Vacation rentals in Chester

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Top-rated vacation rentals in Chester

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Guest favorite
A modern kitchen features sleek cabinetry and stainless steel appliances, with a kitchen island equipped with barstools. The inviting living area is adorned with a comfortable sofa, a coffee table, and a smart TV, illuminated by natural light from large windows.
Apartment in West Philadelphia
4.98 out of 5 average rating, 101 reviews

New Build Close to DT Philly w/Full KTCHN + LNDRY

🌟🏙️ Discover comfort and convenience in our fresh Philly Lux retreat 🏙️🌟 🌇🏦🌞Welcome to your stylish urban haven! This modern apartment offers the perfect mix of comfort and accessibility. Located near downtown, you're just minutes away from the city's best attractions 🎨, dining 🍕, and vibrant nightlife 🎶, all while enjoying a peaceful and cozy space to recharge 💤. Whether you're visiting for work or leisure, this is your ideal home base. Experience the best in modern city living! 🌟

Top guest favorite
Guesthouse in Chester Springs
4.96 out of 5 average rating, 284 reviews

Newly Renovated Chester Springs Guesthouse

The newly renovated one bedroom apartment (that can accommodate up to 5 guests) above the detached garage at Artisan Studios provides a lovely guesthouse retreat. Nestled in the woods in beautiful Chester County, you'll enjoy privacy and seclusion even though you're just a 5 minute drive to anything you could need. We're just 8 miles from the PA Turnpike and only 38 miles (45 minutes to an hour) from Philadelphia. Feel free to bring your pet, as long as they are house broken or litter trained.

Guest favorite
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.
Apartment in Prospect Park
4.9 out of 5 average rating, 216 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 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 Swarthmore
5 out of 5 average rating, 127 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 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, 133 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 favorite
A cozy living area is presented with a dark grey sectional sofa adorned with orange accent pillows. A colorful rug covers the hardwood floor, and a painting depicting a serene pathway hangs on the wall. Natural light enters through large windows, illuminating the inviting space.
Home in Lansdowne
4.89 out of 5 average rating, 150 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 favorite
A rustic stone building with a wooden deck extends over a serene waterway, surrounded by lush greenery. A bench is positioned nearby, inviting relaxation. The structure showcases a blend of natural materials, with a charming entrance that opens to the inviting outdoor space.
Home in Collegeville
5 out of 5 average rating, 123 reviews

The Cottage at the Mill

Welcome to the Cottage at the Mill – we are so thrilled you are here. Let us host you in our one of a kind Pennsylvania home, where you will find yourself immersed in nature and luxury. Our 1800’s Grist Mill is situated on 7 acres, just minutes from Valley Forge Park, the King of Prussia Mall, and the Main Line. The Cottage at the Mill offers a quintessential Montgomery County experience from its architecture to its picturesque surroundings.

Top guest favorite
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, 103 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 favorite
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.
Apartment in Media
4.77 out of 5 average rating, 375 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!

Top guest favorite
The exterior of a red carriage house showcases large, multiple-pane windows, allowing natural light to fill the space. The building is framed by greenery, including flowering plants and bushes, offering a serene garden setting that complements the architecture.
Guesthouse in Kennett Square
4.97 out of 5 average rating, 462 reviews

Longwood Gardens Carriage House

Two miles from Longwood Gardens and six from Winterthur and Brandywine River museums, the apartment is ideally located for exploring Brandywine Valley sites and historic Kennett Square. Situated in a garden with views of a wildflower meadow and horses, it offers a spacious bedroom and bath, cozy kitchen/living combo and washer/dryer. It is modern, super clean, comfortable, and private--an idyllic country escape.

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, 572 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, 105 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

  • 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 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 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 120 vacation rentals in Brookhaven, over 120 vacation rentals in Upland, and over 330 vacation rentals in Woodlyn.

  • 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.

  • 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 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.

  • 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 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 610 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    40 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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