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Vacation rentals in Chesterfield

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Top-rated vacation rentals in Chesterfield

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The entrance of the cottage is framed by lush greenery and decorative plants. A wooden bench is positioned beside the door, and a textured stone wall adds character to the exterior. Pathways lead through a peaceful garden area, offering accessibility to the entrance.

Cottage in New Mills

4.95 out of 5 average rating, 340 reviews

Torr Top Place - Peak district apartment(sleeps 5)

2-bedroom apartment / cottage set within a large stone built property. Sleeps upto 5. Positioned on the edge of the Peak District, centrally located for amenities and situated next to the river. Excellent walks, and close proximity to shops, pubs, restaurants, direct from the doorstep. Train 2 minutes with direct service to Manchester and Sheffield. Ideal for walking, cycling, or restful breaks. Suitable for couples, solo adventurers, families. Private parking and patio with access to garden.

Top guest favorite

The exterior of a rustic stone cottage is showcased, featuring a wooden decking area surrounded by a railing. A covered outdoor seating space is visible, with potted plants enhancing the natural setting. Lush greenery and trees are seen in the background under a clear blue sky.

Barn in Ford, Leek

4.94 out of 5 average rating, 187 reviews

5* Stunning Secluded Luxurious Converted Barn

AWARD WINNING STUNNING SECLUDED RURAL LOCATION-GROUND FLOOR BEDROOM-LOG BURNING STOVE-NO CLEANING FEES You will find it hard to find anywhere else as peaceful & secluded as Ford Wetley Cottage in the Peak District, a beautifully luxurious appointed converted dairy. This unique space is secluded & surrounded by fields, trees, streams, waterfalls, woodland. Peaceful & relaxing, log burning stove, outdoor BBQ & river view decking and beautifully cabin 2 acre field for dogs to explore.EV charging

Top guest favorite

A peaceful scene depicts the still water reflecting the nearby stone buildings and lush greenery. Tall grasses line the banks, enhancing the natural tranquility of the environment. The stone pathway is visible, leading toward a residential area in the background.

Cottage in Derbyshire

4.94 out of 5 average rating, 366 reviews

Millstream Cottage

A Charming Grade 2 listed stone built terraced cottage with an allocated parking space outside the property, conveniently located in the picturesque market town of Bakewell. Very quiet but ideally positioned to explore the beautiful Peak District. There is a bus stop nearby where you can access transport to Manchester and Sheffield. Ideal for families or couples. Highchair and travel cot available on request. A welcome pack will be provided on your arrival to get your stay of to a great start.

Top guest favorite

A wooden table with matching chairs is set on a gravel area, surrounded by greenery. The view showcases expansive fields under a partly cloudy sky, with blue hues dominating the landscape, creating a serene outdoor space for relaxation.

4.97 out of 5 average rating, 173 reviews

Quiet cottage with beautiful surroundings

Welcome to Honeysuckle cottage located in Alton, Staffordshire. Surrounded by green countryside and picturesque walks, our cottage is in nice quiet part of the village and is the perfect rural escape. A short stroll away from the village shops and pubs and a 10 minute drive from the local ice rink, cinema and polar bear experience. With ample free off road parking the cottage is great for families couples or meeting up with friends for a get together. 2 double bedrooms and one single 2 lounges

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, 211 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

Two historic stone towers stand by a calm body of water, mirrored perfectly in its surface. Lush greenery surrounds the scene, with trees displaying autumn colors in the background under a clear blue sky.

Townhouse in Derbyshire

4.89 out of 5 average rating, 123 reviews

Period town house, right in the Heart Of Bakewell

Fabulous loft style living right in the heart of beautiful Bakewell Shops, pubs, restaurants, River and amazing walks on your doorstep. Ideal to explore the stunning dales. Parking permit supplied for 1 vehicle. Sleeps 8 guests in 2 bedrooms & can sleep up to 12 with the use of sofa beds in the lounge area (£25 pppn on request) All in a modern and bright setting. Fully fitted and well equipped kitchen. Fast wi-fi Adaptable sleeping arrangements, to accommodate larger groups and families.

