Best Vacation Homes in Chester County
House
10.0(56 Reviews)
9 Bedrooms
5 Baths
18 Guests
5000 ft²
Fireplace/Heating
Balcony/Terrace
Kitchen
Air Conditioner
US $1,682/Night
7 Nights - US $11,774
House
10.0(12 Reviews)
3 Bedrooms
2 Baths
10 Guests
3326.05 ft²
- Fireplace/Heating
- Balcony/Terrace
Parking- Air Conditioner
US $319/Night
7 Nights - US $2,236
Bed & Breakfast
9.8(57 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
Breakfast- Parking
US $232/Night
7 Nights - US $1,624
Cottage
10.0(345 Reviews)
4 Bedrooms
2 Baths
9 Guests
1400 ft²
Hot Tub- Fireplace/Heating
- Balcony/Terrace
Pet Friendly
US $390/Night
7 Nights - US $2,730
House
10.0(4 Reviews)
1 Bedroom
1 Bath
4 Guests
602.78 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
Internet
US $337/Night
7 Nights - US $2,356
House
10.0(183 Reviews)
2 Bedrooms
2 Baths
6 Guests
980 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $257/Night
7 Nights - US $1,801
Cottage
10.0(101 Reviews)
1 Bedroom
1 Bath
2 Guests
575 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $172/Night
7 Nights - US $1,206
House
10.0(56 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $257/Night
7 Nights - US $1,797
Chester County Luxury Rentals
House
6 Bedrooms
5 Baths
12 Guests
Child Friendly
US $6,555/Night
7 Nights - US $45,882
New
House
4 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Air Conditioner
- Child Friendly
Laundry
US $3,219/Night
7 Nights - US $22,533
House
3 Bedrooms
2 Baths
5 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Child Friendly
US $2,220/Night
7 Nights - US $15,540
House
10.0(9 Reviews)
7 Bedrooms
6 Baths
14 Guests
6400 ft²
Private Pool- Hot Tub
- Fireplace/Heating
Pool
US $2,201/Night
7 Nights - US $15,408
House
9.8(8 Reviews)
7 Bedrooms
5 Baths
16 Guests
4500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $2,142/Night
7 Nights - US $14,996
House
9.8(50 Reviews)
6 Bedrooms
5 Baths
19 Guests
6000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,713/Night
7 Nights - US $11,991
House
10.0(3 Reviews)
6 Bedrooms
4 Baths
14 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,543/Night
7 Nights - US $10,803
House
10.0(1 Review)
9 Bedrooms
5 Baths
18 Guests
5005.22 ft²
- Fireplace/Heating
- Parking
- Internet
- Child Friendly
US $1,224/Night
7 Nights - US $8,568
Chester County Pet Friendly Vacation Rentals
Cottage
10.0(46 Reviews)
1 Bedroom
1 Bath
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $302/Night
7 Nights - US $2,111
House
10.0(3 Reviews)
3 Bedrooms
3 Baths
7 Guests
2497.23 ft²
- Fireplace/Heating
View- Pet Friendly
- Parking
US $738/Night
7 Nights - US $5,166
Hotel
9.4(1003 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Breakfast
- Pet Friendly
US $132/Night
7 Nights - US $922
Cottage
10.0(30 Reviews)
2 Bedrooms
2 Baths
4 Guests
1250 ft²
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $329/Night
7 Nights - US $2,305
House
10.0(1 Review)
4 Bedrooms
3 Baths
8 Guests
2002.09 ft²
- Fireplace/Heating
- View
- Pet Friendly
- Parking
US $578/Night
7 Nights - US $4,048
New
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
850 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $216/Night
7 Nights - US $1,511
Cottage
9.8(231 Reviews)
1 Bedroom
1 Bath
3 Guests
800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $198/Night
7 Nights - US $1,387
House
9.8(35 Reviews)
1 Bedroom
1 Bath
2 Guests
1496 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $229/Night
7 Nights - US $1,600
Chester County Large Vacation Homes
House
10.0(42 Reviews)
5 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $339/Night
7 Nights - US $2,370
Bed & Breakfast
9.1(37 Reviews)
8 Bedrooms
9 Baths
16 Guests
343.1 ft²
- Fireplace/Heating
- Balcony/Terrace
- Parking
- Air Conditioner
US $209/Night
7 Nights - US $1,463
House
10.0(31 Reviews)
5 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $328/Night
7 Nights - US $2,299
House
1 Bedroom
3 Baths
10 Guests
2884.73 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $1,093/Night
7 Nights - US $7,651
House
10.0(28 Reviews)
5 Bedrooms
4 Baths
10 Guests
4500 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $772/Night
7 Nights - US $5,406
House
10.0(25 Reviews)
5 Bedrooms
3 Baths
11 Guests
3961 ft²
- Fireplace/Heating
Ocean View- Balcony/Terrace
- View
US $1,056/Night
7 Nights - US $7,390
Villa
10.0(17 Reviews)
3 Bedrooms
2 Baths
6 Guests
2200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $227/Night
7 Nights - US $1,589
House
10.0(15 Reviews)
4 Bedrooms
2 Baths
12 Guests
32292 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,097/Night
7 Nights - US $7,678
Why Choose Rent By Owner for your Chester County Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Chester County
When should you plan your Vacation Rentals stay?
