Discover Your Ideal Chesterfield District Vacation Rentals for a Memorable Stay in England, United Kingdom
Discover Your Perfect Chesterfield District Vacation Homes
Best Vacation Homes in Chesterfield District
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Chesterfield District Luxury Rentals
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Chesterfield District Pet Friendly Vacation Rentals
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Chesterfield District Large Vacation Homes
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Why Choose Rent By Owner for your Chesterfield District Vacation Rental Homes?
What makes our Vacation Rentals special?
Best Times to Visit Chesterfield District
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit this destination can enhance your experience, as the best seasons may vary depending on your interest in local events, weather conditions, and the region's natural beauty.
Peak Season Highlights
Summer (June to August)
During the summer months, you can enjoy longer daylight hours and typically warmer weather, making it an ideal time for exploring local attractions and outdoor activities in the area.
Spring (March to May)
Spring is a popular season to visit when the region blooms with vibrant colors, offering pleasant temperatures and a lively atmosphere perfect for outdoor exploration.
Off-Season Highlights
Autumn (September to November)
In autumn, the scenery transforms with stunning fall foliage, and fewer crowds allow for a more relaxed experience while still enjoying mild temperatures.
Winter (December to February)
Winter offers a quieter time to stay here with cooler weather and the potential for scenic countryside views, perfect for those seeking tranquility away from peak season crowds.
Weekly Weather Forecast for Chesterfield District
How to Book Your Chesterfield District Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Chesterfield District
Common Vacation Rentals Amenities
What amenities can you expect?
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 or patios to savor meals al fresco in the fresh air
- Benefit from private gardens or landscaped yards ideal for relaxation and outdoor activities
- Make the most of scenic balconies or decks with views of the surrounding countryside
- Utilize accessible parking spaces suitable for exploring this charming region with ease
- Take advantage of nearby walking trails or nature paths for outdoor adventures
- Relax in furnished outdoor seating areas designed for unwinding amidst scenic surroundings
- Access outdoor recreational amenities such as tennis courts, golf courses, or play areas in the vicinity
Top Attractions Around Chesterfield District
What attractions are nearby?
While staying in this destination, you can enjoy a variety of outdoor activities and cultural attractions just moments from your accommodation in Chesterfield District, ensuring a memorable and engaging experience during your visit to the region.

Family Activities
- Chesterfield Canal Walks: Explore the scenic waterways of the region on family-friendly walks along the Chesterfield Canal, offering a peaceful retreat amid nature.
- Pavilion Arts Centre: Enjoy engaging performances and family-friendly shows at this cultural hub situated conveniently within the area, perfect for a day out with loved ones.
- Queens Park: Spend quality time outdoors in this expansive park featuring playgrounds, open fields, and picturesque gardens, ideal for picnics and family adventures.
- Bolsover Castle Exploration: Discover the historic Bolsover Castle nearby, where your family can learn about local history while exploring its impressive medieval architecture.
Adult Activities
- Chesterfield Canal Walks: Explore scenic waterways along the Chesterfield Canal, perfect for enjoying peaceful strolls and discovering the area's natural beauty.
- Historic Chesterfield Market: Visit this vibrant market to experience local culture, browse unique stalls, and indulge in regional specialties.
- Peveril Castle Ruins: Discover the remnants of a medieval fortress offering panoramic views and a glimpse into the area's rich history.
- The Peak District National Park: Embark on outdoor adventures such as hiking or cycling amidst stunning landscapes just outside the region's borders.
Other Places to Stay in Chesterfield District
Chesterfield District Travel Tips
How Can You Make the Most of Your Stay?
- Plan your itinerary wisely: Explore the region’s rich history and local attractions to make the most of your stay in Chesterfield District, ensuring you experience its unique charm.
- Select a well-located vacation rental: Choose accommodations that are conveniently situated near key sites and transport links to maximize your exploration time here.
- Stay connected with local experiences: Engage with local events, markets, and eateries to immerse yourself fully in the culture of this destination.
- Book early for peak seasons: Reserve your vacation rental in advance to secure the best properties and enjoy a stress-free visit during busy times in the area.
Transportation Options
- Chesterfield Railway Station: You can easily access train services connecting to major UK cities, making travel convenient when staying in this part of the region.
- Local Bus Services: The area is well-served by bus routes that provide flexible transportation options for exploring nearby towns and attractions.
- Taxis and Ride-Sharing Services: Taxis and ride-sharing apps offer door-to-door convenience, ideal for quick trips within the district and beyond.
- Car Hire Facilities: Several rental agencies operate here, allowing you to rent a vehicle and enjoy the freedom to explore the region at your own pace.
Local Customs Options
- Harewood House Customs: Embrace the tradition of local hospitality by visiting the nearby Harewood House, where guided tours and cultural events reflect the area's rich history.
- Bank Holiday Celebrations: Participate in annual community festivities during bank holidays, showcasing vibrant parades and traditional entertainment unique to the region.
- Local Craftsmanship: Discover the craftsmanship heritage through visits to artisan markets and workshops that highlight the region's skilled artisans and handmade goods.
- Traditional Pubs and Ale Drinking: Experience the authentic pub culture by enjoying local ales in historic taverns that have served the community for generations here.
Frequently Asked Questions About Chesterfield District?
1. What are the top vacation rentals in Chesterfield District?
There are a lot of options in Chesterfield District. If you plan on staying in the Chesterfield District 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 District:
- Church Villa B&B
- Cedar Holme
- Country Retreat in the Peak District. Great location for cyclists. Pet friendly
- 4 bedroom accommodation in Holymoorside, near Chesterfield
- Charming Croft Cottage on the doorstep of the Peak District near Barlow
- Peak District - 2 Beds - Sleeps 4 - Pet Friendly
- THE OLD GROCERY, pet friendly, with a garden in Barrow Hill
- THE RUMBLINGS 1, pet friendly, character holiday cottage in Barlow
- 2 bedroom accommodation in Calow
- The Old Grocery
2. Which vacation homes in Chesterfield District are best for families?
If you are looking for a family-friendly vacation home in Chesterfield District, 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 District:
3. How many Rentbyowner vacation rentals are available in Chesterfield District?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 155 in the Chesterfield District 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 District.