A patio area features a round wooden table surrounded by six folding chairs. A wooden fence encloses the space, with shrubbery and a large tree visible in the background. A relaxing atmosphere is suggested by the openness of the surroundings and the light blue sky.

4.76 out of 5 average rating, 118 reviews

The Alders Cottage - Stunning views!

Beautiful stone built cottage in the heart of rural Staffordshire with stunning views of the rolling English countryside and just five minutes’ drive from Alton Towers! This stylishly renovated cottage in the lovely village of Alton is bright and airy with Wifi, TV, street parking and a sun trap patio garden. Sleeping six and with country walks, cycle trails and popular pubs nearby Felicity’s Cottage is the ideal cosy base for thrill-seekers and Peak District explorers. Easy self check in!

Top guest favorite

A private entrance unfolds, framed by natural stone and adorned with decorative animal sculptures. A pathway leads to a small garden area filled with colorful flowers, while the entrance door is clearly visible, set against a backdrop of textured stone walls.

Tiny home in Derbyshire

4.96 out of 5 average rating, 581 reviews

Delightful Studio House-superb location!

Our studio has been a complete labour of love and now we're finally ready to share this beautiful little spot. You can wake up and hike until your hearts content, take in the sights in town and end your day reclining on the sofa with a cosy pellet burner. We have ample parking, private entrance, walking distance (1.2miles) to town (bars & restaurants), bus stop to Buxton / Macclesfield. Wifi, Sky TV,Netflix. Non smoking. *We do not have a hob or oven* EV Charger (added cost). Sorry no pets.

A small terrace area features a gravel surface surrounded by greenery. Two metal chairs and a round table are set against the backdrop of the cottage and rolling hills, providing a serene space for outdoor relaxation.

Cottage in Derbyshire

4.97 out of 5 average rating, 160 reviews

Swiss Cottage, a heritage cottage, stunning views

Overlooking the beautiful tree-lined Derwent valley, the South facing Swiss Cottage is uniquely situated to offer panoramic views of the entire gorge and the picture perfect village of Matlock Bath, complete with an array of pretty lights, below. It provides the seclusion of a mountain retreat and access to all the village has to offer by way of a range of eateries from vegan to seafood, excellent pubs and entertainment for children from the Heights of Abraham to rowing on the river.

Top guest favorite

Cottage in Tideswell

4.95 out of 5 average rating, 311 reviews

Lovely Lavender Cottage Tideswell, Buxton

A cosy cottage in a thriving village. Pretty walled garden with garden furniture. Well equipped, with quality linen, towels. Bathroom with separate bath and great power shower. Bedroom one has a double bed and bedroom two has two singles which can be zipped together to make a king size. Great Wi-Fi signal. Family friendly, cot and high chair available. Sorry no pets. Two minute walk into the village situated away from the main road on the hillside. Self check in with key box.

Top guest favorite

The entrance to No. 3 Club Cottages is highlighted by charming stone walls and a light blue front door. A small welcome light fixture is mounted beside the door, and the property number is displayed on a stone plaque next to it. Green foliage frames the entryway.

Cottage in Biggin

4.95 out of 5 average rating, 153 reviews

Cosy Village Cottage in The Peak District

A traditional cottage in the idyllic village of Biggin in the beautiful Peak District. No3 Club Cottages is within walking distance of a popular village pub, Biggin Hall, and children’s play area. With plenty of footpaths, cycle trails and bridleways within walking distance, including the famous Tissington Trail. The Cottage has great views of the countryside, an enclosed garden/courtyard front & rear with seating areas, it also has a log burner for those colder evenings.

