Vacation rentals in Chesterfield

Find and book unique accommodations on Airbnb

Quick stats about vacation rentals in Chesterfield

  • Total vacation rentals

    Explore 130 vacation rentals in Chesterfield

  • Nightly prices starting at

    Chesterfield vacation rentals start at ﺩ.ﺇ 110 per night before taxes and fees

  • Verified guest reviews

    Over 8,120 verified reviews to help you choose

  • Family-friendly vacation rentals

    70 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    120 of Chesterfield vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chesterfield rentals

  • 4.8 Average rating

    Chesterfield stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated vacation rentals in Chesterfield

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
Home in Rowsley
4.98 out of 5 average rating, 304 reviews

Panoramic views, Spring Lambs, Bakewell Chatsworth

The Garden Nook offers complete privacy and is located in a perfect spot for everything. Newly converted and set within 55 acres of impressive private land, gardens, and fruit orchards. A rejuvenating location to unwind and reconnect with nature in such a tranquil environment. The comfy contemporary haven with tasteful decoration, stylish furniture, and spectacular views is the perfect place to relax. Watching lambs skipping around the orchard is a delightful bonus! Tractor experiences available

Top guest favorite
A cosy living room features comfortable seating on two plush sofas, arranged around a central ottoman. A stone fireplace with a woodburner creates a focal point. Exposed beams highlight the ceiling, while the space is adorned with floral cushions and a decorative area rug.
Cottage in Baslow
4.94 out of 5 average rating, 338 reviews

Characterful 2 bed cottage in excellent location

A charming cottage overlooking a babbling, nature-rich brook. Full of character, this peaceful cottage boasts a cosy living room complete with woodburner, underfloor heating and exposed beams, a fabulous kitchen and a stylish bathroom. The cottage is in a superb location with top-class restaurants, the magnificent Chatsworth Estate and truly stunning local walks right on the doorstep. Bikes can be stored in the rear yard making this cottage an ideal base for foodies, cyclists and walkers alike.

Top guest favorite
A spacious lawn leads to a charming stone cottage, surrounded by well-maintained greenery. The bright blue sky and scattered clouds enhance the inviting atmosphere, while the driveway provides access to the property and its scenic surroundings.
Cottage in Derbyshire
5 out of 5 average rating, 279 reviews

Luxury 2 Bedroom Cottage (Sleeps 4) Stunning Views

*AirBnB Best New Host Finalist 2022* A stunning 2 bedroom (Sleeps 4) luxury cottage, nestled in the Peak District countryside, with superb views over Chatsworth House. Outdoor dining, farm animals, private parking (with electric charging) & tranquil walks - all within a short drive of Bakewell, Matlock & the beautiful Derbyshire Dale villages. Fully equipped with everything you will need for your stay, including: Netflix, Amazon Prime & Disney+ BBQ for outdoor dining. Family & Dog Friendly

Top guest favorite
The Tower emerges from a lush green landscape, surrounded by tall trees and manicured grass. The building's robust concrete structure is accented by its original window designs, reflecting the natural beauty of the outdoors in a tranquil setting.
Tower in Bolsover
5 out of 5 average rating, 239 reviews

The Tower

The Tower is the perfect romantic high-end getaway for couples who want to get away from it all in a secluded location and fancy just something different. The Tower has recently been converted for use as a holiday let which was previously an unused ancillary building adjacent to The Water Works, an old water treatment plant near Bolsover, converted to domestic use in 2002 and featured on the Channel 4 programme Grand Designs. Available for single night stays. Discounts on 3+ nights bookings.

Guest favorite
A modern, light-filled living area features a gray sectional sofa adorned with colorful, geometric pillows. A simple wall-mounted shelf is visible on the left, and a front door, partially open, allows natural light to enter the space.
Townhouse in Chesterfield
4.91 out of 5 average rating, 187 reviews

Cheerful 2- Bedroomed Home in Chesterfield.

This beautiful town house is located right on the edge of the Peak District and within walking distance to Chesterfield's iconic Market Town. This 2 bedroomed modern home has everything you need and is the perfect base for visiting all the local attractions Derbyshire has to offer. The locations boasts a 20 min drive to the well loved Peak District. Along with all the wonderful bars, restaurants, gift & coffee shops just a short walk away. Chesterfield's Golf course is just 15min drive away.

