Family-friendly vacation rentals in Kennett Square

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Top-rated family-friendly rentals in Kennett Square

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favourite
A walkway leads toward the entrance of the modern apartment, flanked by colorful foliage and seasonal plants. The path is bordered by manicured gardens, while trees with autumn leaves create a serene backdrop. Natural light brightens the inviting exterior.
Guest suite in Kennett Square
4.94 out of 5 average rating, 131 reviews

Unionville Apartment-Minutes from Longwood Gardens

Bright and open two-story (stairs), modern one-bedroom, 1 bath apartment with central air conditioning, great room, walk-in closet, wood floors, and utility room with washer/dryer. Private parking. Rural setting in Unionville adjacent to ChesLen Preserve. We are also minutes from Longwood Gardens, Plantation Field Events, and Kennett Square, PA. Particularly well suited for travel and business trips to Southern Chester County. 18% off stays over a week. 25% off stays of a month or longer.

Top guest favourite
A cozy living room features a comfortable seating arrangement with a sofa and two armchairs. A wooden coffee table sits on a soft area rug, alongside warm lighting from standing lamps. A ceiling fan adds ventilation, while the staircase and dining area can be seen in the background.
Home in Kennett Square
4.95 out of 5 average rating, 127 reviews

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

Top guest favourite
The exterior of a blue cottage is shown, featuring a gravel pathway leading to the front door. Lush greenery surrounds the home, with a small seating area visible to the left, complemented by colorful flowers and shrubs.
Guesthouse in Kennett Square
4.98 out of 5 average rating, 299 reviews

Blue Lotus - a luxe cottage in Kennett Square

Welcome to the Blue Lotus, a cottage in lovely downtown Kennett Square! Voted 5th coolest town in the U.S. and is home to Longwood Gardens. A quick walk in town makes it easy to enjoy the local food, coffee and culture. Renovated in 2020 & has lovely furnishings, hardwood floors in the main space, a new kitchen, laundry & bathroom. You'll love the intimacy of this space, the private patio, & views of gardens. Great for couples, solo adventurers, & business travelers.

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, 235 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.

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
4.84 out of 5 average rating, 352 reviews

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).

Top guest favourite
The exterior of the Tiny House is showcased, featuring a modern design with a gray metal facade. A welcoming entryway is installed with a wooden door. A brick walkway leads from the grass area to the entrance, framed by trees and landscaping, creating an inviting environment.
Home in Kennett Square
4.89 out of 5 average rating, 106 reviews

Newly built Tiny House in Historic Kennett Square

Custom-built tiny house Cottage with designer touches. Main floor has living area, full bath, and laundry. Loft bedroom with king bed and full ceiling height, accessed by stairs. Fully equipped kitchen with full appliances, cookware, table settings, and coffee. Smart TV, high-speed internet, and on-site parking. Two blocks from downtown Kennett Square dining, shops, and breweries. Near Longwood Gardens and Brandywine Valley attractions. Max 2 guests.

Guest favourite
An open living and dining area features modern furnishings with a round dining table set for four. A vibrant floral accent wall adds character to the space, while a cozy seating area is visible in the background, complemented by natural light from nearby windows.
Townhouse in Kennett Square
4.97 out of 5 average rating, 185 reviews

Homey Retreat in Historic Kennett Square!!

Homey Retreat! A hidden gem tucked away in the bustling historic district of Kennett Square. Walking distance from all shops, restaurants, bars, and entertainment on the main strip. Historic charm and modern upgrades throughout make this a great place to experience and take in the full vibe this great town has to offer. 3 bedrooms, open living room, dining area, fully functioning kitchen, private backyard oasis, with off-street parking.

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
4.91 out of 5 average rating, 314 reviews

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*

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, 557 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, 315 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 living area features a soft, light-colored sofa facing a glass coffee table. Natural light fills the space through large windows, highlighting rustic wooden beams. A dining area with a table and benches is visible in the background, alongside a kitchenette, enhancing the open layout.
Apartment in West Grove
4.97 out of 5 average rating, 180 reviews

Swallow’s Rest: West

This two hundred year old post-and-beam farm building has been converted into two elegant, private apartments that share a common entry. Either apartment can be reserved separately, or both can be shared by a group of guests. The property is located in a quiet and picturesque region that is close to many attractions in southern Chester County.

Top guest favourite
The living room features high ceilings with a textured dark wall, decorated with a world map. A sleek electric fireplace is surrounded by decorative wood stacks. Two sofas face each other, accompanied by a coffee table and indoor plants that add a natural touch to the space.
Loft in Gap
4.98 out of 5 average rating, 300 reviews

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!😊

Popular amenities for Kennett Square family-friendly rentals

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Avg. price$236 CAD$229 CAD$244 CAD$250 CAD$265 CAD$264 CAD$261 CAD$258 CAD$258 CAD$253 CAD$239 CAD$258 CAD
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Quick stats about vacation rentals that are family-friendly in Kennett Square

  • Total vacation rentals

    Explore 10 vacation rentals in Kennett Square

  • Nightly prices starting at

    Kennett Square vacation rentals start at $140 CAD per night before taxes and fees

  • Verified guest reviews

    Over 1,850 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 of Kennett Square vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Kennett Square rentals

  • 4.9 Average rating

    Kennett Square stays are highly rated by guests—averaging 4.9 out of 5!