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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.

Lovely Apartment Above  Cafe Near Peak District - Chesterfield
9.7 289 reviews
Chesterfield
08/21 – 08/23
$157/nighttotal: $314 (2 )

Lovely Apartment Above Cafe Near Peak District

1 2
apartment , Barlow
This apartment is located in Barlow, a charming village on the edge of the Peak District, just a 10-minute drive from Chatsworth House. The apartment enjoys excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. This one-bedroom apartment comfortably accommodates two guests and features a private entrance for added privacy. Enjoy the convenience of a garden, parking, internet, and a self-contained unit with a charming historical setting above a 200-year-old cafe, perfect for a relaxing getaway.
Refurbished Plush Property Great Transport Links - Chesterfield
9.4 284 reviews
Chesterfield
06/26 – 06/28
$364/nighttotal: $728 (2 )

Refurbished Plush Property Great Transport Links

3 4
house , Sheffield
This Sheffield house is located just 3.8 miles from FlyDSA Arena, making it a convenient base for exploring the city and surrounding attractions. With excellent user, location, and cleanliness ratings, you can expect a comfortable and enjoyable stay.
The home has 3 bedrooms and 1 bathroom, comfortably accommodating up to 10 guests. Enjoy amenities like a fully equipped kitchen, a private garden, free parking, and free Wi-Fi, perfect for relaxing and creating lasting memories.
55 M² House ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
Chesterfield
07/07 – 07/08
$220/nightfor 1 night

55 M² House ∙ 2 Bedrooms ∙ 4 Guests

2 1
house , Walton
This Chesterfield, England house rental is conveniently located near Chesterfield Canal (10-minute drive), Queens Park (12-minute drive), and Chatsworth House (15-minute drive), offering easy access to local attractions.
This pet-friendly home boasts 635 square feet of space, featuring two bedrooms, one bathroom, and a fully equipped kitchen, comfortably accommodating up to four guests.
3 Br Bungalow Close To Peak District With Garden - Chesterfield
9.2 5 reviews
Chesterfield
06/26 – 06/28
$414/nighttotal: $828 (2 )

3 Br Bungalow Close To Peak District With Garden

3 4
apartment , South Yorkshire
This Sheffield vacation home, near Endcliffe Park (1.1 miles) and the University of Sheffield (2.5 miles), offers easy access to local attractions like Forge Dam and Whirlowbrook Hall.
This 1180-square-foot (approximately 109 square meters) property features four bedrooms, two bathrooms, accommodates seven guests, and includes a fully equipped kitchen, private garden, and free Wi-Fi.

Best Chesterfield vacation rentals with parking

Modern Cozy Retreat-family-friendly-near City & Peak District - Chesterfield
9.4 204 reviews
Chesterfield
09/03 – 09/06
$178/nighttotal: $534 (3 )

Modern Cozy Retreat-family-friendly-near City & Peak District

3 2
house , Sheffield
This renovated 3-bedroom house is located just a short drive from the FlyDSA Arena and Sheffield Train Station, offering easy access to both entertainment and transportation. The house has received excellent ratings for its cleanliness, location, and overall user experience.
The 970 square foot house can comfortably accommodate up to 10 guests, providing ample space for families or groups of friends. Guests can enjoy a fully equipped kitchen, a private garden, free Wi-Fi, and a picnic area perfect for outdoor relaxation.
3 Bed In Ashover Oc-w30175 - Chesterfield
9.6 5 reviews
Chesterfield
08/21 – 08/23
$265/nighttotal: $530 (2 )

3 Bed In Ashover Oc-w30175

3 2
house , Ashover
The Windmill Granary, a three-bedroom vacation home in Ashover, Derbyshire, is conveniently located 7.9 miles from Chatsworth House and within a 23-mile radius of Buxton Opera House and Clumber Park.
This Ashover rental offers a fully equipped kitchen, free Wi-Fi, on-site parking, a garden, and sleeps up to seven guests, perfect for families or groups visiting the Derbyshire Dales.
Unit 1 Bright & Classy 1-bdr Flat, Fast Wi-fi, Free Parking, Intimate Location - Chesterfield
9.8 5 reviews
Chesterfield
07/07 – 07/08
$164/nightfor 1 night

