Weekend Getaways - Vacation Rentals in Chester County
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Luxury Places to Stay in Chester County
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Top-Rated Vacation Rentals with a Pool in Chester County
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Pet-Friendly Vacation Rentals in Chester County
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Large Vacation Homes & Villas in Chester County
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Wheelchair Accessible Vacation Homes in Chester County
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Chester County Vacation Rentals and Airbnb Places to Stay Under $200
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Instantly Bookable Vacation Homes in Chester County
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About Chester County Vacation Rentals
With more than 343 Chester County vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Weekendgetaways and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Chester County.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Weekendgetaways Chester County, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Chester County. Places to stay near Chester County are 840.39 ft² on average, with prices averaging US $443 a night.
Weekendgetaways makes it easy and safe to find and compare vacation rentals in Chester County with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Top Rental Accommodation Types in Chester County
| Type | Count |
|---|---|
| Vacation Homes | 157 |
| Hotels | 88 |
| Holiday Apartments | 60 |
| Cottages | 17 |
| B&B | 5 |
| Cabin Rentals | 5 |
| Others | 4 |
| Villas | 3 |
| Ski Chalet Rentals | 2 |
Use these Quick Filters to Find a Vacation Rental in Chester County
★ Pro Tip: Weekendgetaways makes it easy to compare the best listings on Weekendgetaways homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Weekendgetaways homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Chester County.
Weather in Chester County
View the weather forecast for Chester County before booking your Chester County Vacation Rentals to confirm your best time to go.
Top Attractions Around Chester County, PA
Weekendgetaways offers a large selection of top attractions around Chester County. Research things to do on your vacation before you visit Chester County.
Other Places to Stay Near Chester County, PA
Complexes around Chester County, PA
Chester County Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Chester County?
There are a lot of options in Chester County. If you plan on staying in the Chester County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Chester County:
- Black Horse - FarmGuest House A Travelers Rest and a Vacationers Haven
- Homey Retreat in Historic Kennett Square!
- Historic Cottage in West Chester PA - Two miles from town.
- NEW! Spacious 3 br single/off steet parking, XBOX, Arcade, Ping Pong
- Historic Home on Gay Street.
- Extravagant Atglen Manor w/Private 60-Acre Land!
- Sanctuary in a 300+ year old restored mill in the countryside. Dog Friendly!
- Ushmila's Nest- private entrance, bedroom & bathroom
- Charming Carriage House in the Heart of Kennett
- Newly renovated in the heart of Kennett Square. 3 miles from Longwood Gardens
How many vacation rentals have private pools in Chester County?
There are 19 vacation rentals with private pools near Chester County. Top-rated homes that have access to a swimming pool include:
Which vacation homes in Chester County are best for families?
If you are looking for a family-friendly vacation home in Chester County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chester County:
How many vacation rentals are available in Chester County?
Currently, the total number of properties listed in 2026 is over 343 in the Chester County area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chester County.
