Wifi
Car parking on site
Enclosed Garden / Patio
- Sleeps up to 2
- 1 bedroom
- 1 bathroom
- Up to 2 pets allowed
4.8
out of 5
7 nights
From
£437
Reserve today for only £25
Chesterfield Cottages
Experience the perfect holiday getaway in Chesterfield with cottages.com. Nestled in the heart of beautiful countryside, Chesterfield offers a unique blend of history, culture, and natural beauty.
Popular Holiday Cottages in Chesterfield
Wifi
Car parking on site
Pub within 1 mile
- Sleeps up to 6
- 3 bedrooms
- 2 bathrooms
- Up to 1 pet allowed
5
out of 5
7 nights
From
£735
Reserve today for only £25
Wifi
Car parking on site
Pub within 1 mile
- Sleeps up to 2
- 1 bedroom
- 1 bathroom
- Up to 1 pet allowed
4.9
out of 5
7 nights
From
£383
Reserve today for only £25
Wifi
Car parking on site
Pub within 1 mile
- Sleeps up to 2
- 1 bedroom
- 1 bathroom
- Up to 1 pet allowed
5
out of 5
7 nights
From
£317
Hot Tub
Car parking on site
Pub within 1 mile
- Sleeps up to 2
- 1 bedroom
- 1 bathroom
- Up to 3 pets allowed
4.7
out of 5
7 nights
From
£423
Reserve today for only £25
Wifi
Car parking on site
Detached
- Sleeps up to 5
- 2 bedrooms
- 2 bathrooms
- Up to 0 pets allowed
4.3
out of 5
7 nights
From
£569
Wifi
Car parking on site
Pub within 1 mile
- Sleeps up to 4
- 2 bedrooms
- 1 bathroom
- Up to 0 pets allowed
4.8
out of 5
7 nights
From
£407
Luxury
Wifi
Car parking on site
- Sleeps up to 4
- 2 bedrooms
- 3 bathrooms
- Up to 0 pets allowed
4.9
out of 5
7 nights
From
£533
Reserve today for only £25
Wifi
Car parking on site
Pub within 1 mile
- Sleeps up to 5
- 3 bedrooms
- 1 bathroom
- Up to 2 pets allowed
4.7
out of 5
7 nights
From
£453
Reserve today for only £25
Wifi
Car parking on site
Enclosed Garden / Patio
- Sleeps up to 4
- 2 bedrooms
- 1 bathroom
- Up to 2 pets allowed
4.8
out of 5
7 nights
From
£387
Reserve today for only £25
Wifi
Car parking on site
Pub within 1 mile
- Sleeps up to 2
- 1 bedroom
- 1 bathroom
- Up to 0 pets allowed
5
out of 5
7 nights
From
£383
Wifi
Car parking on site
Enclosed Garden / Patio
- Sleeps up to 4
- 2 bedrooms
- 2 bathrooms
- Up to 1 pet allowed
4
out of 5
7 nights
From
£483
Dog Friendly Cottages in Chesterfield
Wifi
Car parking on site
Enclosed Garden / Patio
- Sleeps up to 2
- 1 bedroom
- 1 bathroom
- Up to 2 pets allowed
4.8
out of 5
7 nights
From
£437
Reserve today for only £25
Wifi
Car parking on site
Pub within 1 mile
- Sleeps up to 6
- 3 bedrooms
- 2 bathrooms
- Up to 1 pet allowed
5
out of 5
7 nights
From
£735
Reserve today for only £25
Wifi
Car parking on site
Pub within 1 mile
- Sleeps up to 2
- 1 bedroom
- 1 bathroom
- Up to 1 pet allowed
4.9
out of 5
7 nights
From
£383
Reserve today for only £25
Wifi
Car parking on site
Pub within 1 mile
- Sleeps up to 2
- 1 bedroom
- 1 bathroom
- Up to 1 pet allowed
5
out of 5
7 nights
From
£317
Wifi
Car parking on site
Pub within 1 mile
- Sleeps up to 5
- 3 bedrooms
- 2 bathrooms
- Up to 2 pets allowed
7 nights
From
£985
Hot Tub
Car parking on site
Pub within 1 mile
- Sleeps up to 2
- 1 bedroom
- 1 bathroom
- Up to 3 pets allowed
4.7
out of 5
7 nights
From
£423
Reserve today for only £25
Wifi
Car parking on site
Pub within 1 mile
- Sleeps up to 5
- 3 bedrooms
- 1 bathroom
- Up to 2 pets allowed
4.7
out of 5
7 nights
From
£453
Reserve today for only £25
Wifi
Car parking on site
Pub within 1 mile
- Sleeps up to 2
- 1 bedroom
- 1 bathroom
- Up to 1 pet allowed
7 nights
From
£555
Reserve today for only £25
Wifi
Car parking on site
Enclosed Garden / Patio
- Sleeps up to 4
- 2 bedrooms
- 1 bathroom
- Up to 2 pets allowed
4.8
out of 5
7 nights
From
£387
Reserve today for only £25
Wifi
Car parking on site
Enclosed Garden / Patio
- Sleeps up to 4
- 2 bedrooms
- 2 bathrooms
- Up to 1 pet allowed
4
out of 5
7 nights
From
£483
Wifi
Car parking on site
Pub within 1 mile
- Sleeps up to 3
- 1 bedroom
- 1 bathroom
- Up to 1 pet allowed
7 nights
From
£555
