Holiday houses in Chester County

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Top-rated holiday rentals in Chester County

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Guest favourite

Home in Honey Brook

Bunk Room, Pavilion, Pickleball & Swimming Pond

-Pickleball, Basketball & Shuffleboard Court -Swimming Pond with Paddle Boat -Children's Playset & Trampoline -Outdoor Kitchen with Kamado Joe Smoker & 36" Griddle -Newly added LG Smart TV -Peaceful retreat surrounded by acres of woodlands -Additional bunk house sleeps 16, available to rent for $100/night Located in Chester County, minutes from Lancaster County's popular tourist attractions and 1 hour from Philadelphia International Airport. Rock Hollow can be your family's next destination!

4.97 out of 5 average rating, 241 reviews

Top Guest favourite

The exterior of a farmhouse is shown, featuring a covered porch with a swing and decorative elements. A lush green lawn surrounds the home, complemented by vibrant trees offering shade. A quaint path leads to the front door, and manicured flower beds add charm.

Home in Downingtown

Historic Farmhouse

Quaint meticulously restored farmhouse with central AC and excellentWiFi. Experience the peace & tranquility that comes with a rural getaway. A short drive to antiques, United Sports, Oaks Convention Center, Springton Manor, Victory Brewery, Marsh Creek lake, Longwood Gardens, and Amish country, there is something for everyone. Enjoy a large yard, patio, grill, fire pit, and space for the kids! Relax and enjoy the feel of country life with endless opportunities for fun!

4.95 out of 5 average rating, 247 reviews

Top Guest favourite

The historic stone home features a charming log addition surrounded by well-maintained landscaping. A spacious front porch extends across the facade, providing an inviting outdoor area. The setting is accented by trees and open fields, contributing to a serene atmosphere.

Cabin in Gap

The Log House at Twin Brook

A cozy family getaway. While staying here, you will get to live in this historic stone home with a beautiful log addition. The original structure was built in the 1700s and served as the servant's quarters for the stone house across the road where your hosts now live. Set out in the country, you will be delighted with the peaceful environment created by the woods, fields, and buggies going by on the road. The house is set close to the road, so traffic can be heard at times.

4.99 out of 5 average rating, 219 reviews

Top Guest favourite

A spacious two-story home features a blend of modern and historic architectural styles. A welcoming porch with seating arrangements is adorned with string lights, while well-maintained flower gardens and greenery enhance the outdoor setting. The image captures the serene ambiance of the property.

Home in West Chester

The Pump Maker’s House Marshallton Historic Beauty

Situated in the historic village of Marshallton, this home is furnished in country style with lovely antiques and vintage items. The first half of the house was built in 1790 with an addition added in 1830. This house was the childhood home of George McFarland, pump maker. He was the town plumber and made wooden pumps in a shop in the rear. We have just completed an entire rehabilitation with brand new plumbing, electric, hvac, as well as brand new bathrooms and kitchen.

4.97 out of 5 average rating, 118 reviews

Top Guest favourite

A gravel driveway is visible, lined with greenery and shaded by trees. The scene opens up to a grassy area beyond, enclosed by a wooden fence. Sunlight filters through the leaves, creating a tranquil outdoor space.

Apartment in West Chester

West Chester apartment located on horse facility

Our apartment in located in the heart of West Chester PA. Our place is close to restaurants and dining, nightlife, great views, and family-friendly activities. You’ll love Sunset Valley Farm because it is a Horse property with activities on the property (season permitting). Horse lessons, Kayak, creek, fishing, and near all of the local attractions (King of Prussia Mall, Gettysburg, Valley Forge, Brandywine river, Lancaster (Amish country) 40 mins away).

4.84 out of 5 average rating, 417 reviews

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

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.

4.99 out of 5 average rating, 279 reviews

Top Guest favourite

The entrance of a historic farmhouse is framed by lush foliage, revealing a stone façade adorned with wooden shutters and an American flag. A small rocking chair is positioned on the covered porch alongside potted plants and a wooden barrel, creating a welcoming outdoor space.

Farm stay in Coatesville

The Farmer’s House

Historic FARM STAY. Est. In 1757 and hidden from view, it is certain to provide a private getaway! If you have the heart of a "homesteader" or simply want to have a peaceful holiday, this farmette will allow you to travel back in time for a relaxing experience you will not forget! A winding brook and pond are located within short walking distance from the home. Well furnished, this home will impress you with all her comfort and character!

4.93 out of 5 average rating, 128 reviews

Guest favourite

A colonial-style farmhouse is viewed from the driveway, framed by trees and shrubs. The stone bridge leads to the front entrance, where warm lanterns illuminate the pathway. The structure features a charmed exterior with a sloped roof and a welcoming entrance.

Farm stay in Coatesville

Vintage Farmhouse Stay - History Meets Comfort

LONG STAY DISCOUNTS!!! Nestled in the heart of Chester county, the Brandywine Lodge is a colonial and Victorian-themed modern house, just minutes from local Amish farms, the Brandywine River, Longwood Gardens, and various local historic sites. Take your stay to the next level by attending a class we offer on traditional skills such as painting, sourdough making, and plant propagation. Please see below for class lengths and prices.

4.94 out of 5 average rating, 147 reviews

Top Guest favourite

A fireplace with a white mantel serves as a focal point beneath a mounted television. The area is complemented by a colorful wall art piece, with natural wood beams enhancing the ceiling. Light streams through a window, and a small desk with coffee amenities is visible.

Home in West Chester

The Mineral House of West Chester

Unique home in the heart of West Chester, tastefully renovated with fantastic detail, walking distance to all the dining, bars, shops and parks the borough has to offer. This home will bring you back to WC again and again. Do not let the staircase frighten you, it was designed by the late great architect George A Matuszewski for this unique space. Come and enjoy this special property and all the charm West Chester has to offer.

4.97 out of 5 average rating, 504 reviews

Guest favourite

An open living area features a small dining table surrounded by chairs, adjacent to a comfortable corner sofa. Sliding barn doors lead to a bedroom with a spacious bed. A ceiling fan and unique wall art contribute to the inviting ambiance.

Apartment in Kennett Square

Cozy, Creative, One of a Kind

Enjoy activities (ping-pong/dart/board games), then stretch out in the king size bed. Full of host's original art. Driveway parking 10 minutes or less to all that Kennett has to offer (breweries, restaurants, Longwood Gardens, etc.), 1/2 hour to Wilmington or UD, 1 hour to Philadelphia. We live upstairs and you will hear footsteps in the morning before school and afternoons. *Solar Powered*Woman Owned*EV Charger*

4.91 out of 5 average rating, 379 reviews

Top Guest favourite

A living room features a stone fireplace as the focal point, flanked by large windows allowing natural light to fill the space. Two comfortable armchairs and a cozy sectional are arranged around a wooden coffee table, with a warm area rug underfoot.

Home in Honey Brook

The View

Come enjoy The View overlooking Amish farmland and feed the farm animals in the back yard. Watch spectacular sunrises from the deck or overlook the farmers field from the hot tub. Feel the smooth texture and beauty of solid handmade furniture. We have room for the whole family or even several families. Relax knowing your host lives on the adjoining property and is wanting your stay to be all you hoped for and more!

4.96 out of 5 average rating, 196 reviews

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

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.

5.0 out of 5 average rating, 363 reviews