
Vacation rentals in Chesterfield
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Top-rated vacation rentals in Chesterfield
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Dog Friendly, Cosy, Peaceful, Walks, Peak District
The Spinney is our super dog-friendly ground floor self-catering accommodation! We've designed it so that you & your dog have a great holiday! Part of a traditional stone barn conversion located in the Peak District & Derbyshire Dales, the Spinney offers space as well as the comfort of modern living. With cosy underfloor heating throughout, and everything you need for you and your furry friend, we are sure you will have a great time here! Peaceful setting, close to popular visitor attractions!

Chatsworth Cottage
Situated on the edge of the Peak District Park, this is the ideal base for exploring Derbyshire. The Cottage is situated on Chatsworth Road just 10 minutes drive from the ‘Palace of the Peak District’. A short journey and you will discover other wonders of the Peak at places like Matlock, Bakewell, Castleton and Buxton. The historic market town of Chesterfield and the famous Crooked Spire is just a 20 minute walk down the Brampton Mile where you will find some great places to shop, eat & drink.

Characterful 2 bed cottage in excellent location
A charming cottage overlooking a babbling, nature-rich brook. Full of character, this peaceful cottage boasts a cosy living room complete with woodburner, underfloor heating and exposed beams, a fabulous kitchen and a stylish bathroom. The cottage is in a superb location with top-class restaurants, the magnificent Chatsworth Estate and truly stunning local walks right on the doorstep. Bikes can be stored in the rear yard making this cottage an ideal base for foodies, cyclists and walkers alike.

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

The Tower
The Tower is the perfect romantic high-end getaway for couples who want to get away from it all in a secluded location and fancy just something different. The Tower has recently been converted for use as a holiday let which was previously an unused ancillary building adjacent to The Water Works, an old water treatment plant near Bolsover, converted to domestic use in 2002 and featured on the Channel 4 programme Grand Designs. Available for single night stays. Discounts on 3+ nights bookings.

Cheerful 2- Bedroomed Home in Chesterfield.
This beautiful town house is located right on the edge of the Peak District and within walking distance to Chesterfield's iconic Market Town. This 2 bedroomed modern home has everything you need and is the perfect base for visiting all the local attractions Derbyshire has to offer. The locations boasts a 20 min drive to the well loved Peak District. Along with all the wonderful bars, restaurants, gift & coffee shops just a short walk away. Chesterfield's Golf course is just 15min drive away.

The Kennels
Kick off your walking boots, wash down your bike or just park up the car, this freshly converted kennels is the place to relax for a few days. Peaceful and away from it all but close enough to explore the beauty of the Peak District and Chatsworth House. Matlock is a couple of miles away with restaurants, shops and amenities. You can start exploring from the door step; we can help with guides, directions and recommendations. The room can be configured as a luxury Super King or twin beds.

Double bedroom with a view/en-suite/couch area
A large double cosy bedroom with sitting area and en-suite. This upper room in an old barn conversion has its own separate entrance. It is tastefully decorated in a traditional manner to provide a comfortable space to relax in. Stunning views over a pretty garden and surrounding countryside. Wifi/dressing table/desk/fridge. Towels and soaps provided. Tea and coffee provided. Within 100 yards (opposite) from The Hackney House Cafe and The Peacock at Barlow who both serve a hearty breakfast

Cottage by the Park Chesterfield - Peak district
Our COTTAGE is situated with a PARK on our doorstep and 15 min drive to Baslow in the PEAK DISTRICT . Also within walking distance to Chesterfield town center and Chatsworth road. Only a 15 min walk to bars, restaurants, coffee shops, and local boutique shops on Chatsworth Road. It is a short drive to Chatsworth house, Bakewell, Matlock and many of the delightful areas in the Peak district. Our home is cozy and welcoming! We hope you will choose us for your next visit to the area.

One Bedroom Studio with full kitchen & log burner.
Located in the village of Holmesfield in Derbyshire. On the edge of the Peak District with Chatsworth House 10 minutes drive away. Sheffield is a short drive away. The accommodation comprises, kitchen and a King size bed. A sitting room with central heating and log burner, a shower, toilet & sink. Utility room with washing machine, coffee machine and breakfast bar. Stunning views of Derbyshire.Private entrance. Car parking. PLEASE NOTE: NO CHILDREN INCLUDING INFANTS UNDER TWO YEARS OF AGE.

