
Holiday rentals in Chester
Find and book unique accommodation on Airbnb
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 £15 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
Top-rated holiday rentals in Chester
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

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

Scenic Farmhouse Escape in Media
Discover your hideaway behind an 1811 stone farmhouse, set on 2 scenic acres with trails, wildlife, and a garden paradise. A 2021 conversion turned this woodshop into a rustic studio with modern comforts—queen bed, full kitchen, 65" Roku TV, washer/dryer, and a private patio. Enjoy tranquility and nature, minutes from vibrant downtown Media and a short drive to Philadelphia. Ideal for a peaceful retreat or city exploration. Book your stay for a perfect blend of convenience and countryside charm!

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!

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

Cozy Cabin in Wayne
This special cabin is close to everything, making it easy to plan your visit. Lovingly updated to welcome our guests. This spacious 2 bedroom, one and 1/2 bath home is built at the base of an old rock quarry making your stay a very unique experience for the area. Two minutes to Eastern college, 5 minutes to downtown Wayne and King of Prussia. 10 minutes to Villanova and Valley Forge National Park. Lots of great shopping and restaurants and well as nature trails to enjoy.

The Farmer’s House
Historic FARM STAY. Est. In 1757 and hidden from view, it is certain to provide a private getaway! If you have the heart of a "homesteader" or simply want to have a peaceful holiday, this farmette will allow you to travel back in time for a relaxing experience you will not forget! A winding brook and pond are located within short walking distance from the home. Well furnished, this home will impress you with all her comfort and character!

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!

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!
Popular amenities for Chester holiday rentals
Other great holiday rentals in Chester

Charming townhouse in historic Wilmington

Historic Country Schoolhouse with kitchen

“Elegant stay near airport & stadiums.” APT 1

Cozy & Modern Rancher Style Home

Radiant 4-Bed Haven w/ King suite in N. Wilmington

Swarthmore Guesthouse · Walk to College & Train

Rosa 2Bed Apartment by CityLux - 10 mins Airport

Cozy 1br loft in Morton-Easy Acess2 Philly&Airport
When is the best time to visit Chester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £53 | £53 | £54 | £45 | £45 | £47 | £53 | £53 | £53 | £53 | £53 | £53 |
| 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.
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.
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 wifi, over 20 homes with a kitchen, over 20 homes with air conditioning, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Destinations to explore
- New York City Holiday rentals
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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
- 30th Street Station
- Temple University
- University of Delaware
- French Creek State Park
- Drexel University
- Marsh Creek State Park
- Valley Forge National Historical Park
- Independence Hall
- Greater Philadelphia Expo Center & Fairgrounds
- Wissahickon Valley Park





