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Vacation rentals in Chesterfield

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Chesterfield vacation rentals

Self check-in
Pet friendly
Hot tub
Laptop-friendly workspace
Gym

Dog friendly vacation rentals in Chesterfield

Guest favorite
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
4.91 out of 5 average rating, 121 reviews

Cosy Quiet Cottage In Pilsley

Top guest favorite
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
4.94 out of 5 average rating, 397 reviews

17th century cottage in Matlock

Top guest favorite
The exterior of the building showcases a traditional stone structure, featuring a vibrant blue door and several windows. A small garden area with gravel and low plants is visible, creating a quaint and inviting entrance alongside a simple table.
Guesthouse in Derbyshire
4.97 out of 5 average rating, 223 reviews

The Annexe - Belle Vue House

Top guest favorite
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
4.99 out of 5 average rating, 171 reviews

Springwood Cottage Private and Unique

Guest favorite
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
4.84 out of 5 average rating, 411 reviews

Cosy cottage, stunning views near Chatsworth

Guest favorite
A modern kitchen diner features wooden cabinetry and a spacious table with room for six. A bouquet of flowers sits at the center of the table. Appliances include a refrigerator, microwave, and dishwasher, while tiled walls display a mix of earthy colors.
Cottage in Clay Cross
4.93 out of 5 average rating, 225 reviews

Holly Cottage a great place for a country break

Top guest favorite
A panoramic view of rolling green hills and fields is framed by lush trees. The landscape features varying shades of green, with distant hills under a subtly cloudy sky. This serene countryside setting showcases the natural beauty of the surrounding area.
Cottage in Darley Dale
4.95 out of 5 average rating, 246 reviews

The Hideaway, Great views, garden & location

Top guest favorite
A cozy seating area features a plush armchair next to a modern wood-burning stove. The warm glow of the fire creates a welcoming ambiance. A dog rests comfortably on a textured rug placed on the hardwood floor, with bookshelves visible in the background.
Guesthouse in Stretton
4.99 out of 5 average rating, 131 reviews

Swift Retreat - converted farm building

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Vacation rentals with jacuzzis in Chesterfield

Guest favorite
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
4.96 out of 5 average rating, 350 reviews

Hunters Cottage. Wheatsheaf Mews

Top guest favorite
The image showcases Rosewall Cottage, with its charming stone exterior and inviting living spaces. A cozy sitting area features a log burner and wooden beams, while the garden displays vibrant greenery and a peaceful atmosphere, ideal for relaxation.
Cottage in Letwell
4.96 out of 5 average rating, 177 reviews

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

Guest favorite
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 Calver
4.87 out of 5 average rating, 228 reviews

Bridgefoot Cottage - Wild Swimming & Hot Tub

Top guest favorite
A spacious two-story property is framed by greenery, featuring large windows with a welcoming entrance. The gravel driveway leads to the front of the house, where symmetrical planters enhance the facade. Lush trees and flowering plants surround the building, creating a serene outdoor environment.
Home in Derbyshire
4.99 out of 5 average rating, 151 reviews

Highfield House - Rural Retreat Derbyshire

Top guest favorite
A private garden area surrounds the cabin, featuring a hot tub and a circular table with four chairs. Lush greenery and trees provide a natural backdrop, while the cabin's wooden exterior complements the serene outdoor setting.
Guesthouse in Derbyshire
4.99 out of 5 average rating, 284 reviews

The cabin @ white cottage

Top guest favorite
A warm living area features a sectional yellow sofa adorned with decorative pillows, positioned beside a wooden coffee table. A round dining table with metal chairs is set against a kitchen backdrop, complemented by stone flooring and exposed beams. Natural light is captured through elegant curtains.
Cottage in Sookholme
5 out of 5 average rating, 203 reviews

Luxury Country Cottage with Hot Tub

Top guest favorite
A cabin is perched among large boulders, surrounded by lush greenery and distant rolling hills. The exterior features wooden siding and a sloped roof, complemented by a small deck with chairs. The scene highlights a tranquil, nature-focused setting under a cloudy sky.
Hut in Birchover
4.98 out of 5 average rating, 175 reviews

