
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.

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.

Pear Tree Lodge with private HOT TUB and garden
Pear Tree Lodge (with private HOT TUB & garden) is a private and cosy retreat in peaceful surroundings within Henry's Orchard. This unique space is across two floors housing open dining, living and kitchen downstairs with KING SIZE BED and ensuite upstairs. Located close to many woodland walks, pubs, amenities, attractions and transport links in and around Yorkshire and Derbyshire. Please check our GUIDEBOOK for details https://abnb.me/P8eNebqIyib If bringing dogs please add to booking!

The Round House - family house with indoor pool
Architect-designed The Round House sits just above the Peak District village of Rowsley, boasting stunning views towards Haddon Hall and Bakewell. Walk to Chatsworth House (3 miles) across the fields following the River Derwent. Set in 9 acres of peaceful landscaped gardens with wonderful birdlife - but only a few miles from the market town of Bakewell. Plenty of great walks from the house plus all year round indoor heated pool shared with Woodside Cottage - also at the same location.

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.

Peaceful hideaway Baslow Chatsworth, Peak District
Gorse Ridge End is a fresh and airy bungalow superbly situated in the beautiful village of Baslow in the heart of the stunning Peak District National Park. Within walking distance of the Chatsworth Estate, excellent village pubs, restaurants and dramatic gritstone crags and moorlands. In a peaceful village location away from the main road with private garden and plenty of off road parking, this 2 bedroom property provides a tranquil base for a couple or a family.
Popular amenities for Chesterfield house rentals
House rentals with a pool

Charming 6-Bedroom Winster Village, Peak District

Large Modern Décor 3 Bed with Driveway & Garden

Ashbourne Cottage near Dovedale

6 cottages, 46 guests

Grove Farm Cottage

Cuckoo

The Farmhouse

Haddon Grove F'house - with shared pool & games rm
Weekly house rentals

The Old Chapel Luxury Retreat

Lovely house Eckington Sheffield

Cheerful 2-bedroom home with free offroad parking

The Nook - an idyllic rural bolt hole...

Central Bakewell Quiet Luxury

Derbyshire Gem, Peak District

The Old Timber Store - tiny home in a village

Style and Comfort - Welcome to The Bobbin!
Private house rentals

Beautiful 4 bed at gateway to the Peak District

Luxury manor house with hot tub

The Cottage - Derbyshire

A cosy 2 bedroom family friendly living space

Affordable 3 Bed house - Peak District 20 mins

Spacious Scandinavian style hideaway with log fire

Home in Chesterfield

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 | $139 CAD | $167 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!
Destinations to explore
- London Vacation rentals
- Picardy Vacation rentals
- Hebrides Vacation rentals
- Amsterdam Vacation rentals
- Thames River Vacation rentals
- South West England Vacation rentals
- Inner London Vacation rentals
- Rivière Vacation rentals
- Dublin Vacation rentals
- Brussels Vacation rentals
- South London Vacation rentals
- Central London Vacation rentals
- Condo rentals Chesterfield
- Rentals with outdoor seating Chesterfield
- Family-friendly rentals Chesterfield
- Apartment rentals Chesterfield
- Pet-friendly rentals Chesterfield
- Rentals with a patio Chesterfield
- Rentals with a fireplace Chesterfield
- Cabin rentals Chesterfield
- Cottage rentals Chesterfield
- Rentals with a washer and dryer Chesterfield
- House rentals Derbyshire
- House rentals England
- House rentals United Kingdom
- 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