Holiday Cottages in Chesterfield

Holiday Cottages in Chesterfield

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Chesterfield Cottages

  • Snaptrip - Holly Cottage
  • 2

    Derbyshire

    Holly Cottage

    Ref: S1317150

    Reviews 18

    3
    6
    A fantastic cottage located between the towns of Matlock and Chesterfield and on a great bus route for getting around the Peak District with ease a, and a welcoming pub across the road.. Ground Floor: Living room: Freeview TV, TV, Gas...

    From

    £180

    per night
    View

  • Snaptrip - Manor House
  • Derbyshire

    Manor House

    Ref: S4525

    Reviews 95

    5
    10
    The historic market town of Chesterfield acts as the gateway to the Peak District, and has much to offer visitors. The town is famous for its 14th Century church with "Crooked Spire", twisting curiously from its true centre, while the frequent...

    From

    £385

    per night
    View

  • Snaptrip - The Pantiles
  • 2

    Derbyshire

    The Pantiles

    Ref: S1317498

    Reviews 2

    5
    9
    A fantastic house for all the family to gather, located in a great location central to the town amenities and restaurants.. 5 steps to entrance. Ground Floor: Living room: Smart TV, Netflix, Apple TV, Open Fire Dining room: Rayburn, Patio Doors...

    From

    £184

    per night
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  • Snaptrip - Overton
  • 1

    Derbyshire

    Overton

    Ref: S853948

    Reviews 2

    4
    8
    Chesterfield, a historic market town that serves as a gateway to the Peak District, is a popular tourist destination. The town's 14th-century church, known for its "Crooked Spire," which diverges curiously from the building's true centre, has...

    From

    £106

    per night
    View

  • Snaptrip - Oakleigh
  • Derbyshire

    Oakleigh

    Ref: S1332679

    Reviews 29

    2
    3
    Oakleigh is a stylishly furnished, two bedroomed bungalow, ideally located to base yourself for an exciting holiday exploring all that the surrounding areas. All on the Ground Floor: Open plan living space. Living area: Freeview Smart TV, Patio...

    From

    £104

    per night
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  • Snaptrip - Riber View Barn
  • 2

    Derbyshire

    Riber View Barn

    Ref: S1375305

    2
    4
    The small, rural village of Ashover is peacefully situated in the Amber Valley, just five miles from Matlock. The village has several good pubs, including the Crispin Inn, renowned as one of the oldest pubs in the Peak District and The Old Poets’...

    From

    £82

    per night
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  • Snaptrip - The Cottage
  • Derbyshire

    The Cottage

    Ref: S801932

    Reviews 11

    2
    4
    Located on the edge of the Peak District National Park in Derbyshire, between Matlock and Chesterfield, is the tiny village of Stone Edge. Despite being well-known for its industrial past, the hamlet now draws a wide variety of tourists,...

    From

    £111

    per night
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  • Snaptrip - Moor Farm Cottage
  • Derbyshire

    Moor Farm Cottage

    Ref: S778600

    Reviews 32

    2
    4
    The small, rural village of Ashover is peacefully situated in the Amber Valley, just five miles from Matlock. The village has several good pubs, including the Crispin Inn, renowned as one of the oldest pubs in the Peak District and The Old Poets’...

    From

    £155

    per night
    View

  • Snaptrip - Harris House
  • 2

    Derbyshire

    Harris House

    Ref: S1315372

    Reviews 11

    3
    5
    Located on the outskirts of Chesterfield town, this property provides spacious and comfortable accommodation for up to five guests. Ground Floor: Living/dining room: Freeview Smart TV Kitchen: Electric Oven, Electric Hob, Microwave,...

    From

    £78

    per night
    View

  • Snaptrip - Peak Avenue Retreat
  • 1

    Derbyshire

    Peak Avenue Retreat

    Ref: S1250633

    3
    5
    The historic market town of Chesterfield acts as the gateway to the Peak District, and has much to offer visitors. The town is famous for its 14th Century church with "Crooked Spire", twisting curiously from its true centre, while the frequent...

    From

    £84

    per night
    View

  • Snaptrip - Freebirch Barn
  • Derbyshire

    Freebirch Barn

    Ref: S1330448

    Reviews 4

    2
    4
    This light and airy converted barn is conveniently placed for Chatsworth House and the numerous attractions the Peak District has to offer.. Ground Floor: Living room/kitchen: Freeview TV, DVD Player, CD Player, Electric Fire, Electric Oven, Gas...

    From

    £98

    per night
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  • Snaptrip - Carr House Farm
  • 2

    Derbyshire

    Carr House Farm

    Ref: S2149682

    3
    6
    The small hamlet of Waberthwaite is situated on the West Coast of Cumbria within the Lake District National Park, comprising of a scattering of cottages, farm dwellings and a traditional village pub. Waberthwaite enjoys an enviable position amidst...

