
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.

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!

Panoramic views, Spring Lambs, Bakewell Chatsworth
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

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.

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.

Charming grade II listed cottage with hot tub
Chander Hill Cottage is a stylish 3-bedroom barn conversion nestled above the village of Holymoorside, on the edge of the Peak District. This cosy cottage is a perfect base for exploring the countryside, with numerous walks from the door and two pubs just a mile away in the village. Relax in our hot tub with stunning views or warm up by the wood burning stove after a winter walk. The enclosed cottage garden has a patio where you can enjoy a BBQ in the summer. Dogs welcome!

Woolley Lodge Farm Retreat
A brand new fully furnished wooden lodge situated within the grounds of a working farm, with views across open countryside. The cabin has been furnished to a high standard and includes a double bedroom with double bed. The kitchen has a full size fridge with small freezer, full size oven and a microwave. It has a small bathroom with a full size corner shower. It has its own entrance, parking and a beautiful decked area and fire pit and BBQ . Not suitable for children or pets

Cosy self contained studio - Peak District
Set in the glorious Peak District in a rural and peaceful location is our lovely self contained studio. Glorious views and walks over rolling countryside. Close to Chatsworth House and Haddon Hall. With the popular wedding venue (Peak Edge Hotel ) within walking distance and the beautiful market towns of Bakewell, Matlock and Chesterfield (with its famous crooked spire) close by you can easily explore the Peak District from here. Perfect for the Chatsworth Christmas market.

Hidden beauty
A beutiful refurbished part of an old barn. it comprises old with the new. comfortable and spacious with underfloor heating downstairs and super fast broadband. Nearby are 2 local pubs walking distance. Also easy access to the trans Pennines trail. The village is located next to the strines with numerous walks. And plenty of surrounding villages with all amenities. Ideal for a romantic weekend away, walkers, or business people.

Exclusive Detached Retreat+Games Room M1J35 1.5m
A unique duplex property that has a fully furnished games room complete with snooker table, professional air hockey table, surround sound cinema system with a self contained upstairs living space equipped to a high standard. Located in the heart of Ecclesfield you are a short distance from local amenities, woodland walks, pubs and cafes but also only a short distance to the vibrant nightlife in Sheffield. .
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

Cosy studio apartment close to Peak District

Lizzy’s Luxury Cottage

Luxury Peak District Cottage with Hot Tub

Characterful 2 bed cottage in excellent location

The Oaks Hut - with hot tub - Hillside Huts

Pear Tree Lodge with private HOT TUB and garden

Beautiful barn conversion.

Clover View - Hot tub, Sauna & Countryside Views
Other great vacation rentals in Chesterfield

Millstone Cottage - Cosy Peak District Cottage

A cosy 2 bedroom family friendly living space

Cosy 2 bed home CHESTERFIELD

Picturesque Rose Cottage in Winster

Spire View | Chesterfield 2 Bedroom Apartment

The Coach House Harthill

Charming 18th century stone cottage

Derbyshire Gem, Peak District
When is the best time to visit Chesterfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$22,796 GYD | G$23,005 GYD | G$24,469 GYD | G$20,914 GYD | G$21,123 GYD | G$21,123 GYD | G$23,005 GYD | G$24,887 GYD | G$21,750 GYD | G$23,423 GYD | G$22,587 GYD | G$23,005 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 condo rentals in Chesterfield have wifi?
Absolutely! We offer over 10 condo 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$6,274 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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- Peak District National Park
- Alton Towers
- Etihad Stadium
- Chatsworth House
- The Quays
- AO Arena
- Heaton Park
- Motorpoint Arena Nottingham
- Lincoln Castle
- First Direct Arena
- Harewood House
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- Peace Gardens
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