Pet-friendly holiday rentals in Chesterfield

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Top-rated pet-friendly home rentals in Chesterfield

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Top Guest favourite
A traditional stone barn conversion is visible, showcasing a well-maintained exterior with multiple windows and doors. The surrounding gravel driveway leads to a serene countryside setting, highlighted by greenery in the background and a clear blue sky above.
Condo in Holymoorside
4.98 out of 5 average rating, 207 reviews

Dog Friendly, Cosy, Peaceful, Walks, Peak District

The Spinney is our super dog-friendly ground floor self-catering accommodation! We've designed it so that you & your dog have a great holiday! Part of a traditional stone barn conversion located in the Peak District & Derbyshire Dales, the Spinney offers space as well as the comfort of modern living. With cosy underfloor heating throughout, and everything you need for you and your furry friend, we are sure you will have a great time here! Peaceful setting, close to popular visitor attractions!

Top Guest favourite
The living room features a cozy arrangement with a soft beige sofa and armchair, adorned with floral cushions. A low coffee table sits in front of a fireplace, while patterned curtains frame a bright window. A small TV is mounted on the wall above the fireplace.
Cottage in Chesterfield
4.92 out of 5 average rating, 314 reviews

Chatsworth Cottage

Situated on the edge of the Peak District Park, this is the ideal base for exploring Derbyshire. The Cottage is situated on Chatsworth Road just 10 minutes drive from the ‘Palace of the Peak District’. A short journey and you will discover other wonders of the Peak at places like Matlock, Bakewell, Castleton and Buxton. The historic market town of Chesterfield and the famous Crooked Spire is just a 20 minute walk down the Brampton Mile where you will find some great places to shop, eat & drink.

Guest favourite
The exterior of the stone cottage is featured, showcasing its classic design with multiple windows and a welcoming entrance. Hanging flower baskets add a touch of greenery, while the surrounding landscape displays lush grassland and rolling hills in the distance.
Home in Derbyshire
4.87 out of 5 average rating, 377 reviews

Runner Duck Cottage

A bright and airy cottage, comprising of two open plan rooms, a separate shower/WC. The kitchen area is equipped with hob, oven, fridge & microwave. In the downstairs lounge area there is a double pull out sofa bed, TV /DVD. Upstairs there is a king size bed & adjoining shower room/WC. Gas central heating. All bed linen, towels, and a welcome pack are provided. A charming little cottage for up to 4 people. Well behaved dogs are welcome. Immediate access to miles of footpaths & stunning views.

Top Guest favourite
A cozy sitting area features a blue armchair with decorative pillow. A wooden mantel surrounds a small fireplace, flanked by two lamps providing soft illumination. Artwork adorns the walls, and a vintage trunk adds character to the space.
Cottage in Holymoorside
4.98 out of 5 average rating, 326 reviews

Wasp Nest Cottage, Peak District

Sitting on the edge of the Peak District, a stone’s throw from open fields, woodland and moors - sits a 19th Century cosy mill worker’s cottage. Two pubs and a shop are within easy walking distance and Chatsworth House is a beautiful 7 mile wander over the hill. Marvel at the lovely centuries old tree slice, coffee table and huge slice of elm breakfast bar, enjoy chopping boards, pottery and soft furnishings from the local artisans - just some of the magic the Peak District has to offer.

Top Guest favourite
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, 244 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.

Top Guest favourite
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, 288 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 favourite
A wooden entrance door is framed by large planters filled with vibrant flowers and lush greenery. The glass panels of the door are partially frosted, allowing light to filter through. The surrounding area is adorned with hanging baskets overflowing with colorful blooms.
Condo in Dronfield
4.82 out of 5 average rating, 258 reviews

Exclusive & Beautiful Modern Studio Flat

Located on Green Lane, traffic is busy at peak times of the day, however this private studio is perfect for access to the Peak District. There is a kitchen, a spacious bathroom, pull-down double bed (only a small 4 ft double). The flat is best suited for a single person but if you are in a couple and the bed is ok, then this will suit you. The Peak district is just a short car ride away. Restaurants, supermarkets; train station and buses will take you to Sheffield or chesterfield.

Guest favourite
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, 342 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 favourite
The exterior of a stone cottage is displayed against a clear blue sky. Large windows allow light to illuminate the façade, and a set of stone steps leads up to the entrance. Nearby trees provide a natural backdrop, enhancing the overall rustic charm.
Barn in Holymoorside
4.99 out of 5 average rating, 157 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!

Top Guest favourite
Guest suite in Ashover
4.98 out of 5 average rating, 365 reviews

Cosy self contained studio - Peak District

Set in the glorious Peak District in a rural and peaceful location is our lovely self contained studio. Glorious views and walks over rolling countryside. Close to Chatsworth House and Haddon Hall. With the popular wedding venue (Peak Edge Hotel ) within walking distance and the beautiful market towns of Bakewell, Matlock and Chesterfield (with its famous crooked spire) close by you can easily explore the Peak District from here. Perfect for the Chatsworth Christmas market.

Top Guest favourite
The exterior of the cottage features a blend of rustic brick and wooden elements, with a welcoming entrance and landscaped planters. The path is bordered by well-kept greenery, leading toward the charming structure under a partly cloudy sky.
Cottage in Totley
4.99 out of 5 average rating, 260 reviews

Luxury Peak District Cottage with Hot Tub

The Old Stable Block at Bank View Farm has recently been converted into an elegant self-catering holiday cottage with its own private hot tub in a beautiful courtyard garden. The cottage is set in the wonderful landscaped grounds and gardens of bank view farm next to the orchard with its geese and giant tortoises. Set on the edge of the peak district moors with pubs on your doorstep, this is the perfect location for an idyllic rural retreat.

Top Guest favourite
A spacious interior features a warm wood-burning stove adjacent to a comfortable sleeping area. Two inviting armchairs are placed upon a soft area rug. Natural light streams in through the skylight and window, illuminating the simple, yet elegant decor.
Barn in Ashover
5 out of 5 average rating, 117 reviews

Beautiful barn conversion.

Reconnect with nature at this unforgettable escape on the edge of the Peak District. Beautifully finished barn conversion. King sized bed, tv with full Sky package. Log burner. Bathroom with freestanding bath and separate shower. Fully equipped kitchen. Outside seating/bbq area. Village and pubs within walking distance. Fantastic walking area. Stunning views. Plenty of parking.

Popular amenities for Chesterfield pet-friendly home rentals

When is the best time to visit Chesterfield?

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Avg. price$179 NZD$177 NZD$180 NZD$187 NZD$190 NZD$197 NZD$212 NZD$221 NZD$199 NZD$200 NZD$189 NZD$199 NZD
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Quick stats about holiday rentals that are pet-friendly in Chesterfield

  • Total holiday rentals

    Explore 40 holiday rentals in Chesterfield

  • Nightly prices starting at

    Chesterfield holiday rentals start at $51 NZD per night before taxes and fees

  • Verified guest reviews

    Over 3,040 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    40 of Chesterfield holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chesterfield rentals

  • 4.9 Average rating

    Chesterfield stays are highly rated by guests – averaging 4.9 out of 5!