Some info has been automatically translated. Show original language

Family-friendly vacation rentals in Kennett Square

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Kennett Square

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

%{current} / %{total}1 / 1
Top guest favorite
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 favorite
The inviting living area features a warm-toned couch and decorative accent pillows. A circular coffee table sits in front, complemented by a stylish lamp. A wall-mounted TV is visible, along with an open kitchen view, highlighting natural light from nearby windows.
Home in Kennett Square
4.97 out of 5 average rating, 225 reviews

Longwood | Shops & Restaurants | Private Backyard

"We've stayed at AirBnBs all over the world and this was our favorite!" • Walk Score 86 (Walk to cafes, dining, shopping, breweries, etc.) • Fully equipped + stocked kitchen w/ SMEG appliances • Backyard patio w/ fire pit + BBQ grill • Samsung Frame TV • Onsite washer + dryer • Extremely safe neighborhood • Self check-in w/ keypad → 2 mins to Downtown → 10 mins to Longwood Gardens (#1 Botanical Gardens in USA) → 15 mins to Brandywine Battlefield → 25 mins to downtown Philly

Top guest favorite
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 favorite
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 favorite
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 favorite
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*

Top guest favorite
The exterior of a historic carriage home is shown, featuring a charming wooden door framed by a small porch. A textured shingle roof and light-colored siding complement the building's design. Nearby, a gravel pathway leads to outdoor seating, adding to the inviting entrance.
Apartment in Kennett Square
4.95 out of 5 average rating, 109 reviews

The Suite in a carriage house in Kennett Square

Historic carriage house Suite with one bedroom featuring a king bed and luxury linens. Dining for four and a 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 shops, dining, and breweries. Near Longwood Gardens and Brandywine Valley attractions. Ground-floor unit with no steps. Shared laundry.

Guest favorite
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 favorite
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 favorite
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 favorite
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!😊

Top guest favorite
A charming farmhouse features a two-story exterior with white siding and wooden accents. The porch is screened, providing an inviting space to enjoy the surroundings. Colorful autumn leaves blanket the lawn, and string lights are hung for evening ambiance.
Home in Kennett Square
4.98 out of 5 average rating, 193 reviews

Underground Railroad 4 Bedroom Farmhouse

Enjoy everything that Kennett has to offer in this charming 3 bedroom farmhouse right off union street. Relax in the completely renovated Barn that was once part of the underground railroad. Moments away from Longwood Gardens, Winterthur, and lots of shopping and restaurants.

Popular amenities for Kennett Square family-friendly rentals

When is the best time to visit Kennett Square?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR2,861 ZARR2,776 ZARR2,963 ZARR3,030 ZARR3,217 ZARR3,200 ZARR3,166 ZARR3,132 ZARR3,132 ZARR3,064 ZARR2,895 ZARR3,132 ZAR
Avg. temp-1°C0°C5°C11°C16°C21°C23°C22°C19°C12°C7°C2°C

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 R1,693 ZAR 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

  • Wi-Fi availability

    10 of Kennett Square vacation rentals include wi-fi 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!