
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.

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.

Historic J. Pyle House Main St Location Pets OK!
The J. Pyle House, built in 1844, is in the National Historic District of Kennett Square, PA. We are in the heart of walkable downtown Kennett Square and a quick 6 minute drive to Longwood Gardens. The townhome has been lovingly restored to reflect its mid-19th century roots, while providing an updated, cozy place to relax while visiting our quaint town. 45 min to the PHL airport, 25 min to Wilmington, DE, 25 min to West Chester University, 6 min to Longwood Gardens 15 min to Winterthur

Bala Farm Cottage - 2 miles from West Chester
Bala Farm Cottage is a wonderfully cozy stone cottage, located less than 3 miles from the center of West Chester, on a hilltop in a quiet neighborhood. It has a charming study downstairs with a bay window looking out towards majestic trees, and an entry hall that ends with a wet bar, equipped with a mini-fridge, kettle, coffee machine and microwave. The original curved staircase leads to the upstairs bedroom with queen bed and a spacious bathroom. You'll love your stay in the Cottage!

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.

The Blue Lotus - a cottage in Kennett Square
Welcome to the Blue Lotus, a cottage in lovely Kennett Square! Voted 5th coolest town in the U.S. and is home to Longwood Gardens. A quick walk downtown makes it easy to enjoy the local food, coffee and culture. The Blue Lotus has just been completely renovated & has lovely furnishings, hardwood floors in the main space, a new kitchen, laundry & bathroom. You'll love the intimacy of this space. Great for couples, solo adventurers, & business travelers.

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.

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.

*Woodland Chalet* Hot Tub - Fire Pit - Grill
Welcome to your cozy woodland retreat! Nestled in a serene forest, this charming one-bedroom Airbnb offers a perfect blend of style and tranquility. Designed with a modern aesthetic, the space features chic furnishings, warm modern accents, and large windows that invite natural light and breathtaking views of the surrounding trees.

Charming loft apartment
The loft is in a newly renovated barn, located on our small farm in Gap PA. The location is approximately 15 min from Lancaster County’s main attractions. (please see below for more details on location) We have the cutest pony named Snickers who is accompanied by his two bunny friends. He loves when guests stop by to say hi!😊

Glasshouse overlooking the Great Marsh
Come enjoy the Great Marsh of Chester County, PA. We have 600 acres for you to enjoy hiking, bird watching, biking our trails, kayaking/canoeing our marsh or just finding a quite place on the property to enjoy the outdoors. We also have a non-profit on the property called "Great Marsh Institute".
Popular amenities for Chester County outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Gorgeous Victorian Style Home

"The Stay Over" your Home away from Home

Bunk Room, Pavilion, Pickleball & Swimming Pond

Historic Farmhouse

Country Outback Cozy Home *W/Camp Fire Pit*

King’s place, hot tub Pool is closed until Spring

Cozy hideaway on your own corner of our homestead

Downingtown Manor | 1900s Farmhouse w/ Creek Views
Apartment rentals with outdoor seating

Queen Bed, Luxury Studio with Balcony

Spacious apartment in a quiet setting.

Quiet suite in the heart of Amish country.

Carriage House Suite

Stoltzfus Farm Guest House

Apt. 1 at Witmer Estate, Near Amish Attractions

Lemon St. Retreat

Peaceful, country setting on Fountain Hill Farm
Other holiday rentals with outdoor seating

Hilltop Mansion: Farm Views+HotTub+Pool+GameRoom.

West Chester PA THE LOFT your 5 Star romantic stay

Country Cottage

Pyle Cottage, circa 1750

Vintage Farmhouse Stay | History Meets Comfort

A-Frame Getaway on Amish Farm

Private Guest Suite and Entrance

The Stone House between the Streams
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- Rentals with outdoor seating Pennsylvania
- Rentals with outdoor seating United States
- Pennsylvania Convention Center
- Lincoln Financial Field
- Citizens Bank Park
- Hersheypark
- Longwood Gardens
- Dorney Park & Wildwater Kingdom
- Fairmount Park
- Penn's Landing
- Betterton Beach
- Philadelphia Museum of Art
- 30th Street Station
- Diggerland
- French Creek State Park
- Wells Fargo Center
- Marsh Creek State Park
- Philadelphia Zoo
- The Franklin Institute
- Aronimink Golf Club
- Wissahickon Valley Park
- Valley Forge National Historical Park
- Crystal Beach Manor, Earleville, MD
- Independence Hall
- Eastern State Penitentiary
- Franklin Square




