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Chesterfield vacation rentals
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Best Vacation rentals and Airbnb offers in Chesterfield

Browse Vacation Rentals in the Historic District of Chesterfield

Stay in downtown Chesterfield to keep top attractions within walking distance. Browse our central vacation rentals and find your perfect base.

College View - Chesterfield
9.8 16 reviews

College View

apartment
This Chesterfield studio apartment is centrally located, a short walk from Chesterfield train station and the town center, providing easy access to the Peak District National Park.
This newly renovated unit sleeps four guests in two double beds, features a fully equipped kitchen with microwave, fridge, and hob, and offers fast internet and designated workspaces.
The Corner House A-2 Bedroom Town Centre Apartment - Chesterfield
9.7 144 reviews

The Corner House A-2 Bedroom Town Centre Apartment

apartment
This ground floor flat is located within walking distance of Chesterfield's town center and train station, making it easy to explore the area. It has received excellent ratings for cleanliness, location, and user experience. The two-bedroom apartment comfortably accommodates up to five guests, making it ideal for families or groups of friends. Guests have access to a fully equipped kitchen, a dedicated workspace with high-speed internet, and a private parking space.
Spire View | Chesterfield 2 Bedroom Apartment - Chesterfield
9.9 19 reviews

Spire View | Chesterfield 2 Bedroom Apartment

apartment
This Chesterfield, Derbyshire apartment is centrally located, a short walk from the Chesterfield train station and town center, providing easy access to the Peak District National Park.
The two-bedroom, one-bathroom unit sleeps four, features a fully equipped kitchen, designated workspaces, fast internet, and is near affordable parking options starting at $4.75 per day.
Stylish Flat In Chesterfield Peak District - Chesterfield
9.3 45 reviews

Stylish Flat In Chesterfield Peak District

apartment, Chesterfield
This Chesterfield apartment rental, located in the Peak District, offers easy access to attractions like Chatsworth House (13 miles away), Clumber Park (20 miles), and the Utilita Arena Sheffield (14 miles).
This 430-square-foot (40-square-meter) unit features one bedroom, one bathroom, sleeps three guests, and includes a fully equipped kitchen with microwave, washer, free Wi-Fi, and private parking.

Best Chesterfield vacation rentals with air conditioning

The Coach House At Stretton House - Chesterfield
No reviews

The Coach House At Stretton House

house, Stretton
The Coach House, located in Stretton, is 14 miles from Chatsworth House, 20 miles from Clumber Park, and 21 miles from Sherwood Forest, with East Midlands Airport 29 miles away.
This lodging offers 2 bedrooms, 2 bathrooms, air conditioning, a kitchenette, and complimentary WiFi, plus a private terrace and balcony with garden views.
The Urban Residence - Sheffield 6br Group-family Stay - Sleeps 12 - Chesterfield
No reviews

The Urban Residence - Sheffield 6br Group-family Stay - Sleeps 12

house, Victoria
The Urban Residence is located in the Sheffield district of Victoria, offering convenient access to local attractions.
This spacious 1940 square feet apartment accommodates up to 12 guests, featuring 6 bedrooms, 2 bathrooms, a full kitchen, a private terrace, and complimentary private parking.
Cool "Beautiful " 1757 Stone Cottage In Hot Summer - Chesterfield
9.9 39 reviews

Cool "Beautiful " 1757 Stone Cottage In Hot Summer

apartment
This two-bedroom cottage is located in Ashover, a charming village in the Peak District, just a short walk from Dove Dale and 51 other Dales. The cottage sleeps up to four guests and features a fully equipped kitchen with a dishwasher, a comfortable living area, and a private garden with a pergola and BBQ.
Lv8 Chesterfield - Chesterfield
10 1 review

Lv8 Chesterfield

apartment, Chesterfield
This one-bedroom flat in Chesterfield offers convenient access to local attractions, situated 10 miles from Chatsworth House and 14 miles from Utilita Arena Sheffield.
This 590 sq ft rental accommodates up to two guests and features Wi-Fi, a fully equipped kitchen with a dishwasher, and on-site parking.

