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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, 18 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.

Guest favorite
A spacious studio unit features a wooden bunk bed and a full bed on the bottom with a twin bed on top. An open kitchen area is equipped with modern appliances, complemented by a dining table for four. Natural light enters through a window dressed with light curtains.
Apartment in Cobbs Creek
4.93 out of 5 average rating, 341 reviews

Mayor Sponsored and Inspired Block Fresh & Clean!

Our Mayor of Philadelphia once resided near the block and has sponsored this block to keep it nice and neat. Our family has been local to Philadelphia for 30 years and we have renovated the entire building to feel refreshing and spacious while still being affordable. We personally make sure all sheets and towels are washed and clean with sanitizing spray throughout the whole unit after every stay. Space is spotless and we expect nothing less. It is probably cleaner than your own house lol!

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, 309 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.

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
4.91 out of 5 average rating, 150 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

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 👍🏼

Guest favorite
Home in Nether Providence Township
4.83 out of 5 average rating, 6 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. Experience the convenience and comfort of this delightful Airbnb!

Top 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
4.93 out of 5 average rating, 102 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 favorite
A modern living room features a comfortable sectional sofa with decorative cushions. Two windows dressed in sheer curtains allow natural light to fill the space. A small round coffee table sits on a patterned area rug, next to a lamp providing soft illumination.
Apartment in Lansdowne
4.9 out of 5 average rating, 205 reviews

Town & Country III: Private Apt, Minutes from City

Get the best of both town and country during your next trip to Philadelphia. Stay in a well-appointed, modern private apartment in the carriage house of a beautiful brick colonial revival home (built 1890) in quiet Lansdowne, PA - minutes from the airport and downtown Philly. A short walk to regional rail (5 stops to Center City), Lansdowne's popular farmer's market, and local restaurants. Oh and free off-street parking (one spot)!

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, 297 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!

Top 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, 558 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 favorite
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.
Apartment in Wallingford
4.96 out of 5 average rating, 96 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 vacation 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 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 20 vacation rentals in Chester featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do apartment rentals in Chester have wifi?

    Absolutely! We offer over 10 apartment 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 House Rentals in Chester?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a kitchen, over 20 homes with air conditioning, over 10 homes with free parking, over 20 homes with wifi, 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 ﺩ.ﺇ73 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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