
Family-friendly holiday rentals in Chester
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Top-rated family-friendly rentals in Chester
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Private Guest Suite and Entrance
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.

Mayor Sponsored and Inspired Block Fresh & Clean!
Our Mayor of Philadelphia once resided near the block and has sponsored this block to keep it nice and neat. Our family has been local to Philadelphia for 30 years and we have renovated the entire building to feel refreshing and spacious while still being affordable. We personally make sure all sheets and towels are washed and clean with sanitizing spray throughout the whole unit after every stay. Space is spotless and we expect nothing less. It is probably cleaner than your own house lol!

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.

2BR Cozy Apt 1 mi from Airport (PHL) Free Parking
Newly Renovated, centrally located Multi-unit home in a suburban neighborhood. This 1st Floor unit is a 2BR/1BA apartment with a private entrance. Complete with all you need for a work trip, get away or longer stay. The unit features a full kitchen, living room with pull out couch. The Kitchen has full sized stainless steel appliances, dishes, cookware and small kitchen appliances. There is fast Wi-fi, Keyless entry/self check-in, Smart TV's in each room and an in unit Washer and Dryer.

CoZy Super Clean, Sanitized, Disinfected-PEACEFUL.
Beautiful, cozy, sunny room with a super comfy L-shaped sectional sofa. Super clean and spacious fully equipped Eat-in kitchen with dishwasher, stove, oven, microwave, regular and K-Cup coffee makers, Micro-wave, Toaster, Pots, Pans, Utensils, and Silverware all provided. The apartment includes (2) 43" Flat Screen TVs; streaming HULU-Live, Amazon Prime, Disney Plus. Also, a little work desk area provided Free washer/dryer access and Free parking, (short-term lease available).

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

Pennell Apartment- By Neumann Univ
Welcome to the apartment on Pennell! This apartment offers a modern, recently renovated peaceful and private setting right next to the woods! Large windows allow natural light to spill into the open-concept living space. Expect to see deer and other wildlife. Our place is 2 minutes from Barnaby' restaurant, 5 minutes from Linvilla Orchards & Neumann University & also 15 minutes from State Street in Media where you can enjoy food, drinks, shopping and or just strolling.

The Lighthouse
Centrally located in northern Delaware with easy on/off access to 95 and 495. Newer construction, built in 2018. One large bedroom with KING size bed, 1.5 bath, private entrance, living room and full eat in kitchen. Work station area. Twin size pull out in living room. Free WiFi and large smart TVs in living room and bedroom. Deck off of the kitchen and upstairs deck off of the bedroom. Laundry located in bedroom upstairs. NO CLEANING FEE

Tranquil Hilltop Retreat
Escape to a peaceful retreat in our newly remodeled two-bedroom guest cottage, situated atop a scenic hill in Glen Mills. With its light-filled interior and modern amenities, this 1,100 sq ft cottage provides the perfect respite from the hustle and bustle of nearby Media and West Chester. Wake up to the tranquil sounds of nature and enjoy your morning coffee on the cobblestone patio, where you can watch the deer graze in the yard.

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!

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!

Private Suite with Hot tub
Escape to our private guest suite nestled in a quiet residential neighborhood in Delaware County, Pennsylvania. Just one mile from the town of Media and Swarthmore College. Conveniently located close to route 476 and just a 20 minutes drive from Philadelphia and all the major sporting events. Our recently renovated in-law suite offers comfort and convenience for short and medium-term stays.
Popular amenities for Chester family-friendly rentals
Family-friendly home rentals with a hot tub

Sunset River Shack -amazing waterfront view

The Cottage at Marsh Creek (with hot tub!)

Unique Townhouse in Vibrant East Passyunk Square

Pyle Cottage, circa 1750

King’s place, hot tub. Pool is open for summer!

Eclectic Escape Near Longwood Gardens & Mt. Cuba

Mill Road Farmhouse: Restored with Beautiful Pool.

The Vintage Suite at Park House
Family- and pet-friendly home rentals

Cottage w/ Fireplace, King Bed & Fenced in Yard

Spacious Entire Home - Near Philly - Free Parking

Shurs Lane Cottage, EV Charging, Free Parking

Cozy home in west deptford

“The Flat” cozy, comfortable, private 1BDR

The Cottage at the Mill

King size bed condo all cherry wood cabinets/floor

The Mineral House of West Chester
Family-friendly home rentals with a pool

Boutique King 2BR Retreat in Historic Old City

Golfer's Dream | Luxury 1 Bed Apt

Peaceful Retreat with pool and great outdoor space

Private Country Guesthouse Getaway Minutes from UD

The Mint Cottage in Chesapeake City

Lakefront Guesthouse

Newly Renovated Chester Springs Guesthouse

Creekside Private Lower Level Apartment
Quick stats about holiday rentals that are family-friendly in Chester

Total holiday rentals
Explore 10 holiday rentals in Chester

Nightly prices starting at
Chester holiday rentals start at $85 AUD per night before taxes and fees

Verified guest reviews
Over 230 verified reviews to help you choose

Wi-Fi availability
10 of Chester holiday 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
Destinations to explore
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- Pennsylvania Convention Center
- Lincoln Financial Field
- Sesame Place
- Longwood Gardens
- Fairmount Park
- Citizens Bank Park
- Wells Fargo Center
- Philadelphia Museum of Art
- University of Pennsylvania
- Temple University
- Dutch Wonderland
- Bear Creek Ski and Recreation Area
- Diggerland
- Philadelphia Zoo
- 30th Street Station
- Marsh Creek State Park
- Valley Forge National Historical Park
- French Creek State Park
- Wissahickon Valley Park
- Independence Hall
- Eastern State Penitentiary
- The Franklin Institute
- Dover Motor Speedway
- Franklin Square





