
House vacation rentals in Chesterfield
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Top-rated house rentals in Chesterfield
Guests agree: these houses are highly rated for location, cleanliness, and more.

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

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

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!

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.

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.

Pigeon Loft Cottage
This unique self contained peaceful cottage is 250 years old and set in the centre of the beautiful village of Bonsall in the Peak District and within easy reach of all amenities. The cottage was once a Pigeon loft and has been transformed and renovated into a simple characterful living space within the conservation area. Views from the cottage and outside private terrace are stunning. There are choices of walks from the door including 2 pubs cafe and shop within easy walking distance.

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

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.

Cuckoostone Barn - simply stunning!!
Cuckoostone Barn is a stunning property set in the White Peak area of the Peak District. The area is surrounded by nature and the perfect location to sit and watch the wildlife go by, whilst being mesmerised by the uninterrupted views of rolling countryside. Cuckoostone Barn is an excellent base to explore the wonders of the Peak District National Park, with amazing walks and cycle routes on the doorstep, or a place to simply relax and unwind in an idyllic part of the world .

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.

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.

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.
Popular amenities for Chesterfield house rentals
House rentals with a pool

Charming 6-Bedroom Winster Village, Peak District

Ashbourne Cottage near Dovedale

Cuckoo

28 Fentley

The Farmhouse

The Manor House

Badgers Wood

Country Cottage With Shared Swimming Pool
Weekly house rentals

The Cottage - Derbyshire

Spacious Scandinavian style hideaway with log fire

The old stables - sleeps 2 near Dore Station

Home in Chesterfield

Scrumpy's Cottage

Derbyshire Gem, Peak District

Blissful Barry’s

The Little Engine House
Private house rentals

Beautiful 4 bed at gateway to the Peak District

A cosy 2 bedroom family friendly living space

1 Bedroom Terrace in Quiet area

Affordable 3 Bed house - Peak District 20 mins

Lower Holly Barn

Entire HOME lovely terrace cottage style house

Pail End in the Derbyshire Dales

Cosy Bowness House welcomes you.
When is the best time to visit Chesterfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec | 
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 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. temp | 4 °C | 5 °C | 7 °C | 9 °C | 12 °C | 15 °C | 17 °C | 17 °C | 14 °C | 11 °C | 7 °C | 5 °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! 
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- Peak District national park
- Alton Towers
- Etihad Stadium
- Chatsworth House
- The Quays
- Lincoln Castle
- Harewood House
- Sundown Adventureland
- Mam Tor
- Tatton Park
- Royal Armouries Museum
- Holmfirth Vineyard
- Crucible Theatre
- The Nottinghamshire Golf & Country Club
- Science and Industry Museum
- Rufford Park Golf and Country Club
- IWM North
- Shrigley Hall Golf Course
- John Rylands Library
- Cavendish Golf Club
- Derwent Valley Mills
- Daisy Nook Country Park
- Manchester Central Library
- Bosworth Battlefield Heritage Centre