Reserve today for only £25
Wifi
Car parking on site
Pub within 1 mile
- Sleeps up to 4
- 2 bedrooms
- 2 bathrooms
- Up to 2 pets allowed
5
out of 5
7 nights
From
£572
Reserve today for only £25
Luxury Holiday Cottages in Chesterfield
Luxury
Wifi
Car parking on site
- Sleeps up to 4
- 2 bedrooms
- 3 bathrooms
- Up to 0 pets allowed
4.9
out of 5
7 nights
From
£533
Reserve today for only £25
Hot Tub
Luxury
Wifi
- Sleeps up to 10
- 4 bedrooms
- 4 bathrooms
- Up to 0 pets allowed
5
out of 5
7 nights
From
£1,174
Hot Tub
Luxury
Wifi
- Sleeps up to 8
- 4 bedrooms
- 2 bathrooms
- Up to 0 pets allowed
5
out of 5
7 nights
From
£985
Luxury
Wifi
Car parking on site
- Sleeps up to 6
- 3 bedrooms
- 2 bathrooms
- Up to 3 pets allowed
4.8
out of 5
7 nights
From
£779
Luxury
Wifi
Car parking on site
- Sleeps up to 6
- 3 bedrooms
- 2 bathrooms
- Up to 0 pets allowed
5
out of 5
7 nights
From
£749
Self-Catering Holiday Cottages in Chesterfield
Our exclusive selection of Chesterfield cottages provides the ideal accommodation for a truly memorable holiday. Immerse yourself in the rich history of this charming town, known for its ancient market square and iconic crooked spire. Explore the picturesque Peak District National Park, located just a stone's throw away, and discover breathtaking landscapes, tranquil walks, and thrilling outdoor activities. Whether you're seeking a romantic getaway, a family adventure, or a peaceful retreat, our Chesterfield cottages are the perfect base for your holiday. With cottages.com, you can relax and unwind in your own private haven, surrounded by the beauty of Chesterfield. Book your holiday today and create lifelong memories in this enchanting destination. With the largest collection of holiday cottages in Derbyshire, we have the perfect home away from home for you.
More Popular Derbyshire Holiday Cottage Destinations
Explore
Inspiration
Collections
2026 Holiday CottagesAccessible Holiday CottagesChristmas Holiday BreaksCity BreaksCoastal HolidaysCottages with PoolCycling BreaksDog friendlyEaster HolidaysEV Charging Holiday CottagesFamily HolidaysFebruary Half Term BreaksFishing HolidaysGlamping in the UKGolf BreaksHoliday Cottages with Games RoomHot tub breaksLarge Holiday Cottages & Group AccommodationLast Minute DealsLuxury Holiday CottagesMay Half Term HolidayMother's DayNew Years Eve BreaksOctober Half Term BreaksQuality CottagesRomantic GetawaysShort Breaks & Weekends AwaySpring Breaks in the UKSummer Holidays in the UKSustaibable & Eco Friendly CottagesUnique CottagesValentines BreaksWaterside BreaksWinter Breaks in the UK
Destinations
Countries
Regions
All West MidlandsBedfordshireBerkshireBlackdown HillsBuckinghamshireCambridgeshireCheshireConstable CountryCornwallCotswoldsCounty DurhamCranborne Chase and West Wiltshire DownsCumbriaDartmoorDerbyshireDevonDorsetEssexExmoorForest of BowlandForest of DeanGloucestershireGreater LondonHampshireHerefordshireHertfordshireHigh WealdHowardian HillsIsle of WightKentKent DownsLake DistrictLancashireLeicestershireLincolnshireLincolnshire WoldsMalvern HillsMendip HillsNew ForestNidderdaleNorfolkNorfolk BroadsNorfolk CoastNorth Devon CoastNorth PenninesNorth Wessex DownsNorthamptonshireNorthumberlandNorthumberland CoastNottinghamshireOxfordshirePeak DistrictRutlandShakespeare CountryShropshireShropshire HillsSomersetSouth DownsStaffordshireSuffolkSuffolk Coast and HeathsSurreySussexWarwickshireWiltshireWorcestershireWye ValleyYorkshireYorkshire DalesYorkshire Moors
Areas
Sign up for a chance to win £500!
Stay updated on the latest deals, exclusive offers and new holiday destinations by joining the cottages.com newsletter! Register today and automatically be entered into our prize draw to win a £500 voucher.
Click here for terms and conditions. You can opt out anytime by using the unsubscribe link in our emails. We will use your information as per our Privacy Notice.