
Vacation rentals in Chesterfield
Find and book unique accommodations on Airbnb
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

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.

Luxury 2 Bedroom Cottage (Sleeps 4) Stunning Views
*AirBnB Best New Host Finalist 2022* A stunning 2 bedroom (Sleeps 4) luxury cottage, nestled in the Peak District countryside, with superb views over Chatsworth House. Outdoor dining, farm animals, private parking (with electric charging) & tranquil walks - all within a short drive of Bakewell, Matlock & the beautiful Derbyshire Dale villages. Fully equipped with everything you will need for your stay, including: Netflix, Amazon Prime & Disney+ BBQ for outdoor dining. Family & Dog Friendly

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.

The Hollies - Luxury self contained apartment
This garden flat with separate access is located in the heart of Sheffield's academic and healthcare hubs. Nestled between Broomhill, Ecclesall road and 2 miles away from the city centre. Close to Botanical Gardens, Endcliffe park and a short walk to a variety of restaurants and pubs. With an en-suite bathroom, well equipped kitchen and small private patio this apartment is perfect for everything Sheffield has to offer! We have 2 friendly dogs and a cat. We also have free overnight parking.

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.

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

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!

Spacious Scandinavian style hideaway with log fire
The property is in a delightful and secluded position on the south facing side of Darley Hillside with views over the valley. The main living area is on the upper floor, accessed directly from the driveway and car-port via a hallway leading to the master bedroom and ensuite; living room with open log fire, dining area and internal balcony access to 2-storey atrium complete with spiral staircase; cloakroom; toilet, and kitchen with tree top external terrace.

'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 self contained studio - Peak District

Exclusive & Beautiful Modern Studio Flat

Bridgefoot Cottage - Wild Swimming & Hot Tub

Cozy Couples Glamping - Private Hot Tub

Pear Tree Lodge with private HOT TUB and garden

Wasp Nest Cottage, Peak District

Clover View - Hot tub, Sauna & Countryside Views

Stretton Hall Farm - The Annex
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

Close to town, hot tub retreat!

The Stables House, Lomberdale Hall. 4 to 7 guests

Butler's Retreat Tissington Hall Derbyshire

Spire View | Chesterfield 2 Bedroom Apartment

Peaceful hideaway Baslow Chatsworth, Peak District

Derbyshire Gem, Peak District

Litton Mill Retreat, Luxury Converted Mill

The Beehive
When is the best time to visit Chesterfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ400 | ﺩ.ﺇ404 | ﺩ.ﺇ430 | 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 50 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in condo rentals in Chesterfield?
Experience the best of Chesterfield with our condo rentals, starting at about $100 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 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 house rentals in Chesterfield have wifi?
Absolutely! We offer over 70 house 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 ﺩ.ﺇ110 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!
Destinations to explore
- Durham Vacation rentals
- London Vacation rentals
- Picardie Vacation rentals
- Sea of the Hebrides Vacation rentals
- Thames River Vacation rentals
- Amsterdam Vacation rentals
- South West Vacation rentals
- Inner London Vacation rentals
- Rivière Vacation rentals
- Dublin Vacation rentals
- Brussels Vacation rentals
- South London Vacation rentals
- Condo rentals Chesterfield
- Cabin rentals Chesterfield
- Rentals with a patio Chesterfield
- Rentals with outdoor seating Chesterfield
- House rentals Chesterfield
- Pet-friendly rentals Chesterfield
- Family-friendly rentals Chesterfield
- Rentals with a fireplace Chesterfield
- Cottage rentals Chesterfield
- Rentals with a washer and dryer Chesterfield
- Apartment rentals Chesterfield
- Peak District National Park
- Alton Towers
- Etihad Stadium
- Chatsworth House
- The Quays
- Heaton Park
- Motorpoint Arena Nottingham
- Lincoln Castle
- First Direct Arena
- Harewood House
- Tatton Park
- Didsbury Village
- Mam Tor
- Donington Park Circuit
- Utilita Arena Sheffield
- Royal Armouries Museum
- Temple Newsam Park
- Yorkshire Wildlife Park
- Manchester Central Library
- Bowlers Exhibition Centre
- The Piece Hall
- Yorkshire Sculpture Park
- Crucible Theatre
- Manchester Central Convention Complex





