Pet-friendly vacation rentals in Chesterfield

4.93 out of 5 average rating, 344 reviews

Cottage in Chesterfield

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.

WalkabilityPetsBackyard

4.99 out of 5 average rating, 196 reviews

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

Outdoor spacesWalkabilityQuiet

4.98 out of 5 average rating, 236 reviews

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!

WalkabilityOutdoor spacesBiking

4.94 out of 5 average rating, 348 reviews

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.

PetsOutdoor spacesParking

Apartment in Chesterfield

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.

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.

PetsWalkabilityQuiet

4.85 out of 5 average rating, 102 reviews

4.97 out of 5 average rating, 351 reviews

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

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.

WalkabilityOutdoor spacesCleanliness

Apartment in Chesterfield

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.

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.

WalkabilityPetsGetting around

4.96 out of 5 average rating, 294 reviews

4.82 out of 5 average rating, 270 reviews

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.

WalkabilityPetsAccuracy

4.96 out of 5 average rating, 353 reviews

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

WalkabilityOutdoor spacesCheckout

4.99 out of 5 average rating, 198 reviews

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 spacesPetsHot tub

4.98 out of 5 average rating, 394 reviews

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.

WalkabilityPetsSleep quality

4.96 out of 5 average rating, 224 reviews

Cottage in Letwell

Rural cottage! Wood-fired hot tub. Bliss awaits.

Welcome to our home! A charming cottage in a rural village, ideal for couples, families, friends, contractors, business trips & weddings. The property features 2 king-size bedrooms, a children’s bedroom with 3 single beds, plus a ground-floor king bedroom & 3 bathrooms. Enjoy a bespoke kitchen, rain shower, wood burner, parquet flooring, huge garden with play area, hot tub & parking for 3 cars/LWB van. Close to M1, A1, Hodsock Priory, Thoresby, Sherwood Forest & Sheffield.

Outdoor spacesWalkabilityParks

Popular amenities for Chesterfield pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.89 out of 5 average rating, 299 reviews

A view from a bridge showcases a serene countryside scene with a stone cottage nestled among lush greenery. The vibrant leaves of trees frame the picturesque surroundings, while the calm waters of the river reflect the natural beauty. The distant hills provide a backdrop.

Home in Grindleford

Bridgefoot Cottage - Wild Swimming & Hot Tub

WalkabilityOutdoor spacesBackyard

4.83 out of 5 average rating, 499 reviews

A rustic stone cottage is set against a backdrop of rolling hills. A spacious wooden deck extends from the cottage, surrounded by lush green grass and trees. Soft sunlight filters through the foliage, creating a serene outdoor environment.

Home in Derbyshire

Cosy cottage, stunning views near Chatsworth

WalkabilityOutdoor spacesIndoor spaces

4.96 out of 5 average rating, 170 reviews

Home in South Yorkshire

The Little Lodge

PetsOutdoor spacesKitchen

4.91 out of 5 average rating, 269 reviews

A living room area features a dark gray sofa with plaid cushions, positioned beside a small white coffee table. A flat-screen TV is mounted on a wall unit, while light streams through a window with white shutters, creating a bright and welcoming space.

Home in Totley

Charming fully equipped home 5min to Peak District

WalkabilityOutdoor spacesIndoor spaces

4.92 out of 5 average rating, 155 reviews

A charming stone barn exterior is framed by lush greenery. The building features several windows and is adorned with climbing vines and red leaves, creating a natural connection with its surroundings. A stone pathway leads to the entrance, enhancing the inviting appearance.

Home in Derbyshire

Hugo’s Luxury Barn

PetsWalkabilityBackyard

4.99 out of 5 average rating, 335 reviews

The charming stone cottage features a symmetrical facade with large windows, allowing natural light to fill the interior. A spacious patio area is visible in front, providing ample outdoor space. The roof is covered in slate, complementing the warm stone exterior.

