Chesterfield Vacation Rentals, England: house rentals & more

Select from 50 homes, 103 cottages, and other vacation rentals in Chesterfield to find one that's perfect for your trip. Whether you’re staying in a vacation home with friends, family, or even just your pets, you'll have the amenities you expect and more, which might include parking and a hot tub. Whatever you're looking for, you'll find a rental to meet everyone's needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in Chesterfield

Hardwick Hall

Find the best place to stay - Chesterfield

Whittonlodge Sleeps 28 Hottub, Pool table

Sleeps 28 · 9 bedrooms · 9+ bathrooms

Charming Croft Cottage on the doorstep of the Peak District near Barlow

Sleeps 5 · 2 bedrooms · 1 bathroom

Top rated rentals - Chesterfield

Beautiful house with all amenities

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, yards and more
More for less
More space, more privacy, more amenities — more value

Find out more about Chesterfield

Why visit Chesterfield

Stunning outdoor scenery: Chesterfield boasts beautiful parks and lush landscapes, perfect for nature enthusiasts.
Rich cultural heritage: Explore historic buildings and charming houses that reflect the town's fascinating history.
Friendly city centre: Enjoy a vibrant atmosphere with delightful boutiques and cafes for a relaxing day out.
Family-friendly activities: Nearby Central Lonsdale offers a welcoming vibe and activities suitable for all ages.
Diverse accommodation options: Choose from cozy cottages to spacious apartments for a comfortable stay.

Popular types of accommodation in Chesterfield

Discover the charm of Chesterfield with a variety of vacation rentals to suit your needs. Whether you're seeking cozy cottages, spacious apartments, or houses, we have something for everyone. Popular options include bedroom apartments, charming cedar cottages, and delightful holiday cottages. For those planning extended stays, consider our monthly rentals. Whatever your preference, Chesterfield offers the perfect home away from home for your Canadian adventure.

Cottages: The top choice for vacation rentals in Chesterfield, offering a cozy and charming atmosphere perfect for a relaxing getaway.
Apartments: A popular option for those seeking modern amenities and the convenience of self-catering during their stay.
Houses: Ideal for families or groups, these homes provide spacious living areas and a home-like experience.
House Boats: A unique accommodation choice that allows you to enjoy a stay on the water, adding a whimsical touch to your holiday.
Caravan Parks: A budget-friendly option, perfect for those looking to enjoy nature while having access to communal facilities.**

Top attractions in Chesterfield

Chesterfield, England, is perfect for outdoor enthusiasts and those seeking adventure, with a stunning blend of scenery and cultural experiences. Visitors can explore urban parks, historic buildings, and charming historic houses, making it an ideal destination for families and culture seekers alike. Whether you're enjoying the lush landscapes or delving into the rich history, Chesterfield offers a delightful vacation experience for all types of travellers.

Chatsworth House: A magnificent historic house located 12.9km from Chesterfield, Chatsworth House boasts stunning gardens and art collections, offering a glimpse into aristocratic life and culture.
Bolsover Castle: Nestled within Chesterfield, this romantic castle features enchanting architecture and lush gardens, perfect for those seeking a blend of history and charm.
Hardwick Hall: An impressive historic building in Chesterfield, Hardwick Hall showcases exquisite Elizabethan architecture and beautiful grounds, reflecting the rich cultural heritage of the area.

Things to do recommended for couples

For a romantic getaway in Chesterfield, enjoy a concert at Sheffield City Hall for vibrant entertainment, soar with Virgin Balloon Flights for an adventurous experience, or try Sheffield Cable Waterski for outdoor thrills. Each offers unique vibes perfect for couples seeking memorable moments together.

Things to do recommended for families

Families visiting Chesterfield can enjoy wellness and relaxation at Hardwick Hall-Derbyshire Country Park, explore the sports vibes at Bramall Lane, and experience fun at Ponds Forge International Sports Centre, located a short drive away. Perfect for creating memorable family moments!

Things to do recommended for groups

Explore the Meadowhall Shopping Centre for a fun shopping experience, catch a show at the Crucible Theatre for a taste of local culture, and wander through Chesterfield Market for a vibrant atmosphere and unique finds. Perfect activities for a memorable group getaway!

