Winter Short Breaks in South West England

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    A property's star rating is the average of the star ratings received from guests that wish for their review to be published
  • A green metal shepherd hut with two windows and an open door outdoor seating with cushions a fire pit and a barbecue at Shepherds Joy Kennerleigh near Cheriton Fitzpaine
    24
    Kennerleigh near Cheriton Fitzpaine, Devon
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyNo

      5.0★

      Perfect

    • Helpful Holidays rating

    Shepherds Joy is a delightful shepherd's hut, with a private hot tub, situated in the little countryside village of Cheriton Fitzpaine in Devon. (Ref. 1162533)

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

    2 nights from Sat 28th Nov From £331

    Book now
  • A house with a pond surrounded by trees at Lower Moorwood in Moorwood near Bovey Tracey
    New property
    59
    Moorwood near Bovey Tracey, Devon
    • Sleeps8
    • Bedrooms4
    • Pet FriendlyNo

    • Helpful Holidays rating

    Moorwood House, a pleasing single-storey annex near Bovey Tracey, Devon, boasts a hot tub, enclosed patio, and proximity to Dartmoor National Park. (Ref. 1158218)

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

    2 nights from Wed 6th Jan From £681

    Last booked yesterday
    Book now
  • A garden area with outdoor chairs and table in front of a stone cottage at The Barn in Bicknoller
    40
    Bicknoller, Somerset
    • Sleeps9
    • Bedrooms4
    • Pet FriendlyYes

      4.7★

      Outstanding

    • Helpful Holidays rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon

    Outstanding stone barn conversion on a friendly working farm with free range chickens, lambs and acres of meadows to wander free. (Ref. 915884)

    • Pets go free
    • Wi-fi
    • Off-road parking
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly

    2 nights from Sun 29th Nov From £653

    Last booked 6 hours ago
    Book now
  • A living room with a sofa coffee table fireplace TV and open doors leading to a garden at The Hideaway in Lympsham near Brean
    18
    Lympsham near Brean, Somerset
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyYes

      4.9★

      Outstanding

    • Helpful Holidays rating

    This charming, one-bedroom annex rests in Lympsham, near Brean, Somerset. (Ref. 1113531)

    • Pets go free
    • Wi-fi
    • Off-road parking
    • Ground floor bedroom
    • Hot Tub
    • Dishwasher

    2 nights from Sat 28th Nov From £428

    Book now
  • A balcony with a wooden table and four chairs with blue cushions overlooking a town and a river at Kittiwake in Noss Mayo
    Property has offers
    49
    Noss Mayo, Devon
    • Sleeps5
    • Bedrooms3
    • Pet FriendlyNo

      4.9★

      Outstanding

    • Helpful Holidays rating

    This delightful detached cottage is located in Noss Mayo, Devon. (Ref. 1007669)

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

    • 10% off - Fri 17th Jul to 24th Jul 2026

    2 nights from Sat 28th Nov From £493

    Book now
  • An outdoor view of a wooden building with a balcony at Arvor Wetroom Studio 1.0
    New property
    8
    Marhamchurch, Cornwall
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyNo

    • Helpful Holidays rating

    Arvor Wetroom Studio 1.0 is a lovely apartment on Whalesborough Resort and Spa near Marhamchurch, Cornwall, with an open‑plan layout and en‑suite wet room. (Ref. 1196270)

    • Wi-fi
    • Electric car charging
    • Swimming pool
    • Baby-friendly

    2 nights from Sat 28th Nov From £191

    Book now
  • An outdoor patio with cushioned chairs and a table next to a barbecue grill at Tilia Barn in Wincanton
    50
    Wincanton, Somerset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.9★

      Outstanding

    • Helpful Holidays rating

    This excellent, two-bedroom barn conversion rests in Wincanton, Somerset. (Ref. 1052563)

    • Wi-fi
    • Electric car charging
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly

    2 nights from Tue 5th Jan From £482

    Book now
  • A house with patio furniture and a hot tub at Knowle House Okehampton
    Property has offers
    64
    Okehampton, Devon
    • Sleeps9
    • Bedrooms5
    • Pet FriendlyNo

      4.8★

      Outstanding

    • Helpful Holidays rating

    Knowle House is a stunning, five-bedroom home resting in Okehampton, Devon. (Ref. 1192506)

    • Wi-fi
    • Off-road parking
    • Hot Tub
    • Dishwasher
    • Washing machine
    • Baby-friendly

    • 5% off - Fri 14th Aug to 21st Aug 2026

    • 5% off - Fri 28th Aug to 4th Sep 2026

    2 nights from Sat 28th Nov From £1181

    Book now
  • An exterior view of a two story house with wooden and white walls glass balcony railings and a pond with rocks and plants in front at Swallows Dip in Honiton
    60
    Honiton, Devon
    • Sleeps8
    • Bedrooms4
    • Pet FriendlyNo

      5.0★

      Perfect

    • Helpful Holidays rating

    This luxury holiday home is situated in the market town of Honiton in Devon. (Ref. 1046010)

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

    2 nights from Wed 2nd Dec From £947

    Book now
  • A stone building with wooden windows and door surrounded by a paved driveway and a garden with a blossoming tree at Bagtor Granary in Ilsington
    48
    Ilsington, Devon
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyNo

      4.9★

      Outstanding

    • Helpful Holidays rating

    A delightful, three-bedroom barn conversion resting on a working farm in Ilsington, Devon. (Ref. 1079841)

    • Wi-fi
    • Off-road parking
    • Hot Tub
    • Dishwasher
    • Washing machine
    • Baby-friendly

    2 nights from Sat 28th Nov From £708

    Book now
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Winter short breaks in South West England

Stave off those post-summer blues by booking a winter short break in the South West. With Helpful Holidays you can pick from the best of Cornwall, Devon, Dorset and Somerset cottages.

Got a few days annual leave spare that you need to use? Need a quiet break before the chaos of the festive season begins? Or want something to look forward to in the New Year?

If the answer is yes to any of the above, browse these beautiful properties for your next South West winter short break.

Get to Know the West Country on a Winter Short Break

The magnificent scenery of the South West is only made more magical in the low winter sun. From walks through the Mendips on a frosty morning, to fish and chips by Weymouth Beach.

The towns and villages across Dartmoor make for lovely country retreats, with pubs home to welcoming roaring fires to keep you from the cold, alongside tasty, hearty food.

Cornwall’s amazing beaches may be deserted in winter, but the waters are populated with incredible waves and avid surfers. Head to Cornwall on a winter short break and find the best waves all year.

Find your ideal South West Short Break Winter Retreat

Helpful Holidays can accommodate you and your loved ones with a range of properties across the South West.

Bring a big group together at a large holiday cottage before you see in the New Year. Or choose to treat yourself and your loved ones to the finer things at a luxury holiday cottage.

Enjoy the lack of seasonal dog bans on a winter short break with your pet pooch, finding a host of dog-friendly cottages across the South West.

Book your winter short break in South West England with Helpful Holidays today! Book online or talk with one of our experts on the phone.

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