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, 20 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 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.
Flat in Southwest Philadelphia
4.97 out of 5 average rating, 219 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 favourite
A cozy bedroom features a spacious bed dressed in white linens, complemented by decorative pillows. Two lamps provide soft lighting on either side. A sleek television is mounted on the wall, and an electric fireplace adds warmth to the space. Large windows with curtains allow natural light.
Guest suite in Havertown
4.95 out of 5 average rating, 150 reviews

Claremont Cottage

Our one-bedroom suite is the perfect cozy getaway, whether you’re visiting Philadelphia or spending time in the surrounding area. We’re conveniently located near Media, Ardmore, Bryn Mawr, and many local colleges. While you’re here, cozy up to the electric fireplace, or enjoy time in the backyard or local neighborhood. We look forward to having you! Please note: Your "home away from home" is connected to our "home all the time," so please read the full space description before booking. Thanks!

Top guest favourite
Guest house in Media
4.95 out of 5 average rating, 553 reviews

Treetop Studio at Ridley Creek State Park

Enjoy the view of the treetops outside this secluded and bright studio while listening to limitless free music on the smart speaker. Unique touches include exposed beams, sliding barn door and European-style bathroom with large tiled shower. Enjoy original artwork hanging on the walls, a nod to Philadelphia's thriving art scene. Designed and decorated using a combination of American & European influences, the high quality finishes and accessories make this 280 square foot space feel like home.

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, 311 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 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 kitchen features light brown wooden cabinetry and stainless steel appliances, including a gas stove and dishwasher. A round dining table with stylish chairs is positioned near the counter. Granite countertops and a decorative backsplash enhance the space, with natural light highlighting the room.
Home in Prospect Park
4.84 out of 5 average rating, 130 reviews

CoZy Super Clean, Sanitized, Disinfected-PEACEFUL.

Beautiful, cozy, sunny room with a super comfy L-shaped sectional sofa. Super clean and spacious fully equipped Eat-in kitchen with dishwasher, stove, oven, microwave, regular and K-Cup coffee makers, Micro-wave, Toaster, Pots, Pans, Utensils, and Silverware all provided. The apartment includes (2) 43" Flat Screen TVs; streaming HULU-Live, Amazon Prime, Disney Plus.   Also, a little work desk area provided Free washer/dryer access and Free parking, (short-term lease available).

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, 157 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.

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, 206 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.
Flat in Media
4.77 out of 5 average rating, 301 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 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, 564 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, 151 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.

Popular amenities for Chester holiday rentals

When is the best time to visit Chester?

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Avg. price$77 SGD$82 SGD$71 SGD$77 SGD$77 SGD$80 SGD$90 SGD$90 SGD$90 SGD$71 SGD$77 SGD$71 SGD
Avg. temp1°C2°C6°C13°C18°C23°C26°C25°C21°C15°C9°C4°C

Frequently Asked Questions

  • Do house rentals in Chester have air conditioning?

    Absolutely! We offer over 20 house 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 House Rentals in Chester?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with air conditioning, over 20 homes with wifi, over 10 homes with free parking, over 10 homes with a kitchen, 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 $26 SGD 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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