Vacation rentals in Chesterfield

4.94 out of 5 average rating, 187 reviews

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

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

4.94 out of 5 average rating, 366 reviews

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

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.

4.97 out of 5 average rating, 173 reviews

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.

Home in Alton

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

5 out of 5 average rating, 211 reviews

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

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, 122 reviews

A scenic landscape features rolling hills adorned with vibrant purple heather under a colorful sky at sunset. The backdrop showcases distant valleys, while large boulders in the foreground highlight the natural beauty of the area.

Townhouse in Derbyshire

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.

4.76 out of 5 average rating, 118 reviews

A well-lit kitchen showcases a double window with scenic views of rolling greenery. A stainless steel sink is positioned under the window, alongside a dish rack and dish soap. Light beige tiles and a dark countertop create a clean, functional space.

Home in Alton

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!

4.96 out of 5 average rating, 580 reviews

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

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.

4.97 out of 5 average rating, 160 reviews

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

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.

4.95 out of 5 average rating, 311 reviews

Cottage in Tideswell

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.

4.95 out of 5 average rating, 153 reviews

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

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.

4.8 out of 5 average rating, 218 reviews

Cottage in Carsington

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)

4.97 out of 5 average rating, 288 reviews

An outdoor patio area is featured, with a comfortable seating arrangement and a fire pit on a gravel surface. Lush green grass extends to the horizon, framed by scenic countryside views beneath a partly cloudy sky.

Hut in Derbyshire

Hillside Hut - with hot tub & private garden

Hillside Hut is our charming, newly developed, hut located in a secluded position on our smallholding in rural Derbyshire. With its own driveway and dedicated parking, it is situated in a very private 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 front door and fantastic dog-friendly village pubs within walking distance.

Vacation rentals for every style

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Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Chesterfield vacation rentals

Laptop-friendly workspace

Stay near Chesterfield's top sights

Cineworld Cinema Chesterfield19 locals recommend

Linacre Reservoirs16 locals recommend

The Peacock At Barlow14 locals recommend

Chesterfield Market8 locals recommend

Nonnas Chesterfield7 locals recommend

The Tickled Trout7 locals recommend

Pet-friendly vacation rentals in Chesterfield

4.98 out of 5 average rating, 158 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

4.8 out of 5 average rating, 207 reviews

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

Cheedale Lodge

4.87 out of 5 average rating, 175 reviews

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

Cosy Little Cottage in the Peak District

4.87 out of 5 average rating, 160 reviews

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

Harry Eyre Cottage, Castleton, Peak District

4.95 out of 5 average rating, 200 reviews

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

Dog & Cycle friendly house with enclosed garden

4.99 out of 5 average rating, 107 reviews

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

The Old Toffee Shop

4.98 out of 5 average rating, 133 reviews

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

Spacious, dog friendly, one level accommodation.

4.89 out of 5 average rating, 244 reviews

A small stone courtyard is shown, featuring a round wooden table accompanied by two folding chairs. Flower pots with greenery add a touch of nature against the stone wall, while sunlight bathes the area, enhancing the welcoming outdoor space.

Cottage in Birchover

Small cottage in Peak District 1 x King Bed only

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Other great vacation rentals in Chesterfield

4.92 out of 5 average rating, 25 reviews

Home in Derbyshire

Escape to the Peak District National Park

4.86 out of 5 average rating, 64 reviews

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

Home in Hayfield

4.96 out of 5 average rating, 169 reviews

Farm stay in Derbyshire

Luxury newly converted oak cottage

Farm stay in Staffordshire

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.

4.92 out of 5 average rating, 212 reviews

Hot Tub, Indoor Pool & Hay Loft Near Alton Towers

5 out of 5 average rating, 210 reviews

Cottage in Bakewell

Rocking Stone Cottage - Idyllic Rural Retreat

4.99 out of 5 average rating, 260 reviews

A private garden area is surrounded by tall fences and lush greenery. A gravel pathway leads toward the cabin, which features large windows. A seating area is visible, offering a serene view of the landscaped yard, with gentle sunlight filtering through the trees.

Guesthouse in Derbyshire

The cabin @ white cottage

5 out of 5 average rating, 39 reviews

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

Booth Farm - Small party rental