Unit 1 Bright & Classy 1-bdr Flat, Fast Wi-fi, Free Parking, Intimate Location

1 1
apartment , Sheffield
This Sheffield apartment rental is conveniently located four miles from the FlyDSA Arena, offering easy access to Sheffield's attractions.
The 355-square-foot one-bedroom unit sleeps three guests and features a fully equipped kitchen, private balcony with garden views, free Wi-Fi, and on-site parking.
Modern Town House In Chesterfield & The Peaks - Chesterfield
9.0 4 reviews
Chesterfield
06/27 – 07/25
$207/nighttotal: $5796 (28 )

Modern Town House In Chesterfield & The Peaks

3 1
apartment , Newbold
This 3-bedroom apartment is conveniently located in Newbold, just 14 miles from FlyDSA Arena and 13 miles from Chatsworth House. The apartment is highly rated by guests, receiving excellent scores for location, cleanliness, and overall experience.
This spacious 1190 square foot home comfortably sleeps 6 guests. Guests will enjoy a fully equipped kitchen, a private garden and terrace, free Wi-Fi, and 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.

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.

Luxury Apartment - Great Location - Chesterfield
9.4 70 reviews
Chesterfield
07/07 – 07/08
$185/nightfor 1 night

Luxury Apartment - Great Location

1 1
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.
Springwood Cottage - Chesterfield
9.9 260 reviews
Chesterfield
08/08 – 08/09
$308/nightfor 1 night

Springwood Cottage

1 2
apartment , Holmesfield
Springwood Cottage is located in the peaceful village of Holmesfield, just a short drive from Chatsworth House and FlyDSA Arena. The cottage has received excellent ratings for location, cleanliness, and overall user experience.
This one-bedroom apartment offers 520 square feet of space, comfortably accommodating up to four guests. Enjoy a private terrace, a fully equipped kitchen, free Wi-Fi, and free private parking.
Fairfield Snug - Ashover Village Super King-twin - Chesterfield
9.9 7 reviews
Chesterfield
08/21 – 08/23
$116/nighttotal: $232 (2 )

Fairfield Snug - Ashover Village Super King-twin

1 2
apartment , Ashover
This recently renovated Ashover apartment is located 11 miles from Chatsworth House and 20 miles from Utilita Arena Sheffield.
This 240-square-foot flat accommodates up to three guests and features a private terrace, complimentary on-site parking, and free Wi-Fi, with dedicated bicycle parking and an on-site coffee shop available.
The Watchmakers Matlock - Chesterfield
9.6 448 reviews
Chesterfield
07/07 – 07/08
$197/nightfor 1 night

The Watchmakers Matlock

1 1
apartment , Matlock
The Watchmakers Matlock apartment is located in Matlock, Derbyshire, England, 8.5 miles from Chatsworth House and 21 miles from Buxton Opera House, offering easy access to Peak District attractions.
This one-bedroom unit, boasting 280 square feet of space, includes a fully equipped kitchen, free Wi-Fi, private parking, a terrace, and a garden, perfect for a relaxing getaway.

Best Chesterfield vacation rentals with air conditioning

The Urban Residence - Sheffield 6br Group-family Stay - Sleeps 12 - Chesterfield
Chesterfield
09/03 – 09/06
$618/nighttotal: $1854 (3 )

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

6 2
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.
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.
Superb 3 Bed House, Homely Comforts Close To Supermarkets, With Private Parking On Gated Premise - Chesterfield
9.0 8 reviews
Chesterfield
08/21 – 08/23
$1499/nighttotal: $2998 (2 )

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

3 2
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.
Lv8 Chesterfield - Chesterfield
Chesterfield
07/02 – 07/06
$398/nighttotal: $1592 (4 )

Lv8 Chesterfield

1 1
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.
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