Vacation rentals in Chester

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Quick stats about vacation rentals in Chester

  • Total vacation rentals

    Explore 50 vacation rentals in Chester

  • Nightly prices starting at

    Chester vacation rentals start at €17 per night before taxes and fees

  • Verified guest reviews

    Over 710 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Chester vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chester rentals

  • 4.6 Average rating

    Chester stays receive an average rating of 4.6 out of 5 from guests

Top-rated vacation rentals in Chester

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
Home in Nether Providence Township
4.96 out of 5 average rating, 24 reviews

Tranquil Haven: Stylish Home Surrounded by Nature

Welcome to your suburban retreat, 15 minutes from Philadelphia International Airport and 10 minutes from Swarthmore College. This 650 sq ft home features a comfortable living area, one bedroom, and a well-equipped kitchen. Enjoy outdoor space in the front and backyard. Located in the Wallingford-Swarthmore school district, you'll also be minutes away from charming Media, with its shops and dining. 20 minutes from Philadelphia sports center (including Lincoln Financial Field), open for 2026 FIFA.

Top guest favorite
A modern living area features a plush blue sofa paired with a decorative cushion. Light wood flooring complements a wall-mounted flat screen TV and a sleek work desk with an office chair. A doorway leads to the entrance, and a large mirror adds depth to the space.
Apartment in Southwest Philadelphia
4.97 out of 5 average rating, 239 reviews

Nchanted-Luxury unit near Airport w Parking & Yard

Step into style in this cozy 1 bed/1bath 1st floor unit. 2 car driveway. Keypad entry into living room w/ sleeper sofa, work desk, chair & 50 in Samsung smart TV. Kitchen with granite counter is fully equipped w/ everything you need and a breakfast bar to sit and eat meals. Granite is carried onto the bathroom vanity w/ plenty counter & drawer space stocked w/ amenities. BR has queen bed, dresser, walk in closet, smart tv and electric fireplace. Sliding door leads to yard w/ grill and bistro set

Top guest favorite
A bright bedroom features a queen-size bed with plush bedding and decorative pillows. A wooden dresser with a mirror and two lamps are positioned alongside. Natural light filters through the window, highlighting a cozy armchair in the corner. Two doors lead to adjoining spaces.
Guest suite in Wilmington
4.99 out of 5 average rating, 298 reviews

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.

Guest favorite
Apartment in Prospect Park
4.9 out of 5 average rating, 238 reviews

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.

Top guest favorite
A bright sunroom is filled with natural light from large windows, offering views of greenery. It features comfortable seating with colorful cushions, a patterned area rug, and decorative artwork on the wall. A small lamp and a side table complete the inviting space.
Apartment in Swarthmore
4.89 out of 5 average rating, 329 reviews

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.

Guest favorite
The exterior of the Woodlyn single-family home is showcased with a neatly maintained garden featuring various shrubs and plants. Stone steps lead to the entrance, framed by green trees and a clear blue sky, providing a welcoming first impression.
Home in Woodlyn
4.91 out of 5 average rating, 44 reviews

Comfy, Cozy Home by Philly, Airport, I-95, + more!

This charming Woodlyn single will feel like home away from home. Conveniently located off of I-95, trips to Philadelphia, stadiums, or airport are quick & easy. The spacious home sleeps 4 comfortably w/ 2 bedrooms and 2 full bathrooms! Full kitchen, cozy living room, dining room, office, wifi, w/d, and treadmill included! Enjoy the outdoors on the balcony off the master bedroom and bring your furry friends too! NOTE: 5 ⭐️ reviews under previous account (attempting to recover) & elsewhere!

Guest favorite
A cozy living space features a small dining table with four chairs and a television mounted on a dresser. Natural light filters through two windows dressed with dark curtains, while a patterned area rug adds warmth to the wooden floor. A keyboard is positioned in a corner.
Loft in Wilmington
4.92 out of 5 average rating, 158 reviews

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

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, 362 reviews

The Cottage at Marsh Creek (with hot tub!)

Peaceful, renovated cottage with year-round hot tub less than a mile from Marsh Creek State Park and lake! 1 bedroom (with king size bed!), 1 bathroom The park has hiking, fishing & water sports. Close to great dining, breweries, coffee, & other activities, but far enough from town to feel relaxing & somewhat secluded. Dog friendly! You'll have access to the entire home, including the private patio with string lights & hot tub. Follow us on IG! @thecottageatmarshcreek

Top guest favorite
The living room is furnished with two patterned armchairs and a floral couch, creating a comfortable seating area. A ceiling fan is visible above, and natural light enters through a window. An open layout leads to the kitchen, featuring white cabinetry and modern appliances.
Home in Wilmington
4.98 out of 5 average rating, 121 reviews

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

Guest favorite
The cottage exterior features a blend of natural stone and siding, showcasing a green front door. Lush green grass surrounds the home, complemented by trees in the backdrop. A gravel path leads to the entrance, providing access to the peaceful surroundings.
Cottage in Glen Mills
4.91 out of 5 average rating, 126 reviews

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.