Cottage in Carsington

4.8 out of 5 average rating, 218 reviews

Luxury SC Cottage Lake views 6-8 Guests

FULLY REFURBISHED -Fabulous Lakeside cottage with unrivalled views over Carsington Water. The property is South facing, set in over an acre of garden. Beautiful walks, cycling, water & outdoor activities on your doorstep. Fantastic village gastro pub - The Miners Arms (2 min walk) central to over 100 attractions. A Hot tub can be hired in ready for use on arrival (extra charge) Please ask for details. Weekend breaks (Friday-Monday) or Midweek breaks (Monday - Friday)

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Chesterfield vacation rentals

Laptop-friendly workspace

Stay near Chesterfield's top sights

Linacre Reservoirs8 locals recommend

The Peacock At Barlow7 locals recommend

Chesterfield Market3 locals recommend

Nonnas Chesterfield7 locals recommend

The Tickled Trout5 locals recommend

Morrisons5 locals recommend

Dog friendly vacation rentals in Chesterfield

Top guest favorite

A cozy lounge area features a pink armchair positioned next to a wood-burning stove, with a stack of logs visible below. A modern television is mounted above the fireplace, and natural light enters through two window panes with shutters. A lantern and small decorative elements complete the space.

Home in Tideswell

4.98 out of 5 average rating, 108 reviews

A chic retreat in the Peaks

An entrance pathway leads through a wooden exterior to a welcoming doorway. Large windows offer natural light, while a wrought iron gate introduces a secure outdoor area. The stone wall complements the rustic design of the lodge, enhancing the natural surroundings.

Cottage in Chelmorton

4.8 out of 5 average rating, 207 reviews

Cheedale Lodge

A scenic view captures rolling green fields dotted with sheep, extending towards a distant stone farm building surrounded by hills. The landscape is characterized by rustic stone walls and a serene, open sky, evoking a peaceful rural atmosphere.

Cottage in Buxton

4.87 out of 5 average rating, 175 reviews

Cosy Little Cottage in the Peak District

The exterior of a rustic stone cottage is presented, featuring two windows with white curtains and a green door that provides access inside. Flower pots with vibrant blooms are positioned in front of the cottage, complemented by a bright blue sky overhead.

Cottage in Castleton

4.87 out of 5 average rating, 160 reviews

Harry Eyre Cottage, Castleton, Peak District

A modern kitchen is illuminated by pendant lights, featuring wooden cabinetry and slate flooring. A dining table is set with plates and glassware, ready for a meal. Large windows allow for natural light, showcasing views of the garden and surrounding landscape.

Home in Harpur Hill

4.95 out of 5 average rating, 200 reviews

Dog & Cycle friendly house with enclosed garden

Top guest favorite

An outdoor patio area is visible, featuring a rustic wooden table surrounded by scattered chairs. Potted flowers add vibrant color to the space, while nearby stone walls complement the natural setting. Beyond the patio, greenery and distant hills enhance the tranquil atmosphere.

Barn in Castleton

5 out of 5 average rating, 103 reviews

Dog Friendly Speedwell Stable at Speedwell House

Top guest favorite

A tranquil bedroom is presented with two spacious beds adorned with soft white linens and elegant gray throw pillows. Fluffy towels are neatly rolled at the foot of each bed, while natural light illuminates the room, highlighting minimalist decor and a stylish vanity area.

Cottage in Tideswell

4.99 out of 5 average rating, 107 reviews

The Old Toffee Shop

Top guest favorite

A serene pond is surrounded by lush green foliage and trees. Water lilies float on the surface, reflecting the natural beauty of the garden. A wooden structure can be seen in the background, blending with the landscape.

Condo in Derbyshire

4.98 out of 5 average rating, 133 reviews

Spacious, dog friendly, one level accommodation.

Vacation rentals with jacuzzis in Chesterfield

The exterior of a two-story stone coach house is displayed, featuring a steeply pitched roof and large windows framed with wood. A small balcony is visible above the entrance. A driveway made of cobblestones leads to the front door, surrounded by neatly trimmed hedges.

Cottage in High Peak

4.88 out of 5 average rating, 556 reviews

HOT TUB Luxury Converted Barn

Top guest favorite

A three-story family home features a natural stone facade with multiple large windows. The entrance is framed by a small porch and steps leading to the front door, surrounded by a neat lawn and well-maintained pathway.

