Vacation rentals in Chester

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Top-rated vacation rentals in Chester

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Top guest favorite
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, 228 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 favorite
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.
Guesthouse in Chester Springs
4.96 out of 5 average rating, 279 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.

Guest favorite
An outdoor patio area is set with a round glass-topped table surrounded by four metal chairs. A tall umbrella provides shade, while a built-in stone fireplace is visible in the background. The ground is covered with leaves, hinting at a seasonal change.
Guest suite in Paoli
4.96 out of 5 average rating, 299 reviews

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.

Top guest favorite
A comfortable living area features a green sectional sofa adorned with eclectic throw pillows and blankets. Two lamps provide soft lighting, while a round coffee table sits at the center atop a patterned area rug. Plants add a touch of greenery to the space, creating a welcoming environment.
Home in Phoenixville
4.94 out of 5 average rating, 232 reviews

The Phoenixville bnb 15 min walk w/ driveway

Cute, convenient, quiet, sparkling clean bohochic single family home w/ a driveway for parking 2-3 vehicles. Walk 15 minutes downhill or .6 miles to downtown Phoenixville/Bridge Street and the Schuylkill RiverTrail. This small peaceful 2 bedroom has new finishes and is owner operated by an experienced superhost. 1st bedroom has a queen bed and the 2nd has a bunk bed. Come enjoy our porch & inviting backyard with firepit and beautiful lush gardens. Follow our insta @thephoenixvilleairbnb !

Top guest favorite
A charming cottage exterior is surrounded by lush greenery and well-maintained landscaping. The inviting front porch features two turquoise chairs and a small table, with a pathway leading to the entrance. Large windows offer views of nature and enhance the bright atmosphere.
Cottage in Downingtown
4.94 out of 5 average rating, 241 reviews

Silk Purse Cottage-a private, cozy retreat

Silk Purse Cottage (ca. 1920) is in scenic, historic Chester County, PA 6 miles from the PA turnpike. It is a completely renovated, private cottage on a 6 acre property. Perfect spot for a relaxing vacation. Visitors who are interested in gardening, history and outdoor activities will find many opportunities close by. Hike, fish, go boating or mountain biking one mile away at Marsh Creek State Park. Longwood Gardens, Winterthur, Lancaster and Philadelphia are all a short distance by car.

Top guest favorite
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.

Guest favorite
A spacious studio loft features large windows allowing natural light to filter in. A comfortable blue sofa and a small round table with chairs are arranged, while two pendant lamps provide soft lighting. The decor combines elements of texture and color.
Place to stay in Royersford
4.86 out of 5 average rating, 267 reviews

Sweet & Simple

Your own private super sized 1 bedroom studio loft in a unique converted historic building in the center of town! Your little 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 2 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.

Guest favorite
A charming three-story house features a welcoming front porch with white railings. Potted plants and vibrant seasonal flowers are arranged at the entry, while the exterior showcases light siding and multiple windows, contributing to the home's inviting appearance.
Home in Phoenixville
4.94 out of 5 average rating, 251 reviews

Historic House in the Heart of Town

Experience the vibrant heart of Phoenixville with this entire house. Nestled in a tranquil downtown neighborhood, you'll enjoy easy access to a plethora of unique shops, restaurants, markets, and parks just steps away. The property is situated on a peaceful, non-busy, one-way road with ample free street parking. Relax in the large, fully fenced-in private backyard or unwind on the cozy front porch. Equipped with modern amenities, this three-story house is your ideal Phoenixville getaway.

Top guest favorite
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, 309 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

Top guest favorite
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 favorite
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 favorite
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 vacation 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.

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