Top guest favorite
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, 496 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.

Superhost
A bright kitchen area features a wooden dining table surrounded by four metal chairs. Against the wall, a white stove and a black microwave are positioned, with a window allowing natural light. A few decorative elements and wall art enhance the space.
Apartment in Media
4.76 out of 5 average rating, 339 reviews

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!

Popular amenities for Chester vacation rentals

When is the best time to visit Chester?

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Frequently Asked Questions

  • What are the best places to stay in Chester?

    Consider staying near the waterfront or in residential neighborhoods for a quieter atmosphere. Areas around local parks or main streets often have convenient access to shops, dining, and community events.

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

    Kids often enjoy playgrounds at local parks, visits to interactive museums, and seasonal community festivities. Family-friendly restaurants and hands-on art workshops are also popular, especially during school holidays.

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

    Explore the waterfront parks, attend local arts events, and learn about Chester’s history at cultural sites. Community festivals, sports matches, and family-run restaurants are also frequently suggested experiences.

  • How is the weather in Chester?

    Chester has cold winters with temperatures around 26–41°F (-3–5°C) and warm, fairly humid summers near 70–88°F (21–31°C). Rain is distributed throughout the year, so carrying an umbrella or waterproof jacket is suggested.

  • When is the best time to visit Chester?

    Late spring through early fall is often recommended for a visit to Chester, with comfortable temperatures and outdoor community events. Autumn brings colorful foliage across parks and riverfront areas.

  • What are the best places to visit in Chester?

    Popular places include riverfront parks, public art installations, and museums with exhibits on local history and culture. The city’s main squares and gathering spaces are also known for their community activities.

  • What are some hiking trails in Chester?

    Some parks in Chester have walking and biking paths suitable for gentle hikes and nature exploration. Trails along the river or within larger green spaces invite visitors to experience local flora and scenic views.

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

    Families can explore parks with playgrounds, enjoy interactive exhibits at museums or visit community recreation centers. Seasonal festivals, sports events, and local libraries often have programming for children of different ages.

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

    Day trips often include exploring museums, gardens, or historic sites in nearby cities and towns, as well as coastal parks or scenic nature preserves around the region. Many visitors enjoy discovering local markets and seasonal festivals just outside Chester.

  • Are there any pet friendly accommodations available in Chester?

    Many accommodations in Chester welcome pets, especially in residential neighborhoods and near local parks. It’s often suggested to review listings for specific pet policies and nearby outdoor spaces for walks.

  • What are some local tips for visiting Chester?

    Travelers frequently enjoy attending local events or markets to connect with the Chester community. Consider exploring beyond main streets to discover parks and hidden art, and check schedules for cultural or sports activities.

  • What is Chester known for?

    Chester is known for its rich industrial history, ties to the early colonial era, and vibrant local arts and community traditions. The city has riverside parks, historic neighborhoods, and sports facilities that draw residents and visitors alike.

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

    Explore local parks along the river, discover murals and public art around downtown, or visit neighborhood community centers hosting events and workshops. Some travelers enjoy searching for unique eateries or historic sites that highlight Chester’s lesser-known stories.

  • What are the best foods to try in Chester?

    Local favorites include hoagies, cheesesteaks, and soft pretzels, reflecting regional Philadelphia-area flavors. Travelers often find soul food, family-run bakeries, and seafood dishes as part of the area’s culinary traditions.

  • What should I bring for a trip to Chester?

    Pack comfortable walking shoes for exploring parks and local sites, and bring a rain jacket, as weather can be unpredictable. In cooler months, layers and a warm coat are useful, especially from November through March.

  • What is the nightlife in Chester like?

    Chester’s nightlife features neighborhood bars, lively community venues, and occasional live music events. Some visitors enjoy sports venues or local restaurants with evening gatherings and entertainment.

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

    Chester hosts community parades, cultural celebrations, and seasonal fairs throughout the year. Juneteenth events, summer concerts, and neighborhood gatherings are frequently suggested for experiencing local culture.

  • Are there family friendly vacation rentals in Chester?

    Chester has a variety of family-friendly vacation rentals, including entire homes and apartments in residential neighborhoods. Many options provide kitchens, extra space, and amenities suited for families traveling with children.