Holiday rentals in Chester

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Top-rated holiday rentals in Chester

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

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Top guest favourite
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.

Top guest favourite
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.
Guest house in Media
4.99 out of 5 average rating, 74 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
4.68 out of 5 average rating, 111 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 favourite
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.
Flat 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 favourite
A cozy sleeping area features a spacious bed adorned with dark bedding and accented by decorative pillows. A comfortable armchair is positioned nearby, and a small bedside table holds a lamp. A framed artwork and plants enhance the serene ambiance of the room.
Guest suite in Folcroft
5 out of 5 average rating, 47 reviews

Creekside Private Lower Level Apartment

Enjoy this nonsmoking, newly renovated full kitchen and bathroom with quartz countertops. Adjustable tempurpedic bed w lumbar, vibration, under bed lighting, and Ritz Carlton pillows and Hotel Collection bedding will put you in the clouds. Near Boeing, airport (10min) and train station 10 min walk. This is a great quiet place to work from. Apartment is private with a nice (motion detected) lighted brick and concrete path to entrance w patio around back. No stairs. Must be a non smoker!

Top guest favourite
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.
Flat 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.

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.
Flat 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.

Top guest favourite
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 favourite
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
4.93 out of 5 average rating, 105 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.

Guest favourite
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.
Flat in Media
4.78 out of 5 average rating, 299 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 favourite
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, 562 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!

Top guest favourite
An outdoor patio area is arranged with comfortable seating, including a sectional sofa and coffee table, surrounded by greenery. Soft lighting is provided by decorative string lights overhead, creating an inviting ambiance. A spiral staircase leads to an upper level, enhancing the outdoor space.
Flat in Wallingford
4.96 out of 5 average rating, 98 reviews

Private Suite with Hot tub

Escape to our private guest suite nestled in a quiet residential neighborhood in Delaware County, Pennsylvania. Just one mile from the town of Media and Swarthmore College. Conveniently located close to route 476 and just a 20 minutes drive from Philadelphia and all the major sporting events. Our recently renovated in-law suite offers comfort and convenience for short and medium-term stays.

Popular amenities for Chester holiday rentals

When is the best time to visit Chester?

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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 holiday rentals in Chester

  • Total holiday rentals

    Explore 40 holiday rentals in Chester

  • Nightly prices starting at

    Chester holiday rentals start at £15 per night before taxes and fees

  • Verified guest reviews

    Over 560 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 of Chester holiday rentals include wifi 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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