Customers' Choice
Pets stay free
Wifi
Car parking on site
Garden / Patio
- 4 Guests
- 2 Bedrooms
- 1 Bathroom
- 2 Pets
4.9
out of 5
7 nights
From
£651
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
Customers' Choice
Hot Tub
Luxury
Wifi
- 10 Guests
- 4 Bedrooms
- 4 Bathrooms
- 0 Pets
5
out of 5
7 nights
From
£1,346
Customers' Choice
Wifi
Car parking on site
Enclosed Garden / Patio
- 6 Guests
- 3 Bedrooms
- 2 Bathrooms
- 0 Pets
4.9
out of 5
7 nights
From
£607
Customers' Choice
Pets stay free
Wifi
Car parking on site
Pub within 1 mile
- 2 Guests
- 1 Bedroom
- 1 Bathroom
- 2 Pets
4.9
out of 5
7 nights
From
£417
Customers' Choice
Wifi
Car parking on site
Detached
- 2 Guests
- 1 Bedroom
- 1 Bathroom
- 2 Pets
5
out of 5
7 nights
From
£403
Wifi
Car parking on site
Enclosed Garden / Patio
- 4 Guests
- 2 Bedrooms
- 2 Bathrooms
- 1 Pet
4.2
out of 5
7 nights
From
£447
Customers' Choice
Wifi
Car parking on site
Pub within 1 mile
- 4 Guests
- 2 Bedrooms
- 1 Bathroom
- 0 Pets
4.9
out of 5
7 nights
From
£453
Customers' Choice
Pets stay free
Wifi
Car parking on site
Detached
- 8 Guests
- 3 Bedrooms
- 2 Bathrooms
- 2 Pets
4.6
out of 5
7 nights
From
£667
Pets stay free
Wifi
Car parking on site
Pub within 1 mile
- 6 Guests
- 3 Bedrooms
- 2 Bathrooms
- 2 Pets
4.2
out of 5
7 nights
From
£533
Customers' Choice
Wifi
Car parking on site
Pub within 1 mile
- 2 Guests
- 1 Bedroom
- 1 Bathroom
- 0 Pets
4.9
out of 5
7 nights
From
£413
Dog Friendly Cottages in Chesterfield
Customers' Choice
Pets stay free
Wifi
Car parking on site
Garden / Patio
- 4 Guests
- 2 Bedrooms
- 1 Bathroom
- 2 Pets
4.9
out of 5
7 nights
From
£651
Customers' Choice
Pets stay free
Wifi
Car parking on site
Pub within 1 mile
- 2 Guests
- 1 Bedroom
- 1 Bathroom
- 2 Pets
4.9
out of 5
7 nights
From
£417
Customers' Choice
Wifi
Car parking on site
Detached
- 2 Guests
- 1 Bedroom
- 1 Bathroom
- 2 Pets
5
out of 5
7 nights
From
£403
Wifi
Car parking on site
Enclosed Garden / Patio
- 4 Guests
- 2 Bedrooms
- 2 Bathrooms
- 1 Pet
4.2
out of 5
7 nights
From
£447
Customers' Choice
Pets stay free
Wifi
Car parking on site
Detached
- 8 Guests
- 3 Bedrooms
- 2 Bathrooms
- 2 Pets
4.6
out of 5
7 nights
From
£667
Pets stay free
Wifi
Car parking on site
Pub within 1 mile
- 6 Guests
- 3 Bedrooms
- 2 Bathrooms
- 2 Pets
4.2
out of 5
7 nights
From
£533
Wifi
Car parking on site
Enclosed Garden / Patio
- 10 Guests
- 4 Bedrooms
- 3 Bathrooms
- 3 Pets
4.8
out of 5
7 nights
From
£1,061
Wifi
Car parking on site
Enclosed Garden / Patio
- 4 Guests
- 2 Bedrooms
- 2 Bathrooms
- 1 Pet
5
out of 5
7 nights
From
£513
Luxury Holiday Cottages in Chesterfield
Customers' Choice
Hot Tub
Luxury
Wifi
- 10 Guests
- 4 Bedrooms
- 4 Bathrooms
- 0 Pets
5
out of 5
7 nights
From
£1,346
Customers' Choice
Luxury
Wifi
Car parking on site
- 7 Guests
- 3 Bedrooms
- 2 Bathrooms
- 3 Pets
4.7
out of 5
7 nights
From
£741
Pets stay free
Wifi
Enclosed Garden / Patio
Pub within 1 mile
- 12 Guests
- 5 Bedrooms
- 3 Bathrooms
- 2 Pets
7 nights
From
£1,266
Customers' Choice
Luxury
Wifi
Car parking on site
- 4 Guests
- 2 Bedrooms
- 3 Bathrooms
- 0 Pets
5
out of 5
7 nights
From
£503
See more cottages in Chesterfield
