Family-friendly holiday 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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Guest favourite
A welcoming corner of the suite features a round table with two black chairs beneath a historic sign. Soft natural light enters through the door, highlighting a wooden dresser and decorative items along the walls. A textured rug enhances the cozy atmosphere.
Apartment in Kennett Square
4.79 out of 5 average rating, 141 reviews

Kennett Square romantic 1 bedroom efficiency

Historic Kennett Square, mushroom capital of the world, is in beautiful Chester County. In the historic district.You can walk to our exquisite restaurants, shopping and Hiking trails. Longwood Gardens, a mile drive away! Now a bit about our lovely bedroom suite.. during The pandemic we closed our antique store. We incorporated both antiques and contemporary pieces to reflect the ambiance of our shop. Free parking, out front, and a easy walk from car, no steps, into your private entrance. Enjoy!♥️

Top Guest favourite
A cozy living area is furnished with a slipcovered sectional sofa and two blue slipper chairs surrounding a glass coffee table. Natural light filters through patterned curtains, highlighting a vintage rug on hardwood floors. The space connects to a dining area and staircase leading to the upper levels.
Home in Kennett Square
4.99 out of 5 average rating, 155 reviews

Historic Downtown D. Clark House Dog Friendly!

The historic Dorothy Clark House, built around 1907, is in the National Historic District of Kennett Square, PA. We are downtown in the heart of the walkable Kennett Square Borough! This twin home has been lovingly restored to reflect its early 20th century roots, while providing a cozy place to relax while visiting our quaint town. We hope you’ll fall in love with the home like we have! 45 min to Philadelphia airport, 25 min to Wilmington 25 min to WCU, 6 min to Longwood, 15 min to Winterthur

Top Guest favourite
A cozy living area features a dark brown leather sectional sofa facing a 55” HDTV. A round table with fresh flowers is positioned near the sliding glass doors, which provide natural light and a view of the outdoor patio. Light-colored dining chairs are arranged around a wooden dining table.
Apartment in Chadds Ford
4.92 out of 5 average rating, 308 reviews

Spacious & Peaceful, Pvt, 3mi Longwood Gardens

Comfy & Spacious Private Downstairs Suite in 2 acres of nature Private Pool Heated end of May to Sept 3 mi to Longwood Gardens aka “America’s Versailles”. Amazing! Ask about guest passes to the Gardens w/2 night stays. Winterthur, Brandywine River Museum, Wineries & more 3 Bedrms, 4 beds Beautiful lg bathrm & Powder room Dining/TV rm Kitchen: Convection oven, Cooktop, Microwave, Keurig coffee maker WiFi, 55” HDTV Full size washer, dryer, refrigerator Gentle Pets welcome! *No Smoking, No Parties

Top Guest favourite
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
4.98 out of 5 average rating, 248 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 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, 262 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.

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
4.98 out of 5 average rating, 259 reviews

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.

Guest favourite
The exterior of a charming carriage home is displayed, featuring intricate woodwork and a variety of window shapes. The structure includes a distinctive turret and a red brick chimney. Vibrant flowers surround the entrance, enhancing the inviting appearance.
Apartment in Kennett Square
4.89 out of 5 average rating, 212 reviews

Luxury Apartment in Kennett Square

Historic carriage house Apartment with 2 bedrooms (king & double) and shared Jack-and-Jill bath. Spacious living room with pull-out sofa, dining for 6, work desk, and fully equipped kitchen with full appliances and coffee. Smart TVs, 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; no steps. Shared laundry.

Top 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, 199 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.

Top 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
4.92 out of 5 average rating, 336 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 favourite
The exterior of a red carriage house showcases large, multiple-pane windows, allowing natural light to fill the space. The building is framed by greenery, including flowering plants and bushes, offering a serene garden setting that complements the architecture.
Guesthouse in Kennett Square
4.97 out of 5 average rating, 466 reviews

Longwood Gardens Carriage House

Two miles from Longwood Gardens and six from Winterthur and Brandywine River museums, the apartment is ideally located for exploring Brandywine Valley sites and historic Kennett Square. Situated in a garden with views of a wildflower meadow and horses, it offers a spacious bedroom and bath, cozy kitchen/living combo and washer/dryer. It is modern, super clean, comfortable, and private--an idyllic country escape.

Guest favourite
A living room is presented with a neutral color palette featuring green walls. Comfortable seating includes a spacious sofa and two armchairs. A wooden coffee table occupies the center, while a TV is mounted on a cabinet. Natural light enters through large windows, and a staircase is visible in the background.
Home in Kennett Square
4.92 out of 5 average rating, 120 reviews

Longwood Kennett Newly Renovated

Lovely renovated and newly decorated duplex, close to downtown Kennett Square and all of the great activities nearby. Walk Score 73 (Walk to cafes, dining, shopping, breweries, etc.) 9 min walk to Downtown Kennett for more restaurants and shopping 2 min walk to restaurants 9 mins drive to Longwood Gardens (#1 Botanical Gardens in USA) 25 mins drive to downtown Philly 25 mins drive to Wilmington

Top Guest favourite
Guesthouse in Kennett Square
4.98 out of 5 average rating, 307 reviews

Blue Lotus - a luxe cottage in Kennett Square

Escape to the Blue Lotus, a serene cottage located in walkable downtown Kennett Square and within minutes from the world-famous Longwood Gardens. Thoughtfully designed for rest and connection with deep rich color & themed around the Lotus flower, Lilly pads, Ferns, Birds & nature. This intimate retreat offers peaceful garden views, cozy luxury, and the perfect setting to unwind.

Popular amenities for Kennett Square family-friendly rentals

When is the best time to visit Kennett Square?

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Avg. price$236 AUD$229 AUD$245 AUD$250 AUD$265 AUD$264 AUD$261 AUD$259 AUD$259 AUD$263 AUD$256 AUD$260 AUD
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Quick stats about holiday rentals that are family-friendly in Kennett Square

  • Total holiday rentals

    Explore 10 holiday rentals in Kennett Square

  • Nightly prices starting at

    Kennett Square holiday rentals start at $140 AUD per night before taxes and fees

  • Verified guest reviews

    Over 1,990 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    10 of Kennett Square holiday 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!