Cottage in Sheffield

4.98 out of 5 average rating, 205 reviews

Holly House - Quiet Retreat

A spacious hot tub is surrounded by a textured wall of green foliage, illuminated by blue lights. The water creates a soothing, steamy ambiance, with built-in seating designed for multiple guests. Ambient lighting adds a calming touch to the overall atmosphere.

Home in Nottinghamshire

4.96 out of 5 average rating, 375 reviews

Close to town, hot tub retreat!

The exterior of a newly converted barn cottage is displayed, featuring rustic stone walls and a slate roof. Several windows allow natural light to enter, while two wooden benches are placed on the patio, inviting relaxation. Lush greenery is visible in the background.

Farm stay in Derbyshire

4.96 out of 5 average rating, 169 reviews

Luxury newly converted oak cottage

Top guest favorite

Place to stay in Onecote

4.99 out of 5 average rating, 273 reviews

Woodland Retreat with Hot Tub in Onecote

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, 261 reviews

The cabin @ white cottage

Top guest favorite

Cottage in Derbyshire

4.95 out of 5 average rating, 115 reviews

Peak District - Howard Park lodge. Hot tub.

Top guest favorite

A spacious hot tub is positioned within a sheltered area featuring wooden paneling. Water is visibly swirling inside, with a floating device gently resting on the surface. Soft lighting enhances the serene atmosphere, providing a private space for relaxation.

Home in Hollinsclough

4.96 out of 5 average rating, 185 reviews

Axe Edge View

Other great vacation rentals in Chesterfield

A spacious living area features two dark blue sofas with decorative cushions, positioned on a light-colored area rug. Natural light enters through windows dressed with soft shades. A side table holds decorative items, while a mirror reflects the room's layout. A dining area is visible in the background.

Home in Derbyshire

4.92 out of 5 average rating, 25 reviews

Escape to the Peak District National Park

The semi-detached Victorian property displays a stone façade with large windows. A well-maintained garden features green grass, blooming flowers, and a small pathway leading to the entrance. The structure is framed by trees and bushes, providing a natural setting.

Home in Hayfield

4.86 out of 5 average rating, 64 reviews

Home in Hayfield

An outdoor dining area is surrounded by lush planters filled with colorful flowers. A large stone patio features a table with light blue chairs, complemented by a tall umbrella. In the background, two brick ovens are visible, adding to the inviting outdoor space.

Farm stay in Staffordshire

4.92 out of 5 average rating, 212 reviews

Hot Tub, Indoor Pool & Hay Loft Near Alton Towers

Top guest favorite

Cottage in Bakewell

5 out of 5 average rating, 210 reviews

Rocking Stone Cottage - Idyllic Rural Retreat

Top guest favorite

A stylish hanging chair is positioned beside a stone wall, surrounded by lush greenery and blooming flowers. A nearby window offers a view into the home, framed by the vibrant plants, creating a serene outdoor seating area.

Home in Derbyshire

5 out of 5 average rating, 39 reviews

Booth Farm - Small party rental

Top guest favorite

The exterior of the apartment building is shown, featuring a stone facade and a large floor-to-ceiling window. The building is situated beside a grassy area, with a wooden gate leading to the front path, showcasing a clear blue sky and lush greenery in the background.

Condo in Buxton

4.96 out of 5 average rating, 177 reviews

Buxton apartment, free parking and stunning views

An inviting entrance to Critchlow Cottage is framed by lush green ivy climbing the stone exterior. A wrought iron gate leads to a pathway surrounded by well-maintained hedges and grass, providing access to the front door.

Cottage in Earl Sterndale

5 out of 5 average rating, 9 reviews

Dog-friendly Critchlow Cottage in Earl Sterndale

Top guest favorite

A round glass table is set on a wooden deck, surrounded by a dark wicker seating arrangement. The expansive views of rolling hills and greenery in the distance are visible beyond the railing, providing a serene backdrop.

Farm stay in Cauldon

4.99 out of 5 average rating, 84 reviews

Escape to the country

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.

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