Top guest favorite
A stone exterior of the building is highlighted, featuring a prominent navy-blue door framed by two windows. Soft lighting enhances the entrance, surrounded by a neatly landscaped area with low shrubs and pavers leading to the door.
Cottage in Matlock
4.99 out of 5 average rating, 284 reviews

The Kennels

Kick off your walking boots, wash down your bike or just park up the car, this freshly converted kennels is the place to relax for a few days. Peaceful and away from it all but close enough to explore the beauty of the Peak District and Chatsworth House. Matlock is a couple of miles away with restaurants, shops and amenities. You can start exploring from the door step; we can help with guides, directions and recommendations. The room can be configured as a luxury Super King or twin beds.

Guest favorite
A charming two-story cottage is presented with a welcoming façade featuring pale pink and cream walls. A quiet street is visible alongside, with a parking space indicated. Lush trees line the road, enhancing the serene environment of the neighborhood.
Townhouse in Chesterfield
4.87 out of 5 average rating, 114 reviews

Cottage by the Park Chesterfield - Peak district

Our COTTAGE is situated with a PARK on our doorstep and 15 min drive to Baslow in the PEAK DISTRICT . Also within walking distance to Chesterfield town center and Chatsworth road. Only a 15 min walk to bars, restaurants, coffee shops, and local boutique shops on Chatsworth Road. It is a short drive to Chatsworth house, Bakewell, Matlock and many of the delightful areas in the Peak district. Our home is cozy and welcoming! We hope you will choose us for your next visit to the area.

Top guest favorite
A spacious studio is seen, featuring a wooden double bed and a breakfast bar with stools. Comfy chairs are positioned near a large television. Soft carpeted flooring complements the pastel-colored walls, and kitchen appliances are visible in the background, providing functional living space.
Apartment in Chesterfield
4.96 out of 5 average rating, 293 reviews

Cosy studio apartment close to Peak District

Cosy,private ,self contained upstairs studio with own entrance , double bed with en suite, dual ring halogen hob ,combination microwave and oven , television with free sat ,free wifi ,integrated fridge freezer ,breakfast bar and stools . Comfy chairs to relax! On the main bus route into Chesterfield and the Peak District ,10 mins to Chatsworth,20 mins to Bakewell and lots of walks in the area. Many bars ,coffee shops and restaurants within walking distance . We look forward to meeting you.

Guest favorite
A comfortable living area is furnished with a gray sectional sofa and two leather armchairs. A glass coffee table is positioned centrally, and a wooden cabinet stands against the wall, adding storage space. Double doors lead to the outside, allowing natural light to enter.
Home in Chesterfield
4.96 out of 5 average rating, 350 reviews

The Long Hall 2 bed ground floor annexed apartment

Long Hall has been lovingly converted into a 6-person, ground floor, annexed apartment, within a quiet housing estate, a short distance from the Peak District. Two large double bedrooms, with rainfall shower en-suites, and a large open-plan living area dining and kitchen area and a large, shared enclosed patio and garden area Long Hall suits leisure and tourist staycations, as well as trade or professional workers, who wish for a home from home. SKY Sports and Movies included

Top guest favorite
Barn in Holymoorside
4.99 out of 5 average rating, 190 reviews

Charming grade II listed cottage with hot tub

Chander Hill Cottage is a stylish 3-bedroom barn conversion nestled above the village of Holymoorside, on the edge of the Peak District. This cosy cottage is a perfect base for exploring the countryside, with numerous walks from the door and two pubs just a mile away in the village. Relax in our hot tub with stunning views or warm up by the wood burning stove after a winter walk. The enclosed cottage garden has a patio where you can enjoy a BBQ in the summer. Dogs welcome!

Superhost
The living area features a comfortable gray sofa, accompanied by decorative cushions. A light wooden bookshelf holds various books, while a dining table adorned with a vase of roses occupies the foreground. The space is filled with natural light from nearby windows.
Condo in Chesterfield
4.83 out of 5 average rating, 144 reviews

The Corner House A-2 Bedroom Town Centre Apartment

A stylish ground-floor apartment in a beautifully converted 1800s home, recently refurbished to a high standard and exclusively used for Airbnb guests. The property features two double bedrooms, a full bathroom plus a separate toilet, and a fully equipped open-plan kitchen/diner with a sofa bed - perfect for relaxing stays. Within walking distance of Chesterfield town centre and train station, with allocated parking for one car.

Top guest favorite
A modern two-story home features a clean white exterior with large windows and a circular accent window. A wooden fence offers privacy to the front yard, which displays a paved pathway leading to the entrance. The sky is partly cloudy, creating a serene backdrop.
Home in Chesterfield
4.98 out of 5 average rating, 272 reviews

'Rose House' Modern 3 Bedroom Detached House

Located a mile from Chesterfield town centre. The property consists of a large open plan lounge/kitchen, 2 double bedrooms and 1 single room with bunk beds. The garden is south facing and there is private parking. There are a range of bars, cafe's, restaurants and local amenities just a short walk from the property. Chatsworth House, Haddon Hall and Peak District are 15 minutes drive away.

