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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.

Spire Haven - Chesterfield
9.9 22 reviews

Spire Haven

house, Chesterfield
Spire Haven is a vacation home located in Chesterfield, just a short drive from Chatsworth House, Utilita Arena Sheffield, and Clumber Park. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The home features four bedrooms and two bathrooms, with a total floor area of 1560 square feet. It offers a fully equipped kitchen, a comfortable seating area, a TV, a garden, free parking, and Wi-Fi, along with nearby opportunities for golfing and cycling.
Lv8 Chesterfield - Chesterfield
10 1 review

Lv8 Chesterfield

apartment
This unique dungeon-themed apartment is centrally located in Chesterfield, Great Britain, just a short walk from shops, restaurants, and the famous Crooked Spire.
This designer flat accommodates two guests with one bedroom and one bathroom, offering air conditioning and internet, and is an ideal escape for couples seeking a memorable getaway.
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.
The Corner House - Modern Chesterfield Town Centre Apartments - Chesterfield
9.4 194 reviews

The Corner House - Modern Chesterfield Town Centre Apartments

apartment, Chesterfield
The Corner House apartment complex is located in Chesterfield town center, just a short drive from Chatsworth House, FlyDSA Arena, and Clumber Park. The apartments have consistently received excellent ratings for cleanliness, location, and overall user experience.
These modern apartments are equipped with everything you need for a comfortable stay, including a fully equipped kitchen, flat-screen TV, and complimentary Wi-Fi. Enjoy the convenience of on-site parking and explore the surrounding area with ease.

Best Chesterfield vacation rentals with air conditioning

Affordable 1br Flat By Ankers Short Term Lets Matlock Bath With Exclusive Summer Savings - Chesterfield
9.1 12 reviews

Affordable 1br Flat By Ankers Short Term Lets Matlock Bath With Exclusive Summer Savings

apartment, Matlock Bank
This Matlock Bank apartment rental is conveniently located near Chatsworth House (8.7 miles), Alton Towers (20 miles), and Buxton Opera House (21 miles), offering easy access to popular attractions.
The one-bedroom unit sleeps six guests comfortably in king-size beds and features free Wi-Fi, a fully equipped kitchen, air conditioning, parking, and a flat-screen TV.
Hip Hideaway In The Trendiest Part Of Town - Chesterfield
9.7 6 reviews

Hip Hideaway In The Trendiest Part Of Town

house, Nether Edge
This 2-bedroom vacation home in Nether Edge offers free WiFi and parking, located 4.8 miles from Utilita Arena Sheffield and 13 miles from Chatsworth House.
This allergy-free residence accommodates up to 6 guests with a kitchen featuring an oven and microwave, air conditioning, and a terrace with city views.
Spacious 4 Bed Home For Families & Contractors. - Chesterfield
10 1 review

Spacious 4 Bed Home For Families & Contractors.

house, Sheffield
This 4-bedroom house in Sheffield offers a convenient location with easy access to local amenities.
This spacious 1130-square-foot residence accommodates up to 12 guests and features air conditioning, a full kitchen with a dishwasher and microwave, complimentary Wi-Fi, and private parking.
Superb 3 Bed House, Homely Comforts Close To Supermarkets, With Private Parking On Gated Premise - Chesterfield
9.0 8 reviews

Superb 3 Bed House, Homely Comforts Close To Supermarkets, With Private Parking On Gated Premise

house, Sheffield
This 3-bedroom house is located in Sheffield, just 2.5 miles from the FlyDSA Arena, offering easy access to the city center and its attractions. The house has received excellent ratings for user experience, location, and cleanliness.
The home has 1610 square feet of space and can accommodate up to 5 guests. Guests can enjoy features like air conditioning, a fully equipped kitchen, a private garden, and free parking on the premises.

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.

Springwood Barn No1 Forest - Chesterfield
9.9 9 reviews

Springwood Barn No1 Forest

house, Holmesfield
Springwood Barn No. 1, a Holmesfield house rental, is located 9.4 miles from Chatsworth House and 10 miles from the FlyDSA Arena.
This 680-square-foot (approximately 63 square meter) property boasts one bedroom, two bathrooms, and accommodates up to seven guests, featuring a private garden, free parking, Wi-Fi, and a fully equipped kitchen.
1885 The Retreat - Chesterfield
9.1 19 reviews

1885 The Retreat

apartment, Matlock
This recently renovated 1885 historic apartment in Matlock offers convenient access to regional attractions, located 7.5 miles from Chatsworth House and 22 miles from Alton Towers, with East Midlands Airport 30 miles away.
This 380 sq ft flat accommodates up to 5 guests, features a private terrace, complimentary WiFi, a fully equipped kitchen, and allows pets, all within a non-smoking environment.
Kspace @ The Point - Chesterfield
9.2 1800 reviews

Kspace @ The Point

apartment, Sheffield
This Sheffield apartment is conveniently located in the city center, just a short walk from the City Hall and Crucible Theatre, and less than a mile from the train station. Guests have consistently rated this apartment as excellent for location, cleanliness, and overall experience.
The apartment has one bedroom and one bathroom, comfortably accommodating up to two guests. The apartment features modern amenities, including a kitchen with a fridge, microwave oven, and dishwasher, as well as a terrace or balcony, perfect for enjoying the city views.
Derbyshire Holiday Cottages - Chesterfield
9.5 146 reviews

Derbyshire Holiday Cottages

house, Holmesfield
This Derbyshire Holiday Cottage is located in Holmesfield, Derbyshire, just 9 miles from Chatsworth House and 11 miles from the Sheffield Arena.
The two-bedroom home comfortably sleeps 7 guests and offers a fully-equipped kitchen, a terrace, a garden, free Wi-Fi, and free private parking.

