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Chesterfield vacation rentals
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Best Vacation rentals and Airbnb offers in Chesterfield

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.

Bolsover Castle View - Chesterfield
8.8 83 reviews
Chesterfield
08/08 – 08/09
$134/nightfor 1 night

Bolsover Castle View

2 2
apartment , Bolsover
Bolsover Castle View, a two-bedroom apartment in Bolsover, Derbyshire, offers easy access to Bolsover Castle and is within a 13-18 mile radius of Clumber Park, Sherwood Forest, and Chatsworth House.
This 860-square-foot rental features a fully equipped kitchen, free Wi-Fi, a garden, parking, and accommodates up to seven guests with amenities including a washing machine and baby safety gate.
House ∙ 3 Bedrooms ∙ 6 Guests - Chesterfield
9.7 10 reviews
Chesterfield
07/02 – 07/06
$254/nighttotal: $1016 (4 )

House ∙ 3 Bedrooms ∙ 6 Guests

3 1
house , Hundall
Ellencroft is a peaceful cottage located in the Peak District, a short drive from Chatsworth House and Haddon Hall, with Bolsover Castle and Hardwick Hall also nearby, situated 750 yards from the nearest pub in Hundall.
This family-friendly house sleeps six guests in three bedrooms and features a well-equipped kitchen with a microwave and dishwasher, a lounge with WiFi, extensive gardens, and parking for up to four cars.
The Rumblings 3, Barlow - Chesterfield
Chesterfield
07/04 – 07/08
$127/nighttotal: $508 (4 )

The Rumblings 3, Barlow

1 1
apartment , Dronfield
This end-of-terrace cottage is located one mile from Barlow village, near Chesterfield, providing a base for exploring the Peak District and attractions like Chatsworth House and Sheffield City Hall.
This family-friendly rental accommodates up to five guests with one bedroom and one bathroom, featuring a playroom, a woodburner, and off-road parking for one vehicle.
Meersbrook Luxury Duplex Apartment - Chesterfield
9.1 137 reviews
Chesterfield
07/04 – 07/08
$126/nighttotal: $504 (4 )

Meersbrook Luxury Duplex Apartment

1 1
apartment , Sheffield
The Meersbrook Luxury Duplex Apartment is located in the Meersbrook district of Sheffield, just 39km from both Clumber Park and Cusworth Hall, offering easy access to both attractions and the beautiful green spaces of Sheffield. The apartment has received excellent ratings for cleanliness, location, and overall experience.
The duplex apartment offers 600 square feet of space, perfect for a family or group of up to four guests. The apartment includes a private garden, terrace, free Wi-Fi, a modern kitchen with a fridge, freezer, and microwave, and a comfortable living area.

Best Chesterfield vacation rentals with parking

Corner Studio Apartment In Sheffield - Chesterfield
9.0 65 reviews
Chesterfield
07/04 – 07/08
$83/nighttotal: $332 (4 )

Corner Studio Apartment In Sheffield

1 1
studio , Sheffield
This Sheffield studio apartment is conveniently located near the Utilita Arena, approximately 2.4 miles away, offering easy access to major attractions like Chatsworth House (14 miles) and Cusworth Hall (24 miles).
The self-catering unit features a kitchenette with a microwave and toaster, accommodates up to three guests, includes free parking and Wi-Fi, and boasts excellent cleanliness and location ratings.
Tapton View - Modern Stay Near Chesterfield Town Center, Train Station & The Peak District - Chesterfield
9.3 11 reviews
Chesterfield
07/04 – 07/08
$185/nighttotal: $740 (4 )

Tapton View - Modern Stay Near Chesterfield Town Center, Train Station & The Peak District

2 1
house , Brimington
Tapton View, a modern vacation home in Brimington, Derbyshire, England, offers easy access to Chesterfield town center, the train station, and the Peak District National Park, with Chatsworth House approximately 14 miles and FlyDSA Arena about 15 miles away.
This 600-square-foot rental property features two bedrooms, one bathroom, and accommodates up to 11 guests, boasting amenities such as free Wi-Fi, free parking, a fully equipped kitchen, and a sun terrace.
2 Bed Apartment In Chesterfield With Free Parking - Sleeps Upto 5 - Perfect For Workers & Professionals - Hosted By Stayhostsave - Chesterfield
9.0 2 reviews
Chesterfield
08/21 – 08/23
$204/nighttotal: $408 (2 )

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

2 2
apartment , Chesterfield
This 2-bedroom, 2-bathroom flat in Chesterfield offers a convenient location in a district with easy access to local attractions.
This pet-friendly apartment accommodates up to 9 guests and includes complimentary high-speed Wi-Fi, a fully equipped kitchen, and a flat-screen TV, ideal for a peaceful, non-smoking stay prohibiting parties.
The Gatehouse-uk11836 - Chesterfield
8.9 11 reviews
Chesterfield
06/26 – 06/28
$308/nighttotal: $616 (2 )

The Gatehouse-uk11836

2 2
house , Dronfield
The Gatehouse-uk11836 is a vacation home located in Dronfield, just 8.8 miles from FlyDSA Arena and within easy reach of other attractions like Chatsworth House and Clumber Park. The home has earned excellent ratings for its location, cleanliness, and overall experience.
The vacation rental has two bedrooms and can accommodate up to four guests. It offers a fully equipped kitchen, a private garden, free parking, and free Wi-Fi, making it a comfortable and convenient option for families or groups of friends.

