Holiday houses 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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Guest favourite
The bedroom features a spacious bed with a decorative blue and white bedding set. Nightstands with lamps sit on either side, and a large piece of wall art hangs above the bed. A cozy seating area includes a glass table and stylish decor. Natural light enters through a nearby window.
Home in Prospect Park
4.84 out of 5 average rating, 127 reviews

By PHL airport - A++Clean, Disinfected, Sanitized.

A 1 bedroom & 1 bath fully furnished apartment in a quiet suburban neighborhood, 10 minutes from the PHL airport - Free Parking - Super clean, disinfected and sanitized after each guest check-out. - High-Speed Wi-Fi with Netflix, Amazon & Hulu-Live. - Eat-in kitchen with electric stove & regular and K-cup coffee. - Washer and Dryer facility located in the Gym/Laundry room (Gym currently closed). I can add a guest Gym membership to local Gym (30 days or more). - Available for long-term stays.

Guest favourite
Cottage in Chadds Ford
4.88 out of 5 average rating, 194 reviews

Cozy Historic Spring House in Chadds Ford!

Welcome Friends!! This COZY, cute, historic, Spring House is minutes away from Terrain at Styers Wedding Venue. (If you are a bride, you'll want to get ready here!) It is minutes from World-Renowned Longwood Gardens, Chadds Ford Village, (the Conservancy now offers over 5 miles of hiking/walking trails) Minutes from Andrew Wyeth Home, Brandywine River Museum, Brandywine Battlefield, Wineries, 5-star restaurants, shopping, AND it sits on the same property as the #1 Antique Shop in Chester County.

Top Guest favourite
A stand-alone carriage house features a charming cedar shake exterior, framed by lush greenery and colorful pink azaleas. The structure includes multiple windows, allowing natural light to filter through. A well-kept lawn leads to the inviting front door.
Barn in Wayne
5 out of 5 average rating, 100 reviews

World Cup Star Carriage House:PhillyVillanovaWayne

Escape to this tucked away apartment in a Main Line carriage house. Located 5 min from Villanova University & downtown Wayne; 10 min from King of Prussia; short walk to Radnor Train Station gets you to Philadelphia in 30 min with access to NYC and D.C. With a private entrance, full kitchen, bath, and bedroom, we preserved the cedar shake exterior, wood beams & floors, & exposed the cupola. Perfect for university visits, Valley Forge National Park, or Philly access without staying in the city.

Top Guest favourite
A sunlit meditation room features gold-painted walls and a pitched ceiling. Indoor plants surround a red cloth table displaying decorative items, including a Buddha statue and crystals. A large window allows natural light to fill the space, enhancing the peaceful ambiance.
Apartment in Swarthmore
4.89 out of 5 average rating, 321 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
Apartment in Prospect Park
4.9 out of 5 average rating, 221 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
The exterior features a stone and brick facade with ornamental ironwork gates. A four-step entry leads to the front door, positioned beside a concrete walkway. A staircase is visible along the side, providing access to the rear of the property.
Home in Roxborough
4.95 out of 5 average rating, 320 reviews

Shurs Lane Cottage, EV Charging, Free Parking

Our newly renovated cottage in Philadelphia is in the exciting, hip neighborhood of Manayunk. Enjoy countless indoor and outdoor restaurants, walking along Main Street shops, biking, and hiking on local and nearby trails. Sit on the back patio and watch the happenings from above. Private parking is free and safe, including a NEMA 14-50 receptacle for your EV/plug-in hybrid. Please bring your own plug-in device. Commercial License #890 819 Rental License #893142

Top Guest favourite
Home in Lansdowne
4.89 out of 5 average rating, 155 reviews

Charming historical home near Philadelphia

This 3 story victorian home sits on a treelined street nestled between a Quaker school and picturesque stone church. The 3rd floor apartment is resident occupied and the 1st and 2nd floors consist of 2+ bedrooms, kitchen, dining room and LR solely for AirBNB guests. Cozy up with a good book, cook a meal in the well appointed kitchen, relax by the outdoor fire pit and find your zen in the garden. Wifi and 2 parking spaces. Welcome to the Honeysuckle Hideout.

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, 114 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

Guest favourite
The exterior of a cottage is framed by lush greenery, featuring a winding brick pathway leading to the entrance. A decorative lamppost stands beside the path, surrounded by well-maintained landscaping that enhances the property's inviting charm.
Cottage in Glen Mills
4.91 out of 5 average rating, 118 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.

Superhost
Apartment in Media
4.77 out of 5 average rating, 327 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 fire pit surrounded by several chairs is set among a carpet of autumn leaves. The area is enclosed by a wooden fence, with a hammock and a small structure visible in the background, creating a cozy gathering space in the woods.
Guest suite in Media
4.98 out of 5 average rating, 592 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 hot tub is illuminated with soft blue lights, situated under a wooden pergola adorned with string lights. The serene ambiance is created by the gentle glow, offering an inviting space for relaxation in the evening.
Apartment in Wallingford
4.95 out of 5 average rating, 118 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

  • 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.

  • 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 30 vacation rentals in Chester featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Where should I stay in Chester?

    Make yourself at home in Chester by choosing from our most frequently booked neighborhoods. We have over 130 vacation rentals in Brookhaven, over 130 vacation rentals in Upland, and over 350 vacation rentals in Woodlyn.

  • 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.

  • Do house rentals in Chester have a kitchen?

    Absolutely! We offer over 20 house rentals with a kitchen in Chester. Enjoy a tailored experience with all the comforts you desire.

  • 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.

  • Do house rentals in Chester have free parking?

    Absolutely! We offer over 20 house rentals with free parking in Chester. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Chester

  • Total holiday rentals

    Explore 50 holiday rentals in Chester

  • Nightly prices starting at

    Chester holiday rentals start at $33 NZD per night before taxes and fees

  • Verified guest reviews

    Over 680 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Chester holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chester rentals

  • 4.5 Average rating

    Chester stays receive an average rating of 4.5 out of 5 from guests

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