Pet-friendly holiday rentals in Chesterfield

Apartment in Holymoorside

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.

4.98 out of 5 average rating, 220 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 house in Derbyshire

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.

4.99 out of 5 average rating, 189 reviews

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

5 out of 5 average rating, 274 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

*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

4.89 out of 5 average rating, 286 reviews

The image captures a serene evening view from a private hot tub, with clear glass doors leading into a cozy indoor space. Outside, an expansive landscape of greenery and distant fields is seen under a twilight sky, creating a peaceful atmosphere.

Farm stay in Ashover

Clover View - Hot tub, Sauna & Countryside Views

Nestled on the countryside moors of Beeley, Clover View is a beautifully modern cottage ideally located a short drive from Bakewell, Chatsworth House, Matlock, and breathtaking landscapes of the Peak District. Sleeping up to 4 guests in superb accommodation with a cosy, contemporary feel – perfect for couples, families, or friends looking for a countryside escape. Step outside to your private hot tub or to feed the goats, its an ideal spot to relax and take in the stunning countryside views

4.99 out of 5 average rating, 271 reviews

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

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.

4.96 out of 5 average rating, 292 reviews

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

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.

4.91 out of 5 average rating, 267 reviews

A spacious lounge area features a modern sectional sofa, complete with decorative pillows. Soft light is provided by a standing lamp, highlighting the room's neutral tones. An archway leads towards a dining space that includes stylish pendant lighting, creating an inviting atmosphere.

Cottage in Derbyshire

Lizzy’s Luxury Cottage

Welcome to Lizzy’s Cottage! Nestled in the heart of the Peak District, Lizzy’s Cottage offers a luxurious escape for couples and families. Surrounded by breathtaking countryside, the cottage provides a peaceful retreat, while being just a short drive from popular destinations such as Bakewell, Chatsworth, Matlock, and Matlock Bath. At Knabb Farm, we offer private parking for all guests, and our 7 acres of private land provide plenty of space to explore and enjoy the stunning surroundings.

4.99 out of 5 average rating, 166 reviews

A modern hut is set on a gravel patio, surrounded by manicured grass. Large glass doors provide views of the interior, complemented by wooden paneling on the exterior. Potted flowers are placed at the entrance, and a seating area is visible in the outdoor space.

Cabin in Derbyshire

The Willows Hut - with hot tub - Hillside Huts

The Willows - Hillside Huts - *brand-new August 2025* Our charming, The Willows Hut, is our latest addition, joining The Oaks Hut on our smallholding in rural Derbyshire. With a shared driveway, its own dedicated parking & private enclosed garden, it is situated in a secluded spot enjoying stunning countryside views. Enjoy the most magnificent sunsets as you kick back and relax in this calm, stylish space. Bring your wellies! There are many countryside walks from the from the doorstep!

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.

4.96 out of 5 average rating, 346 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

4.99 out of 5 average rating, 178 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!

4.85 out of 5 average rating, 554 reviews

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

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.

4.87 out of 5 average rating, 549 reviews

A wooden hot tub is positioned outdoors, surrounded by tranquil countryside. Rolling hills form a scenic backdrop, and a wooden ladder leads to the tub. A peaceful atmosphere is enhanced by the natural setting and distant trees.

Tent in Edale

Cozy Couples Glamping - Private Hot Tub

**Updated for 2026** Escapism at its finest. Find yourself rested and renewed at our idyllic glamping site nestled amongst the rolling hills of the Peak District. Updated and improved for Spring - Summer 2026! - We specialise in couples experiences; Birthdays, Anniversaries, Engagements, reach out to us to discuss how we can help make your occasion special. We guarantee that here, you can truly experience the meaning of a retreat.

Popular amenities for Chesterfield pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.95 out of 5 average rating, 399 reviews

The exterior of the cottage is showcased, featuring a stone facade with multiple windows. Double French doors lead to a patio area, where a hot tub is positioned on the stone-paved ground. A clear blue sky creates a bright, inviting atmosphere.

Home in Tibshelf

Hunters Cottage. Wheatsheaf Mews

4.98 out of 5 average rating, 323 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

4.99 out of 5 average rating, 127 reviews

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

Country Cottage with great outside space & views

4.9 out of 5 average rating, 191 reviews

The renovated stone barn features a tidy exterior with a porch and flower beds filled with colorful plants. A gravel driveway leads to the entrance, and a spacious lawn area is visible. The surrounding hills create a serene countryside backdrop.