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.

Destinations nearby

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.

Stay Angels - Hidden Gem - Chesterfield
8.4 24 reviews
Chesterfield
08/08 – 08/09
$253/nightfor 1 night

Stay Angels - Hidden Gem

1 2
apartment , Nether Edge
This Nether Edge apartment rental is conveniently located approximately 5.1 miles from the Utilita Arena Sheffield and 14 miles from Chatsworth House.
The 540-square-foot (50-square-meter) unit features one bedroom, one bathroom, and accommodates up to five guests, offering a private garden, free parking, and a fully equipped kitchen with a dishwasher and microwave.
Matlock Town Centre Flat Near Transport Links - Chesterfield
8.6 6 reviews
Chesterfield
08/21 – 08/23
$167/nighttotal: $334 (2 )

Matlock Town Centre Flat Near Transport Links

1 2
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.
Park House Studio - Chesterfield
9.0 203 reviews
Chesterfield
08/21 – 08/23
$159/nighttotal: $318 (2 )

Park House Studio

1 2
studio , Matlock
Park House Studio, a Derbyshire apartment rental in Matlock, is conveniently located 9 miles from Chatsworth House and 22 miles from Buxton Opera House.
This 270-square-foot (approximately 25-square-meter) studio apartment in Matlock sleeps two guests and features a fully equipped kitchen with a dishwasher, a private terrace, free parking, and free Wi-Fi.
Little Manor - Chesterfield
8.5 52 reviews
Chesterfield
07/05 – 07/09
$119/nighttotal: $476 (4 )

Little Manor

2 1
house , Chesterfield
Little Manor is located in Chesterfield, just 14 miles from Chatsworth House and 15 miles from Utilita Arena Sheffield, making it a great base for exploring the area. The house receives very good ratings for location, cleanliness, and user experience.
This two-bedroom home can comfortably accommodate up to 10 guests. Little Manor offers a garden, patio, outdoor dining area, picnic area, free parking, and free Wi-Fi, ensuring a comfortable and enjoyable stay.

Best Chesterfield vacation rentals with air conditioning

The Stables East Lodge Country House - Chesterfield
8.1 17 reviews
Chesterfield
07/02 – 07/06
$442/nighttotal: $1768 (4 )

The Stables East Lodge Country House

3 1
house , Great Rowsley
This three-bedroom house in Great Rowsley, Peak District, is 3.8 miles from Chatsworth House and offers easy access to other attractions like Buxton Opera House.
The 3,900-square-foot home features three bathrooms, sleeps up to 13 guests, includes a fully equipped kitchen, air conditioning, a patio, a garden, free Wi-Fi, and free private parking.
Exceptional 3 Bed House With Homely Comforts, Close To Fast Food, Supermarkets And City Centre - Chesterfield
9.2 25 reviews
Chesterfield
07/02 – 07/06
$444/nighttotal: $1776 (4 )

Exceptional 3 Bed House With Homely Comforts, Close To Fast Food, Supermarkets And City Centre

3 1
apartment , Sheffield
This 3-bedroom apartment is located just a short distance from the city center, offering easy access to Sheffield Train Station and popular attractions like FlyDSA Arena. It's also conveniently close to fast food restaurants and a supermarket for your convenience. The apartment has consistently received excellent ratings from guests for its cleanliness, location, and overall experience.
This spacious 1130 square foot apartment features a fully equipped kitchen, a washing machine, and free Wi-Fi. Enjoy the garden, free parking, and private check-in/check-out for a relaxing and comfortable stay.
Small 1 Bed Apartment - Free Parking!!! - Chesterfield
8.8 12 reviews
Chesterfield
08/21 – 08/23
$141/nighttotal: $282 (2 )

Small 1 Bed Apartment - Free Parking!!!

1 2
apartment , Victoria
This Victoria apartment rental is conveniently located off City Road, approximately 3.4 miles from the FlyDSA Arena and within a 20-30 mile radius of other attractions.
This 320-square-foot unit features one bedroom, one bathroom, and accommodates up to five guests, offering free WiFi, private parking, and a fully equipped kitchen including an oven, microwave, and coffee maker.
Superb 3 Bed House, Homely Comforts Close To Supermarkets, With Private Parking On Gated Premise - Chesterfield
9.0 8 reviews
Chesterfield
07/04 – 07/08
$375/nighttotal: $1500 (4 )

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

3 1
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.
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