Family-friendly holiday rentals in Chester County

Beautiful Studio Guest Suite near Parkesburg

Cozy & Private, the suite has everything you'll need for a comfortable and relaxing stay. A fully equipped kitchen with a Keurig Coffee Maker. King Sized Bed, Living Area w a pullout couch to sleep 4 guests total, Spacious bathroom with a tub/shower combo, a large private backyard with a BBQ grill. Just a few minutes drive to grocery stores. Located less than an hours drive from Philadelphia. Within 40 min drive to Longwood Gardens, King of Prussia Mall, Amish Attractions, and Lancaster. NO TV.

Newly Renovated Chester Springs Guesthouse

The newly renovated one bedroom apartment (that can accommodate up to 5 guests) above the detached garage at Artisan Studios provides a lovely guesthouse retreat. Nestled in the woods in beautiful Chester County, you'll enjoy privacy and seclusion even though you're just a 5 minute drive to anything you could need. We're just 8 miles from the PA Turnpike and only 38 miles (45 minutes to an hour) from Philadelphia. Feel free to bring your pet, as long as they are house broken or litter trained.

A 650 SF Condo| Walking distance to Amtrak station

If you are looking for a quiet and convenient location in the Paoli area for a comfortable stay, welcome to East Central Ave. Close to shops, restaurants, walking trails, and the Paoli train station. This suite is a basement, but it has a private entrance, full bathroom and a patio. The kitchen has white cabinets with appliances, including a stove, an oven, a coffee maker, a toaster, kettle, and a refrigerator. Ideal for family of 5, 1 bedroom with a queen bed for 2 and 2 sofa cum beds for 3.

Historic J. Pyle House Main St Location Dogs 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 Peaceful Nook A-Frame + Sauna

The Peaceful Nook, built by Zook Cabins is the perfect place for a romantic getaway, or a peaceful time in nature. The A-frame is one of the best glamping experiences you will find! With heat and AC, a luxurious bed, kitchenette, hammock, rain shower, bath house, sauna, flat top griddle, fire pit (firewood included) chairs under the stars, and the unparalleled connection to nature - Robes also provided! What better way to spend a few nights to fully re-energize yourselves!

West Chester apartment located on horse facility

Our apartment in located in the heart of West Chester PA. Our place is close to restaurants and dining, nightlife, great views, and family-friendly activities. You’ll love Sunset Valley Farm because it is a Horse property with activities on the property (season permitting). Horse lessons, Kayak, creek, fishing, and near all of the local attractions (King of Prussia Mall, Gettysburg, Valley Forge, Brandywine river, Lancaster (Amish country) 40 mins away).

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.

The Farmer’s House

Historic FARM STAY. Est. In 1757 and hidden from view, it is certain to provide a private getaway! If you have the heart of a "homesteader" or simply want to have a peaceful holiday, this farmette will allow you to travel back in time for a relaxing experience you will not forget! A winding brook and pond are located within short walking distance from the home. Well furnished, this home will impress you with all her comfort and character!

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.

Broad Run Suite- West Bradford Township

The comfy suite is located on a private 4- acre wooded lot, with a stream, in scenic Chester County. The private suite, which is attached to the house, has its own entrance and all the comforts of home...close to West Chester and Downingtown, Longwood Gardens, historic sites, Brandywine River Museum, several nature preserves, SEPTA Regional Rail and Amtrak lines, and much more. Come relax in this beautiful, scenic location.

3 King Beds | Scenic Amish Flower Farm Retreat

Experience the best of both worlds: the peace of a working Amish flower farm with direct access to Philadelphia’s 2026 events. Perfect for groups or families attending the World Cup, the 250th Anniversary celebrations, or the MLB All-Star game, our home offers a rare 3-King-bed layout just 3 minutes from the Parkesburg Amtrak station. Avoid the city crowds and retreat to floral vistas and high-end comfort

Peaceful Retreat with pool and great outdoor space

Peaceful and spacious home on a 2 acre lot with a small above ground pool. Great outdoor space with fire pit and seating area. Located just minutes from beautiful Lancaster County. 15 to 30 minutes from most local attractions. Philadelphia is about an hour away. There is an Amish farm market nearby. Our place is great for families with children, couples, business travelers and more.