Home in Derbyshire

Cheerful 2-bedroom home with free offroad parking

4.99 out of 5 average rating, 104 reviews

Home in Bakewell

Knowsley Cottage - Central - Hot Tub - EV Charger

4.88 out of 5 average rating, 286 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

4.96 out of 5 average rating, 112 reviews

The exterior of Fox Cottage features stone walls adorned with climbing greenery. A blue front door is framed by a lantern and surrounded by plants. The cottage is set against a backdrop of trees and a gravel path, with a nearby area for parking.

Home in Tansley

Fox Cottage at Yew Tree Farm

4.94 out of 5 average rating, 189 reviews

A grand manor house with a brick facade and symmetrical design is set against a clear blue sky. Lush green lawns frame the property, which is accentuated by tall trees and several parked vehicles. Four chimneys rise above the roofline, contributing to the estate's historic charm.

Home in Nottinghamshire

Stunning Countryside Manor — Hot Tub & Parking

Pet-friendly home rentals with a pool

Holiday park in Derbyshire

A light and airy caravan is positioned within a grassy area, featuring a spacious decking area surrounded by a low fence. An umbrella provides shade for outdoor seating, with well-maintained landscaping visible. The clear blue sky enhances the inviting outdoor space.

4.88 out of 5 average rating, 32 reviews

Caravan near Tissington Trail

4.95 out of 5 average rating, 400 reviews

Cottage in Fenny Bentley

Luxury Peak District Home - 2 miles from Ashbourne

4.94 out of 5 average rating, 95 reviews

Home in Doncaster

Large Modern Décor 3 Bed with Driveway & Garden

Holiday park in Derbyshire

5 out of 5 average rating, 33 reviews

The Tissington Retreat, Ashbourne Heights

4.98 out of 5 average rating, 60 reviews

Cabin in Derbyshire

Loki’s Lodge@ Ashbourne Heights holiday park

An open plan dining area features a wooden table surrounded by several chairs, complemented by a decorative plate display on the wall. Exposed beams highlight the ceiling. A comfortable seating area with light upholstery is visible in the background, providing a cozy space for relaxation.

Home in Bakewell

4.89 out of 5 average rating, 19 reviews

Buttercup Down - shared heated pool & games room

4.92 out of 5 average rating, 53 reviews

A spacious dining area features a long wooden table with comfortable upholstered chairs, accommodating multiple guests. A large vase filled with flowers serves as a focal point. The open kitchen can be seen in the background, showcasing modern appliances and a warm aesthetic.

Home in Brassington

Spacious Dog Friendly Cottage by Carsington Water

A sitting room is presented with cozy seating arrangements on either side. A glass coffee table is centered on an ornate area rug, while a woodburning stove is positioned against a warm-toned wall. A television is mounted nearby, enhancing the room’s inviting atmosphere.

Home in Derbyshire

4.8 out of 5 average rating, 5 reviews

Pippinwell

Private, pet-friendly home rentals

4.94 out of 5 average rating, 87 reviews

A spacious bedroom is shown with a large bed featuring a patterned duvet and soft grey blankets. Two bedside tables with lamps are positioned on either side. Natural light enters through the window, casting a warm glow, while an adjoining bathroom door is visible.

Cottage in Chesterfield

The Olde Coach House - Cottage with Hot Tub

4.97 out of 5 average rating, 214 reviews

Cottage in Letwell

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

4.86 out of 5 average rating, 36 reviews

An exterior view of the cottage reveals a charming stone facade under a clear blue sky. A large tree stands nearby, and the entrance features gray doors complemented by lanterns. Natural greenery is visible in the background, enhancing the tranquil rural setting.

Guest house in Barlow

Delightful Country Cottage

4.95 out of 5 average rating, 449 reviews

Cottage in Winster

Gorgeous romantic cosy cottage retreat with views

The exterior of the brick house is showcased, featuring a charming door with a small balcony above. Large windows allow natural light in, while the well-maintained driveway provides ample space for parking. A clear blue sky enhances the welcoming appearance of the property.

4.97 out of 5 average rating, 62 reviews

Home in Chesterfield

4.93 out of 5 average rating, 30 reviews

Charming 18th century stone cottage

4.91 out of 5 average rating, 35 reviews

A light-filled living area features a comfortable sectional sofa in soft gray, complemented by decorative pillows. A dark coffee table occupies the center space, while large glass doors open to a private outdoor seating area, enhancing the connection to nature.

Home in Brimington

Blissful Barry’s

A cozy living area is presented with a brown sofa adorned with decorative cushions. A wooden coffee table sits in front, complemented by a patterned area rug. A wall-mounted television and a decorative shelf enhance the space, which is warmed by a stove and illuminated by natural light.