Family-friendly holiday rentals in Kennett Square

Apartment in Kennett Square

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.

4.82 out of 5 average rating, 160 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!♥️

Indoor spacesFamilyWalkability

4.96 out of 5 average rating, 175 reviews

Historic J. Pyle House Main St Local Host

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

FamilyIndoor spacesHospitality

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.

4.98 out of 5 average rating, 269 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

KitchenFamilyCheckout

Cottage in Lincoln University

4.97 out of 5 average rating, 160 reviews

Thunder Hill Retreat - Spacious/Deck/Hot tub

Welcome to Thunder Hill Retreat, the perfect getaway for the whole family seeking peace and tranquility. Nestled amidst a serene wooded area, it offers a picturesque setting atop a hill, offering breathtaking views of a nearby creek. Immerse yourself in nature and witness the beauty of abundant wildlife right from the comfort of the deck. Come and experience the tranquility and beauty of this hidden gem, where you can find solace, fun, and rejuvenation in the heart of nature.

Indoor spacesKitchenTV

Place to stay in West Chester

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.

4.99 out of 5 average rating, 278 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.

KitchenIndoor spacesLocation

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, 219 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.

Indoor spacesKitchenAccess

Apartment in Kennett Square

The entrance to the Loft is framed by vibrant greenery and colorful flower pots. A brick pathway leads to the door, flanked by two large planters filled with lush plants. The exterior displays a combination of red and cream siding, under a clear blue sky.

4.88 out of 5 average rating, 221 reviews

Luxury Loft in in Kennett Square

Historic carriage house Loft with 2 bedrooms (queen & double) and 1 full bath. Spacious living room with pull-out sofa, dining for 6, work desk, and well-equipped kitchen with full appliances and coffee. Smart TV, high-speed internet, combo washer/dryer, and 1 parking space. Two blocks from downtown Kennett Square shops, dining, and breweries. Near Longwood Gardens and Brandywine Valley attractions. Second-floor unit; stairs required.

Indoor spacesKitchenGetting around

A bright living room features floor-to-ceiling windows allowing natural light to fill the space. A plush sofa is accompanied by two armchairs, and a TV is mounted above a contemporary fireplace. A textured area rug adds warmth, creating a cozy gathering spot.

4.97 out of 5 average rating, 147 reviews

Spacious 3BR Historic Home | Walk Downtown+Parking

✨ The Walton House, built in 1846, is located in the National Historic District of Kennett Square, PA. We are walking distance to downtown Kennett Square and a short drive to local Brandywine Valley points of interest. ✨ The home has been lovingly maintained to reflect its mid 19th century beginnings, while providing a modern, comfortable place to rest while visiting our lovely town. We hope you enjoy the home as much as we do!

Indoor spacesKitchenNearby

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, 377 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*

FamilyKitchenQuiet

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, 479 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.

KitchenFamilyQuiet

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.

4.92 out of 5 average rating, 132 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

Indoor spacesKitchenQuiet

Guesthouse in Kennett Square

4.98 out of 5 average rating, 323 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.

KitchenFamilyQuiet

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

4.96 out of 5 average rating, 188 reviews

A living room features a stone fireplace as the focal point, flanked by large windows allowing natural light to fill the space. Two comfortable armchairs and a cozy sectional are arranged around a wooden coffee table, with a warm area rug underfoot.

Home in Honey Brook

The View

FamilyIndoor spacesWi-Fi

4.97 out of 5 average rating, 156 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 open for summer!

Indoor spacesKitchenCondition

4.99 out of 5 average rating, 234 reviews

Home in Gordonville

15 min to Sight & Sound-Hot Tub-EV-Plug-Firepit

FamilyIndoor spacesBackyard

4.91 out of 5 average rating, 116 reviews

The exterior of the lodge is surrounded by lush greenery, showcasing a spacious driveway leading to a two-car garage. Colorful blooming flowers are seen in the landscaped gardens, enhancing the tranquil ambiance. The lodge features a rustic design with a welcoming porch and a natural stone chimney.

Home in Oxford

Beautiful Large Home in Private Woods with Hot Tub

KitchenIndoor spacesAccuracy

4.98 out of 5 average rating, 243 reviews

An A-frame cabin is surrounded by lush greenery, featuring large glass windows that reflect the surrounding trees. A wooden deck extends from the cabin, complemented by a wooden fence that provides privacy. A gravel pathway leads to the entrance, enhancing the outdoor setting.

Cabin in Narvon

Hillside Haven |Hot Tub & Sauna

Indoor spacesKitchenHospitality

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.