Frequently Asked Questions about vacation rentals in Chesterfield

  • What should a first-time visitor not miss in Chesterfield?

    You definitely want to see the Crooked Spire, it's a must-see for any visitor to Chesterfield. You should also check out the Chesterfield Museum and Art Gallery, it's a great way to learn about the town's history. And don't forget to take a stroll through the beautiful Queen's Park.
  • What are the best Airbnb and vacation rentals in Chesterfield?

    3 Bedroom House Near Woods - Edge Of Peak District, The Long Hall 2 Bed Ground Floor Annexed Apartment and The Barn At Woodland View are the most popular Airbnb and vacation rentals in Chesterfield among travelers.

  • Which neighborhood in Chesterfield should you consider for a vacation rental?

    The town center is a good choice, it's close to all the main attractions and has plenty of restaurants and shops. If you're looking for something a bit quieter, you might consider the residential neighborhoods of Newbold or Brimington, they're still close to the town center but have a more relaxed atmosphere.
  • What are the most popular Airbnbs in Chesterfield?

  • What are the top family-friendly attractions in Chesterfield?

    The Chesterfield Museum and Art Gallery has a lot of interactive exhibits that kids will love. You should also check out the Chesterfield Canal, it's a great place for a family walk or bike ride. And if you're looking for something a bit more adventurous, the National Trust's Hardwick Hall is just a short drive away.
  • What are the best vacation rentals with a pool in Chesterfield?

    Manor House, Family Fun Party House Pool - Bar - Sauna - Cinema and Tawny Owl Barn are the best vacation rentals with a pool in Chesterfield.

  • When is the best time to book a vacation rental in Chesterfield?

    You'll want to book your vacation rental in advance, especially if you're traveling during peak season, which is typically from June to August. If you're looking for a more affordable option, you might consider traveling during the shoulder seasons, which are spring and fall.
  • What are the best rentals for families and kids in Chesterfield?

  • What are the best budget-friendly activities in Chesterfield?

    You can walk or bike along the Chesterfield Canal, it's a great way to see the town and enjoy the scenery. You can also visit the Queen's Park, it's a beautiful park with a playground, a cafe, and a bandstand. And don't forget to check out the Chesterfield Museum and Art Gallery, it's free to enter.
  • What are the best rentals or Airbnbs with a jacuzzi in Chesterfield?

    The best vacation rentals or Airbnb with a jacuzzi in Chesterfield are Spahome With Hottub Sauna Bbq & Pool Table, Manor House and Hot Tub House Close To Woodland And Peak District.

  • What are the best restaurants with local dishes in Chesterfield?

    The Crooked Spire pub is a popular spot for traditional British food. The Tap & Barrel is another good option, it's known for its burgers and craft beers. And if you're looking for something a bit more upscale, you might try The Old Vicarage, it's a fine dining restaurant with a focus on local ingredients.
  • What are the best walking or cycling routes in Chesterfield?

    The Chesterfield Canal towpath is a great option for a leisurely walk or bike ride. The Chesterfield to Worksop cycle route is a longer, more challenging route that takes you through the Derbyshire countryside. And if you're looking for a shorter walk, the Queen's Park has a number of trails to choose from.
  • Are there pet-friendly attractions in Chesterfield?

    Queen's Park is pet-friendly and has a dog walking area. You can also take your dog for a walk along the Chesterfield Canal towpath.
  • What are the benefits of choosing a vacation rental in Chesterfield?

    Vacation rentals offer more space and privacy than a hotel. They're also often more affordable, especially if you're traveling with a group. And many vacation rentals have kitchens, which allows you to cook your own meals and save money on dining out.
  • What are the top sports attractions and facilities in Chesterfield?

    The Proact Stadium is home to Chesterfield FC, a professional football club. You can also find a number of other sports facilities in Chesterfield, including the Queen's Park, which has a tennis court and a bowling green. The Chesterfield Leisure Centre also offers a variety of fitness classes and swimming pools.