    From

    £80

    per night
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  • Snaptrip - Smithy Apartment
  • 2

    Derbyshire

    Smithy Apartment

    Ref: S1317168

    Reviews 3

    2
    6
    A great apartment, perfect for a walkers base whilst exploring the Peak District with cosy, friendly pub below.. 8 steps to entrance. All on the First Floor: Living room: Freeview TV, Electric Fire, Sofa Bed (Double) Dining room. Kitchen:...

    From

    £50

    per night
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  • Snaptrip - The Bobbin
  • 2

    Derbyshire

    The Bobbin

    Ref: S1326616

    Reviews 37

    2
    4
    This cottage is perfect for outdoor enthusiasts with walking and cycle trails from the doorstep, or perhaps enjoy a get together with family or friends or romantic break away in beautiful surroundings.. Ground Floor: Open plan living...

    From

    £109

    per night
    View

  • Snaptrip - Spire Haven
  • Derbyshire

    Spire Haven

    Ref: S525509

    Reviews 25

    4
    8
    Chesterfield, the historic market town that serves as the Peak District's gateway, has a lot to offer visitors. The town's 14th-century church is known for its "Crooked Spire," which twists strangely from its actual centre, and the town's regular...

    From

    £120

    per night
    View

  • Snaptrip - The Loft at The George
  • 2

    Derbyshire

    The Loft at The George

    Ref: S517500

    Reviews 29

    4
    8
    Clay Cross is a small village near the Peak District National Park's boundary. There are numerous shops, taverns, and superb restaurants in the town. The old market town of Chesterfield, which serves as the gateway to the Peak District and has...

    From

    £94

    per night
    View

  • Snaptrip - Tuliptree
  • Derbyshire

    Tuliptree

    Ref: S375576

    Reviews 22

    2
    4
    Resting in the picturesque Amber Valley and only five miles away from the thriving town of Matlock, is the quaint village of Ashover. You will find everything you need right on your doorstep in Ashover, from a selection of welcoming pubs,...

    From

    £116

    per night
    View

  • Snaptrip - 4 Bed Cottage in Chesterfield
  • 1

    Derbyshire

    4 Bed Cottage in Chesterfield

    Ref: S2201438

    4
    8
    Additional information and rules . Please enquire if you wish to bring more than 1 dog - 4 bedrooms – 2 king-sizes, 1 double, 1 twin - 2 bathrooms – 1 en-suite shower room with WC, 1 family bathroom with bath, separate shower and WC, plus 1...

    From

    £194

    per night
    View

  • Snaptrip - 4 Bed Cottage in Chesterfield
  • Derbyshire

    4 Bed Cottage in Chesterfield

    Ref: S229999

    4
    10
    Additional information and rules No dogs allowed - 4 bedrooms: 1 king, 2 doubles, 1 bedroom with 4 single beds - 2 upstairs bathrooms, 2 downstairs bathrooms, additional toilet accessed from outside - 2 Woodburners - Ample off road parking ...

    From

    £455

    per night
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  • Snaptrip - Rent My Spa Home with Pool table, Hottub and Sauna
  • 2

    Derbyshire

    Rent My Spa Home with Pool table, Hottub and Sauna

    Ref: S2141003

    7
    20
    The historic market town of Chesterfield acts as the gateway to the Peak District, and has much to offer visitors. The town is famous for its 14th Century church with "Crooked Spire", twisting curiously from its true centre, while the frequent...

    From

    £1263

    per night
    View

  • Snaptrip - Woodthorpe Cruck Cottage
  • Derbyshire

    Woodthorpe Cruck Cottage

    Ref: S162153

    Reviews 86

    3
    6
    Clay Cross is a small town resting close to the Peak District National Park and houses a selection of shops, pubs and restaurants. Within a few miles you will find the market town of Chesterfield which is known as the gateway to the Peak District....

    Check for price

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  • Snaptrip - Barn View
  • 1

    Derbyshire

    Barn View

    Ref: S1330045

    Reviews 35

    2
    6
    A charming stone-built cottage with lovely countryside views, set within a great location to explore Derbyshire.. Ground Floor: Living/dining room: 49" Freeview Smart TV, DVD Player, Electric Fire, Sofa Bed (Double) Kitchen: Electric Oven,...

    From

    £87

    per night
    View

  • Snaptrip - Yew Tree Cottage
  • 3

    Derbyshire

    Yew Tree Cottage

    Ref: S1312026

    Reviews 26

    3
    6
    Tucked away in the countryside of Holymoorside, this quiet, a perfect base for walking, cycling and exploring the Peak District.. 2 steps to entrance. Ground Floor: Living room: Smart TV, Sky, Woodburner Kitchen/dining room: Breakfast Bar,...

    Check for price

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  • Snaptrip - The Pig Sty
  • 2

    Derbyshire

    The Pig Sty

    Ref: S1327127

    Reviews 36

    2
    4
    The Pig Sty is perfect for relaxing in beautiful surroundings, actively exploring the Peak District or visiting many of the tourist attractions in the area.. Ground Floor: Living room: Freeview TV, DVD Player, Soundbar, Bluetooth Speaker,...

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    Showing 25 - 48 of 113 properties

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