Popular amenities for Chesterfield vacation rentals

When is the best time to visit Chesterfield?

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Avg. priceﺩ.ﺇ 400ﺩ.ﺇ 404ﺩ.ﺇ 430ﺩ.ﺇ 367ﺩ.ﺇ 371ﺩ.ﺇ 371ﺩ.ﺇ 404ﺩ.ﺇ 437ﺩ.ﺇ 382ﺩ.ﺇ 411ﺩ.ﺇ 397ﺩ.ﺇ 404
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Frequently Asked Questions

  • What are the best places to stay in Chesterfield?

    Look for accommodations around the town center, Hasland, or the Brampton area, which have convenient access to shops and local attractions. Neighborhoods near parks may appeal to those seeking a quieter stay.

  • What are the best things to do in Chesterfield with kids?

    Queen’s Park has playgrounds and open spaces, while local museums and swimming pools provide indoor options. Family-friendly events and seasonal activities add variety throughout the year.

  • What are some of the best things to do in Chesterfield?

    Explore outdoor markets, visit the Church of St Mary and All Saints with its iconic spire, and relax in Queen’s Park. The town has museums, cozy cafés, and easy access to countryside trails.

  • How is the weather in Chesterfield?

    Chesterfield experiences cool winters around 35–44°F (2–7°C), and milder summers averaging 54–71°F (12–22°C). Rain is common year-round, so a waterproof jacket is useful most seasons.

  • When is the best time to visit Chesterfield?

    Late spring and summer are often recommended for milder temperatures and longer daylight hours. Autumn brings colorful foliage, while winter is cooler and tends to be wetter.

  • What are the best places to visit in Chesterfield?

    Enjoy the unique Church of St Mary and All Saints, stroll through Queen’s Park, or discover local history at Chesterfield Museum. The outdoor market brings a lively atmosphere on market days.

  • What are some hiking trails in Chesterfield?

    Explore scenic paths in Queen's Park, wander the countryside around the Peak District, or stroll along canal towpaths. These trails provide a blend of nature, parkland, and gentle walking routes.

  • What are some family activities we can do in Chesterfield?

    Explore the play areas in Queen’s Park, visit local museums, or enjoy leisure centers with swimming and sports facilities. Family walks and outdoor events are frequently suggested on weekends.

  • What are some of the best day trip ideas from Chesterfield?

    Visit the countryside around the Peak District, explore historic stately homes, or tour nearby market towns. Nature reserves and heritage attractions are frequently suggested for day excursions.

  • Are there any pet friendly accommodations available in Chesterfield?

    Pet-friendly stays are available in Chesterfield, particularly around residential neighborhoods and near green spaces. Many hosts welcome pets and provide guidance on local dog walks.

  • What are some local tips for visiting Chesterfield?

    Arriving early for market days is frequently suggested, as you’ll find fresh produce and handmade goods. Carrying an umbrella is helpful, and locals often stroll Queen’s Park for relaxation.

  • What is Chesterfield known for?

    Chesterfield is known for its historic crooked church spire, vibrant outdoor markets, and access to the Peak District. The town blends local heritage with countryside appeal.

  • What are the best hidden gems to explore in Chesterfield?

    Wander lesser-known paths around the Chesterfield Canal, discover small galleries, or enjoy tucked-away cafés in Brampton. These spots provide quieter alternatives to main attractions.

  • What are the best foods to try in Chesterfield?

    Chesterfield has traditional pies, locally baked bread, and hearty pub fare. Afternoon tea is frequently suggested, with sweet treats and locally made cakes featured in cafés.

  • What should I bring for a trip to Chesterfield?

    Pack waterproof clothing and comfortable walking shoes, as rain can happen in any season. Layers are useful for changing temperatures, and a camera may help capture historic architecture and scenery.

  • What is the nightlife in Chesterfield like?

    Chesterfield has a mix of traditional pubs, relaxed bars, and venues with live music. The town center and Brampton area are known for welcoming atmospheres and community events.

  • What are the most popular events or festivals in Chesterfield?

    The Chesterfield Market Festival and annual medieval-themed events are often recommended. Seasonal celebrations, including local fairs and arts festivals, mark highlights on the town’s calendar.

  • Are there family friendly vacation rentals in Chesterfield?

    Many rentals in Chesterfield have family-friendly amenities and are located near parks, shopping, or leisure centers. Options often include homes or apartments with spacious layouts.