Vacation rentals in Chester

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Top-rated vacation rentals in Chester

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

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Top guest favorite
An open living area showcases vaulted ceilings with exposed wooden beams. A light gray sectional sofa is positioned near a coffee table, while a flat-screen TV is mounted on the wall opposite. Soft sunlight illuminates the space, enhancing the inviting atmosphere.
Home in Swarthmore
5 out of 5 average rating, 19 reviews

Swarthmore Guesthouse

Welcome to this stylish and comfortable 1BR, 1.5BA home in Swarthmore! Just a few blocks from the college, The Ville, and train, this newly remodeled gem sleeps 2 and blends charm with modern flair. Once a bike shop, it now boasts an open concept layout with exposed beams, full kitchen, 2 TVs, washer/dryer, private entrance, and AC/heat with ceiling fans. Light, bright, and airy—perfect for short or long stays in a prime location. Enjoy the whole house to yourself! No smoking,no parties,no pets.

Superhost
A cozy living area is highlighted by a brown sofa and a wooden bench. A wall-mounted TV is visible across from the seating, while artwork adorns the wall. Natural light enters through a doorway in the background, enhancing the welcoming atmosphere.
Apartment in East Parkside
4.92 out of 5 average rating, 53 reviews

Private & Cozy West Philly Apartment Free Parking

Welcome to your home away from home in the heart of West Philadelphia's vibrant Parkside neighborhood! Convenient and comfortable accommodations close to the city's top universities and hospitals! UPenn, CHOP, Jeff Located in the charming Parkside section of West Philadelphia, our Airbnb is just a stone's throw away from schools like U Penn, Drexel, St. Joes and more making it perfect for visiting students, parents, or anyone looking to explore the academic and cultural treasures of the area.

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, 310 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.

Top guest favorite
A modern living area features a light grey sofa with decorative pillows, positioned on polished hardwood flooring. A wooden coffee table sits beside a sleek television stand. The open space leads to a contemporary kitchen with two barstools visible in the background.
Apartment in Morton
5 out of 5 average rating, 122 reviews

Lovely 1-bedroom unit with parking on premises

Kick back and relax in this calm, very private, stylish space, in a safe and quiet neighborhood. The apartment is in mint condition and recently renovated. We are within walking distance (9 blocks) to the Media/Elwin SEPTA Regional Rail, which takes you to Center City Philadelphia. We are also only a one-mile walk to the beautiful Swarthmore College Campus. We are 2.5 miles from I-476, I-95, supermarkets, restaurants, and the Springfield Mall. The PHL airport is 15 minutes away.

Top guest favorite
A cozy living area features a brown sofa against a soft pink wall. Natural light enters through two large windows, illuminating a round wooden coffee table with books. A unique, curved chair and modern floor lamp complete the inviting space.
Apartment in Fishtown
4.95 out of 5 average rating, 59 reviews

Cozy, Walkable Studio in Fishtown

This cozy and stylish studio apartment located in Fishtown Urby offers the perfect blend of comfort and convenience. Rest and relax in your bedroom nook while enjoying a fully-equipped kitchen with updated appliances, cookware, and utensils and a living area with North Front St. facing double pane windows that is outfitted with a Sonos speaker and a smart TV. Walk to popular restaurants and bars in the area, or stay right at home with on-site restaurant and bar, Percy.

Guest favorite
The living room features a large sectional sofa and a centered ottoman. Natural light enters through two windows, complemented by sheer curtains. A modern television is mounted on the wall, and an abstract painting adds color. A potted plant and decorative items are present.
Apartment in Media
4.93 out of 5 average rating, 107 reviews

Lemon St. Retreat

A quaint 2 bedroom apartment located a stones throw from downtown Media (state street). The neighborhood is full of great restaurants, coffee shops, bars and parks. The house has a newly finished front & back deck, a newly finished kitchen and a bathroom with tub perfect for relaxing. Media is the perfect neighborhood for a weekend or week getaway! Train station a couple blocks away, 20 mins from Philly and Philly airport. If in need for longer stays message me 👍🏼

