Pet-friendly holiday rentals in Chesterfield

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Chesterfield

Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.

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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.
Apartment in Holymoorside
4.98 out of 5 average rating, 188 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!

Guest favourite
The image presents a modern kitchen featuring sleek cabinetry and essential appliances. A cozy lounge area with neutral tones showcases a comfortable seating arrangement and a television. The spacious bedroom boasts a wooden bed frame and soft linens. A stylish bathroom includes a bathtub and waterfall shower. A scenic walking trail bordered by trees is depicted in the last image.
Home in Pilsley
4.92 out of 5 average rating, 137 reviews

Cosy Quiet Cottage In Pilsley

A beautiful, refurbished, one bedroomed cottage in a peaceful small village location, just a couple of minutes walk onto the Five Pits Trail and other great walks, yet still in close proximity to local amenities. The perfect place to enjoy a home from home getaway; self check in, full kitchen, glorious large bathroom space with bath and waterfall shower, comfy lounge area with large TV, extremely spacious cosy king bedroom and front and rear enclosed patio areas for your four legged friends!

Top guest favourite
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 Darnall
5 out of 5 average rating, 233 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 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, 309 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, 220 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.
Flat in Chesterfield
4.96 out of 5 average rating, 284 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.
Apartment in Dronfield
4.82 out of 5 average rating, 255 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, 334 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
Guest suite in Ashover
4.98 out of 5 average rating, 356 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.

Guest favourite
The exterior of Pepper Cottage is visible, showcasing a traditional stone façade with multiple windows. Access steps lead up to the entrance, and a low fence borders the well-kept garden area. The surrounding neighborhood features a mix of architecture under a bright blue sky.
Cottage in Derbyshire
4.95 out of 5 average rating, 197 reviews

Pepper Cottage- pet-friendly, stylish & cosy

Pepper Cottage is a stylish yet traditional workman's cottage with a modern garden room extension situated on Church Street, about 5-10mins walk into the centre of Matlock. It is ideal for dog-owners as it has a fenced garden and easy access to the High & Pic Tor for walks with fantastic views across Matlock & down to Matlock Bath. The front of the cottage looks up to Riber Castle. There is a lockable garden shed for bikes. Ideal for couples & families with older children.

Top guest favourite
A charming stone cottage is visible, framed by lush greenery and flowering plants. The two-story structure features a sloped roof and a chimney, with a pathway leading to the entrance. Rolling hills are seen in the background, under a partly cloudy sky.
Home in Ashover
5 out of 5 average rating, 116 reviews

Country Cottage with great outside space & views

Relax in our stunning two-bedroom slice of Derbyshire heaven! Amazing walks and local pubs >1 mile away. Large terrace with fabulous views over the valley & a range of seating. 2 double bedrooms, 1 ensuite & large family bathroom. Significant renovations recently & has a highly specified kitchen inc. range. Log burner in living room & Smart TVs in Kitchen, Living room & main bedroom. WIFI & office to keep in touch with work whilst relaxing in comfort & style.

Guest favourite
A charming stone cottage with a slate roof is set among gravel landscaping. A vibrant green door, adorned with diamond-shaped glass, is framed by neatly trimmed boxwood hedges. A small potted tree adds a touch of greenery to the inviting entrance.
Barn in Clay Cross
4.85 out of 5 average rating, 510 reviews

Stretton Hall Farm - The Annex

Our holiday cottages & glamping pods are located on our 100 acre farm on the edge of the Peak District. The Annex is a modern barn conversion with a luxurious interior, designed to make it feel like a home away from home. Secluded down a 1/4 mile private driveway in a courtyard with the other cottages, the Annex has a quiet feel to it where you can truly relax. We are contractor friendly, please message us for work stays that are Monday to Friday.

Popular amenities for Chesterfield pet-friendly home rentals

When is the best time to visit Chesterfield?

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Avg. price$138 SGD$136 SGD$139 SGD$144 SGD$147 SGD$152 SGD$164 SGD$170 SGD$153 SGD$143 SGD$140 SGD$151 SGD
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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 $39 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,800 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

    30 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!