Holiday rentals in Chester

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Top-rated holiday rentals in Chester

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Top guest favourite
A spacious studio bedroom is illuminated by natural light from the skylight and large arched window. The area features a Queen bed dressed in soft linens, a cozy seating arrangement with light-colored armchairs, and warm wooden furnishings, creating a harmonious atmosphere.
Cottage in Downingtown
4.97 out of 5 average rating, 227 reviews

The Cottage at Hoffman Barn

The Cottage at Hoffman Barn is a freestanding modern studio cottage located on what was once a dairy farm. The cottage is filled with eclectic art and modern appliances. Outside, your private deck is surrounded by mature specimen trees, birds and nature! You will love the charming waterfall patio and freedom to walk most of the four acre property including visits to goats and chickens at the stable. Most amenities needed for a lovely private getaway or a productive business trip are included.

Top guest favourite
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.
Guest house in Chester Springs
4.96 out of 5 average rating, 278 reviews

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.

Top guest favourite
A charming outdoor dining area features a table covered with a floral tablecloth, surrounded by metal chairs. A bottle and glasses sit atop the table. Views of horse fields and a historic barn are visible, framed by wooden railings and greenery.
Guest suite in Spring City
5 out of 5 average rating, 224 reviews

Country getaway on a horse farm, Bryn Taran Farm

Country farm, but quick drive to major historical and entertainment sites and events. Private, secluded accommodation adjacent to 275 yr old farmhouse. Includes an expansive porch with seating, a table for outdoor dining overlooking a garden, horse fields and historic barn. You have a private entrance to your own elegant living space with all modern amenities, including full-size kitchen appliances, an ample dining area with a view outdoors and a spacious bedroom with en-suite bathroom/shower.

Top guest favourite
A cozy living area is highlighted by warm wooden flooring, featuring a comfortable brown sofa adorned with decorative pillows. A round wooden table rests on a striped rug, while a soft daybed offers additional seating. Natural light filters through large windows, enhancing the inviting space.
Place to stay in Royersford
4.93 out of 5 average rating, 275 reviews

Sweet City Retreat

Your own private super sized 2 bedroom 2 story loft in a unique converted historic building in the center of town! Your home away from home with everything you need to be extremely cozy! A taste of the old with the new offering quality, style, and comfort, in a great location! Free private parking for up to 3 cars right in front of your loft. 3 PM CHECK IN/11 AM CHECK OUT (More details in "other things to note") GPS the Wawa in Royersford, PA 19468 for an approximate location.

Top guest favourite
A bright and airy living area features a brown leather couch and a wooden coffee table on a patterned rug. Natural light filters through sheer curtains by a cozy reading chair. The open-plan space includes a kitchen visible in the background, highlighted by modern fixtures.
Cottage in Downingtown
4.98 out of 5 average rating, 305 reviews

The Cottage at Marsh Creek (with hot tub!)

Cottage less than a mile from Marsh Creek State Park! Relax in the YEAR ROUND HOT TUB, enjoy the 50" Smart TV, & sleep in the comfy gel memory foam king size bed! The house comes with two inflatable SUP board. Dog friendly! Peaceful surroundings. The park has tons of trails for hiking, as well as fishing & water sports. You'll have access to the entire home, including the private patio & hot tub. 15 minutes to great coffee & dining. Follow us on IG! @thecottageatmarshcreek

Guest favourite
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.
Flat in West Chester
4.84 out of 5 average rating, 356 reviews

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).

Top guest favourite
A quaint cottage is surrounded by green foliage and vibrant flower beds. The exterior features white siding and large windows, allowing natural light to fill the interior. A small patio area is visible, suitable for outdoor seating.
Cottage in Chester Springs
4.97 out of 5 average rating, 241 reviews

Charming cottage under the pines. No cleaning fee.

Relax in our tiny cottage overlooking the fields of Chester County. View the beautiful St. Matthews church from your bedroom window. Livingroom has comfortable pull down couch. Kitchen and bathroom are newly renovated. Enjoy the peaceful enclosed back porch to wind down after a day of hiking or horseback riding on local trails and parks, boating at nearby Marsh Creek or spending the day in the quaint nearby towns and/or historic Philadelphia.

Top guest favourite
An a-frame home is showcased, featuring a spacious deck with modern outdoor seating arrangements. A fire pit sits on a stone patio, surrounded by greenery. Large windows reflect the surrounding trees, inviting natural light into the living space. A barbecue grill is positioned nearby.
Chalet in Birdsboro
4.96 out of 5 average rating, 241 reviews

Luxury Chalet with Mountain Views & Hot Tub

Escape to this luxurious A-frame chalet nestled in Birdsboro, Pennsylvania, providing breathtaking mountain vistas. Delight in the warmth of the cozy fireplace, unwind in the hot tub, and utilize the outdoor kitchen for culinary adventures. This chalet is ideal for relaxation and rejuvenation, with convenient access to nearby trails for hiking, opportunities for fishing, and the chance to go canoeing. It's a genuine retreat from the everyday.

Top guest favourite
A rustic stone building with a wooden deck extends over a serene waterway, surrounded by lush greenery. A bench is positioned nearby, inviting relaxation. The structure showcases a blend of natural materials, with a charming entrance that opens to the inviting outdoor space.
Home in Collegeville
5 out of 5 average rating, 116 reviews

The Cottage at the Mill

Welcome to the Cottage at the Mill – we are so thrilled you are here. Let us host you in our one of a kind Pennsylvania home, where you will find yourself immersed in nature and luxury. Our 1800’s Grist Mill is situated on 7 acres, just minutes from Valley Forge Park, the King of Prussia Mall, and the Main Line. The Cottage at the Mill offers a quintessential Montgomery County experience from its architecture to its picturesque surroundings.