Popular destinations

Find the Best Vacation Rentals with Balconies in Chesterfield

Elevate your stay in Chesterfield with a vacation rental featuring a private balcony and stunning city skyline views.

Somersall Park Studio - Chesterfield
9.8 433 reviews

Somersall Park Studio

studio, Chesterfield
Somersall Park Studio is located in Chesterfield, just a short drive from Chatsworth House and FlyDSA Arena, making it a convenient base for exploring the area. This studio consistently receives excellent ratings for its cleanliness, location, and overall experience.
The studio is equipped with everything you need for a comfortable stay, including a kitchen with a fridge and microwave, a private patio, and a garden. Enjoy amenities like free Wi-Fi, barbecue facilities, and a continental breakfast, plus views of the inner courtyard and city.
Matlock Holiday Homes Apartment 5 - Chesterfield
8.5 10 reviews

Matlock Holiday Homes Apartment 5

apartment, Matlock
This Matlock town center apartment offers a central location, conveniently close to public transport and 7.7 miles from Chatsworth House.
The 370-square-foot (approximately 34-square-meter) unit features one bedroom, one bathroom, a fully equipped kitchen with a fridge and microwave, a balcony, and sleeps up to three guests.
Stylish Apartment In Great City Location, Parking Possible - West One - Chesterfield
8.9 10 reviews

Stylish Apartment In Great City Location, Parking Possible - West One

apartment, Sheffield
West One apartment, a Sheffield rental located 600 yards from the city center, offers convenient access to Sheffield's attractions, including the Utilita Arena (4 miles away) and Chatsworth House (16 miles away).
This 550-square-foot (approximately 51 square meters) one-bedroom unit sleeps three, features a fully equipped kitchen with a dishwasher and microwave, a private garden, on-site parking, and free Wi-Fi.
Little Fairfield - Chesterfield
9.0 4 reviews

Little Fairfield

apartment, Ashover
This one-bedroom apartment in Ashover is located at Little Fairfield, offering convenient access to Chatsworth House, 11 miles away, and the Utilita Arena Sheffield, 20 miles away.
This 190-square-foot unit accommodates up to two guests and features complimentary on-site parking, free Wi-Fi, a fully equipped kitchenette, and an on-site coffee shop.

Our Favorite Family-Friendly Vacation Rentals in Chesterfield

These family-friendly vacation rentals in Chesterfield offer spacious layouts and easy access to top city attractions.

Bobbin Cottage Retreat In Matlock - Chesterfield
10 1 review

Bobbin Cottage Retreat In Matlock

cottage, Matlock
This Matlock cottage is located on the southeastern edge of the Peak District National Park, offering convenient access to local amenities and outdoor activities, and is just a short distance from the Matlock Bath Cable Car Station and Heights of Abraham Cable Car Station.
This family-friendly rental accommodates up to six guests in three bedrooms and features a sitting room with a woodburning stove, a rear garden with a patio, and roadside parking, making it a suitable base for visiting attractions like Gulliver's Kingdom theme park and the market town of Bakewell.
Cottage ∙ 1 Bedroom ∙ 2 Guests - Chesterfield
No reviews

Cottage ∙ 1 Bedroom ∙ 2 Guests

cottage, Ashover
Little Mill is a first-floor cottage located in Ashover, Derbyshire, by the River Amber, 5 miles from Matlock and close to Chatsworth House and Haddon Hall.
This cottage accommodates 2 guests in 1 bedroom and features a kitchen with a fridge and microwave, an en-suite shower room, a garden, and is pet-friendly with a designated off-lead area.
The Bell Chime, Renovated 3 Bedroom Cottage In Matlock - Chesterfield
9.0 51 reviews

The Bell Chime, Renovated 3 Bedroom Cottage In Matlock

house, Matlock Bank
The Bell Chime, a renovated 1926 cottage in Matlock Bank, Derbyshire, is conveniently located 8.9 miles from Chatsworth House and 22 miles from Buxton Opera House.
This three-bedroom, two-bathroom house offers 1,390 square feet of space, comfortably accommodating up to 11 guests with amenities including free Wi-Fi, a dishwasher, and a private garden; nearby attractions include hiking trails and the Peak District National Park.
Ippleton House - Great Mix Of Town And Country - Chesterfield
9.4 99 reviews

