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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 paved patio with stone tiles, surrounded by a brick wall and a wooden fence.

    2. a quiet semi rural property located in bolsover

    A paved patio with a wooden gate and brick walls.

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

    A paved patio with stone tiles, surrounded by a brick wall and a wooden fence.

    4. a Quiet Semi Rural Property Located in Bolsover

    A paved patio with a wooden gate and brick walls.

    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 bedroom with a bed, a nightstand, a lamp, a window, and a staircase leading to an outdoor area.

    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 staircase with a framed flower artwork on the wall.

    12. Charming Cottage in Grindleford, Peak District

    A residential property with a large garden, a patio area, and a view of a forested hill.

    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 residential property with a sliding glass door leading to a patio area.

    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

    Front of property

    18. No 4

    A modern dining area with a glass table, two chairs, and a vase with flowers.

    19. Cheerful and Cosy 4 bedroom House

    A modern living room with a grey sofa, a dining table with chairs, a black fireplace, and a wall clock.

    20. Cozy Sheffield Guest Room with Shared Facilities

    Decorative detail

    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.