Some info is shown in its original language. Translate

House vacation rentals in Chesterfield

Find and book unique houses on Airbnb

Top-rated house rentals in Chesterfield

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

%{current} / %{total}1 / 1
Top guest favourite
A modern kitchen area features a central island with seating, completed by stylish light fixtures above. A large window offers a view of lush greenery outside, while contemporary art adds a touch of color to the neutral walls. The space invites comfort and functionality.
Home in Rowsley
4.98 out of 5 average rating, 269 reviews

Panoramic views idyllic, hill farm Nr Bakewell

The Garden Nook offers complete privacy and is located in a perfect spot for everything. Newly converted and set within 55 acres of impressive private land, gardens, and fruit orchards. A rejuvenating location to unwind and reconnect with nature in such a tranquil environment. The comfy contemporary haven with tasteful decoration, stylish furniture, and spectacular views is the perfect place to relax. Watching lambs skipping around the orchard is a delightful bonus! Tractor experiences available

Guest favourite
A spacious garden area is visible, featuring a variety of colorful flowers in pots, including bright yellow and pink blooms. A well-maintained lawn extends into the distance, accompanied by tree line and greenery. A soft play structure and garden shed are also included in the scene.
Home in Wingerworth
4.89 out of 5 average rating, 272 reviews

Oakdale - Our Quest retreat

Idyllically situated at the entrance to Hardwick Wood, Wingerworth, 2 miles from Chesterfield and all amenities, yet totally secluded. Close to Chatsworth & Peak District. Fully fitted kitchen all appliances including tumble drier & dishwasher. Underfloor zoned central heating. Log burner. Fully fitted bathroom with bath and shower. Separate shower/wc. Fully fitted bedrooms with ample wardrobes and drawers ideally suited to a family of 4. Sleeps 4 in one double and 1 set of bunks, cot available

Guest favourite
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
4.92 out of 5 average rating, 135 reviews

Cosy Quiet Cottage In Pilsley

A beautiful, refurbished, one bedroomed cottage in a peaceful small village location, just a couple of minutes walk onto the Five Pits Trail and other great walks, yet still in close proximity to local amenities. The perfect place to enjoy a home from home getaway; self check in, full kitchen, glorious large bathroom space with bath and waterfall shower, comfy lounge area with large TV, extremely spacious cosy king bedroom and front and rear enclosed patio areas for your four legged friends!

Guest favourite
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
4.83 out of 5 average rating, 438 reviews

Cosy cottage, stunning views near Chatsworth

If you want peace and solitude with stunning sunset views in a comfy, lived-in, dog-friendly place of your own Copy Wood Cottage is your ideal location. Situated on a steep hill above the Derwent Valley, it’s a short drive or good walk to Chatsworth and Bakewell and Matlock. Nestled on the edge of Beeley Moor Copy Wood sits below woodland and is surrounded by fields grazed by sheep. A short walk down brings to Rowsley village. We now have an EV Charger for guest’s use, just contact me on cost.

Top guest favourite
A scenic view captures rolling green hills under a colorful sky at sunset. A tranquil river flows through the valley, with a quaint white building nestled among the trees. A signpost directs visitors towards Monsal Dale, indicating nearby walking paths.
Home in Bakewell
4.97 out of 5 average rating, 124 reviews

Monsal View Cottage

A beautiful space with exquisite views set at the iconic viewpoint of Monsal Head. This is the perfect base to really enjoy all that the Peak District has to offer- including the most epic view of all at Monsal Head and the Headstone Viaduct. ** Pets allowed on request ** Located at Hobb’s Cafe so you have a quaint little cafe right next door! Enjoy breathtaking views all to yourself in the mornings and evenings. Please check out Hobb’s Cafe online to fully see the location of this cottage.

Guest favourite
A modern kitchen space is shown with white cabinetry and a wooden island table. Stainless steel appliances, including built-in ovens and a refrigerator, are featured. Natural light floods in through a window above the sink and a stable door leading to the garden.
Home in Curbar
4.96 out of 5 average rating, 157 reviews

Sleeps 6- Views of Curbar gap & near to Chatsworth

Edge Cottage is nestled in the picturesque village of Curbar with magnificent views of Curbar Edge. This 2 bedroomed cottage has a stylish home from home feel with lots of little touches, free Wifi, free parking & a cottage garden to enjoy. Spacious cottage for 4, but can sleep 6. A great base to visit Chatsworth House, Haddon Hall, Castleton, Hathersage and the Hope Valley. Dog friendly, we charge an additional £30 per dog for the duration of your stay. We can accept up to 1 dog.

