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  4. Chester
  5. Rentals by Owner

Discover Your Perfect Chester Rentals by Owner

Chester Rentals by Owner

More Top-Rated Rentals by Owner in Chester Area

Why Choose Rent By Owner for your Chester vacation rental?

What makes our Rentals by Owner 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 Rentals by Owner stay?

Choosing the right time to visit this destination can enhance your experience, allowing you to enjoy the area's unique charm and natural beauty when the weather and local events are at their best.

Peak Season Highlights

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Summer (June to August)

During the warm summer months, you'll experience the region at its liveliest, making it an ideal time for outdoor activities and enjoying the scenic beauty.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
autumn
Fall (September to November)

Autumn brings a vibrant display of foliage, offering a picturesque setting that enhances your stay here. The pleasant weather makes it perfect for exploring the local area.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 45°F to 55°F

Off-Season Highlights

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Winter (December to February)

The colder months see fewer visitors, creating a peaceful atmosphere for those seeking tranquility and cozy accommodations in this destination.

Average Temperature Daytime: 30°F to 40°F - Nighttime: 15°F to 25°F
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Spring (March to May)

Early spring offers mild weather and blooming landscapes, though fewer tourists visit during this shoulder season which often results in more relaxed rental options.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 35°F to 45°F

Weekly Weather Forecast for Chester

How to Book Your Chester vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. 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 Rentals by Owner in Chester Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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 a private outdoor patio or deck to relax and take in the scenic views of the region.
  • Make use of a spacious backyard perfect for outdoor dining, barbecues, or simply unwinding amidst nature.
  • Take advantage of well-maintained gardens or landscaped areas to explore and enjoy the local flora.
  • Utilize outdoor fire pits or fireplaces for cozy evenings under the stars with friends or family.
  • Benefit from access to nearby hiking trails or walking paths that showcase the area's natural beauty.
  • Relax by an outdoor swimming pool if your rental offers this luxury, ideal for warm summer days.
  • Use outdoor recreational equipment such as bikes, kayaks, or paddleboards, often available for guest use in this destination.

Top Attractions Around Chester

What attractions are nearby?

In this charming area, you can enjoy a variety of outdoor activities and local attractions that showcase the natural beauty and culture of the region, making it an ideal destination for your stay through Rent By Owner in Chester, New York.

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Family Activities

  • The Hudson Highlands Nature Museum: Engage with interactive exhibits and explore scenic trails that make this museum a perfect family outing spot in the region.
  • : Discover outdoor adventures such as hiking, picnicking, and boating in one of the area's most popular natural destinations for families.
  • The New York State Thruway Visitor Center: Learn about the region’s history and enjoy informational displays, making it an educational experience for all ages during your stay here.
  • Local Farmers Markets: Enjoy fresh produce, homemade treats, and local crafts at nearby markets that offer a taste of the area's vibrant community life for families visiting Chester.
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Adult Activities

  • Hiking at the Harriman State Park: Discover scenic trails and outdoor adventures just a short drive from your rental, offering a perfect way to explore the natural beauty of the region.
  • Visiting Bear Mountain State Park: Enjoy outdoor activities such as picnicking, kayaking, or simply taking in breathtaking views at this popular destination nearby.
  • Exploring Local Art and Culture: Immerse yourself in regional art galleries and cultural exhibits that highlight the area's rich history and vibrant community spirit.
  • Savoring Regional Cuisine: Dine at local eateries that serve up fresh, regional flavors, adding a delicious touch to your stay here in the region.

Other Places to Stay in Chester, NY

Goosepond Mountain State Park
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Sugar Loaf
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The Rock Sports Complex
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Castle Fun Center
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Chester Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local dining options: Discover the area's culinary scene by trying charming eateries and cafes near your rental to experience authentic regional flavors.
  • Plan outdoor activities: Take advantage of nearby parks and recreational areas to enjoy scenic walks, hikes, or leisurely picnics that showcase the natural beauty of this region.
  • Visit seasonal events and festivals: Check the local calendar for community gatherings and festivities that offer a glimpse into the area’s vibrant culture and traditions.
  • Utilize your rental’s amenities: Maximize your stay by making full use of the facilities offered in your vacation home, ensuring a comfortable and convenient visit here.

Transportation Options

  • New York State Thruway (Interstate 87): You can access the region conveniently via this major highway, connecting Chester to New York City and beyond for quick travel options.
  • Stone Ridge Bus Service: This regional bus service offers reliable transportation for exploring nearby towns and places of interest within the area.
  • Local Taxi Services: Local taxi companies provide flexible and on-demand transportation around the region, ideal for short trips or airport transfers.
  • Chester Train Station: Although limited, nearby train services connect here to larger networks, facilitating convenient travel to New York City and other parts of the state.

Local Customs Options

  • Local Farmers' Markets: Embrace the tradition of visiting farmers' markets in the area, where you can experience the region's fresh produce and community spirit firsthand.
  • Seasonal Festivals: Participate in seasonal festivals that celebrate local harvests and cultural heritage, adding a memorable touch to your stay here.
  • Historic Preservation Practices: Respect the area's commitment to preserving its historical sites and architecture, ensuring your interactions honor local customs.
  • Community Celebrations: Join in on neighborhood gatherings and events that foster a welcoming atmosphere central to the regional way of life.

Frequently Asked Questions About Chester Rentals by Owner

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 Rentbyowner vacation rentals are available in Chester?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 36 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. 

3. How do I find the specific cancellation policy for my rental by owner in Chester, New York?

The cancellation policy is detailed in the listing description of each property. To ensure you understand the terms, review the policy on the rental's page or contact the owner directly through the booking platform for clarification.

4. What amenities are typically included in a rental by owner in this area?

Amenities vary by property, but common features include Wi-Fi, parking, kitchens, and outdoor spaces. For exact details, please check the individual listing, or reach out to the owner to confirm what is offered during your stay.

5. Are pets allowed in rentals by owner in Chester, New York?

Pet policies differ depending on the property. You can find this information in the listing description, or contact the owner directly to inquire about bringing your pet and any associated fees or restrictions.

6. What is the process for checking in and out of a rental by owner in this region?

Check-in and check-out procedures are specified in each listing. Typically, owners provide instructions prior to arrival. Contact the owner directly through the platform if you need additional guidance or have special requests during your stay.

7. Can I modify or extend my booking in Chester, New York once confirmed?

Modifications and extensions depend on the owner's policies and availability. To request changes, contact the owner as early as possible through the reservation platform to discuss your options and ensure a smooth adjustment.

More Rentals You May Like Near Chester

More Top-Rated Rentals by Owner in Chester Area