What do I need to keep in mind when booking a vacation in Chesterfield

If you're planning a trip with a group, family, pets, or seeking extended stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

Traveling to Chesterfield with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for all of these options and more on Vrbo.
Traveling to Chesterfield with young kids: Travelling with young children can present some challenges. It's important to prioritize their comfort and safety, as well as provide suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
Taking your pets with you to Chesterfield: For many, a family getaway isn’t truly fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
Planning for a long term stay visiting Chesterfield: If you’re seeking vacation rentals with special offers for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to consider features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Chesterfield

Chesterfield offers a delightful mix of adventure and culture, perfect for your vacation. Wander through its friendly city centre, where charming boutiques and cafes await. Explore nearby regions like Central Lonsdale, known for its relaxing atmosphere and family-friendly vibe. With plenty of vacation rentals available, you can easily immerse yourself in the local scene and enjoy the scenic beauty of this welcoming area.

Sheffield: Sheffield is a vibrant city located 16.1km from Chesterfield, known for its stunning outdoor adventures and scenic landscapes. It offers a variety of recreational areas and an impressive arena entertainment facility, perfect for sports fans and event-goers. Shop at its bustling shopping centres or explore the surrounding natural beauty in nearby national parks. Don’t miss the chance to visit local landmarks like the renowned stadium, which frequently hosts exciting events that reflect the city’s rich cultural scene.
Bakewell: Just 17.7km away from Chesterfield, Bakewell is a charming market town that beckons visitors with its outdoor activities and picturesque scenery. Known for its delightful recreational areas and scenic hiking trails, it's an ideal spot for nature enthusiasts. Golf lovers can enjoy the local golf courses, while history buffs will appreciate the nearby historic houses that reflect the town’s heritage. Bakewell is also famous for its delicious Bakewell pudding, a sweet treat that you must try during your visit.
Matlock: Located 14.5km from Chesterfield, Matlock is a beautiful town that captivates visitors with its outdoor attractions and breathtaking scenery. Enjoy thrilling rides on the cable car gondola, which provides stunning views of the surrounding landscapes. Matlock's recreational areas are perfect for relaxing walks and picnics. You can also explore nearby national parks and monuments that highlight the region's natural beauty and historical significance, making it a fantastic choice for an adventurous day trip.

Best time to go to Chesterfield

If you're planning a trip to Chesterfield, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April, July and September, while off-peak times, like October to December tend to have fewer bookings and better deals.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	38.3°F (3.5°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
February	39.4°F (4.1°C)	No Rain (Dry)	Mostly Cloudy	Average	Slightly Low
March	42.3°F (5.7°C)	No Rain (Dry)	Mostly Cloudy	Average	Slightly Low
April	46.2°F (7.9°C)	No Rain (Dry)	Mostly Cloudy	Slightly High	Average
May	51.8°F (11.0°C)	Light Rain	Mostly Cloudy	Average	Average
June	57.2°F (14.0°C)	Light Rain	Mostly Cloudy	Average	Average
July	60.8°F (16.0°C)	Light Rain	Mostly Cloudy	Slightly High	Slightly High
August	60.3°F (15.7°C)	Light Rain	Mostly Cloudy	Average	Slightly High
September	56.5°F (13.6°C)	No Rain (Dry)	Mostly Cloudy	Slightly High	Average
October	50.7°F (10.4°C)	Light Rain	Mostly Cloudy	Slightly Low	Average
November	44.1°F (6.7°C)	Light Rain	Mostly Cloudy	Slightly Low	Average
December	40.1°F (4.5°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly High

Booking with Vrbo is simple

Are you hoping to save on your next journey? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you could enjoy substantial savings by opting for a longer stay. To discover a Vrbo property that suits your budget, simply use our filters to narrow down your options by price, location, and type of vacation rental. We're here to help you make the most of your travel experience!

Vrbo Trips: Planning made easy

Vrbo's Trip Board provides you with a convenient platform to plan new adventures, refine your travel arrangements, or keep track of your existing bookings. Your saved or reserved properties are thoughtfully categorized into Potential, Upcoming, or Current Trips for easy access. To discover the features of Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

The friendly area of Chesterfield awaits your stay

Come and experience Chesterfield and its churches, culture and theater scene. Well known for its bars, parks and restaurants, this welcoming city won't disappoint. With a vacation rental, you get a home away from home. Many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Chesterfield

Are you hoping to discover things to do while you're in town? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Chesterfield a fun spot to vacation. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

Gulliver's Valley (9 mi / 14.5 km)
Gulliver's Kingdom (10 mi / 16.2 km)
Tropical Butterfly House, Wildlife and Falconry Centre (12.3 mi / 19.7 km)
Walesby Forest (17.5 mi / 28.2 km)
Goyt Valley (17.7 mi / 28.4 km)
Dore and Totley Golf Club (6.7 mi / 10.8 km)

Exploring the natural features in Chesterfield

Whether you're an active traveler or just want to appreciate the scenery, Chesterfield is a great place to get outside. These are some of the area's most stunning sights, all within 30 miles (48.2 km) of the city center:

Peak District National Park (18.4 mi / 29.7 km)
Chatsworth House Labyrinth (7.8 mi / 12.5 km)
Rother Valley Country Park (8.4 mi / 13.5 km)
Creswell Crags (9.6 mi / 15.4 km)
Heights of Abraham Cable Car Station (9.7 mi / 15.6 km)
Endcliffe Park (9.9 mi / 15.9 km)

How to get to and around Chesterfield

The nearest airport is in Doncaster (DSA-Sheffield), located 24.3 mi (39.1 km) from the city center. If you're unable to find a flight that fits your schedule, you might consider flying into Nottingham (NQT), which is 26 mi (41.9 km) away.

