
Holiday rentals in Chester
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Top-rated holiday rentals in Chester
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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. 20 minutes from Philadelphia sports center (including Lincoln Financial Field), open for 2026 FIFA.

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 recently remodeled guesthouse 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 & parking, and AC/heat with ceiling fans. Perfect for short or long stays in a prime location. Enjoy the whole house to yourself! No smoking, no parties, no pets.

The Butler Pride
This is and corner property fenced row home, very nice house okay block. Parking can be a challenge at times but otherwise the other amenities especially being so close to interstate 95 and the city of Philadelphia outweigh the parking issue. NOTICE: As per (COVID-19) safety, cleaning, and sanitizing requirements, This home has been thoroughly cleaned and sanitized by the owners clean up crew. Also for your convenience included are disinfectant spray and wipes. Close to PHL airport+stadiums.

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.

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.

Comfy, Cozy Home by Philly, Airport, I-95, + more!
This charming Woodlyn single will feel like home away from home. Conveniently located off of I-95, trips to Philadelphia, stadiums, or airport are quick & easy. The spacious home sleeps 4 comfortably w/ 2 bedrooms and 2 full bathrooms! Full kitchen, cozy living room, dining room, office, wifi, w/d, and treadmill included! Enjoy the outdoors on the balcony off the master bedroom and bring your furry friends too! NOTE: 5 ⭐️ reviews under previous account (attempting to recover) & elsewhere!

“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.

New NoLibs Cozy Studio
Location! Located in Northern Liberties and a few blocks from Fishtown, the restaurant options are endless. Walk down North 2nd Street or over to Frankford Ave for just about any cuisine you can think of. 5 Minute drive to Old City and 10 minute drive to Center City. Walk to your show at the Fillmore or a quick drive to The Met. Enjoy a spacious new construction studio with a cozy Queen Bed, full Kitchen, full Bath, Laundry Closet and private Balcony!

The Millhaus
This is the original "tiny house." Built in 1766, the Millhaus sits on a 32-acre historic site with the Knauer Mill, Horseshoe Trail, and French Creek. Take a short hike along the water's edge to Saint Peter’s Village for coffee & pastries, or dinner & drinks. Recharge with modern touches like onsite massage and private fitness amenities, available by appointment. Stay put and unwind—or venture out and explore the best of PA from this beautiful location!

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

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)!

The World Cup Cape Cod - 10 Min to Philly Stadium
Perfect for PHL airport travelers & FIFA World Cup fans! Quick, direct highway access to Lincoln Financial Field with dedicated free parking (4 parking spots). Conveniently located just: - 10 mins from PHL International Airport - 15 mins from PHILADELPHIA’s Lincoln Financial, Enjoy quality time at our cozy house, featuring 4 driveway parking spots & an overly spacious gated backyard. Book now for a memorable stay!
Popular amenities for Chester holiday rentals
Other great holiday rentals in Chester

Cozy 1br Loft in Morton-Easy Access 2Phily&Airport

Cozy & Modern Rancher Style Home

The Prestige Pitch House

Main Line Haven - Near City

Creekside Lower Level Apartment near PHL

Lemon St. Retreat

Immaculate 1 BR w/ Roof Deck|Old City|Premium View

Jacuzzi/Game Room/Close to Airport/Philly Stadiums
When is the best time to visit Chester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €60 | €60 | €62 | €52 | €52 | €53 | €60 | €60 | €60 | €60 | €60 | €60 |
| Avg. temp | 1°C | 2°C | 6°C | 13°C | 18°C | 23°C | 26°C | 25°C | 21°C | 15°C | 9°C | 4°C |
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 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 holiday rentals in Chester

Total holiday rentals
Explore 50 holiday rentals in Chester

Nightly prices starting at
Chester holiday rentals start at €17 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 & child-friendly amenities

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
40 of Chester holiday rentals include wifi 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
Destinations to explore
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- Lincoln Financial Field
- Sesame Place
- Pennsylvania Convention Center
- Longwood Gardens
- Citizens Bank Park
- Wells Fargo Center
- Fairmount Park
- University of Pennsylvania
- Philadelphia Museum of Art
- Dutch Wonderland
- Bear Creek Ski and Recreation Area
- Diggerland
- Philadelphia Zoo
- Dover Motor Speedway
- Temple University
- 30th Street Station
- French Creek State Park
- University of Delaware
- Marsh Creek State Park
- Drexel University
- Valley Forge National Historical Park
- Independence Hall
- Greater Philadelphia Expo Center & Fairgrounds
- Wissahickon Valley Park





