Family-friendly vacation rentals in Chester

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Chester

  • Total vacation rentals

    Explore 10 vacation rentals in Chester

  • Nightly prices starting at

    Chester vacation rentals start at G$18,783 GYD per night before taxes and fees

  • Verified guest reviews

    Over 260 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    10 of Chester vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chester rentals

  • 4.7 Average rating

    Chester stays receive an average rating of 4.7 out of 5 from guests

Top-rated family-friendly rentals in Chester

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

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Guest favorite
A light-filled living area features a stylish blue couch adorned with patterned cushions. A modern dining table is situated nearby, surrounded by four wooden stools. Two windows provide natural light, highlighting the space's calm ambiance.
Condo in Media
4.9 out of 5 average rating, 137 reviews

Lovely 2-bedroom Condo with Free Parking

Kick back and relax in this calm, stylish newly renovated space. It is on the second floor in a two-story building, located in a bamboo forest. A shopping mall is around the corner. Riddle Village and Riddle Hospital are nearby. A 4 min drive to Elwyn or Wawa Septa Train Station, 18 min drive to Philadelphia International Airport, 25 min to UPenn. Easy access to Media downtown area with lots of restaurants. Hope you'll enjoy the wall pictures that I brought back from different national parks.

Indoor spacesFamilyAccuracy

Top guest favorite
A bright bedroom features a queen-size bed with plush bedding and decorative pillows. A wooden dresser with a mirror and two lamps are positioned alongside. Natural light filters through the window, highlighting a cozy armchair in the corner. Two doors lead to adjoining spaces.
Guest suite in Wilmington
4.99 out of 5 average rating, 300 reviews

Private Suite & sitting room in Brandywine Valley

Seeking a romantic getaway or respite from a long work day? You'll love relaxing "at home" in your private 1 BR suite. We are located in a tree lined quiet community. Convenient shopping & restaurants are within walking distance. Short & extended rentals for business travelers or those relocating. Minutes from historic Chadds Ford & the scenic Brandywine Valley, plan to tour our Wine & Ale Trail, hike our greenways or experience the many duPont Chateau's with their glorious gardens & grounds.

Indoor spacesFamilyAmenities

Guest favorite
Apartment in Prospect Park
4.9 out of 5 average rating, 240 reviews

Cozy 2BR Apt 2 mi from Airport (PHL) Free Parking

Feel at home in this beautifully renovated private first-floor apartment, ideally located in a quiet suburban neighborhood with easy access to local attractions, restaurants, shopping, & major roadways. This spacious 2BR/1BA apartment is equipped with everything you need for a relaxing stay. Enjoy a private entrance, fast Wi-Fi, contactless self check-in, Smart TVs in bedrooms & living room, & the comfort of an in-unit washer & dryer. The fully equipped kitchen makes it easy to prepare meals.

KitchenFamilyAccess

Top guest favorite
A bright sunroom is filled with natural light from large windows, offering views of greenery. It features comfortable seating with colorful cushions, a patterned area rug, and decorative artwork on the wall. A small lamp and a side table complete the inviting space.
Apartment in Swarthmore
4.89 out of 5 average rating, 331 reviews

Skylight second floor apartment

Second, 3rd floor apartment. Apartment includes a master bedroom with a full sized bed and a guest bedroom with 2 twin beds. Private bathroom. There is a dining area with refrigerator, sink,microwave,induction hot pate convection toaster oven, coffee maker, french press dining table,Alexa and LCD TV. The dining area does NOT have a STOVE. 3rd floor meditation room with skylights and sitting area with LCD. ALL APARTMENT AREA IS PRIVATE. Home backs up to woods and back garden. NO CLEANING FEES.

Indoor spacesFamilyAir conditioning

Top guest favorite
Apartment in Collingdale
4.94 out of 5 average rating, 113 reviews

FIFA WORLD CUP Private Luxury APT near PHL airport

Welcome to our newly renovated Airbnb! Experience the epitome of comfort and style in our 1-bedroom haven. Fall in love with the beautiful bathroom, boasting modern fixtures and an indulgent ambiance. The fully remodeled kitchen is a chef's dream, equipped with top-of-the-line appliances. With space for up to 3 guests, our Airbnb offers a perfect retreat for couples or small families. Immerse yourself in luxury and make unforgettable memories in this meticulously designed haven.

