
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.

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

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

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

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

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

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

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

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

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

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

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

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
Family-friendly home rentals with a hot tub

Modern Home in heart of Fish-town & private yard
FamilyKitchenWifi

The Cottage at Marsh Creek (with hot tub!)
Indoor spacesFamilyGrill

Unique Townhouse in Vibrant East Passyunk Square
Indoor spacesKitchenQuiet

Radiant 4-Bed Haven w/ King suite in N. Wilmington
Indoor spacesKitchenHospitality

Private Backyard Oasis w/ Hot Tub 30 mins 2 Philly
FamilyKitchenParks

Cozy 2BR Guesthouse/Hot Tub - Near Philly
FamilyIndoor spacesBackyard

🚙 Private Garage 🏙 Center City Roofdeck w 🔥Hot Tub
KitchenFamilyLocation

Eclectic Escape Near Longwood Gardens & Mt. Cuba
KitchenFamilyPets
Family- and pet-friendly home rentals

Vintage Farmhouse Haven-Private Guesthouse
FamilyKitchenSleep quality

Tranquil Hilltop Retreat
FamilyIndoor spacesGrill

Melrose Place 3BD Oasis
FamilyKitchenHospitality

"The Stay Over" your Home away from Home
KitchenIndoor spacesBackyard

“The Flat” cozy, comfortable, private 1BDR
KitchenFamilyOutdoor spaces

Charming cottage under the pines. No cleaning fee.
Indoor spacesFamilyLaundry

King size bed condo all cherry wood cabinets/floor
FamilyKitchenHeating

Immaculate 1 BR w/ Roof Deck|Old City|Premium View
KitchenIndoor spacesSleep quality
Family-friendly home rentals with a pool

Boutique King 2BR Retreat in Historic Old City
Indoor spacesFamilyBackyard

Carriage House with Pool in Lower Merion Township
FamilyKitchenSleep quality

Carriage House in Landenberg
KitchenIndoor spacesParks

Private Country Guesthouse Getaway Minutes from UD
FamilyKitchenOutdoor spaces

Your own peaceful, natural retreat!
FamilyKitchenBackyard

Lakefront Guesthouse
KitchenFamilyParks

Newly Renovated Chester Springs Guesthouse
FamilyIndoor spacesOutdoor spaces

Creekside Private Lower Level Apartment
KitchenFamilyValue
Destinations to explore
- New York Vacation rentals
- Philadelphia Vacation rentals
- Washington Vacation rentals
- Boston Vacation rentals
- Ocean City Vacation rentals
- Pittsburgh Vacation rentals
- Virginia Beach Vacation rentals
- Niagara Falls Vacation rentals
- Jersey City Vacation rentals
- Baltimore Vacation rentals
- Newark Vacation rentals
- Richmond Vacation rentals
- Sesame Place
- Pennsylvania Convention Center
- Longwood Gardens
- Wells Fargo Center
- Citizens Bank Park
- University of Pennsylvania
- Fairmount Park
- Philadelphia Museum of Art
- Dutch Wonderland
- Temple University
- Bear Creek Ski and Recreation Area
- University of Delaware
- Drexel University
- Amish Village
- Dover Motor Speedway
- Diggerland
- French Creek State Park
- Philadelphia Zoo
- 30th Street Station
- Marsh Creek State Park
- Greater Philadelphia Expo Center & Fairgrounds
- Independence Hall
- Wissahickon Valley Park
- Valley Forge National Historical Park





