Holiday houses in Chester County

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Top-rated holiday rentals in Chester County

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Top Guest favourite
A greenhouse made of glass panels is surrounded by thriving garden beds filled with various plants. Lush greenery and flowering plants are present in the landscaped area. A well-maintained lawn with neat stripes leads up to the greenhouse, enhancing the serene outdoor setting.
Apartment in Honey Brook

Farm Stay at Solidrock Guest House

Solid Rock close to mini golfing, major golf courses, shopping, Amish tourist areas, restaurants, historical land marks and areas, parks, lakes and hiking. We have a great place for married couples, families with children, and the business travelers. We have a master bedroom with a corner whirlpool tub and private restroom and a smaller bedroom also containing its own private shower/washroom. we easily sleep four adults and have extra mattresses for others who would like to sleep on the floor.

4.94 out of 5 average rating, 186 reviews
Top Guest favourite
Guesthouse in West Chester

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!

4.97 out of 5 average rating, 258 reviews
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, 242 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, 217 reviews
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, 409 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, 278 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!

QuietOutdoor spacesHospitality

4.93 out of 5 average rating, 127 reviews
Guest favourite
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, 144 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, 500 reviews
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!

FamilyCleanliness

4.96 out of 5 average rating, 191 reviews
Guest favourite
Home in Chester Springs

Experience the charm of a historical getaway

Take it easy at this unique and tranquil getaway. Step back into time in this historic 1735 house transformed into a beautiful retreat by Jeff & Janelle, as seen on the Magnolia Network. The Inn can accommodate up to 9 people in 4 comfortable bedrooms. So, grab your friends and family and escape into a one-of-a-kind stone home, right in the heart of Pennsylvania.

4.93 out of 5 average rating, 120 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, 358 reviews

Popular amenities for Chester County holiday rentals