KitchenFamilyNearby

Top guest favorite
A bright living area designed for relaxation features a comfortable gray sofa and a cozy armchair, complemented by wooden flooring and exposed beams. Large windows bring in natural light, while decorative curtains add a touch of warmth. A dining table is positioned invitingly nearby.
Home in Wilmington
4.87 out of 5 average rating, 106 reviews

Dog Friendly Cottage with Fully Fenced in Yard

Welcome to The Cottages on Orchard, a charming 1BR/1BA cottage built in 1920 by author Victor Thaddeus. Nestled on a natural wooded lot, this bright & airy home is entirely fenced in, perfect for up to two guests with dogs. Conveniently located in whimsical Ardentown, Delaware, the cottage is just 2 minutes from I-95 South & 10 minutes from downtown Wilmington, offering easy access to local attractions. Enjoy the surrounding woods, hiking trails, creek, & more. READ HOUSE RULES

Indoor spacesFamilyBackyard

Top guest favorite
A cozy living space features a small dining table with four chairs and a television mounted on a dresser. Natural light filters through two windows dressed with dark curtains, while a patterned area rug adds warmth to the wooden floor. A keyboard is positioned in a corner.
Loft in Wilmington
4.92 out of 5 average rating, 163 reviews

Quiet Empty Nest - North Wilmington

Forget your worries in this spacious and serene space. Short drive to train lines for explorers. Bellevue State Park 1 mile away with biking and hiking 27 miles of trails. Rockwood Museum & Brandywine Valley attractions all a short drive. This is the second floor with steeper narrower steps. A private entrance. There are window air conditioners in living room and bedroom. TV is basic with no cable (30+)channels. We look forward to making your stay enjoyable and comfortable

Indoor spacesKitchenValue

Top guest favorite
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
4.92 out of 5 average rating, 183 reviews

Sweet home w/pool & woods at peaceful Glen Mills

IMPORTANT – PLEASE READ BEFORE BOOKING: This is a private home in a quiet residential neighborhood. Maximum occupancy is 8 people at all times. NO parties, events, or unauthorized gatherings. Violations may result in termination of the stay and a charge of up to $500, subject to Airbnb policies. Please read all House Rules before booking. Relax with your family in peaceful Glen Mills, near Ridley Creek State Park, Longwood Gardens, Philadelphia Airport and Wilmington.

FamilyKitchenQuiet

Top guest favorite
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
4.99 out of 5 average rating, 276 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.

FamilyKitchenQuiet

Top guest favorite
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
4.97 out of 5 average rating, 498 reviews

The Mineral House of West Chester

Unique home in the heart of West Chester, tastefully renovated with fantastic detail, walking distance to all the dining, bars, shops and parks the borough has to offer. This home will bring you back to WC again and again. Do not let the staircase frighten you, it was designed by the late great architect George A Matuszewski for this unique space. Come and enjoy this special property and all the charm West Chester has to offer.

KitchenIndoor spacesAccuracy

Superhost
A bright kitchen area features a wooden dining table surrounded by four metal chairs. Against the wall, a white stove and a black microwave are positioned, with a window allowing natural light. A few decorative elements and wall art enhance the space.
Apartment in Media
4.76 out of 5 average rating, 342 reviews

Media's Hidden Gem!

Welcome to Media's Hidden Gem! Nestled on a quiet block in everybody's hometown Media. Just a couple blocks from all that downtown has to offer. Enjoy some time away on the nice deck, and check out the completely renovated bathroom. You won't be dissapointed with this one. Perfect set up for the weekend away or the business traveler. We went above and beyond to make sure this is a space you can call home!

Indoor spacesKitchenParks

Top 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
4.97 out of 5 average rating, 613 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!

Indoor spacesFamilyBackyard

Popular amenities for Chester family-friendly rentals