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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 23 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.
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.
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.
The Corner House - Modern Chesterfield Town Centre Apartments - Chesterfield
9.5 192 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

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.
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.
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.
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.

Sheffield City Centre Apartment & Balcony - Chesterfield
9.7 201 reviews

Sheffield City Centre Apartment & Balcony

apartment, Sheffield
This Sheffield city center apartment, located within 700 yards of the city center and 4 miles from the Utilita Arena, offers easy access to Sheffield's attractions.
This 580-square-foot (approximately 54 square meters) two-bedroom, one-bathroom unit sleeps four and includes a private balcony, free Wi-Fi, on-site parking, and a fitness center.
1 Coach House Mews - Matlock Bath - Chesterfield
9.7 219 reviews

1 Coach House Mews - Matlock Bath

apartment, Matlock Bank
This apartment is located in Matlock Bank, a quiet area just a short drive from attractions like Chatsworth House and Buxton Opera House. It has excellent ratings for location, cleanliness, and user experience. This two-bedroom apartment offers 750 square feet of space and can comfortably accommodate up to four guests. Amenities include a fully equipped kitchen, a private patio, a garden, parking, and free Wi-Fi, ensuring a comfortable and enjoyable stay.
Lavender Cottage - Chesterfield
9.4 52 reviews

Lavender Cottage

house, Holmesfield
Lavender Cottage, a one-bedroom house in Holmesfield, Derbyshire, is conveniently located 7 miles from Chatsworth House and 12 miles from the FlyDSA Arena.
This Holmesfield vacation rental sleeps four, features a fully equipped kitchen with a dishwasher and microwave, free Wi-Fi, and private parking, and offers a peaceful retreat near Buxton Opera House, Clumber Park, and the Eco-Power Stadium.
Luxury Apartment - Great Location - Chesterfield
8.9 76 reviews

Luxury Apartment - Great Location

apartment, Ecclesall
This Ecclesall apartment rental is conveniently located six miles from the Utilita Arena Sheffield and fourteen miles from Chatsworth House.
The 910-square-foot (84.5-square-meter) one-bedroom, one-bathroom unit sleeps three guests and boasts a fully equipped kitchen, terrace, free parking, and free Wi-Fi.

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.

Spire Haven - Chesterfield
9.9 26 reviews

Spire Haven

apartment
Spire Haven is a pet-free, non-smoking apartment in Chesterfield, Derbyshire, just a short walk from a local shop and pub. The apartment has excellent user, location, and cleanliness ratings, making it a great choice for travelers.
The apartment comfortably sleeps eight guests in four bedrooms and two bathrooms. Spire Haven offers modern appliances, a private garden, and convenient parking for three cars, making it a perfect base for exploring Derbyshire.
The Old Hayloft-uk39431 - Chesterfield
10 5 reviews

The Old Hayloft-uk39431

cottage, Dronfield
This Dronfield apartment, a first-floor unit in a converted barn on a 40-acre estate near the Peak District National Park, offers easy access to Sheffield and Chesterfield.
The one-bedroom, one-bathroom rental sleeps two, features a fully equipped kitchen with a dishwasher, free Wi-Fi, and provides parking for two cars; a travel cot, highchair, and stairgate are available.
Wasp Nest Cottage, Peak District - Chesterfield
9.9 346 reviews

Wasp Nest Cottage, Peak District

apartment
This charming 19th-century cottage sits on the edge of the Peak District, just a short walk from open fields, woodland, and moors, with two pubs, a shop, and Chatsworth House a scenic 7-mile stroll away. This cozy abode has received excellent ratings for its location, cleanliness, and overall experience.
The cottage features two bedrooms, one bathroom, and can accommodate up to four guests. Guests can enjoy a fully equipped kitchen, a conservatory space, a private garden patio, and the option to light a fire for added warmth.
Unit 5 Comfortable 1-br Apartment, For 3, Parking, Near Bramall Lane, Unlimited Wi-fi - Chesterfield
9.5 2 reviews

Unit 5 Comfortable 1-br Apartment, For 3, Parking, Near Bramall Lane, Unlimited Wi-fi

apartment, Sheffield
This 1-bedroom flat in Sheffield is located 3.7 miles from the Utilita Arena Sheffield and 14 miles from Chatsworth House.
This family-friendly apartment offers 140 square feet of space, accommodates up to 5 guests, and includes a fully equipped kitchen with a dishwasher, microwave, and fridge, plus free WiFi, on-site parking, a private garden, and a washing machine.

Best Chesterfield vacation rentals with parking

All Inn Mews 1 - Home Crowd - Chesterfield
9.7 6 reviews

All Inn Mews 1 - Home Crowd

apartment
Thorntree Lodge - Chesterfield
9.5 2 reviews

Thorntree Lodge

house, Ashover
The Corner House - Modern Chesterfield Town Centre Apartments - Chesterfield
No reviews

The Corner House - Modern Chesterfield Town Centre Apartments

apartment, Chesterfield
The Painted Terrace - Peaceful Home In Calow Near The Royal Hospital - Chesterfield
No reviews

The Painted Terrace - Peaceful Home In Calow Near The Royal Hospital

house, Chesterfield

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.

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

Top Dog-Friendly Vacation Rentals in Chesterfield

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

2 Bedroom Lux House In Sheffield - Chesterfield
No reviews

2 Bedroom Lux House In Sheffield

apartment, Woodseats
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
2 Bedroom Accommodation In Kelstedge, Near Matlock - Chesterfield
9.0 4 reviews

2 Bedroom Accommodation In Kelstedge, Near Matlock

cottage, Kelstedge, near Matlock
Blue Lagoon Retreat Escape Free Parking 14ppl - Chesterfield
9.7 3 reviews

Blue Lagoon Retreat Escape Free Parking 14ppl

house, Sheffield

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 ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
10 7 reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage, Eckington
215 M² House ∙ 7 Bedrooms ∙ 20 Guests - Chesterfield
9.5 11 reviews

215 M² House ∙ 7 Bedrooms ∙ 20 Guests

house
Central Blue Haven Retreat Free Parking 8ppl! - Chesterfield
9.0 19 reviews

Central Blue Haven Retreat Free Parking 8ppl!

apartment, Victoria
Cottage ∙ 4 Bedrooms ∙ 8 Guests - Chesterfield
No reviews

Cottage ∙ 4 Bedrooms ∙ 8 Guests

cottage

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.

The Olde Coach House - Chesterfield
9.4 12 reviews

The Olde Coach House

house, Chesterfield
Stunning Barn With Hot Tub On Secluded Farm - Chesterfield
10 14 reviews

Stunning Barn With Hot Tub On Secluded Farm

gîte
The Bungalow - Chesterfield
No reviews

The Bungalow

house, Matlock
Wigley Farm House Cottage - Chesterfield
9.3 3 reviews

Wigley Farm House Cottage

house, Chesterfield
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