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  3. Keene
  4. Chesterfield
  5. Rentals by Owner

Discover Your Perfect Chesterfield Rentals by Owner

Chesterfield Rentals by Owner

3.1 (25 Reviews)
Cabin
Econo Lodge
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
More Top-Rated Rentals by Owner in Chesterfield Area

Why Choose Rent By Owner for your Chesterfield 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 Chesterfield

When should you plan your Rentals by Owner stay?

Choosing the ideal time to vacation here can enhance your experience, so consider visiting during the region's most pleasant seasons to enjoy optimal weather and local events while booking your rental by owner with confidence on Rent By Owner.

Peak Season Highlights

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Summer (June to August)

During the summer months, you can enjoy the warm weather and longer daylight hours, making it ideal for outdoor activities and exploring the region.

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

Fall is a popular time to visit when the foliage reaches its peak, offering stunning natural scenery throughout this destination.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F

Off-Season Highlights

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Spring (April to May)

In spring, you’ll find fewer visitors and enjoy the scenic renewal of the landscape as blossoms begin to bloom.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 30°F to 40°F
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Winter (December to February)

Winter offers a quieter experience with opportunities to enjoy the peaceful snowy landscapes, perfect for those seeking solitude or winter sports.

Average Temperature Daytime: 20°F to 35°F - Nighttime: 10°F to 20°F

Weekly Weather Forecast for Chesterfield

How to Book Your Chesterfield 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 Chesterfield

More Top-Rated Rentals by Owner in Chesterfield 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

  • You can enjoy spacious outdoor seating areas, perfect for relaxing and taking in the scenic views of the region.
  • Many rentals offer access to private or shared patios and decks to enhance your outdoor experience.
  • Expect well-maintained gardens or landscaped yards that add to the charming atmosphere here.
  • It’s common to find outdoor fire pits or barbecue grills, ideal for evening gatherings or cooking al fresco.
  • Some properties include amenities such as a swimming pool or hot tub for outdoor leisure.
  • Outdoor recreational features like walking trails or fishing spots are often available nearby.
  • Many rentals come equipped with outdoor dining areas, making it easy to enjoy meals amidst nature's beauty.

Top Attractions Around Chesterfield

What attractions are nearby?

While staying here, you can enjoy a variety of outdoor activities nearby, including hiking, boating, and exploring scenic trails that showcase the natural beauty of the region.

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Family Activities

  • Chesterfield Town Beach: Engage in a day of swimming and picnicking at this scenic lakeside spot, perfect for family relaxation in the area.
  • King Pine State Park: Explore the numerous hiking trails and enjoy outdoor activities amid the natural beauty that surrounds here, making it ideal for family adventures.
  • Chesterfield Gorge Natural Area: Discover stunning geological formations and enjoy educational walks through the gorge, offering an engaging experience for all ages.
  • Local Farm Visits: Experience farm life with family-friendly tours and activities at nearby farms, providing both fun and educational opportunities in the region.
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Adult Activities

  • Hiking and Nature Trails: Explore the scenic trails around Chesterfield, where you can enjoy a peaceful hike amid natural beauty and tranquil landscapes.
  • Paddling and Boating on Local Lakes: Experience the area's lakes firsthand by renting a kayak or paddleboard to immerse yourself in the serene waters and stunning views.
  • Wildlife Watching: Visit nearby protected areas to observe various local species in their natural habitat, perfect for outdoor enthusiasts seeking connection with nature.
  • Fishing Excursions: Cast your line in the region's prime fishing spots, offering chances to relax and unwind during your stay in this charming destination.

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Chesterfield Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead: Research local attractions and activities to tailor your stay in the region, ensuring you make the most of your visit.
  • Book Early: Secure your rental by owner well in advance to access the best properties and enjoy a stress-free arrival here.
  • Embrace Nature: Take advantage of the area's scenic outdoor spaces for hiking, fishing, or relaxing amidst the natural beauty that surrounds you.
  • Connect Locally: Support the community by exploring local markets and dining options, enriching your experience in this charming destination.

Transportation Options

  • Chesterfield Transportation Services: Local transportation providers offer convenient options for exploring the area and reaching nearby destinations with ease.
  • Closest Airports: The region is served by regional airports that facilitate easy access for travelers arriving from distant locations, making your trip more seamless.
  • Taxi and Rideshare Options: Reliable taxi services and popular rideshare apps provide flexible and quick transportation around here for your comfort and convenience.
  • Car Rental Agencies: Several car rental agencies are available nearby to help you explore the scenic region at your own pace during your stay.

Local Customs Options

  • New England Hospitality Norms: Visitors often find that locals here value friendliness and politeness, making your stay in the area welcoming and comfortable.
  • Respect for Natural Spaces: When exploring this region, it's customary to follow Leave No Trace principles, ensuring the preservation of its scenic beauty for future visitors.
  • Community Events and Gatherings: Participating in local events such as seasonal festivals or farmers' markets is a common way to connect with residents during your stay.
  • Environmental Conservation Practices: In this area, respecting conservation efforts and adhering to guidelines around outdoor activities are appreciated by the community and enhance your experience.

Frequently Asked Questions About Chesterfield Rentals by Owner

1. What are the top vacation rentals in Chesterfield?

There are a lot of options in Chesterfield. If you plan on staying in the Chesterfield area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Chesterfield:

2. How many Rentbyowner vacation rentals are available in Chesterfield?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 31 in the Chesterfield 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 Chesterfield. 

3. What is the cancellation policy for rental properties in Chesterfield, New Hampshire?

Cancellation policies vary by individual rental owner. To understand the specific terms for your chosen property, please review the listing details or contact the owner directly.

4. Are there any additional fees I should be aware of when booking a rental by owner in the area?

Additional fees such as cleaning, service charges, or security deposits are usually specified in the listing. Be sure to read the full description and reach out to the owner if you have questions about extra costs.

5. How do I ensure the rental property in the region meets my needs?

You can verify the amenities, house rules, and photos provided in the listing. Contact the owner directly for any specific requirements or clarifications before confirming your reservation.

6. What is the process for checking in and checking out of rentals in this destination?

Check-in and check-out procedures are typically outlined by the owner within the listing. For a smooth experience, communicate with the owner ahead of your arrival to confirm details and access instructions.

7. Is it safe to stay in a rental by owner in the area?

Rental safety measures are maintained by individual owners, and reviews from previous guests can provide insight. Always review the listing and contact the owner if you have safety concerns or need additional reassurance.

More Rentals You May Like Near Chesterfield

More Top-Rated Rentals by Owner in Chesterfield Area