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

Springwood Cottage Private and Unique
Springwood Cottage is ideally situated in a beautiful location on the edge of Derbyshire is completely self contained with its own entrance and private garden area with parking outside. The Cottage is completely newly built in 2020 and designed to the highest standard. Well behaved Dogs welcome, we are happy to accommodate 2 dogs, please request if you have more than 2. A deluxe super kingsized bed (6 x6 foot) with the most up to date memory foam mattress and a comfortable sofa bed in the lounge

The Old Coach House. 5-star. Parking. EV charger.
“Loved staying here”. Off street parking. Ultra fast WiFi. Perfectly located in leafy Nether Edge village, 10 minutes from city centre and Peak District. Near to local shops, pubs, cafés and restaurants. Everything you need for the perfect stay: Private off-street parking: Yes. Big comfortable beds: Yes. Powerful shower: Yes. Washing machine: Yes. New kitchen: Yes. Spotlessly clean: Yes. Ultra-fast 1GB fibre optic broadband/Wi-Fi: Yes. Ev charger: Yes. Charm, character, history? Yes. Yes. Yes!

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

2 En-suite rural luxury cottage Ashover Derbyshire
Rural luxury 2 bedroomed en-suite cottage with kingsize bed & twin or superking. Both bedrooms have en-suite facilities one with walk in rain shower and twin with shower over bath. Ideally situated for the Peak District, Bakewell, & Chatsworth. Underfloor heating throughout and looks out onto its own woodland with picnic bench plus 2 more seating areas ideal for 2 couples. BBQ & table & chairs with cushions. Perfect for chilling out with views and walks from the doorstep. Pub 10 minute walk.

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.

Lizzy’s Luxury Cottage
Welcome to Lizzy’s Cottage! Nestled in the heart of the Peak District, Lizzy’s Cottage offers a luxurious escape for couples and families. Surrounded by breathtaking countryside, the cottage provides a peaceful retreat, while being just a short drive from popular destinations such as Bakewell, Chatsworth, Matlock, and Matlock Bath. At Knabb Farm, we offer private parking for all guests, and our 7 acres of private land provide plenty of space to explore and enjoy the stunning surroundings.

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.

Self-contained studio in amazing rural location
This comfortable studio with amazing views, lots of outdoor space, walks from the doorstep and pubs with good food nearby is perfect for couples looking to re-charge their batteries in a rural location. It has a well-equipped kitchen, including dishwasher, White Company linen, underfloor heating with independent controls, it's own combi-bolier for hot water, tv and wi-fi. It is on the edge of the Peak District with many local attractions, such as Chatsworth and Hardwick Hall.

The Old Chapel Apartments
The Old Chapel Apartment 2 Positioned on a beautiful village high street in the heart of Sherwood Forest, our two brand new apartments are in a renovated former Methodist Chapel and truly at the centre of village life. Beautifully-appointed and furnished in a luxurious modern style, each sleeping up to four people, they are perfect for couples looking for a little space or families and friends holidaying together. We look forward to hosting you!

'Rose House' Modern 3 Bedroom Detached House
Located a mile from Chesterfield town centre. The property consists of a large open plan lounge/kitchen, 2 double bedrooms and 1 single room with bunk beds. The garden is south facing and there is private parking. There are a range of bars, cafe's, restaurants and local amenities just a short walk from the property. Chatsworth House, Haddon Hall and Peak District are 15 minutes drive away.
Popular amenities for Chesterfield vacation rentals
Pet-friendly vacation rentals in Chesterfield

Cosy studio apartment close to Peak District

Luxury Cottage Green Cottage, Peak District

20 Lacemarket Panorama

Cosy self contained studio - Peak District

Gorgeous romantic cosy cottage retreat with views

Wagon Lea is a delightful converted Railway Wagon,

Hay Loft Flat

Swift Retreat - converted farm building
Pet-friendly boutique hotels in Chesterfield

Family Room in Hotel; Near Alton towers & JCB

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
Other great vacation rentals in Chesterfield

A beautiful barn in the heart of the Peak District

Lovely Lavender Cottage Tideswell, Buxton

Cosy Home from Home, Private Hot tub, Sunset Views

Cosy 2 bed home CHESTERFIELD

Spire View | Chesterfield 2 Bedroom Apartment

Charming 18th century stone cottage

Pet-Friendly Cosy Cottage in Chesterfield

Blissful Barry’s
When is the best time to visit Chesterfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$22,803 GYD | G$23,012 GYD | G$24,477 GYD | G$20,920 GYD | G$21,129 GYD | G$21,129 GYD | G$23,012 GYD | G$24,895 GYD | G$21,757 GYD | G$23,431 GYD | G$22,594 GYD | G$23,012 GYD |
| 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 vacation rentals in Chesterfield?
Chesterfield has more than 70 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Chesterfield?
Experience the best of Chesterfield with our house rentals, starting at about $30 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 vacation rentals in Chesterfield?
Four-legged friends are welcome in Chesterfield. Choose from more than 50 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Chesterfield?
Yes! Work meets play with ease at over 50 vacation 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 200 vacation rentals in Chesterfield, and over 200 vacation rentals in Brimington.
Do apartment rentals in Chesterfield have a kitchen?
Absolutely! We offer over 10 apartment 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 120 vacation rentals in Chesterfield

Nightly prices starting at
Chesterfield vacation rentals start at G$6,276 GYD per night before taxes and fees

Verified guest reviews
Over 7,680 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
110 of Chesterfield vacation rentals include wi-fi 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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