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
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, 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.

Guest favourite
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.
Flat in Prospect Park
4.9 out of 5 average rating, 211 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.

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, 116 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 favourite
A sunlit sunroom features large windows surrounded by vibrant greenery. A well-maintained lawn is visible with flowering shrubs in shades of pink, complemented by a wheelbarrow nearby. The brick exterior of the home provides a classic touch to the inviting outdoor space.
Flat in Wilmington
4.82 out of 5 average rating, 398 reviews

“McDaniels Corner” (Cozy Home in North Wilmington)

When you step into "McDaniel's Corner" you get a Quiet and Modern Feel in a 'Cozy' Early Twentieth Century brick home. This cozy home has our guests feeling comfortable and relaxed while providing modern day luxuries in this historic home. You can’t beat this central location close to Longwood gardens, Winterthur, the Nemours Estate and so much more. There are also tons of great restaurants, bars, supermarkets, coffee shops, Nemours Children’s Hospital and so much more to see and do.

Guest favourite
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, 146 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 favourite
An open-concept living space is illuminated by natural light from large windows. A dark futon is adorned with orange decorative pillows, complemented by a low coffee table. A lamp provides additional light, while patterned curtains frame the windows. A doorway leads to the entrance.
Flat in Media
4.91 out of 5 average rating, 153 reviews

Pennell Apartment- By Neumann Univ

Welcome to the apartment on Pennell! This apartment offers a modern, recently renovated peaceful and private setting right next to the woods! Large windows allow natural light to spill into the open-concept living space. Expect to see deer and other wildlife. Our place is 2 minutes from Barnaby' restaurant, 5 minutes from Linvilla Orchards & Neumann University & also 15 minutes from State Street in Media where you can enjoy food, drinks, shopping and or just strolling.

Top guest favourite
The front entrance of the home features a well-maintained pathway bordered by lush greenery and flowering plants. An elegant lamp post stands beside the path, illuminating the approach to the entrance where double doors and a decorative American flag are positioned.
Flat in Chadds Ford
4.99 out of 5 average rating, 229 reviews

Silo Suite

Welcome to our charming suite located in the heart of the historic Brandywine Valley. Nestled within the entrance of a beautifully converted 12,000 square foot barn home, this space offers a truly unique and memorable stay. Our special place is perfectly situated between the renowned Brandywine River Museum and the Chadds Ford Winery, and in just minutes, you can explore the enchanting beauty of Longwood Gardens or dive into the world of history at Winterthur.

Guest favourite
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.
Flat in Lansdowne
4.9 out of 5 average rating, 197 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)!

Guest favourite
A three-story building is presented, featuring a red roof and neutral-painted exterior. A landscaped yard is visible, complemented by a low fence and mature trees. Sidewalk and street access are provided in front, with clear blue skies framing the scene.
Flat in Media
4.76 out of 5 average rating, 363 reviews

Expanded & Updated Downtown Media Gem!

Recently renovated apartment in the heart of everybody's hometown, Media! We made it more cozy and welcoming than before but still so close to everything Downtown Media has to offer. This cozy apartment comes nicely equipped with everything needed for your stay. This one bedroom one bathroom 3rd floor walk up apartment will be your perfect getaway in Media. Come relax and enjoy all that this wonderful location has to offer you!

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, 553 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
A light-filled living room is visible, featuring a comfortable couch adorned with decorative pillows. A patterned rug lies beneath a coffee table and a small console table, providing a cozy atmosphere. A window allows natural light to brighten the space.
Guest suite in Nether Providence Township
4.93 out of 5 average rating, 142 reviews

Private Room near Swarthmore Widener & PHL Airport

Centrally-located private with own entrance, 1 bedroom, w/ living room and private bath suite. Conveniently located near Swarthmore College & Train Station(5 min) Widener University(5 min), Media (10 min), & the Philadelphia Airport (12 min). There is Private keyless entry for easy check-in. We live above the suite, and are available most times if you need anything.

Guest favourite
The open-concept kitchen and living area features modern appliances, a spacious countertop, and two high-backed stools. A large television is mounted on the wall, while warm lighting highlights the hardwood floors. A doorway leads to a separate room in the distance.
Flat in Wilmington
4.95 out of 5 average rating, 124 reviews

The Penthouse at Park Place- King bed-

Escape to a stylish retreat in the heart of Wilmington! This charming 3rd-floor penthouse (walk-up) loft blends modern comforts with historic character. Enjoy exposed brick, hardwood floors, and a cozy atmosphere, perfect for your next getaway. (You will need to provide government-issued photo ID to us and a $500 security deposit may be charged at the host's discretion)

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 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 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 air conditioning, over 10 homes with wifi, 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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