
House holiday rentals in Chester
Find and book unique houses on Airbnb
Top-rated house rentals in Chester
Guests agree: these houses are highly rated for location, cleanliness and more.

Stylish 3-Bdrm Home Near Airport, Stadiums & City
Enjoy comfort, style, and convenience in this beautifully decorated 3-bedroom home in a quiet neighborhood. Just minutes from Phila Airport, I-95, sports stadiums, and public transportation, you’ll have quick access to all the city’s highlights. Explore local shops, dine nearby, or unwind in Sharon Hill Park. A short drive takes you to Center City for nightlife and museums, or to Delaware for tax-free shopping. Ideal for both business travelers and families seeking a peaceful, convenient stay.

Cozy 3B Townhouse Near Sport Complex & Casino
Easy check-in/check-out with an electronic keypad. Located in South Philadelphia, the area is convenient for family, couples, and friends to stay at. Within walking distance to Sport complex, parks, casino, and more! Accessible to public transportation. It is accessible to Philadelphia’s historic sites and attractions like Chinatown or Center City by car and/or public transportation. Free and private parking (one car) in a back yard+ free street parking. Super close to the Whitman Plaza.

702 Mid Atlantic
Single family home located off Interstate 295 convenient to Philadelphia (15 min) and Atlantic City ( 45 min). Professionally landscaped with blue stone patio, deck and water garden in fenced private yard. Located in lovely suburban community along the Delaware River across from the Philadelphia Airport in South Jersey. Spacious for a family of 8 or less with a full kitchen, family room, living room, dining area and sunroom. Must be 25 yrs to book , show ID and be present at check in.

Step away for shopping, dining, bar. Quite street.
Welcome to this cozy and newly renovated house! It's in a great location, the surroundings are quiet but are near a lively Mainline town. You'll find bars, restaurants, stores, SEPTA/Amtrack stations, and Suburban Square within walking distance. It's also near many colleges such as Haverford College, Bryn Mawr College, Villanova University, and more. It's near the center city of Philadelphia and the King of Prussia mall. The most important thing is the security around the neighborhood.

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).

Shurs Lane Cottage, EV Charging, Free Parking
Our newly renovated cottage in Philadelphia is in the exciting and hip walking 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 NEMA 14-50 receptacle for your EV/plug-in hybrid. Bring your own plug-in device, please. Commercial License #890 819 Rental License #893142

The Chill Pad Deluxe in Cherry Hill
Welcome to the Chill Pad Deluxe hosted by Brandon & Hannah, located in a charming neighborhood Cherry Hill, New Jersey. This stunning home offers a comfortable and convenient retreat for your stay in the area. As you step inside, you'll be greeted by a furnished interior designed with your comfort in mind. The spacious living area features plush seating and three inviting bedrooms, allowing you to relax and unwind after a long day of exploring or working in the city.

Drexel Hill Charm I 4bdr 2.5bath I Free Parking
Close to Drexelbrook wedding venue, Kings Mills venue, and Springfield Country club. Centrally located between Philadelphia International Airport, Swarthmore College, center city. No cleaning fee + No chore list The home is two stories + a renovated basement with 2.5 baths. The 3 bedrooms are located on 2nd level with 2 full baths. A renovated basement with 4th bd, movie room, office space, mini fridge, and half bath. 90% of previous guests give a 5-star rating.

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.

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.

Historic Home on Gay Street.
Welcome to historic downtown West Chester, PA. This freshly renovated historic home boasts 2 Queen bedrooms and 2 full baths, sleeping 6. Amenities and accommodation await behind the lavender door. This home is nestled on one of the most desirable blocks in the borough that boasts 260 years of history. Convenience, history, haven, and limitless adventures begin with your stay at 236 W Gay street. Take a look behind the lavender door.

The Mineral House of West Chester
Unique home in the heart of West Chester, tastefully renovated with fantastic detail, walking distance to all the dining, bars, shops and parks the borough has to offer. This home will bring you back to WC again and again. Do not let the staircase frighten you, it was designed by the late great architect George A Matuszewski for this unique space. Come and enjoy this special property and all the charm West Chester has to offer.
Popular amenities for house rentals in Chester
House rentals with a pool

Oasis

5 BDRM City Oasis - Indoor Pool

Modern Home in heart of Fish-town & private yard

Game Day Getaway for fans/ family. Great Location

Charming house in Glassboro

Waterfront Winter on the river 2025/26 available!

Comfort, Fun, & charming! - 5BR oasis w/ Pool

Lakefront Guesthouse
Weekly house rentals

Very cozy 3 bedroom house close to everything

Cozy Cape in Newtown Square Pets Welcome ⚡️Free EV⚡️

Quaint farmhouse

Main Line Haven - Near City

Swarthmore Guesthouse

The Butler Pride

The Cozy Corner in N. Wilmington w/ Queen Bed

Media Oasis: Voted Best Place & Train to Philly!
Private house rentals

Cozy Philly Cottage + Parking

The hookah spot

Melrose Place 3BD Oasis

Single level home, private yard, kid/pet friendly

Charming 4BR in Historic District

Huge Sun Soaked Apt In Quiet Neighborhood

Stylish Home | Near Philly | Fireplace | Parking

Cute, cozy and convenient 2BR w/ office
Quick stats about house rentals in Chester

Total holiday rentals
Explore 20 holiday rentals in Chester

Nightly prices starting at
Chester holiday rentals start at £15 per night before taxes and fees

Verified guest reviews
Over 250 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 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
Destinations to explore
- Plainview Holiday rentals
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- Pennsylvania Convention Center
- Lincoln Financial Field
- Citizens Bank Park
- Sesame Place
- Fortescue Beach
- Longwood Gardens
- Fairmount Park
- Penn's Landing
- Philadelphia Museum of Art
- 30th Street Station
- Diggerland
- French Creek State Park
- Wells Fargo Center
- Marsh Creek State Park
- Philadelphia Zoo
- The Franklin Institute
- Aronimink Golf Club
- Wissahickon Valley Park
- Valley Forge National Historical Park
- Crystal Beach Manor, Earleville, MD
- Independence Hall
- Renault Winery
- Franklin Square
- Eastern State Penitentiary