Pet-friendly holiday rentals in Chesterfield

Find and book unique pet-friendly homes on Airbnb

Quick stats about holiday rentals that are pet-friendly in Chesterfield

  • Total holiday rentals

    Explore 50 holiday rentals in Chesterfield

  • Nightly prices starting at

    Chesterfield holiday rentals start at $70 NZD per night before taxes and fees

  • Verified guest reviews

    Over 3,400 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Chesterfield holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Chesterfield rentals

  • 4.9 Average rating

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

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 well-maintained pathway leads to a beautifully designed cottage surrounded by lush greenery. The property features manicured hedges and trees, with a clear blue sky overhead, creating a welcoming entrance to the private garden area.
Guesthouse in Derbyshire

Springwood Cottage Private and Unique

Springwood Cottage is ideally situated in a beautiful location on the edge of Derbyshire is completely self contained with its own entrance and private garden area with parking outside. The Cottage is completely newly built in 2020 and designed to the highest standard. Well behaved Dogs welcome, we are happy to accommodate 2 dogs, please request if you have more than 2. A deluxe super kingsized bed (6 x6 foot) with the most up to date memory foam mattress and a comfortable sofa bed in the lounge

WalkabilityPetsNearby

5.0 out of 5 average rating, 200 reviews
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

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!

Outdoor spacesPetsGetting around

4.98 out of 5 average rating, 238 reviews
Top Guest favourite
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

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.

PetsWalkabilityFamily

4.94 out of 5 average rating, 352 reviews
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 Derbyshire

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

PetsWalkabilityValue

5.0 out of 5 average rating, 285 reviews
Superhost
A bedroom is featured with a spacious bed dressed in floral bedding. A wooden wardrobe with mirrors stands beside the bed. A bedside lamp provides soft illumination, while neatly folded towels are placed at the foot of the bed, offering a sense of comfort and convenience.
Apartment in Chesterfield

The Hideaway

Surround yourself with style in this standout space. Modern recently refurbished basement apartment with secure drive. It comprises of 1 bedroom with king size bed with Premier Inn mattress. It has a kitchen/lounge with pull out sofa bed that sleeps 2. The kitchen is equipped with microwave, fridge, air fryer, kettle, toaster and all utensils. Includes all bedding and towels. Shower room. 10 min walk to the chesterfield canal. Shops, pubs and restaurants are all within walking distance.

WalkabilityOutdoor spacesAmenities

4.86 out of 5 average rating, 104 reviews
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.
Guest suite in Matlock

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.

PetsWalkabilityHeating

4.99 out of 5 average rating, 304 reviews
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

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.

PetsOutdoor spacesBathroom

4.96 out of 5 average rating, 296 reviews
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

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.

WalkabilityPetsAmenities

4.82 out of 5 average rating, 272 reviews
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

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

PetsOutdoor spacesHeating

4.96 out of 5 average rating, 354 reviews
Top Guest favourite
Barn in Holymoorside

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!

Outdoor spacesWalkabilityLong stay

4.99 out of 5 average rating, 203 reviews
Top Guest favourite
Guest suite in Ashover

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.

PetsWalkabilityBathroom

4.98 out of 5 average rating, 394 reviews
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

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.

Outdoor spacesPetsComfort

4.99 out of 5 average rating, 177 reviews

Popular amenities for Chesterfield pet-friendly home rentals

Pet-friendly home rentals with a pool

Top Guest favourite
Cottage in Fenny Bentley

Boutique Retreat, Summer Pool, Peak District

Outdoor spacesPetsLong stay

4.95 out of 5 average rating, 417 reviews
Guest favourite
The private terrace features a hot tub with views of rolling green hills under a clear blue sky. A comfortable seating area is visible, providing a serene spot to relax and enjoy the landscape, bordered by lush greenery and a stone wall.
Cottage in Derbyshire

Romantic Peak District Spa Cottage •Hot Tub & Pool

WalkabilityPetsIndoor spaces

4.83 out of 5 average rating, 138 reviews
Guest favourite
The entrance to the cottage is framed by rustic brick and stone walls. A wooden door with glass panels provides access, while a small outdoor area features a round table and two chairs on pebbled ground. A welcome sign is visible above the door.
Cottage in Brassington

Dog Friendly Ground Floor Cottage with Shared Pool

WalkabilityPetsAccess

4.83 out of 5 average rating, 101 reviews
Top Guest favourite
A rustic retreat is positioned among tall trees, accented by well-maintained landscaping. Stone steps lead to a wooden structure featuring large glass doors. Outdoor seating is visible on the patio, surrounded by a variety of green and flowering plants, under a clear blue sky.
Shepherd’s hut in Warsop

Luxury Shepherd's Retreat with Hot Tub

Outdoor spacesWalkabilityBarbecue

4.98 out of 5 average rating, 133 reviews
Guest favourite
A serene outdoor setting features a circular stone table surrounded by four black metal chairs. A natural pond with overgrown vegetation is visible, with a rural stone house in the background. The landscape reflects a tranquil countryside atmosphere, complemented by bare trees and scattered plant life.
Guesthouse in Derbyshire

Dog Friendly Retreat

Outdoor spacesPetsBarbecue

4.8 out of 5 average rating, 142 reviews
Superhost
Farm stay in Ashover

Family Home Getaway - Hot Tub, Sauna & Swim Spa

WalkabilityPetsComfort

4.88 out of 5 average rating, 64 reviews
Top Guest favourite
An open living area features a light and airy design, showcasing two sofas with plaid cushions. A round coffee table is placed in front of the seating. The kitchen area is visible in the background, equipped with modern appliances, while a dining table for four is positioned nearby.
Cabin in Derbyshire

Loki’s Lodge@ Ashbourne Heights holiday park

Outdoor spacesPetsGetting around

4.99 out of 5 average rating, 81 reviews
Top Guest favourite
Holiday park in Derbyshire

The Tissington Retreat, Ashbourne Heights

WalkabilityOutdoor spacesLocation

4.98 out of 5 average rating, 42 reviews

When is the best time to visit Chesterfield?

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Avg. price$205 NZD$203 NZD$206 NZD$227 NZD$229 NZD$243 NZD$220 NZD$229 NZD$206 NZD$208 NZD$196 NZD$206 NZD
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