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Vacation rentals in Chesterfield

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Top-rated vacation rentals in Chesterfield

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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4.85 out of 5 average rating, 124 reviews

Riverdale View - birds bees river & trees +garden

"Superb location, beautiful cottage" down the cobbled footpath towards the river. Private terrace & garden, heritage decor, hi speed Broadband. Soak in the roll top bath gazing at the fossil wall. Pull off your walking boots & rest on the church pew. Dim the lights, snuggle up with a glass of wine & cosy fire. Outdoor bistro table with nature all around. River 30 steps down for walks & swim! 3 pubs serve food & grocery shops nearby “undoubtedly the most lovely, wonderful place we have stayed at”

Top guest favorite

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

The entrance features a vibrant green door with a brass knocker and a plaque reading 'Millstream Cottage.' A welcome mat lies at the threshold, greeting guests, while stonework enhances the cottage's character. The exterior is well-maintained and inviting.

4.94 out of 5 average rating, 370 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 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.

5 out of 5 average rating, 215 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.

4.88 out of 5 average rating, 125 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 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.

4.78 out of 5 average rating, 125 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

4.95 out of 5 average rating, 587 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.

4.91 out of 5 average rating, 108 reviews

Stylish cottage inc. breakfast, sleeps 4

FREE Breakfast at the Old Original Bakewell pudding shop Welcome basket on arrival - Loaf of Bakewell Bakery bread, Pint of milk, bottle of Wine, bottle of local beer and the Old Original Bakewell Pudding Within a minuet’s walk of the shops, restaurants, pubs, cafes and the river Wye and large car parks *Walking, climbing and cycling on your door step *Outdoor area for al fresco dining *Cosy log burner in the living area *One parking space included *free WI-FI *Small dogs allowed

Top guest favorite

4.95 out of 5 average rating, 154 reviews

Cosy Village Cottage in The Peak District

A traditional cottage in the idyllic quiet 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.

Top guest favorite

4.95 out of 5 average rating, 312 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.

4.8 out of 5 average rating, 220 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)

4.97 out of 5 average rating, 298 reviews

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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Popular amenities for Chesterfield vacation rentals

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.

4.98 out of 5 average rating, 110 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.

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.

4.86 out of 5 average rating, 180 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.

4.87 out of 5 average rating, 161 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.

4.95 out of 5 average rating, 202 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.

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.

4.99 out of 5 average rating, 107 reviews

The Old Toffee Shop

Top guest favorite

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.

4.89 out of 5 average rating, 244 reviews

Small cottage in Peak District 1 x King Bed only

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.

4.88 out of 5 average rating, 563 reviews

HOT TUB Luxury Converted Barn

An inviting indoor space features a dining table surrounded by sleek, high-backed chairs. Soft lighting casts a warm glow over the area, where a hot tub is positioned nearby, complemented by lush greenery on the walls for a serene atmosphere.

4.96 out of 5 average rating, 387 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.

4.96 out of 5 average rating, 172 reviews

Luxury newly converted oak cottage

Top guest favorite

A wooden lodge is nestled among lush greenery, surrounded by trees. A comfortable hammock is seen hanging nearby, while a path leads to the lodge's entrance. The scene conveys a sense of tranquility, inviting a connection with nature.

4.99 out of 5 average rating, 278 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.

4.99 out of 5 average rating, 271 reviews

The cabin @ white cottage

Top guest favorite

A large six-person hot tub is set against a backdrop of lush greenery, with jets of water creating gentle bubbles. The scene is complemented by a softly lit sky at sunset, adding a calming atmosphere to the outdoor space.

4.98 out of 5 average rating, 150 reviews

Luxury 4 bedroom, 3 bath, hot tub. Pet friendly.

Top guest favorite

A charming stone gate house is depicted, featuring a sloped roof and prominent front gable. Large windows allow natural light to fill the interior. Surrounded by lush greenery, the entrance includes a gated pathway leading to a gravel area, enhancing the serene outdoor setting.

4.95 out of 5 average rating, 115 reviews

Peak District - Howard Park lodge. Hot tub.

Top guest favorite

A comfortable living room features luxury reclining sofas adorned with decorative pillows. A wooden coffee table sits centrally on a light wood floor. Natural light enters through large windows, and a cozy fireplace adds warmth to the space, complemented by a rustic stone surround.

4.96 out of 5 average rating, 188 reviews

Axe Edge View

Other great vacation rentals in Chesterfield

Top guest favorite

4.99 out of 5 average rating, 110 reviews

Rowan Tree Cottage

4.92 out of 5 average rating, 216 reviews

Hot Tub, Indoor Pool & Hay Loft Near Alton Towers

Top guest favorite

5 out of 5 average rating, 212 reviews

Rocking Stone Cottage - Idyllic Rural Retreat

The exterior of a rustic stone cottage is highlighted, featuring a double-height glass entryway. Two small outdoor tables and chairs are set on a stone patio, surrounded by a well-maintained lawn and lush greenery. Flowers adorn the window ledges, adding a touch of color.

4.98 out of 5 average rating, 529 reviews

Woodcock Farm - Luxury self-catering cottages

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.

4.96 out of 5 average rating, 179 reviews

Buxton apartment, free parking and stunning views

Top guest favorite

4.96 out of 5 average rating, 214 reviews

Gag Barn Nr Thorpe (Peak District/Dovedale)

Top guest favorite

A stone exterior of a two-story house is highlighted against a clear blue sky. The building features a set of steps leading to a door adorned with flower boxes. A small outdoor area is visible with a circular table and two decorative figurines.

4.95 out of 5 average rating, 422 reviews

Gramps's - exquisite 2 bed home, comfy & cosy

Top guest favorite

5 out of 5 average rating, 124 reviews

Self-Catering, Log Burner, Cosy, Peak District

Quick stats about vacation rentals in Chesterfield

Total rentals
100 properties
Nightly prices starting at
€ 18 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 Brimington, and over 180 vacation rentals in Chesterfield.
How much does it cost to stay in condo rentals in Chesterfield?
Experience the best of Chesterfield with our condo rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there house rentals with a dedicated workspace in Chesterfield?
Yes! Work meets play with ease at over 20 house rentals in Chesterfield featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly house rentals in Chesterfield?
Four-legged friends are welcome in Chesterfield. Choose from more than 10 house rentals for guests traveling with pets.
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.
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.

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