The HolliesWoodend BungalowYew Tree CottagePriestfield Grange - Chestnut CottageAlton Hall CottageSouth Carolina Farm HouseThe BarnThe Old ChurchOakleighThe BobbinLings Farm CottageHolly CottageClearviewBarn ViewThe Mill CottageStone CottageHillcrestGreenwell CottageThe Chantry - The Garden HousePriestfield Grange - Willow CottageStubley Hollow Farm - The Old HayloftBryn Tor - The Gardener’s HouseStubley Hollow Farm - Barn Owls NestFreebirch BarnHolly CottageMiners CottageStubley Hollow Farm - Little HivePlum Tree HouseSmithy ApartmentHarris HouseThe Chantry - The Gatehouse
Priestfield Grange - Chestnut CottageThe Old ChurchThe Malt ShovelPerkins CottageThe Chantry - The Garden HouseSpringwood Cottages - Merlyn BarnBryn Tor - The Gardener’s HouseSmithy ApartmentMill Farm Cottages - The NookStubley Hollow Farm - The Old HayloftMill Farm Cottage - Kingfisher CottageOak Tree RetreatFreebirch BarnPlum Tree HouseHarris HouseHolly CottageSpringwood Cottages - Springwood CottageWoodend BungalowThe Chantry - The GatehouseStubley Hollow Farm - Barn Owls NestMill Farm Cottages - Bluebell CottageMiners CottageAcorn CottageSpringwood Cottages - Forest BarnGreenwell CottagePriestfield Grange - Willow CottageStubley Hollow Farm - Little Hive
Acorn CottageAshover CottageSpringwood Cottages - Springwood CottageSpringwood Cottages - Merlyn BarnSmithy ApartmentHarris HouseThe Chantry - The GatehouseMill Farm Cottages - The NookSpringwood Cottages - Forest BarnMill Farm Cottages - Cherry Tree CottageMill Farm Cottages - Bluebell CottageMill Farm Cottage - Kingfisher CottageOak Tree Retreat
The HolliesGreen Farm Holiday Cottages - Tawny Owl BarnGreen Farm Cottages - The Old Cow ShedWoodend BungalowBathurst CottageYew Tree CottageAlton Hall CottageSouth Carolina Farm HouseThe BarnThe Old ChurchOakleighGreen Farm Holiday Cottages - The Pig StyLings Farm CottageHolly CottageClearviewThe StablesThe Malt ShovelBarn ViewPerkins CottageThe Mill CottageWest BarnHillcrestGreenwell CottageStubley Hollow Farm - The Old HayloftBryn Tor - The Gardener’s HouseBoundary CottageWoodview LodgeFreebirch BarnThe PantilesHolly CottageMiners CottageStubley Hollow Farm - Little HivePlum Tree HouseAcorn CottageSpringwood Cottages - Springwood CottageSpringwood Cottages - Merlyn BarnSpringwood Cottages - Forest Barn
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
2027 Holiday CottagesAccessible Holiday CottagesChristmas cottagesCity BreaksCoastal CottagesCottages with a games roomCottages with a PoolCottages with SaunaCycling BreaksDog-friendly CottagesEaster HolidaysEV Charging Holiday CottagesFamily HolidaysFebruary Half Term BreaksFishing holidaysGlamping holidaysGolf BreaksHoliday cottages near a pubHot tub breaksJames CollectionLarge CottagesLast Minute DealsLodgesLuxury Holiday CottagesMay Half Term HolidayNew Years Eve BreaksOctober Half Term BreaksQuality CottagesRomantic GetawaysShort Breaks & Weekends AwaySpring Breaks in the UKSummer Holidays in the UKSustainable & Eco Friendly CottagesUnique CottagesValentines BreaksWaterside BreaksWinter Cottages
Destinations
Countries
Regions
BedfordshireBerkshireBlackdown HillsBuckinghamshireCambridgeshireCheshireConstable CountryCornwallCotswoldsCounty DurhamCranborne Chase and West Wiltshire DownsCumbriaDartmoorDerbyshireDevonDorsetEast AngliaEssexExmoorForest 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 HeathsSurreySussexWarwickshireWest MidlandsWiltshireWorcestershireWye ValleyYorkshireYorkshire DalesYorkshire Moors
Areas