Discover Your Perfect Chester Vacation Homes

Best Vacation Homes in Chester

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9.8 (15 Reviews)
Bed & Breakfast
Raritan Inn
  • Parking
  • Balcony/Terrace
  • Security/Safety
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Chester Pet Friendly Vacation Rentals

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Why Choose Rent By Owner for your Chester Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Chester

When should you plan your Vacation Rentals stay?

To make the most of your stay, consider visiting during the shoulder seasons when this destination offers a peaceful atmosphere and favorable weather for exploring the area’s charming surroundings.

Peak Season Highlights

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May to June

During late spring to early summer, the area experiences warm weather ideal for outdoor activities and exploring local scenery.

Average Temperature Daytime: 70-80°F - Nighttime: 50-60°F
spring
September to October

Early fall offers crisp air and colorful foliage, making it a popular time for enjoying scenic drives and outdoor recreation.

Average Temperature Daytime: 65-75°F - Nighttime: 45-55°F

Off-Season Highlights

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January to February

Mid-winter months are quieter, with cooler temperatures perfect for those seeking a peaceful retreat in a cozy vacation rental.

Average Temperature Daytime: 30-40°F - Nighttime: 20-30°F
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November to December

Late fall into early winter is less busy, offering a tranquil atmosphere suitable for relaxing getaways before the holiday season begins.

Average Temperature Daytime: 40-50°F - Nighttime: 30-40°F

Weekly Weather Forecast for Chester

How to Book Your Chester 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

More Top-Rated Vacation Rentals in Chester Area

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 areas perfect for al fresco meals amidst the scenic surroundings.
  • Relax in a private backyard with lush landscaping and space for outdoor recreation.
  • Take advantage of a swimming pool to cool off during the warmer months in this region.
  • Make the most of a spacious patio or deck area ideal for entertaining guests.
  • Explore nearby hiking trails and nature walks directly from your rental property.
  • Benefit from outdoor fireplaces or fire pits, providing cozy evenings under the stars.
  • Have access to well-maintained gardens or outdoor spaces that highlight the area's natural beauty.

Top Attractions Around Chester

What attractions are nearby?

Nearby, you can enjoy a variety of outdoor activities and local attractions that showcase the charm of this destination’s surroundings, making your stay here both relaxing and memorable.

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Family Activities

  • Stroll through the Roxbury Land Trust preserves: Experience family-friendly outdoor adventures just a short drive from Chester, where you can enjoy scenic walking trails and nature exploration.
  • Visit Patriots Path Conservation Area: Engage in outdoor activities such as hiking and picnicking in this beautiful area that offers a peaceful escape within reach of your vacation rental.
  • Explore local farm stands and markets: Taste fresh, local produce and treats while supporting regional farmers, making it a delightful activity for families staying nearby.
  • Enjoy family fun at local parks: Spend quality time at parks with playgrounds and open spaces designed for children, ideal for relaxing days in this part of New Jersey.
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Adult Activities

  • Historic Downtown Chester: Explore charming boutiques, cafes, and local art galleries in the area's vibrant downtown district, perfect for leisurely daytime outings.
  • Patriot's Path Trail: Enjoy scenic hiking and biking along this popular trail that winds through the region, offering stunning views and outdoor adventure opportunities.
  • Ridgewood Reservoir: Experience peaceful nature walks and birdwatching at this tranquil reservoir setting, ideal for relaxation amid natural beauty.
  • Local Wineries and Breweries: Sample regional wines and craft beers at nearby vineyards and breweries, enhancing your taste of the area's culinary scene.

Other Places to Stay in Chester, NJ

The Streets of Chester Shopping Center
The Streets of Chester Shopping Center Vacation Rentals
Chubb Park
Chubb Park Vacation Rentals
Alstede Farms
Alstede Farms Vacation Rentals
Cooper Gristmill
Cooper Gristmill Vacation Rentals
Kay Environmental Center
Kay Environmental Center Vacation Rentals
Hacklebarney Farm Cider Mill
Hacklebarney Farm Cider Mill Vacation Rentals
More Places to Stay Near Chester

Chester Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Attractions: Take time to discover the nearby attractions that showcase the unique charm of this destination, making your stay more memorable.
  • Plan Your Activities: Schedule outdoor adventures or cultural experiences in advance to maximize your time in this area’s vibrant community.
  • Choose the Right Accommodation: Select a well-reviewed vacation rental that offers comfort and convenience, ensuring a relaxing retreat during your visit.
  • Embrace the Local Cuisine: Savor regional flavors by visiting local eateries or preparing meals in your rental to enjoy the area's culinary delights.

Transportation Options

  • Chester Train Station: Offering convenient rail access, this station connects you to major cities and makes exploring the broader region easy.
  • Interstate 80: As a primary highway nearby, it provides straightforward road travel for those arriving by car or planning scenic drives through the area.
  • Local Bus Services: These affordable transportation options help you navigate within Chester and reach surrounding destinations comfortably.
  • Rental Car Services: Several providers in town offer reliable vehicle rentals, giving you the freedom to explore the region at your own pace.

Local Customs Options

  • Local Greeting Customs: You’ll notice that friendly handshakes and warm welcomes are a customary way to greet neighbors here, reflecting the region's welcoming spirit.
  • Community Events: Participating in local festivals and seasonal gatherings provides a wonderful opportunity to experience authentic regional traditions and connect with residents.
  • Dining Etiquette: When enjoying meals at community restaurants or homes, expect a focus on leisurely dining and sharing conversations, embodying the area's communal values.
  • Respect for Nature: Respect for the natural environment is deeply rooted here, so be mindful of local conservation practices during outdoor activities and exploring the area's scenic spots.

Frequently Asked Questions About Chester?

1. What are the top vacation rentals in Chester?

There are a lot of options in Chester. If you plan on staying in the Chester 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:

2. How many vacation rentals have private pools in Chester?

There are 7 vacation rentals with private pools near Chester. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Chester are best for families?

If you are looking for a family-friendly vacation home in Chester, 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:

4. How many Rentbyowner vacation rentals are available in Chester?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 214 in the Chester 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. 

5. What is the cancellation policy for vacation rentals in Chester, New Jersey?

Cancellation policies vary by listing; please review the specific terms on the property’s page or contact the owner directly to understand the options available for your reservation.

6. How do I find available vacation rentals in Chester, New Jersey?

Use the search filters on this site to narrow down your options based on dates, amenities, and preferences, ensuring you find the perfect accommodation here in the region.

7. Are there any additional fees I should be aware of when booking a vacation rental in Chester, New Jersey?

Additional fees such as cleaning, service charges, or taxes are typically listed during the booking process; review the detailed listing to understand all costs before confirming your reservation.

8. What amenities can I expect from vacation rentals in this area?

Most properties offer essential amenities like Wi-Fi, parking, and kitchen facilities, but it’s best to check each listing for specific features to suit your needs during your stay.

9. How can I contact the property owner if I have questions about my stay in Chester, New Jersey?

You can reach out directly through the messaging system provided on the listing page to ask any questions or clarify details before finalizing your booking.