
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.

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.

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

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.

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.

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).

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.

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.

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*

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.

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.

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
Family-friendly home rentals with a hot tub

Quiet Cottage - Hot Tub and Creek mins from City

West Chester PA THE LOFT your 5 Star romantic stay

The Cottage at Marsh Creek (with hot tub!)

*Woodland Chalet* Hot Tub - Fire Pit - Grill

See Wild Deer From The Front Porch! *With Hot-Tub*

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

Eclectic Escape Near Longwood Gardens & Mt. Cuba

Lucy's Log Cabin Cottage in the Woods
Family- and pet-friendly home rentals

Tranquil Hilltop Retreat

"The Stay Over" your Home away from Home

Hideaway Cottage

Charming cottage under the pines. No cleaning fee.

The Mineral House of West Chester

Creekside Forest Nature Retreat : Mongolian Yurt

Carriage House at Amish country

Sunset Dome Rustic Camping | King Bed | Small Farm
Family-friendly home rentals with a pool

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

The Grey Wolf (studio-style loft suite)

Peaceful Retreat Pool and great outdoor space

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

Private Country Guesthouse Getaway Minutes from UD

Ode to the '70's - hot tub & pool in Honey Brook

Lakefront Guesthouse

Newly Renovated Chester Springs Guesthouse
When is the best time to visit Kennett Square?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 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 |
| Avg. temp | -1 °C | 0 °C | 5 °C | 11 °C | 16 °C | 21 °C | 23 °C | 22 °C | 19 °C | 12 °C | 7 °C | 2 °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 $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!
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