Discover Your Perfect Chesterfield Vacation Homes

Why Choose Rent By Owner for your Chesterfield 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 Chesterfield

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit this destination can enhance your experience, as the distinct seasons in the region offer unique opportunities for outdoor activities and relaxation throughout the year.

Peak Season Highlights

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Summer (June to August)

During the summer months, the area experiences warm and inviting weather, making it ideal for outdoor activities and exploring scenic landscapes.

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

Autumn brings vibrant foliage and crisp air, creating a picturesque setting that attracts visitors seeking the region's colorful displays.

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

Off-Season Highlights

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Winter (December to February)

The winter season offers serene snowy landscapes, perfect for cozy stays and winter sports enthusiasts exploring here.

Average Temperature Daytime: 25°F to 35°F - Nighttime: 10°F to 20°F
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Spring (March to May)

As the region transitions into warmer weather, spring features blooming flora and mild conditions, ideal for quiet getaways before the summer rush.

Average Temperature Daytime: 45°F to 55°F - Nighttime: 30°F to 40°F

Weekly Weather Forecast for Chesterfield

How to Book Your Chesterfield 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 Chesterfield

More Top-Rated Vacation Rentals in Chesterfield 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 spacious outdoor areas perfect for relaxing and taking in the scenic views surrounding Chesterfield.
  • Take advantage of private decks or patios ideal for outdoor dining or morning coffee.
  • Explore landscaped gardens or lawns that provide a peaceful setting for outdoor activities.
  • Make use of outdoor fire pits to gather with family and friends during cool evenings.
  • Benefit from access to furnished balconies offering panoramic vistas of the region’s natural beauty.
  • Utilize private or shared outdoor grills to prepare meals amidst the fresh air.
  • Experience the serenity of nearby nature trails or wooded areas right from your rental property.

Top Attractions Around Chesterfield

What attractions are nearby?

In this charming destination, you can enjoy a variety of outdoor activities nearby, including scenic hiking trails, kayaking on pristine waters, and exploring tranquil parks that showcase the natural beauty of the region.

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Family Activities

  • Chesterfield Family Nature Walks: Discover scenic trails perfect for exploring the natural beauty that surrounds this destination, offering a peaceful way for families to enjoy the outdoors together.
  • Local Farm Visits: Experience a hands-on farming experience at nearby farms where children can learn about agriculture and perhaps even meet some friendly farm animals.
  • Community Events and Festivals: Check out seasonal festivals and community events that provide fun and engaging activities suitable for all ages here in the region.
  • Lake Activities: Spend a day enjoying swimming, kayaking, or picnicking by the tranquil lakes close to the area, making it an ideal spot for family outdoor adventures.
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Adult Activities

  • Hiking Trails: Explore scenic trails that provide stunning views and a peaceful escape into the natural beauty of the region.
  • Bird Watching: Discover a variety of bird species in the area’s protected habitats, perfect for enthusiasts seeking tranquil observation spots.
  • Local Art Galleries: Visit charming galleries showcasing regional artists, offering unique pieces that capture the spirit of the destination.
  • Historic Site Tours: Delve into the area's rich history by touring well-preserved sites and learning about its cultural heritage.

Other Places to Stay in Chesterfield, NH

Asbury United Methodist Church
Asbury United Methodist Church Vacation Rentals
More Places to Stay Near Chesterfield

Chesterfield Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for Local Events: Check the regional event calendar to align your stay with local festivals or community gatherings, enriching your experience here.
  • Explore Outdoor Activities: Take advantage of the outdoor opportunities available in this area, such as hiking or fishing, to fully immerse yourself in the region's natural beauty.
  • Select a Prime Location: Opt for vacation rentals that are centrally located within the region to easily access popular spots and enjoy more convenience during your visit.
  • Discover Local Cuisine: Sample authentic dishes at nearby eateries or consider hosting a cooking night in your rental to experience regional flavors firsthand.

Transportation Options

  • Chesterfield Transit Services: Local transit options provide convenient transportation around this destination, making it easy to explore the area without a car.
  • Rental Car Services: Major rental agencies in the region offer reliable vehicles for your stay, giving you the freedom to discover nearby attractions at your own pace.
  • Taxi and Rideshare Options: Taxis and rideshare services are readily available here, offering flexible and quick transportation for your travel needs within this destination.
  • Nearby Public Airports: The regional airports near here connect you to major cities, facilitating smooth arrivals and departures during your visit.

Local Customs Options

  • New Hampshire's Local Craftsmanship: You’ll find that handcrafted goods and traditional craftsmanship are cherished here, offering a glimpse into the area's rich artisanal heritage.
  • Seasonal Celebrations: Participating in seasonal festivals and community events is a common way visitors engage with local traditions and enjoy the region’s vibrant cultural scene.
  • Hospitality Etiquette: Warm greetings and a friendly attitude are customary, reflecting the region’s reputation for welcoming visitors with genuine hospitality.
  • Respect for Nature: Environmental conservation and respect for the natural surroundings are integral to local customs, encouraging eco-friendly practices during your stay.

Frequently Asked Questions About Chesterfield?

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 vacation rentals have private pools in Chesterfield?

There are 1 vacation rentals with private pools near Chesterfield. Top-rated RBO homes that have access to a swimming pool include:

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

If you are looking for a family-friendly vacation home in Chesterfield, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chesterfield:

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 63 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. 

5. What is the cancellation policy for vacation rentals in Chesterfield, New Hampshire?

Cancellation policies vary by property and listing. You should review the specific cancellation terms outlined in the rental details or contact the homeowner directly to understand your options regarding cancellations.

6. Are there any specific check-in and check-out times for vacation rentals in Chesterfield, New Hampshire?

Check-in and check-out times are determined by each property owner. Details are usually included in the property listing, so be sure to review these before booking or reach out to the host for clarification.

7. How do I know if a vacation rental in Chesterfield, New Hampshire, is suitable for my needs?

Property descriptions provide information about amenities, size, and location. You can also contact the owner to ask specific questions or request additional details to ensure the rental meets your travel requirements.

8. Are pet-friendly vacation rentals available in this area?

Many properties specify whether they accommodate pets. To find pet-friendly options, use the filter options on the listing platform or contact the owner directly to confirm if pets are allowed.

9. What should I do if I encounter issues during my stay in a vacation rental in Chesterfield, New Hampshire?

If you experience problems, reach out to the property owner or local support team listed in the booking details. They will assist you in resolving any concerns promptly to ensure a comfortable stay.