Ippleton House - Great Mix Of Town And Country

apartment
Ippleton House is located on the outskirts of Chesterfield, close to the Peak District National Park, making it a great base for exploring both the historic town and the stunning countryside. This apartment has received excellent ratings for location, cleanliness, and user experience.
This three-bedroom home comfortably sleeps six guests, with a unique layout featuring a bathroom on the ground floor, bedrooms on the first floor, and a large double bedroom in the attic extension. The apartment offers a private garden, parking, internet access, and a fully equipped kitchen including a fridge, freezer, microwave, and dishwasher, making it perfect for a relaxing and enjoyable stay.

Best Chesterfield vacation rentals with parking

Commuters Getaway Chesterfield - Chesterfield
10 2 reviews

Commuters Getaway Chesterfield

house, Chesterfield
House ∙ 1 Bedroom ∙ 2 Guests - Chesterfield
9.4 10 reviews

House ∙ 1 Bedroom ∙ 2 Guests

house, Hollins
2 Bed Lovely Home Close To City Center & Rail Station - Chesterfield
9.3 43 reviews

2 Bed Lovely Home Close To City Center & Rail Station

apartment, Chesterfield
Ling Farm Cottage - Chesterfield
9.8 83 reviews

Ling Farm Cottage

house, Holmewood

Popular Luxury Vacation Rentals in Chesterfield

Experience the best of the city in a luxury vacation rental in Chesterfield, where high-end design meets a prime location.

Modern 3 Bed Home, Chesterfield - Chesterfield
9.2 9 reviews

Modern 3 Bed Home, Chesterfield

apartment, Chesterfield

Top Dog-Friendly Vacation Rentals in Chesterfield

Discover dog-friendly vacation rentals in Chesterfield situated perfectly for city walks and nearby dog parks.

Chatsworth Cottage - Chesterfield
9.9 337 reviews

Chatsworth Cottage

apartment
Cedar Holme - Chesterfield
10 69 reviews

Cedar Holme

house, Chesterfield
Contractor Friendly 3br Sleeps 5 - Chesterfield
10 1 review

Contractor Friendly 3br Sleeps 5

house, Duckmanton
Rent My Spa Home With Pool Table Hottub And Sauna - Chesterfield
9.9 170 reviews

Rent My Spa Home With Pool Table Hottub And Sauna

house, Chesterfield

Top-Rated Vacation Rentals with a Pool in Chesterfield

Choose a vacation rental in Chesterfield with a swimming pool for a proper workout or a leisurely dip right in the heart of the city.

Cottage ∙ 1 Bedroom ∙ 4 Guests - Chesterfield
No reviews

Cottage ∙ 1 Bedroom ∙ 4 Guests

cottage
Cottage ∙ 4 Bedrooms ∙ 8 Guests - Chesterfield
9.3 10 reviews

Cottage ∙ 4 Bedrooms ∙ 8 Guests

cottage
Cottage ∙ 3 Bedrooms ∙ 4 Guests - Chesterfield
9.3 9 reviews

Cottage ∙ 3 Bedrooms ∙ 4 Guests

cottage
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
10 7 reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage, Eckington

Check Out Vacation Rentals with a Hot Tub in Chesterfield

Unwind at the end of a busy city day with a private hot tub at these hand-selected vacation rentals in Chesterfield.

Ty Gambo - Chesterfield
9.5 9 reviews

Ty Gambo

house, Matlock
Moorhay Retreat With Private Hot Tub - Chesterfield
9.3 223 reviews

Moorhay Retreat With Private Hot Tub

apartment
Cottage ∙ 3 Bedrooms ∙ 6 Guests - Chesterfield
No reviews

Cottage ∙ 3 Bedrooms ∙ 6 Guests

cottage
37 Steps - Luxury Retreat Above Matlock Bath - Chesterfield
No reviews

37 Steps - Luxury Retreat Above Matlock Bath

house, Matlock Bank
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