Family-friendly vacation rentals in Kennett Square

Guest suite in Kennett Square

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.

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.

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.

4.95 out of 5 average rating, 129 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

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.

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

Guesthouse in Kennett Square

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.

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.

4.99 out of 5 average rating, 237 reviews

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

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.

Townhouse in Kennett Square

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.

4.97 out of 5 average rating, 186 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.

Apartment in Kennett Square

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.

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*

Apartment in Kennett Square

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.

4.95 out of 5 average rating, 110 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.

Guesthouse in Kennett Square

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.

4.97 out of 5 average rating, 461 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.

5 out of 5 average rating, 315 reviews

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.

4.98 out of 5 average rating, 300 reviews

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

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!😊

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.

4.98 out of 5 average rating, 194 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

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.97 out of 5 average rating, 713 reviews

A charming bungalow is nestled among lush greenery, featuring a welcoming front porch with two black chairs. The exterior is framed by tall trees, enhancing the sense of tranquility. Flower beds with vibrant plants surround the house, inviting guests to enjoy the natural beauty.

Cottage in Lancaster

Quiet Cottage - Hot Tub and Creek mins from City

4.98 out of 5 average rating, 126 reviews

A modern kitchen showcases dark cabinetry and stainless steel appliances, complemented by a spacious granite island with seating. Natural light floods the area through large windows, highlighting the wooden ceiling beams. The open layout connects to a cozy sitting area featuring a light-colored couch and accent chair.

Loft in West Chester

West Chester PA THE LOFT your 5 Star romantic stay

4.98 out of 5 average rating, 304 reviews

A bright and airy living area features a brown leather couch and a wooden coffee table on a patterned rug. Natural light filters through sheer curtains by a cozy reading chair. The open-plan space includes a kitchen visible in the background, highlighted by modern fixtures.

Cottage in Downingtown

The Cottage at Marsh Creek (with hot tub!)

4.91 out of 5 average rating, 210 reviews

A bright living room features large windows adorned with sheer white curtains, providing views of the surrounding landscape. Two checkered chairs and a comfortable sofa frame a central wooden coffee table, creating a cozy gathering space complemented by decorative accents on the walls.

Cottage in Lancaster

Amish Cottage, Hot Tub, on Mill Creek

4.98 out of 5 average rating, 144 reviews

Home in Quarryville

*Woodland Chalet* Hot Tub - Fire Pit - Grill

Farm stay in Lincoln University

A charming stone cottage is surrounded by lush greenery. The red roof contrasts with the natural landscape. A spacious deck features outdoor seating, providing a serene view of the garden and rolling grassy hills beyond.

4.96 out of 5 average rating, 156 reviews

Pyle Cottage circa 1750

4.95 out of 5 average rating, 283 reviews

A covered pergola with string lights offers shade over the hot tub, positioned on a wooden deck. The lush green grass surrounds the area, stretching towards an open field framed by trees, showcasing the tranquil rural landscape.

Farm stay in Christiana

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

4.95 out of 5 average rating, 225 reviews

Cottage in Charlestown

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

Family- and pet-friendly home rentals

4.93 out of 5 average rating, 101 reviews

The cottage exterior features a blend of natural stone and siding, showcasing a green front door. Lush green grass surrounds the home, complemented by trees in the backdrop. A gravel path leads to the entrance, providing access to the peaceful surroundings.

Cottage in Glen Mills

Tranquil Hilltop Retreat

4.94 out of 5 average rating, 378 reviews

An interior space is divided into two main areas. One side features a queen bed and a twin bed, along with a cozy seating area. The other side showcases a living area with a sofa, a kitchen table, a bar area, and various seating options.

Home in West Chester

"The Stay Over" your Home away from Home

Guest suite in Peach Bottom

A spacious room features a king-sized bed framed by framed photographs. A wooden chair sits beside a small table with a plant. Sliding glass doors open to a private balcony, allowing natural light to fill the space.

5 out of 5 average rating, 161 reviews

Conowingo Creek Casual

Cottage in Chester Springs

A quaint cottage is surrounded by green foliage and vibrant flower beds. The exterior features white siding and large windows, allowing natural light to fill the interior. A small patio area is visible, suitable for outdoor seating.

4.97 out of 5 average rating, 240 reviews

Charming cottage under the pines. No cleaning fee.

4.97 out of 5 average rating, 459 reviews

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

4.99 out of 5 average rating, 162 reviews

An interior view of the yurt showcases a spacious bed dressed in a light green blanket, positioned against a backdrop of wood lattice walls. A decorative rug lies beneath the bed, with a small nightstand beside it. A chair and potted plant add subtle decor to the space.

Yurt in Elkton

Creekside Forest Nature Retreat : Mongolian Yurt

4.88 out of 5 average rating, 135 reviews

The exterior features a welcoming porch with two rocking chairs positioned beside a small table. Colorful flowerbeds, with a variety of plants and flowers in bloom, enhance the entrance. The upper windows are adorned with green trim, complementing the home's classic design.

Guesthouse in Gap

Carriage House at Amish country

4.99 out of 5 average rating, 132 reviews

The Historic Walton House by RPG

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 194 reviews

A serene view captures the home nestled amidst green grass and trees. The pool glistens in the sunlight, surrounded by a spacious patio and seating area. Rolling farmland stretches across the horizon under a soft, cloudy sky.

Villa in Paradise

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

4.97 out of 5 average rating, 129 reviews

A two-story house is surrounded by lush greenery and colorful plants. The exterior features a mix of brick and siding, complemented by purple shutters. A set of stairs leads to the front door, while a shaded porch provides a welcoming entryway.

Home in Coatesville

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

4.86 out of 5 average rating, 118 reviews

An open and airy living space showcases a dining area with a wooden table surrounded by white chairs. Natural light pours through large windows, illuminating the polished wood floors. A sectional couch is positioned in the corner, while the kitchen and other areas are visible in the background.

Home in Coatesville

Peaceful Retreat Pool and great outdoor space

4.97 out of 5 average rating, 151 reviews

A private deck is presented with woven seating arrangements, including a unique hanging chair and a sofa. A round table is placed at the center, surrounded by natural greenery. The wooden flooring and patterned rug enhance the outdoor relaxation space.

Guesthouse in Elk Mills

Private Country Guesthouse Getaway Minutes from UD

4.94 out of 5 average rating, 127 reviews

A panoramic view showcases a clear swimming pool surrounded by a spacious deck. Lounge chairs and umbrellas are positioned along the poolside, with lush greenery and trees in the background. The inviting outdoor space provides a serene atmosphere for relaxation.

Home in Downingtown

Lakefront Guesthouse

4.99 out of 5 average rating, 151 reviews

The inground pool is framed by lounge chairs and shaded seating areas. A welcome sign is displayed near the pool, with a clear blue sky and greenery visible in the background, showcasing a serene outdoor space perfect for relaxation.

Villa in Leola

Beautiful split level home,with pool and hottub

4.98 out of 5 average rating, 119 reviews

The exterior of a single-story brick home is featured, showcasing a neatly paved driveway and a well-maintained front yard. Colorful flower beds surround the entrance, complemented by large potted plants on the porch. The inviting facade exudes a sense of warmth and welcoming.

Home in Kinzers

Country Land Guest House