Winter Short Breaks in South West England

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    How reviews work

    A property's star rating is the average of the star ratings received from guests that wish for their review to be published
  • A house with a pond surrounded by trees at Lower Moorwood in Moorwood near Bovey Tracey
    59
    Moorwood near Bovey Tracey, Devon
    • Sleeps8
    • Bedrooms4
    • Pet FriendlyNo

      5.0★

      Perfect

    • 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 €796

    Book now
  • A barn style house with gravel driveway and green field at Shepherd's Barn Between Milborne St Andrew and Winterborne Whitechurch
    Property has offers
    24
    Between Milborne St Andrew and Winterborne Whitechurch, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

      5.0★

      Perfect

    • Helpful Holidays rating

    A superb, detached barn conversion set in the countryside near Winterborne Whitechurch. (Ref. 5188)

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

    • 5% off - Wed 1st Jul to 31st Aug 2026

    2 nights from Sun 6th Dec From €634

    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 €577

    Last booked 2 days ago
    Book now
  • An outdoor dining area with a table and chairs at Fieldstone Barn in North Tawton
    New property
    43
    North Tawton, Devon
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

    • Helpful Holidays rating

    Fieldstone Barn is a lovely, dog-friendly barn conversion in North Tawton, Devon, featuring countryside views, ground-floor living, and off-road parking. (Ref. 1202188)

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

    2 nights from Sat 28th Nov From €517

    Last booked yesterday
    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 €1108

    Last booked 2 days ago
    Book now
  • An exterior view of a rustic building with tiled roof and multiple glass doors opening onto a cobblestone courtyard with potted plants and a garden area at The Shippon in Honiton
    35
    Honiton, Devon
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyNo

      5.0★

      Perfect

    • Helpful Holidays rating

    The Shippon is a spacious and inviting home, with characterful yet chic features, perfect for a couples retreat at Lower Lye, in the Blackdown Hills AONB. (Ref. 1087064)

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

    2 nights from Mon 30th Nov From €587

    Last booked yesterday
    Book now
  • A lawn with a stone wall and a wooden building with glass doors at Owl Lodge in Wedmore
    27
    Wedmore, Somerset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyNo

      5.0★

      Perfect

    • Helpful Holidays rating

    A stylish wooden lodge nestled just outside the village of Wedmore in Somerset. (Ref. 1100431)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Ground floor bedroom
    • Hot Tub
    • Dishwasher

    2 nights from Sat 28th Nov From €782

    Book now
  • A blue house with a stone retaining wall and a balcony above a street at Ingledene in Brixham
    Property has offers
    41
    Brixham, Devon
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyNo

      4.9★

      Outstanding

    • Helpful Holidays rating

    A beautiful reverse-level, detached house resting in Brixham, Devon. (Ref. 1123266)

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

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

    • 5% off - Fri 25th Sep to 16th Oct 2026

    2 nights from Sat 28th Nov From €593

    Last booked yesterday
    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 €828

    Last booked 2 days ago
    Book now
  • A wooden outdoor dining table with chairs on a lawn in front of a large building with red tiled roof at The Stables in Watchfield near Highbridge
    39
    Watchfield near Highbridge, Somerset
    • Sleeps5
    • Bedrooms3
    • Pet FriendlyNo

      5.0★

      Perfect

    • Helpful Holidays rating

    The Stables is a superb barn conversion resting in Watchfield, Somerset. (Ref. 1112503)

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

    2 nights from Sat 28th Nov From €523

    Last booked yesterday
    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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