Guest favourite
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.
Home in Chesterfield
4.96 out of 5 average rating, 332 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

Top guest favourite
The exterior of the cottage is adorned with a blend of natural stone and light-colored wood accents. Vibrant flowers in pink, white, and purple surround the entrance, enhancing the welcoming appearance. Two windows above the door allow natural light to brighten the charming facade.
Home in Youlgreave
4.99 out of 5 average rating, 216 reviews

Willow Cottage Newly renovated quaint cottage

Nestled away in the village of Youlgrave, in the heart of the Peak District National Park this newly renovated cottage is the perfect bolt hole for couples, friends and single travellers looking to get away from it all. It is a great place for walkers and cyclists with access to the Limestone Way, White Peak Way and the Alternative Pennine Way. There are three public houses which all serve home cooked food using local produce and there are two bakeries, a deli and post office.

Top guest favourite
A spacious bedroom features a large, comfortable bed dressed in pristine white linens. Two nightstands with lamps are positioned on either side, offering gentle illumination. A wardrobe is visible, and the soft beige walls create a calming environment.
Home in Baslow
4.94 out of 5 average rating, 415 reviews

Comfortable cottage on the Chatsworth Estate

Yeldwood Farm Cottage is a beautiful barn conversion on our farm, just outside Baslow. The self-catering cottage sleeps 2 guests, in a Super-King size (or Twin) master bedroom. The cottage comprises a fully equipped kitchen, dining room, sitting room and bathroom with a large bath and shower. We are ideally situated on the Chatsworth Estate within the Peak District, close to Chatsworth House itself, Haddon Hall, Bakewell, Eyam, Matlock, Castleton, Buxton and Sheffield.

Top guest favourite
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
5 out of 5 average rating, 112 reviews

Country Cottage with great outside space & views

Relax in our stunning two-bedroom slice of Derbyshire heaven! Amazing walks and local pubs >1 mile away. Large terrace with fabulous views over the valley & a range of seating. 2 double bedrooms, 1 ensuite & large family bathroom. Significant renovations recently & has a highly specified kitchen inc. range. Log burner in living room & Smart TVs in Kitchen, Living room & main bedroom. WIFI & office to keep in touch with work whilst relaxing in comfort & style.

Top guest favourite
Home in South Yorkshire
4.97 out of 5 average rating, 106 reviews

The Little Lodge

Kick back and relax in this calm, stylish space. The Little Lodge is a brand new renovated annex attached to a charming Victorian Lodge from the 1800s. Situated in a picturesque and peaceful conservation area on a private road in the leafy suburb of Ranmoor Sheffield. The Little Lodge is only 15minutes away from Sheffield's main train station and sits of the foothills of South Yorkshire's famous Peak District. Ideal for a city break or a Rambler's retreat.

Top guest favourite
An open-plan living space features original stone walls and sleek wooden flooring. A dining table sits in the foreground, while cozy seating with soft cushions is arranged nearby. A staircase leads to an upper level with a spacious bed visible through glass balustrades.
Home in Bradwell
4.99 out of 5 average rating, 225 reviews

Unique & stylish converted Chapel - Peak District

Welcome to Heather View Chapel, a beautifully converted retreat in the heart of the Peak District National Park. Our brilliant housekeepers ensure the Chapel is spotlessly clean for your arrival. Designed with care, it’s the perfect place for family and friends to relax and make memories. Located in picturesque Hope Valley, it’s ideal for exploring trails, hills, and the great outdoors. If you love nature and adventure, you’ll love staying here!

Popular amenities for Chesterfield house rentals

When is the best time to visit Chesterfield?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$133 CAD$134 CAD$133 CAD$147 CAD$141 CAD$138 CAD$166 CAD$161 CAD$157 CAD$158 CAD$151 CAD$155 CAD
Avg. temp4 °C5 °C7 °C9 °C12 °C15 °C17 °C17 °C14 °C11 °C7 °C5 °C

Quick stats about house rentals in Chesterfield

  • Total vacation rentals

    Explore 60 vacation rentals in Chesterfield

  • Nightly prices starting at

    Chesterfield vacation rentals start at $42 CAD per night before taxes and fees

  • Verified guest reviews

    Over 3,690 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    60 of Chesterfield vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chesterfield rentals

  • 4.8 Average rating

    Chesterfield stays are highly rated by guests—averaging 4.8 out of 5!

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