If you're traveling by train, the main station serving the city is Chesterfield Station.

Frequently asked questions

What is the best area to stay in Chesterfield when booking a vacation rental?

Ashover is one of the more popular locations to find a Vrbo vacation home in Chesterfield. Choose from our comfy stays and then prepare to discover this destination like a local.

What is the most popular type of vacation rental accommodation in Chesterfield?

Based on our research, cottages are the most desirable type of vacation property in Chesterfield. But having said that, everyone’s idea of the perfect trip can differ. Vrbo has vacation homes of all shapes and sizes, and we’ll help you to find the perfect fit for you.

How much does it cost to rent a vacation rental in Chesterfield?

Season, length of stay and property type are some of the things that can determine the price of a vacation home. Simply add your travel dates to find your ideal fit. From comfy cabins to expansive villas, all Vrbo vacation rentals provide amazing value.

How much does it cost to rent a beach house in Chesterfield?

When you travel and the size and style of the property will influence how much you’ll pay for your beachside vacation rental. Click on your Chesterfield travel dates to view your available options on Vrbo. Looking for basics like WiFi, or perks like a private pool? Use the filters to choose the amenities and features you want in your beach house.

Are there pet-friendly vacation rentals in Chesterfield?

With 70 vacation rentals that allow pets, your furry best friend can join in on your Chesterfield vacation. Use the filter tool to search our pet-friendly vacation rentals and find a stay that’ll set tails wagging on Vrbo.

What are popular rental amenities in Chesterfield?

The most popular rental amenities people prefer in Chesterfield are a fireplace, a firepit and a barbecue grill. Whether you’re on the road with family, pals or even pets, Vrbo vacation homes provide the best amenities for fun and relaxation with the people you cherish the most.

Are there large group vacation rentals in Chesterfield?

Chesterfield has eight vacation rentals that can host 10 or more guests. These properties come with plenty of space to share good times with your favorite people.

Are there vacation rentals in Chesterfield that welcome kids?

With 70 family-friendly vacation properties available in Chesterfield, now is a fantastic time to introduce the kiddos to the wonders of travel. Simply check our “Properties good for families” filter to locate stays that feature amenities perfect for families on the move, like full kitchens, pools, bunk beds and entertainment areas.

What are the top attractions for families in Chesterfield?

Keeping the kiddos entertained during your vacation in Chesterfield is a breeze with these fabulous family-friendly attractions:

Bolsover Castle
Barrow Hill Roundhouse Railway Centre
Chesterfield Museum & Art Gallery

Are there one-bedroom vacation rentals in Chesterfield?

Yes, Chesterfield has eight one-bedroom rentals available. Usually located in popular areas thanks to their compact size, a one-bedroom property is perfect if you’re traveling with your partner or a pal. And with home comforts like air conditioning and more privacy than a standard hotel, you’ll be able to kick back while discovering this exciting destination.

Can I find two-bedroom vacation rentals in Chesterfield?

Gather your besties and relax in total privacy and comfort in one of the 24 two-bedroom vacation properties Chesterfield has to offer.

Are there vacation rentals with WiFi in Chesterfield?

Chesterfield has eight vacation rentals with WiFi, so you’ll be able to stay connected during your vacation. Simply check the “WiFi” box in our handy search filter to find the perfect property. From streaming TV shows with the family to sending emails, these Vrbo homes make it a cinch to go online.

How old do you have to be to rent a vacation rental in Chesterfield?

You’ll have to check with the Chesterfield vacation property you’re considering on Vrbo as the minimum age differs. However, generally it’s 16, 18 or 21.

How long can I rent a vacation rental in Chesterfield for?

The amount of time you can rent a Chesterfield vacation home for varies depending on the property. Just put in your preferred travel dates to see available options offering extended stays. They have all the things you need to make your extended getaway more comfortable and convenient, such as kitchens and laundries. Some Vrbo vacation homes may also offer discounted weekly or monthly prices, so you can stay even longer for less.