Choosing the right time to vacation here can enhance your experience, as seasonal changes in this destination influence everything from outdoor activities to local events, helping you make the most of your stay in the region.
Peak Season Highlights
Late Spring to Early Summer (May to June)
During this time, you can enjoy warm weather and lush landscapes, making it ideal for outdoor activities and exploring the area's scenic beauty.
Average Temperature Daytime: 70-85°F - Nighttime: 50-65°F
Fall (September to October)
This season features vibrant foliage and comfortable temperatures, perfect for experiencing local events and the serene countryside.
Average Temperature Daytime: 65-75°F - Nighttime: 45-55°F
Off-Season Highlights
Winter (December to February)
The winter months bring cooler temperatures and quieter surroundings, making it an excellent choice for a peaceful getaway in the region.
Average Temperature Daytime: 30-45°F - Nighttime: 20-30°F
Early Spring (March to April)
At this time, the area begins to awaken with the promise of warmer days ahead, offering a tranquil atmosphere before peak season kicks in.
Average Temperature Daytime: 45-60°F - Nighttime: 30-40°F
Weekly Weather Forecast for Chester County
How to Book Your Chester County Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Chester County
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining with a private patio or barbecue grill area in your Chester County getaway.
- Relax by the pool to unwind after exploring the scenic countryside of the region.
- Take advantage of spacious yards perfect for outdoor activities and family gatherings.
- Explore picturesque walking trails or bike paths accessible from your outdoor space.
- Make use of garden spaces or landscaped grounds for a peaceful retreat in nature.
- Spend evenings around an outdoor fire pit, ideal for storytelling and making s'mores.
- Access waterfront views or nearby lakes that invite kayaking, fishing, or simply enjoying the scenery.
Top Attractions Around Chester County
What attractions are nearby?
Discover a variety of outdoor activities, cultural experiences, and scenic attractions just moments from your stay in Chester County, Pennsylvania, where you can immerse yourself in the region’s charming countryside and vibrant local events.
Family Activities
- Longwood Gardens: Explore the renowned botanical gardens, where families can enjoy stunning displays, seasonal outdoor activities, and educational programs in a beautiful setting.
- Chester County Historical Society: Discover local history through interactive exhibits and family-friendly tours that provide insight into the region's rich heritage.
- Strasburg Rail Road: Experience a scenic train ride on a historic steam locomotive, offering an engaging adventure for all ages in this charming area.
- Oaks Amusement Park: Spend a fun-filled day with classic rides, arcade games, and outdoor activities designed to entertain the whole family here in the region.
Adult Activities
- Cultural Tours and Historic Sites: Explore the rich history of this destination by visiting its renowned historic sites and engaging in cultural tours that reveal the area's unique heritage.
- Gourmet Dining and Culinary Events: Savor exceptional cuisine at the area's top restaurants or participate in culinary events to experience the region's vibrant food scene firsthand.