4.97 out of 5 average rating, 196 reviews

Pyle Cottage, circa 1750

KitchenIndoor spacesComfort

4.98 out of 5 average rating, 243 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.

Indoor spacesKitchenPool

4.96 out of 5 average rating, 482 reviews

A well-maintained exterior view of the house features a porch with a hot tub and seating area. Lush green fields surround the property, with a mix of cloud and blue sky creating a serene atmosphere. The driveway leads gently up to the entrance.

Farm stay in Atglen

Refined Lavender Farm Escape with a Luxurious Spa

Indoor spacesFamilyValue

Family- and pet-friendly home rentals

4.89 out of 5 average rating, 154 reviews

A cozy living area features a bright orange sofa accompanied by a light wooden coffee table on a plush rug. A spiral staircase is situated in the corner, leading to the upper level, while a small dining table is set by a window, enhancing the space's functionality.

Apartment in West Grove

Cozy Nook on Prospect

Indoor spacesKitchenWalkability

Apartment in Chadds Ford Junction

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.

4.91 out of 5 average rating, 334 reviews

Spacious&Peaceful, Private, 3mi Longwood Garden

FamilyIndoor spacesAir conditioning

Apartment in West Chester

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.

4.84 out of 5 average rating, 409 reviews

West Chester apartment located on horse facility

Indoor spacesKitchenTV

4.92 out of 5 average rating, 195 reviews

A cozy fire pit area is surrounded by multiple outdoor chairs placed on gravel. Soft lighting from lanterns accentuates the natural setting, while a wooden cabin stands in the background, integrated into the surrounding trees.

Tiny home in Narvon

CountrySide Hut - Firepit- Cozy Loft - volleyball

FamilyIndoor spacesSleep quality

4.96 out of 5 average rating, 197 reviews

A cozy living area features two brown leather chairs with decorative pillows, positioned near a stone fireplace. A wooden staircase leads to an upper level, and a coffee table occupies the center of the space, resting on a patterned black and white rug.

Cabin in Oxford

Secluded Log Cabin Escape on Private Pond & Acres

FamilyKitchenAir conditioning

4.97 out of 5 average rating, 499 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

KitchenFamilyCondition

4.91 out of 5 average rating, 129 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

FamilyIndoor spacesParks

4.98 out of 5 average rating, 193 reviews

A welcoming living area features a large red sectional sofa, positioned around a circular area rug. A light-colored coffee table sits in the center. A television is mounted on the wall, and natural light fills the space through a large window, complemented by a side table and decorative elements.

Home in Wilmington

Cozy Cottage near it all in Wilmington

KitchenIndoor spacesWalkability

Family-friendly home rentals with a pool

Guest suite in West Chester

A functional kitchen is equipped with dark wood cabinets and granite countertops. Appliances include a stainless steel refrigerator, oven, and microwave. Natural light streams in through a door leading to the outside, and a small dining table is set against the patterned wall.

4.99 out of 5 average rating, 299 reviews

Your own peaceful, natural retreat!

KitchenFamilyLayout

4.92 out of 5 average rating, 187 reviews

A dining area is presented with a large wooden table surrounded by six light-colored chairs. Soft light fixtures hang overhead, and large windows are adorned with flowing drapes. A sideboard with decorative items complements the space, which is finished with warm wooden flooring.

Home in Glen Mills

Sweet home w/pool & woods at peaceful Glen Mills

KitchenFamilyPool

4.96 out of 5 average rating, 134 reviews

Home in Peach Bottom

Secluded home pool & waterfall - Amish community

Indoor spacesKitchenPool

4.84 out of 5 average rating, 135 reviews

Home in Coatesville

Peaceful Retreat with pool and great outdoor space

FamilyIndoor spacesAmenities

4.89 out of 5 average rating, 171 reviews

The large inground pool is surrounded by a spacious patio featuring lounge chairs and shaded areas. A gazebo offers seating, while a water slide provides an entertaining feature. Lush greenery and a treeline offer a serene backdrop.

Guest suite in Oxford

Cozy country pool getaway that's pet allowed!

FamilyIndoor spacesTV

Guesthouse in Chester Springs

A bedroom features a spacious bed with a light grey blanket, flanked by two nightstands with lamps providing soft lighting. A dresser with drawers and a woven basket are positioned nearby. A large mirror reflects the tranquil space, enhancing its openness.

4.96 out of 5 average rating, 304 reviews

Newly Renovated Chester Springs Guesthouse

Indoor spacesKitchenSolo travel

Villa in Leacock-Leola-Bareville

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.

4.99 out of 5 average rating, 191 reviews

Beautiful split level home,with pool and hottub

KitchenIndoor spacesView