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 G$4,185 GYD per night before taxes and fees

  • Verified guest reviews

    Over 680 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Chester vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chester rentals

  • 4.5 Average rating

    Chester stays receive an average rating of 4.5 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
4.95 out of 5 average rating, 20 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, 237 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 seating area is presented with two comfortable chairs and a small table, illuminated by natural light from large windows. The space features a mounted television on the wall and a simple white bed with a light blanket, creating a relaxing ambiance.
Guesthouse in Media
4.99 out of 5 average rating, 89 reviews

Scenic Farmhouse Escape in Media

Discover your hideaway behind an 1811 stone farmhouse, set on 2 scenic acres with trails, wildlife, and a garden paradise. A 2021 conversion turned this woodshop into a rustic studio with modern comforts—queen bed, full kitchen, 65" Roku TV, washer/dryer, and a private patio. Enjoy tranquility and nature, minutes from vibrant downtown Media and a short drive to Philadelphia. Ideal for a peaceful retreat or city exploration. Book your stay for a perfect blend of convenience and countryside charm!

Superhost
The front entrance of the row home features a white door with a large stone archway above. A set of steps leads to the door, flanked by an iron railing. The brick facade is complemented by white window frames, conveying a traditional residential charm.
Home in Chester
4.69 out of 5 average rating, 115 reviews

The Butler Pride

This is and corner property fenced row home, very nice house okay block. Parking can be a challenge at times but otherwise the other amenities especially being so close to interstate 95 and the city of Philadelphia outweigh the parking issue. NOTICE: As per (COVID-19) safety, cleaning, and sanitizing requirements, This home has been thoroughly cleaned and sanitized by the owners clean up crew. Also for your convenience included are disinfectant spray and wipes. Close to PHL airport+stadiums.

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, 325 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
A bright living room is displayed, featuring a blue sectional sofa and a glass coffee table atop an area rug. Natural light enters through a large window, framed by light-colored curtains. A ceiling fan is positioned above, and a black armchair is located in the corner.
Apartment in Prospect Park
4.91 out of 5 average rating, 232 reviews

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.

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, 43 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, 154 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
An inviting porch area is highlighted with wooden rocking chairs, a rustic bench, and potted plants. Natural stone flooring leads to the entrance, surrounded by lush greenery from the trees that provide shade and a sense of tranquility.
Cabin in Wayne
4.99 out of 5 average rating, 103 reviews

Cozy Cabin in Wayne

This special cabin is close to everything, making it easy to plan your visit. Lovingly updated to welcome our guests. This spacious 2 bedroom, one and 1/2 bath home is built at the base of an old rock quarry making your stay a very unique experience for the area. Two minutes to Eastern college, 5 minutes to downtown Wayne and King of Prussia. 10 minutes to Villanova and Valley Forge National Park. Lots of great shopping and restaurants and well as nature trails to enjoy.

Top guest favorite
The entrance of a historic farmhouse is framed by lush foliage, revealing a stone façade adorned with wooden shutters and an American flag. A small rocking chair is positioned on the covered porch alongside potted plants and a wooden barrel, creating a welcoming outdoor space.
Farm stay in Coatesville
4.93 out of 5 average rating, 115 reviews

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!

Superhost
A spacious dining area is presented with a long wooden table set for eight, featuring blue placemats and white dishes. Lush green plants in large blue pots add a touch of nature. The background reveals a cozy living space with natural light from two windows.
Home in Brookhaven
4.89 out of 5 average rating, 9 reviews

The World Cup Cape Cod - 10 Min to Philly Stadium

Perfect for PHL airport travelers & FIFA World Cup fans! Quick, direct highway access to Lincoln Financial Field with dedicated free parking (4 parking spots). Conveniently located just: - 10 mins from PHL International Airport - 15 mins from PHILADELPHIA’s Lincoln Financial, Enjoy quality time at our cozy house, featuring 4 driveway parking spots & an overly spacious gated backyard. Book now for a memorable stay!

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
4.77 out of 5 average rating, 333 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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Avg. priceG$14,648 GYDG$14,648 GYDG$15,066 GYDG$12,555 GYDG$12,555 GYDG$12,974 GYDG$14,648 GYDG$14,648 GYDG$14,648 GYDG$14,648 GYDG$14,648 GYDG$14,648 GYD
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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Chester?

    Chester has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in apartment rentals in Chester?

    Experience the best of Chester with our apartment rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in Chester?

    Yes! Work meets play with ease at over 30 vacation rentals in Chester featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do apartment rentals in Chester have air conditioning?

    Absolutely! We offer over 10 apartment rentals with air conditioning in Chester. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Chester have a kitchen?

    Absolutely! We offer over 20 house rentals with a kitchen in Chester. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Chester have wifi?

    Absolutely! We offer over 20 house rentals with wifi in Chester. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Chester have free parking?

    Absolutely! We offer over 20 house rentals with free parking in Chester. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Chester?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with wifi, over 20 homes with a kitchen, over 20 homes with air conditioning, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

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