- Outdoor Recreation and Nature Walks: Discover the natural beauty through outdoor activities such as hiking, biking, or leisurely nature walks in scenic parks and preserved areas nearby.
Other Places to Stay in Chester County, PA
Downingtown
East Brandywine Township
Tredyffrin Township
Brandywine Valley
Easttown Township
Kennett Township
Kennett Square
Malvern
West Whiteland Township
Pottstown
Chester County Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Attractions: Take time to visit the area's renowned historical sites and scenic parks to truly appreciate the region's unique charm.
- Plan Your Dining Experience: Savor the local cuisine by exploring nearby farms, markets, and restaurants that showcase the region’s fresh and authentic flavors.
- Utilize Seasonal Activities: Make the most of the season by engaging in outdoor pursuits or cultural events that are popular here during your stay.
- Choose the Right Vacation Rentals: Opt for well-reviewed vacation rentals in convenient locations to enjoy a comfortable and authentic experience during your visit.
Transportation Options
- Chester County Transportation Services: You can rely on regional transit options that connect you to key destinations within the area, making it easy to explore local attractions during your stay.
- Philadelphia International Airport: This major airport is conveniently situated nearby, offering numerous domestic flights and ground transportation options for easy access to your vacation rentals in the region.
- Amtrak Rail Service: The train service provides a comfortable and efficient way to reach the area from major cities along the East Coast, enhancing your travel flexibility.
- Local Taxi and Rideshare Services: Taxis and rideshare providers are readily available here, providing convenient transportation options to and from your vacation rental property in Chester County.
Local Customs Options
- Philly Cheesesteak Tradition: You can enjoy the local culinary custom of savoring authentic Philly cheesesteaks, a beloved regional specialty that reflects the area's rich food heritage.
Chester County Vacation Rental Frequently Asked Questions
1. 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:
- Lakewood Retreat, come and enjoy .
- 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
- Extravagant Atglen Manor w/Private 60-Acre Land!
- Historic Home on Gay Street.
- 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
2. How many vacation rentals have private pools in Chester County?
There are 21 vacation rentals with private pools near Chester County. Top-rated RBO homes that have access to a swimming pool include:
3. 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:
4. How many Rentbyowner vacation rentals are available in Chester County?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 340 in the Chester County area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Chester County.
5. What is the cancellation policy for vacation rentals in Chester County, Pennsylvania?
Cancellation policies vary by property, so it is important to read the specific listing details or contact the owner directly to understand the terms and any applicable fees.
6. How do I find vacation rentals in Chester County that allow pets?
You can filter your search based on pet-friendly options available in the area, but be sure to review the individual listing’s pet policy or reach out to the owner for clarification.
7. Are there any minimum stay requirements for booking a vacation rental in this region?
Minimum stay requirements differ between properties, so it’s advisable to check the specific listing details or communicate directly with the owner before booking.
8. What amenities are typically included in vacation rentals here?
Amenities vary by property, but many rentals offer essentials like Wi-Fi, parking, and kitchen facilities. Review the listing description to see what’s included or contact the owner for more information.
9. How do I ensure my booking is secure and reliable in Chester County?
Booking through verified listings ensures a trustworthy process. Always read reviews, confirm the ownership details, and communicate directly with hosts when necessary to guarantee a smooth experience.
Chester County Top Rated Vacation Rentals
House
10.0(29 Reviews)
4 Bedrooms
3 Baths
8 Guests
26910 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $684/Night
7 Nights - US $4,790
House
10.0(10 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $672/Night
7 Nights - US $4,701
House
10.0(6 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $563/Night
7 Nights - US $3,938
House
9.6(18 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Private Pool
- Hot Tub
Spa- Fireplace/Heating
US $400/Night
7 Nights - US $2,797
House
9.6(15 Reviews)
4 Bedrooms
4 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $590/Night
7 Nights - US $4,129
Hotel
9.2(780 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
US $145/Night
7 Nights - US $1,013
Hotel
9.2(462 Reviews)
1 Bath
- Pool
- Breakfast
- Kitchen
- Parking
US $213/Night
7 Nights - US $1,494
Hotel
9.2(340 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
US $162/Night
7 Nights - US $1,137
