
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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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!

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.

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.
Popular amenities for Chester County outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Historic Farmhouse

Phoenix Walk

Downingtown Manor | 1900s Farmhouse w/ Creek Views

Cozy hideaway on your own corner of our homestead

Cute Cape Cod in Lancaster County

Eclectic Escape Near Longwood Gardens & Mt. Cuba

Historic House in the Heart of Town

Sunrise Guesthouse, walk to Kitchen Kettle Village
Apartment rentals with outdoor seating

Quiet suite in the heart of Amish country.

Private Suite with Hot tub

Stoltzfus Farm Guest House

Carriage House Suite

Lemon St. Retreat

Peaceful, country setting on Fountain Hill Farm

Amish farmland view: peaceful

King's Suite
Other holiday rentals with outdoor seating

Newly Renovated Chic Farmhouse with Creek access

Sparkling Clean Suite in Amish Country w/ Hot Tub

1 Bedroom Condo in Trolley Square

Fox Creek Cabin, private wooded property w/ stream

Newly Renovated Chester Springs Guesthouse

Quiet, Country Church, Lancaster County

Lucy's Log Cabin Cottage in the Woods

Farm stay! sleeps 8 Lancaster County, PA
Destinations to explore
- Cottage rentals Chester County
- Condo rentals Chester County
- Fitness-friendly rentals Chester County
- Loft rentals Chester County
- Rentals with a hot tub Chester County
- Cabin rentals Chester County
- Bed and breakfasts Chester County
- Rentals with a fireplace Chester County
- Private suite rentals Chester County
- Family-friendly rentals Chester County
- Rentals with pools Chester County
- Pet-friendly rentals Chester County
- Rentals with breakfast Chester County
- Boutique hotels Chester County
- Rentals with a washing machine and dryer Chester County
- House rentals Chester County
- Tiny house rentals Chester County
- Rentals with a patio Chester County
- Farmstay rentals Chester County
- Townhouse rentals Chester County
- Rentals with lake access Chester County
- Apartment rentals Chester County
- Hotel rooms Chester County
- Rentals with a fire pit Chester County
- Guesthouse rentals Chester County
- Rentals with outdoor seating Pennsylvania
- Rentals with outdoor seating United States
- Pennsylvania Convention Center
- Lincoln Financial Field
- Longwood Gardens
- Citizens Bank Park
- Hersheypark
- Fairmount Park
- Dorney Park & Wildwater Kingdom
- Philadelphia Museum of Art
- Wells Fargo Center
- Penn's Landing
- Bear Creek Ski and Recreation Area
- Betterton Beach
- Diggerland
- French Creek State Park
- Philadelphia Zoo
- The Franklin Institute
- Wissahickon Valley Park
- Marsh Creek State Park
- Valley Forge National Historical Park
- Independence Hall
- Spruce Street Harbor Park
- Eastern State Penitentiary
- Hershey's Chocolate World
- Franklin Square