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.

The Loft - Chesterfield
9.0 105 reviews

The Loft

house, Dronfield
The Loft is located in a quiet area of Dronfield, just 11 km from Chatsworth House and within easy reach of other attractions like FlyDSA Arena, Buxton Opera House, and Clumber Park. The house has received excellent ratings for its location, cleanliness, and overall user experience.
The three-bedroom home spans 1400 square feet and offers a variety of amenities for a comfortable stay. Guests can enjoy a swimming pool, jacuzzi, sauna, spa, fitness center, and a garden, along with free parking and Wi-Fi.
2 Bed House - Near Central Sheffield - Fast Wi-fi - Chesterfield
10 3 reviews

2 Bed House - Near Central Sheffield - Fast Wi-fi

apartment, Sheffield
This 2-bedroom house is located near central Sheffield, offering convenient access to the Utilita Arena Sheffield (2.9 miles) and other regional attractions.
This family-friendly apartment offers 2 bedrooms, 1 bathroom, and sleeps up to 5 guests, featuring free Wi-Fi, a fully equipped kitchen, and free private parking.
75 M² House ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
No reviews

75 M² House ∙ 2 Bedrooms ∙ 4 Guests

house, Bolsover
Castle View, a newly renovated house in Bolsover, offers convenient access to the M1 motorway (Junction 29a, 5 minutes away).
This 890-square-foot home features two bedrooms, one bathroom, and sleeps four, boasting an open-plan layout, a fully equipped kitchen with new appliances, smart home technology (Google Nest and Hive), and a garden with ample on-street parking.
Ashover Cottage - Chesterfield
8.7 26 reviews

Ashover Cottage

apartment
Beeley Cottage sits on the edge of the Darwin Lake holiday village, close to Matlock and the Peak District National Park. The apartment receives excellent location ratings and very good user ratings, with cleanliness rated as good.
The 3-bedroom, 3-bathroom home can comfortably accommodate up to 6 guests. Beeley Cottage offers a range of amenities, including a well-equipped kitchen, flexible sleeping arrangements, ensuite bathrooms, a ground floor bedroom, and access to the Darwin Lake holiday village's activities and amenities.

Best Chesterfield vacation rentals with parking

Excellent Studio Balcony Apartment In Sheffield - Chesterfield
9.2 104 reviews

Excellent Studio Balcony Apartment In Sheffield

studio, Sheffield
Lovely House Eckington Sheffield - Chesterfield
9.8 121 reviews

Lovely House Eckington Sheffield

apartment
Prime Serviced Apartments Sheffield Center - Chesterfield
9.2 213 reviews

Prime Serviced Apartments Sheffield Center

studio, Sheffield
Little Hive-uk39430 - Chesterfield
9.8 31 reviews

Little Hive-uk39430

house, Dronfield

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.

Chatsworth Stables - Chesterfield
9.4 104 reviews

Chatsworth Stables

house, Newbold

Top Dog-Friendly Vacation Rentals in Chesterfield

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

Cottage-sdb Privée Avec Douche-the Olde Coach Hous - Chesterfield
9.9 109 reviews

Cottage-sdb Privée Avec Douche-the Olde Coach Hous

cottage
2 Bed Apartment In Chesterfield With Free Parking - Sleeps Upto 5 - Perfect For Workers & Professionals - Hosted By Stayhostsave - Chesterfield
9.0 2 reviews

2 Bed Apartment In Chesterfield With Free Parking - Sleeps Upto 5 - Perfect For Workers & Professionals - Hosted By Stayhostsave

apartment, Chesterfield
Little Manor - Chesterfield
8.3 57 reviews

Little Manor

house, Chesterfield
Middlecroft - Chesterfield
8.6 143 reviews

Middlecroft

apartment, 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.

The Loft, Pet Friendly, Character Holiday Cottage In Millthorpe - Chesterfield
8.0 1 review

The Loft, Pet Friendly, Character Holiday Cottage In Millthorpe

cottage, Dronfield
Blue Lagoon Retreat Escape Free Parking 14ppl - Chesterfield
9.7 3 reviews

Blue Lagoon Retreat Escape Free Parking 14ppl

house, Sheffield
Green Haven Sheffield 2 Bath Parking 14ppl - Chesterfield
10 1 review

Green Haven Sheffield 2 Bath Parking 14ppl

house, Nether Edge
Habberjam Farm: Swimming Pool, Sauna, Hot Tub - Chesterfield
10 41 reviews

Habberjam Farm: Swimming Pool, Sauna, Hot Tub

gîte

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.

Spa Home With Hottub And Sauna - Chesterfield
No reviews

Spa Home With Hottub And Sauna

house, Chesterfield
Beautiful Stone Barn With Hot Tub On A Quiet Farm - Chesterfield
10 1 review

Beautiful Stone Barn With Hot Tub On A Quiet Farm

house, Eckington
Cherry Tree Farm, Family Friendly, With Hot Tub In Chesterfield - Chesterfield
No reviews

Cherry Tree Farm, Family Friendly, With Hot Tub In Chesterfield

apartment, Chesterfield
The House @ Sitwell Arms Hotel - Chesterfield
8.7 8 reviews

The House @ Sitwell Arms Hotel

house, Renishaw