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A historic church with a tall spire, arched windows, and a clock tower.

Chesterfield Vacation Rentals

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    Check prices for these dates

    Check prices for these dates, December 13–14, 2026

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    Our top choices for Chesterfield vacation homes

    1. 2bed - Garden-pets-freeparking-m1connections

    A patio with stone tiles, a wooden fence, and a flower bed with plants and flowers.

    2. a quiet semi rural property located in bolsover

    A compact kitchen with a black refrigerator, a toaster, a sink, and a stove.

    3. 2bed - garden-pets-freeparking-M1connections

    A patio with stone tiles, a wooden fence, and a flower bed with plants and flowers.

    4. a Quiet Semi Rural Property Located in Bolsover

    A compact kitchen with a black refrigerator, a toaster, a sink, and a stove.

    5. 3-bed House - Sleeps 6 - Free Parking - Garden

    A dining table set with black plates, bowls, and cutlery, a fruit basket, and a centerpiece with green plants.

    6. Charress House, 6/7 Bedrooms, 10 beds, 3 bathrooms Contractors/Friends/Families.

    A living room with a large sectional sofa, a television, a fireplace, and a mirror.

    7. Cozy Double Bedroom with Private Bathroom

    A corner house with a bay window, a white door, and a brick wall.

    8. Robin Hood Tower

    A stone house with a wooden bench in front, a car parked nearby, and a stone wall in the background.

    9. Stay Angels ~ Hidden Gem of Sheffield

    A stone building with a large arched entrance, a small circular window, and a door with a number plate.

    10. 3 Bed House Sleeps 5 - Free Parking - Tv & WiFi

    A neatly made bed with a plaid blanket, a decorative pillow, and a rolled towel on the bed.

    11. Serene Homes Sheffield | Peaceful Ensuite Velux Room for Rest & Focus

    A corner house with a bay window, a door, and a small fenced area.

    12. Charming Cottage in Grindleford, Peak District

    Three wine glasses on a wooden table with a house and greenery in the background.

    13. Clean Spacious Walkley Home, 8pp, Free Street Parking

    A grand staircase with ornate railings and a patterned carpet.

    14. Charming & Stylish Home-Heeley, Heart of Sheffield

    A hotel room with a large bed, a mirror, two windows with curtains, and a chandelier.

    15. Stylish Private Guest Suite | Sleeps 5 | Free Parking |Near City & Peak District

    A bedroom with a bed, a chair, a desk, a TV, and a mirror.

    16. 2-bed Hillside House - Sleeps 4, Garden & Parking

    A hotel room with a large bed, a mirror, two windows with curtains, and a chandelier.

    17. Old Nags Head

    Restaurant

    18. No 4

    A modern living room with a sofa, coffee table, and a TV. There is a kitchen in the background with a stove, oven, and cabinets.

    19. Cheerful and Cosy 4 bedroom House

    A modern bedroom with two beds, a window with blinds, a radiator, and a dark door.

    20. Cozy Sheffield Guest Room with Shared Facilities

    Living room

    Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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    Learn more about Chesterfield

    Climb the 'Crooked Spire' of St. Mary's Church for views across this historic market town. Wander through the open-air market, then explore nearby Chatsworth House in the Peak District.

    See all hotels in Chesterfield

    A historic church with a tall spire, arched windows, and a clock tower.