Chesterfield -Peak District-Chatsworth-EV Charger
Welcome to our ground floor studio, private entrance, bathroom, kitchenette with fridge freezer, microwave, double bed, wall-mounted TV. PAYG EV Charger - Ideal for business travellers and couples seeking a relaxing break. Located on a quiet, tree-lined avenue. Minutes from Chatsworth Road's bars and restaurants. Close to the Peak District, Chatsworth House, Buxton, Bakewell, and Matlock, guest access via a coded key lock. Nestled near the Hipper Valley bike trail for a peaceful retreat.

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
Popular amenities for Chesterfield vacation rentals
Pet-friendly boutique hotels in Chesterfield

Peveril Suite at Cheshire Mews Castleton

Mam Tor Suite at Cheshire Mews Castleton

Winnats Suite at Cheshire Mews Peak District

Deluxe Double @George Wright Boutique Hotel & Bar

Speedwell Suite at Cheshire Mews Peak District

Blue John Suite at Cheshire Mews Castleton
Pet-friendly vacation rentals in Chesterfield

Lizzy’s Luxury Cottage

Willow Cottage Newly renovated quaint cottage

Gorgeous romantic cosy cottage retreat with views

Luxury Peak District Cottage with Hot Tub

Luxury Country Cottage with Hot Tub

The Hideaway. Great views, garden & location

Swift Retreat - converted farm building

Wasp Nest Cottage, Peak District
Other great vacation rentals in Chesterfield

Butler's Retreat Tissington Hall Derbyshire

Self contained annex - Peak District riverside

Courtyard Cottage -With Japanese Whirlpool Bath

The Old Coach House. 5-star. Parking. EV charger.

Panoramic views, April lambing, Nr Chatsworth

Magical Historic Barn Conversion

The Old Bank Luxury Serviced Apartment Derbyshire

Exclusive Detached Retreat+Games Room M1J35 1.5m
When is the best time to visit Chesterfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ331 | ﺩ.ﺇ334 | ﺩ.ﺇ342 | ﺩ.ﺇ367 | ﺩ.ﺇ371 | ﺩ.ﺇ371 | ﺩ.ﺇ404 | ﺩ.ﺇ437 | ﺩ.ﺇ382 | ﺩ.ﺇ411 | ﺩ.ﺇ397 | ﺩ.ﺇ404 |
| 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 |
Frequently Asked Questions
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.
How much does it cost to stay in apartment rentals in Chesterfield?
Experience the best of Chesterfield with our apartment 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 pet-friendly house rentals in Chesterfield?
Four-legged friends are welcome in Chesterfield. Choose from more than 30 house rentals for guests traveling with pets.
Are there house rentals with a dedicated workspace in Chesterfield?
Yes! Work meets play with ease at over 30 house rentals in Chesterfield featuring dedicated workspaces. Stay connected and productive in your home away from home.
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 Chesterfield, and over 180 vacation rentals in Brimington.
Do house rentals in Chesterfield have a kitchen?
Absolutely! We offer over 60 house rentals with a kitchen in Chesterfield. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Chesterfield have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Chesterfield. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Chesterfield have free parking?
Absolutely! We offer over 50 house rentals with free parking in Chesterfield. Enjoy a tailored experience with all the comforts you desire.
Quick stats about vacation rentals in Chesterfield

Total vacation rentals
Explore 110 vacation rentals in Chesterfield

Nightly prices starting at
Chesterfield vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

Verified guest reviews
Over 7,360 verified reviews to help you choose

Family-friendly vacation rentals
60 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
100 of Chesterfield vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Chesterfield rentals

4.9 Average rating
Chesterfield stays are highly rated by guests—averaging 4.9 out of 5!
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- Peak District National Park
- Alton Towers
- Etihad Stadium
- Chatsworth House
- AO Arena
- The Quays
- Manchester Central Convention Complex
- Motorpoint Arena Nottingham
- First Direct Arena
- Heaton Park
- Lincoln Castle
- Victoria Warehouse
- Harewood House
- Tatton Park
- Mam Tor
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- Utilita Arena Sheffield
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- Wythenshawe Park
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- Manchester Central Library