Superhost
A modern living area is featured, showcasing a blue velvet sofa adorned with decorative pillows. A light-colored coffee table sits in front of the sofa, complemented by a vibrant flower arrangement. A sleek television is positioned on a white media unit, with dining space visible in the background.
Apartment in Southwest Philadelphia
4.85 out of 5 average rating, 26 reviews

Apartment in Philly, Airport and Stadium Nearby

Welcome to your home away from home! this charming and cozy apartment is perfectly located 7 minutes from airport and 12 minutes to downtown Philly - ideal for both leisure and business travelers. The floor is fully furnished with a cozy bedroom, bathroom, and an additional full sofa bed. There is a 65’ tv so you can relax after a long day travel in city. We do not allow to smoking in the house. Easy access convenient self check in and washer/dryer in unit.

Superhost
A cozy living area features a modern orange sofa paired with a decorative rug in soft colors. A small round coffee table sits in front, while a dining table with yellow chairs is visible. Wall art and plants enhance the inviting space.
Guest suite in West Oak Lane
4.9 out of 5 average rating, 264 reviews

Private 1BR Suite • Dedicated Parking

This private 1-bedroom suite offers a quiet, comfortable stay for couples, solo travelers, and business guests. The entire space is yours, featuring a queen-size bed, walk-in shower, streaming TV, and high-speed Wi-Fi. The kitchenette has a fridge, microwave, and coffee maker for easy meals. A dedicated workspace makes remote work simple. Best of all, you’ll have your own private, dedicated parking spot just steps from the entrance for added convenience.

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
4.97 out of 5 average rating, 94 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

Top guest favorite
A modern studio space features a full size bed topped with dark blue pillows. A flat-screen TV is mounted on the wall opposite the bed. A small desk area is equipped with a computer and two seating options: a round stool and a wooden chair. A closet provides storage, while natural light filters through a window adorned with minimal blinds.
Apartment in Callowhill
5 out of 5 average rating, 82 reviews

Summer Studio | Center City + Convention Area

Centrally located, modern studio apartment that has everything you need for a cozy, clean and comfortable stay. Perfect for solo or couples coming for work or taking in Philadelphia’s many world class attractions and food offerings. The Convention Center, Reading Terminal Market and Chinatown are minutes away. Philly’s other notable attractions such as the Art Museum and Liberty Bell are less than a 20 minute walk away.

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
4.78 out of 5 average rating, 298 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!

Guest favorite
A forest path is surrounded by tall trees and dense greenery, with ferns lining the ground. The sunlight filters through the leaves, creating a serene atmosphere for hikers. The trail, partially obscured by foliage, invites exploration into the natural surroundings.
Guest suite in Media
4.98 out of 5 average rating, 561 reviews

The Welcoming Woods

Enjoy the quiet of the woods as you relax in your private space. The studio is minutes away from downtown Media where you can enjoy the shops & restaurants on State St or take a 20 minute ride into Philadelphia. Attractions include Tyler Arboretum, Ridley Creek State Park,Longwood Gardens,Linvilla Orchards & local wineries in Brandywine & Chadds Ford PA. The woods are waiting to welcome you!

Popular amenities for Chester vacation rentals

When is the best time to visit Chester?

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Avg. priceG$12,555 GYDG$13,392 GYDG$11,509 GYDG$12,555 GYDG$12,555 GYDG$12,973 GYDG$14,647 GYDG$14,647 GYDG$14,647 GYDG$11,509 GYDG$12,555 GYDG$11,509 GYD
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Frequently Asked Questions

  • 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.

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

    Experience the best of Chester with our house rentals, starting at about $20 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 20 vacation rentals in Chester featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • 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.

  • 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.

  • Do house rentals in Chester have a kitchen?

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

  • Do house rentals in Chester have free parking?

    Absolutely! We offer over 10 house rentals with free parking in Chester. Enjoy a tailored experience with all the comforts you desire.

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

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Chester

  • Total vacation rentals

    Explore 40 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 560 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 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

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