Boulder Field Cabin and Hot Tub

Guest favorite
The exterior of the lodge features a blend of traditional brickwork and modern architectural elements. Surrounded by lush greenery, the building showcases large windows and a welcoming entrance, set against a clear blue sky, emphasizing its peaceful and picturesque surroundings.
Home in Eckington
4.98 out of 5 average rating, 202 reviews

Pear Tree Lodge with private HOT TUB and garden

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Other great vacation rentals in Chesterfield

Top guest favorite
A cozy lounge is presented with a light-colored sofa adorned with textured cushions and a throw. A flat-screen television is mounted on the wall opposite, and a sleek console table holds decorative items. Natural light filters through a glass door, leading to the outdoors.
Cottage in Derbyshire
4.96 out of 5 average rating, 157 reviews

Lizzy’s Luxury Cottage

Top guest favorite
A charming stone cottage is surrounded by lush greenery and manicured lawns, with neatly trimmed hedges framing the entrance. A gravel driveway leads to the front, complemented by mature trees and landscaped areas, providing a serene and inviting outdoor space.
Cottage in Derbyshire
5 out of 5 average rating, 218 reviews

Luxury 2 Bedroom Cottage (Sleeps 4) Stunning Views

Top guest favorite
A grand historical building showcases architectural details, with multiple stories and large windows reflecting natural light. A spacious lawn in front is bordered by a stone pathway that leads to the entrance. Visitors are seen walking along the path, framed by greenery and blue skies.
Cottage in Holymoorside
4.98 out of 5 average rating, 288 reviews

Wasp Nest Cottage, Peak District

Superhost
A doorway opens to reveal a view of a lush garden and the surrounding countryside. Natural light pours in, illuminating the interior space with a warm glow. The doorway features a decorative wrought iron railing and is framed by soft drapes, creating a welcoming entryway.
Guest suite in Barlow
4.93 out of 5 average rating, 103 reviews

Double bedroom with a view/en-suite/couch area

Guest favorite
Cabin in Barlow
4.92 out of 5 average rating, 153 reviews

FULLY HEATED OAKTREE RETREAT EDGE OF 60ACRE ESTATE

Top guest favorite
A gravel pathway leads through a peaceful enclave surrounded by greenery, with rustic buildings on either side. Flowering plants and trees line the pathway, enhancing the serene atmosphere of this quiet setting.
Apartment in Sheffield/Chesterfield
4.99 out of 5 average rating, 167 reviews

Peaceful setting, close to amenities and transport

Top guest favorite
The entrance to Gravediggers Cottage is framed by a stylish brick wall and features large glass doors that invite natural light inside. A small stone pathway, bordered by decorative plants and flowers, leads to the entrance, enhancing the cottage's welcoming appeal.
Barn in Bolsover
4.97 out of 5 average rating, 106 reviews

Gravediggers Cottage

Superhost
A cozy outdoor seating area features a stone fireplace, emitting a warm glow. Wooden beams create an inviting ceiling, while the walls consist of slatted wood for a semi-closed feel. A table surrounded by black wicker chairs is adorned with soft, light-colored throws.
Barn in Clay Cross
4.85 out of 5 average rating, 471 reviews

Stretton Hall Farm - The Annex

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Quick stats about vacation rentals in Chesterfield

  • Total rentals

    100 properties

  • Nightly prices starting at

    G$4,184 GYD before taxes and fees

  • Total number of reviews

    6.2K reviews

  • Family-friendly rentals

    50 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

Frequently Asked Questions

  • Where should I stay in Chesterfield?

    Make yourself at home in Chesterfield by choosing from our most frequently booked neighborhoods. We have over 180 vacation rentals in Chesterfield, and over 180 vacation rentals in Brimington.

  • Are there vacation rentals with a dedicated workspace in Chesterfield?

    Yes! Work meets play with ease at over 50 vacation rentals in Chesterfield featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in house rentals in Chesterfield?

    Experience the best of Chesterfield with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Chesterfield?

    Four-legged friends are welcome in Chesterfield. Choose from more than 30 vacation rentals for guests traveling with pets.

  • Do house rentals in Chesterfield have self check-in?

    Absolutely! We offer over 20 house rentals with self check-in in Chesterfield. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Chesterfield?

    Chesterfield has more than 40 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore

  1. Airbnb
  2. United Kingdom
  3. England
  4. Derbyshire
  5. Chesterfield