Home in Great Longstone

Chert Cottage, Great Longstone, Bakewell Peak Dist

Outdoor spacesPetsLaundry

4.9 out of 5 average rating, 123 reviews

A warm living area is adorned with an orange sofa, layered with decorative pillows. A low table rests atop a patterned rug, while a guitar leans against a natural wood shelf featuring books and plants. Two windows invite natural light into the space.

Home in Grindleford

Peak District Home from Home!

WalkabilityOutdoor spacesAccuracy

4.85 out of 5 average rating, 419 reviews

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

Runner Duck Cottage

Outdoor spacesWalkabilityGetting around

Pet-friendly home rentals with a pool

4.95 out of 5 average rating, 413 reviews

Cottage in Fenny Bentley

Boutique Retreat, Summer Pool, Peak District

WalkabilityOutdoor spacesLong stay

4.83 out of 5 average rating, 101 reviews

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

Outdoor spacesWalkabilityShared spaces

4.98 out of 5 average rating, 132 reviews

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

PetsOutdoor spacesCondition

4.8 out of 5 average rating, 142 reviews

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

PetsWalkabilityDecor

4.83 out of 5 average rating, 138 reviews

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

WalkabilityOutdoor spacesCheck-in

4.88 out of 5 average rating, 64 reviews

Farm stay in Ashover

Family Home Getaway - Hot Tub, Sauna & Swim Spa

WalkabilityOutdoor spacesHeating

4.99 out of 5 average rating, 78 reviews

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

PetsWalkabilityCheck-in

Holiday park in Derbyshire

The Tissington Retreat, Ashbourne Heights

WalkabilityPetsSleep quality

4.98 out of 5 average rating, 41 reviews

Private, pet-friendly home rentals

5.0 out of 5 average rating, 282 reviews

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

PetsOutdoor spacesBackyard

Vacation home in Matlock Town

A charming country farmhouse is positioned among vibrant flowerbeds filled with sunflowers and colorful blooms. The home’s stone exterior is complemented by large windows reflecting the blue sky. Lush greenery frames the entrance, inviting guests to explore the surrounding gardens.

Peak District Country Farmhouse

WalkabilityOutdoor spacesView

4.96 out of 5 average rating, 165 reviews

4.94 out of 5 average rating, 455 reviews

The exterior of the stone cottage is framed by a vibrant garden filled with colorful flowers. Large windows provide natural light, and solar panels can be seen on the roof. A rustic stone wall adds charm to the property, creating an inviting entrance.

Cottage in Matlock

17th century cottage in Matlock

PetsWalkabilityQuiet

Cottage in South Yorkshire

The stone exterior of the property is framed by lush greenery, featuring wooden doors that open to a welcoming entrance. A gravel driveway is visible, with a low wooden fence marking the boundary and a clear blue sky overhead.

The Stables

PetsWalkabilityLocation

4.95 out of 5 average rating, 110 reviews

4.98 out of 5 average rating, 163 reviews

The kitchen features a rustic design with shaker-style cabinetry and wooden countertops. A farmhouse sink is positioned under a window, complemented by modern appliances. A wooden dining table and chairs offer a cozy dining space, illuminated by warm lighting and natural materials.

Barn in Eyam

Jacobs Barn, Eyam

Outdoor spacesPetsNearby

4.98 out of 5 average rating, 122 reviews

A wooden gate spans a gravel driveway, bordered by stone walls and lush green trees. In the background, a rustic building can be seen among the foliage, set in a peaceful and natural environment. The setting reflects a tranquil country atmosphere.

Cottage in Bradfield

Cosy cottage with private garden

Outdoor spacesWalkabilityGetting around

4.98 out of 5 average rating, 101 reviews

An open-plan living area features a vibrant blue sofa with colorful cushions. A glass coffee table sits atop a textured rug, while a modern kitchenette is visible in the background. Natural light fills the space through two windows, highlighting the clean lines and inviting design.

Condo in South Yorkshire

“Your Sheffield home away from home”

PetsWalkabilityIndoor spaces