Top guest favourite
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, 462 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.

Top guest favourite
Home in Chester Springs
4.94 out of 5 average rating, 102 reviews

Experience the charm of a historical getaway

Take it easy at this unique and tranquil getaway. Step back into time in this historic 1735 house transformed into a beautiful retreat by Jeff & Janelle, as seen on the Magnolia Network. The Inn can accommodate up to 9 people in 4 comfortable bedrooms. So, grab your friends and family and escape into a one-of-a-kind stone home, right in the heart of Pennsylvania.

Top guest favourite
A charming cottage is nestled among lush greenery, with a large window inviting natural light. The exterior features a sloping roof and a stone wall, accentuating the surrounding landscape of rolling hills and fields.
Cottage in Coatesville
5 out of 5 average rating, 320 reviews

Charming cottage on 50 acre Chester County farm

Frog Hollow Cottage is a newly renovated getaway located in the heart of the Chester County’s rolling farmland and equestrian community. Overlooking beautiful pastures, the cottage was formerly the large painting studio of Delaware Valley artist Peter Sculthorpe. The studio has been re-imagined as a peaceful retreat for families, friends and couples.

Popular amenities for Chester holiday rentals

Frequently Asked Questions

  • What are the best places to stay in Chester Springs?

    Many visitors choose accommodations in restored farmhouses, countryside homes, or rentals close to nature preserves for a peaceful stay. Booking within residential neighborhoods is also popular for a local experience.

  • What are the best things to do in Chester Springs with kids?

    Chester Springs has nature preserves for easy walks, family-friendly art spaces, and pick-your-own farms during harvest seasons. Outdoor play areas and interactive museums nearby add to the variety for children.

  • What are some of the best things to do in Chester Springs?

    Explore historic buildings, walk scenic nature preserves, and visit local art centers around Chester Springs. Many guests also enjoy seasonal markets and regional wineries nestled in the countryside.

  • How is the weather in Chester Springs?

    Chester Springs has cold winters around 23–43°F (-5–6°C), and warm summers near 64–84°F (18–29°C) with moderate rainfall throughout the year. Spring and autumn bring comfortable temperatures and colorful scenery.

  • When is the best time to visit Chester Springs?

    Late spring through early fall is often recommended, when temperatures typically range from 50–84°F (10–29°C) and local landscapes are at their greenest. Autumn brings changing leaves and regional harvest events around the area.

  • What are the best places to visit in Chester Springs?

    Art galleries, nature preserves, and historic sites shaped by Pennsylvania’s early history are often recommended for visitors in Chester Springs. Local markets and scenic gardens also draw guests throughout the year.

  • What are some hiking trails in Chester Springs?

    Chester Springs has a variety of wooded trails in nature preserves, as well as gentle paths suitable for families and casual walkers. Trails often pass historic sites, creeks, and areas rich in local flora and fauna.

  • What are some family activities we can do in Chester Springs?

    Families frequently explore local parks, visit historic sites, or enjoy workshops at community art centers around Chester Springs. Seasonal events, such as farm tours and nature walks, provide learning experiences and fun for all ages.

  • What are some of the best day trip ideas from Chester Springs?

    Popular day trips from Chester Springs include visits to nearby botanical gardens, living history museums, and hiking in state parks around the region. Local farms and small towns also frequently attract guests interested in exploring Pennsylvania’s countryside.

  • Are there any pet friendly accommodations available in Chester Springs?

    Many accommodations in Chester Springs welcome pets, with some rentals featuring outdoor space for dogs or easy access to trails and parks. It is helpful to check each property’s specific pet policy before booking.

  • What are some local tips for visiting Chester Springs?

    Pack layers for changing weather and comfortable shoes for exploring trails or historic sites. Check out local farmers’ markets for fresh foods, and consider booking ahead if visiting during local arts events or fall foliage season.

  • What is Chester Springs known for?

    Chester Springs is known for its rural landscapes, historic architecture, and connections to Pennsylvania’s early colonial past. The area frequently draws visitors interested in art spaces and nature preserves.

  • What are the best hidden gems to explore in Chester Springs?

    Around Chester Springs, visitors often discover art galleries, preserved historic mills, and quiet nature trails less traveled by crowds. Seasonal wildflower meadows and locally owned farm markets are also frequently suggested.

  • What are the best foods to try in Chester Springs?

    Regional foods frequently suggested in Chester Springs include Pennsylvania Dutch pies, fresh produce from nearby farms, and locally made cheeses. Many area eateries incorporate seasonal ingredients into their menus.

  • What should I bring for a trip to Chester Springs?

    Pack weather-appropriate layers, rain gear, comfortable walking shoes, and sun protection. Bringing reusable water bottles and a camera can also enhance outings on local trails or visits to historic sites.

  • What is the nightlife in Chester Springs like?

    Chester Springs has a low-key nightlife scene with cozy pubs, wine bars, and occasional live music events at local venues. Many visitors choose to unwind in relaxed settings or gather at community cafes.

  • What are the most popular events or festivals in Chester Springs?

    Local art fairs, seasonal farmers’ markets, and community festivals—often held in late spring or autumn—are popular around Chester Springs. Music performances and heritage celebrations highlight the area’s creative and historic spirit.

  • Are there family friendly vacation rentals in Chester Springs?

    Chester Springs has a variety of family friendly vacation rentals, including houses with larger yards, kitchens, and multiple bedrooms. Many neighborhoods are surrounded by parks and outdoor activities for all ages.

  1. Airbnb
  2. United States
  3. Pennsylvania
  4. Chester County
  5. Chester