine River museums, the apartment is ideally located for exploring Brandywine Valley sites and historic Kennett Square. Situated in a garden with views of a wildflower meadow and horses, it offers a spacious bedroom and bath, cozy kitchen/living combo and washer/dryer. It is modern, super clean, comfortable, and private--an idyllic country escape.

Top Guest favourite
A forest path is surrounded by tall trees and dense greenery, with ferns lining the ground. The sunlight filters through the leaves, creating a serene atmosphere for hikers. The trail, partially obscured by foliage, invites exploration into the natural surroundings.
Guest suite in Media
4.98 out of 5 average rating, 567 reviews

The Welcoming Woods

Enjoy the quiet of the woods as you relax in your private space. The studio is minutes away from downtown Media where you can enjoy the shops & restaurants on State St or take a 20 minute ride into Philadelphia. Attractions include Tyler Arboretum, Ridley Creek State Park,Longwood Gardens,Linvilla Orchards & local wineries in Brandywine & Chadds Ford PA. The woods are waiting to welcome you!

Top Guest favourite
A charming cottage is nestled among lush greenery, with a large window inviting natural light. The exterior features a sloping roof and a stone wall, accentuating the surrounding landscape of rolling hills and fields.
Cottage in Coatesville
5 out of 5 average rating, 324 reviews

Charming cottage on 50 acre Chester County farm

Frog Hollow Cottage is a newly renovated getaway located in the heart of the Chester County’s rolling farmland and equestrian community. Overlooking beautiful pastures, the cottage was formerly the large painting studio of Delaware Valley artist Peter Sculthorpe. The studio has been re-imagined as a peaceful retreat for families, friends and couples.

Top Guest favourite
A cozy guest room features a queen-sized bed adorned with a blue throw. A comfortable armchair and a wicker chair provide additional seating. Natural light enters through two windows, and a ceiling fan offers ventilation. Artwork adds character to the warm green walls.
Guest suite in Coatesville
4.98 out of 5 average rating, 179 reviews

Broad Run Suite- West Bradford Township

The suite is located on a private 4- acre wooded lot, with a stream, in scenic Chester County. The private suite has its own entrance and all the comforts of home...close to West Chester, Longwood Gardens, historic sites, Brandywine River Museum, SEPTA Regional Rail and Amtrak lines, and much more. Come relax in this beautiful location.

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