Cheltenham Holiday Cottages

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Your search returned 45 cottages.

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  • A small stone cottage with climbing plants and gravel in front at Hazel Manor Wing in Painswick
    43
    Painswick, Gloucestershire
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.7★

      Outstanding

    • Manor Cottages rating

    A very smart and spacious country retreat! (Ref. 988694)

    • Wi-fi
    • Off-road parking
    • Ground floor bedroom
    • Dishwasher
    • Washing machine

    7 nights from £718

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • A wooden footbridge over a pond leading to a stone building with a tiled roof at Jackdaw's Roost in Cheltenham
    25
    Cheltenham, Gloucestershire
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.8★

      Outstanding

    • Manor Cottages rating

    This quaint adult only country cottage is situated in The Leigh, Gloucestershire. (Ref. 991352)

    • Off-road parking
    • Ground floor bedroom
    • Washing machine

    7 nights from £409

    Secure your holiday with a 30% deposit* Book now
  • The Garden Retreat - 1159770 - photo 1
    32
    Winchcombe, Gloucestershire
    • Sleeps2
    • Bedrooms1
    • PetsNo

      5.0★

      Perfect

    • Manor Cottages rating

    8 Gloucester Street is a charming house in Winchcombe, Gloucestershire, situated in the Cotswolds, boasting a woodburning stove and an enclosed garden. (Ref. 1159770)

    • Wi-fi
    • Off-road parking
    • Dishwasher
    • Washing machine

    7 nights from £471

    Secure your holiday with a 30% deposit* Book now
  • A side entrance to a brick house with a black metal gate with a Beechnt Cottage sign and a garden with green grass and trees in the background at Beechnut Cottage in Tewkesbury
    26
    Tewkesbury, Gloucestershire
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.9★

      Outstanding

    • Manor Cottages rating

    A stylish ground-floor cottage resting in Aston on Carrant, Tewkesbury. (Ref. 952307)

    • Wi-fi
    • Off-road parking
    • Ground floor bedroom
    • Dishwasher

    7 nights from £368

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • A wooden building with potted plants and gravel driveway at Wellinghill Lodge in Cheltenham
    27
    Cheltenham, Gloucestershire
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.9★

      Outstanding

    • Manor Cottages rating

    A stunning, detached lodge situated in Cheltenham, Cotswolds. (Ref. 1010167)

    • Wi-fi
    • Off-road parking
    • Ground floor bedroom

    7 nights from £396

    Secure your holiday with a 30% deposit* Book now
  • A street view of a row of old stone houses with chimneys and flower boxes at Fern Cottage in Winchcombe
    26
    Winchcombe, Gloucestershire
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.9★

      Outstanding

    • Manor Cottages rating

    This is a mid-terrace cottage situated in the town of Winchcombe, Gloucestershire in the Cotswolds. (Ref. 1012253)

    • Wi-fi
    • Off-road parking
    • Dishwasher
    • Washing machine

    7 nights from £675

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • A driveway leading to a house with wooden front door and garage surrounded by plants and greenery at The Gables in Sheepscombe
    46
    Sheepscombe, Gloucestershire
    • Sleeps8
    • Bedrooms4
    • PetsYes

      4.9★

      Outstanding

    • Manor Cottages rating

    A beautiful four-bedroom holiday home resting in Sheepscombe, Gloucestershire. (Ref. 1116058)

    • Wi-fi
    • Off-road parking
    • Hot Tub
    • Dishwasher

    7 nights from £1622

    Secure your holiday with a 30% deposit* Book now
  • A gravel driveway leading to a large brick house surrounded by trees and grass at The Coach House Apartment in Bredon
    29
    Bredon, Worcestershire
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.9★

      Outstanding

    • Manor Cottages rating

    A stunning first-floor apartment situated in the rural village of Bredon in Worcestershire. (Ref. 1061403)

    • Wi-fi
    • Off-road parking
    • Baby-friendly

    7 nights from £392

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • A brick exterior of a house with two doors and windows with climbing plants and a white bench outside at River Cottage in Tewkesbury
    21
    Tewkesbury, Gloucestershire
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.8★

      Outstanding

    • Manor Cottages rating

    A 14th century, Grade II listed property situated within the town of Tewkesbury. (Ref. 988216)

    • Wi-fi
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Sky TV

    7 nights from £401

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • A cottage with a red door and climbing plants around it and windows with flowers in them at Runnymede in Tewkesbury
    Property has offers
    38
    Tewkesbury, Gloucestershire
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.8★

      Outstanding

    • Manor Cottages rating

    A charming Grade II listed cottage resting in the historic riverside town of Tewkesbury, Gloucestershire. (Ref. 1071199)

    • Wi-fi
    • Off-road parking
    • Hot Tub
    • Washing machine

    • 5% off - Mon 20th Oct 2025 to 31st Jan 2026

    7 nights from £580

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
Most relevant
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