Winchester Holiday Cottages

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British Travel Award Winners!

We are delighted to announce that we have been awarded 'Best UK Holiday Cottage/Self Catering Booking Company' at the British Travel Awards.

Winchester Holiday Cottages

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Your Winchester, Hampshire search returned 27 cottages

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Map View
The exterior of a two story house with a red tiled roof and wooden porch at Coombe Place House in Meonstoke
72
Meonstoke, South Downs National Park, SO32
  • Sleeps15
  • Bedrooms8
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

A grand, eight-bedroom home resting in Meonstoke, Hampshire. Countryside views. In AONB. Pet-friendly. Large. Open fire. Close to amenities. Droxford 1.7 miles; New Alresford 11.6 miles. (Ref. 1124828)

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

7 nights from £2247

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A large green lawn with a wide tree and a brick house with solar panels at Meon Boscage in Meonstoke
47
Meonstoke, South Downs National Park, SO32
  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A charming holiday home nested in the countryside near Meonstoke, Hampshire. Woodburning stove. Dog-friendly. In South Downs National Park. New Alresford 10.1 miles; Winchester 12.1 miles; Portsmouth 15.4 miles (Ref. 1113322)

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

7 nights from £1190

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A barn-style house with a gravel driveway and hedges along a road at Little Barn in Stockbridge
26
Stockbridge, Hampshire, SO20
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Little Barn is a stunning holiday home tucked away in the rural outskirts of Stockbridge, a charming town in Hampshire. Pet-friendly. Smart TV. Dishwasher. Winchester 10.1 miles; Salisbury 15.9 miles; Southampton 17.3 miles. (Ref. 1136243)

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

7 nights from £773

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A dark wooden house with solar panels on the roof and a fenced grassy yard at Suetts Farm Barns in Bishops Waltham
33
Bishop's Waltham, South Downs National Park, SO32
  • Sleeps6
  • Bedrooms3
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

Suetts Farm Barns, a stunning lodge, with a fire pit, located on the rural outskirts of Bishop's Waltham within the South Downs National Park in Hampshire. Southampton 12.1 miles; Portsmouth 14.4 miles. (Ref. 1126450)

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

7 nights from £972

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A single story wooden house with a gravel driveway and green plants in front at The Roost in Cheriton near Alresford
27
Cheriton near Alresford, South Downs National Park, SO24
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A wonderful single-storey cottage resting in Cheriton near Alresford. Woodburning-stove. Dog-friendly. Ground-floor living. Countryside views. Winchester 7.3 miles; Basingstoke 25.2 miles; Guildford 33.5 miles. (Ref. 1115307)

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

7 nights from £654

Last booked 2 days ago
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A white two-story house with a blue door and multiple windows surrounded by bushes and a black iron fence at Coppice Hill House in Bishop's Waltham
46
Bishop's Waltham, Hampshire, SO32
  • Sleeps9
  • Bedrooms4
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Coppice Hill House is a splendid holiday cottage nestled in Bishop's Waltham, Hampshire. Enclosed garden. Family-friendly. Hot tub. Private driveway. Winchester 10.9 miles; Southampton 10.9 miles; Portsmouth 13.8 miles; New Forest National Park 16 miles. (Ref. 1150056)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room

7 nights from £1416

Last booked yesterday
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A riverside patio with potted plants and green wooden chairs next to a brick wall and railing at RiverGem - Riverside Coach House in Winchester
15
Winchester, Hampshire, SO23
  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

RiverGem - Riverside Coach House is a lovely, pet-friendly first-floor apartment situated in the historic city of Winchester in Hampshire near amenities. Southampton 12.3 miles; North Wessex Downs AONB 13.4 miles; Basingstoke 18.8 miles. (Ref. 1012228)

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

7 nights from £700

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A black wooden house with a gravel yard and outdoor table with six chairs at Barley Cottage in Beauworth near Cheriton
34
Beauworth near Cheriton, South Downs National Park, SO24
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A stunning single-storey barn conversion resting in Beauworth near Cheriton, Hampshire. Original features. Pet-friendly. Open-plan. Woodburning stove. In National Park. New Alresford 4.1 miles; Winchester 7.9 miles; Southampton 15.7 miles. (Ref. 1119351)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £689

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The Granary - 1173555 - photo 1
New property
39
Upper Swanmore near Swanmore, South Downs National Park, SO32
  • Sleeps8
  • Bedrooms4
  • PetsNo

  • Tourist Board rating

The Granary is a wonderful holiday home located in the small village of Upper Swanmore near Swanmore in Hampshire with a Smart TV and enclosed garden. Bishop's Waltham 3.2 miles; Southampton 13.3 miles; Portsmouth 16.4 miles (Ref. 1173555)

  • Wi-fi
  • Off-road parking

7 nights from £1016

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A red brick house with white framed windows and bushes along the front with a stone pathway at Squirrel's Leap in Micheldever
26
Micheldever, Hampshire, SO21
  • Sleeps4
  • Bedrooms2
  • PetsYes

  • Sykes rating

Squirrel's Leap is a welcoming, detached house situated near a pub in Micheldever, Hampshire, boasting an electric fire, Smart TV, and enclosed garden. Southampton 18.9 miles; Reading 31.8 miles; Portsmouth 36.2 miles. (Ref. 1169788)

  • Wi-fi
  • Off-road parking
  • Dishwasher

7 nights from £594

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A bubbling hot tub on a wooden deck surrounded by trees at Blackwood Forest Golden Oak in Blackwood Forest
15

Holiday Park

Blackwood Forest, Hampshire, SO21
  • Sleeps2
  • Bedrooms1
  • PetsNo

Get close to nature in Forest Holidays Golden Oak cabin, nestled among 60 cabins in 270-hectares of Blackwood Forest, Hampshire. (Ref. 1146741)

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

7 nights from £1135

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A cabin with large windows surrounded by tall trees and green plants at Blackwood Forest Silver Birch in Blackwood Forest
16

Holiday Park

Blackwood Forest, Hampshire, SO21
  • Sleeps4
  • Bedrooms2
  • PetsNo

Forest Holidays Silver Birch cabin is one of 60 cabins surrounded by a 270-hectare beech wood at Blackwood Forest, Hampshire. (Ref. 1146654)

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

7 nights from £1020

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A wooden cabin with large windows among tall pine trees and grassy vegetation at Blackwood Forest Golden Oak in Blackwood Forest
18

Holiday Park

Blackwood Forest, Hampshire, SO21
  • Sleeps8
  • Bedrooms4
  • PetsYes

Surrounded by beech trees, Forest Holidays Golden Oak cabin is one of 60 woodland cabins in Blackwood Forest, Hampshire. (Ref. 1146683)

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

7 nights from £1815

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A wooden cabin with a fenced porch surrounded by trees in a forest at Blackwood Forest Golden Oak in Blackwood Forest
16

Holiday Park

Blackwood Forest, Hampshire, SO21
  • Sleeps4
  • Bedrooms2
  • PetsYes

Unwind in Forest Holidays Golden Oak cabin; surrounded by a 270-hectare beech wood in Blackwood Forest, Hampshire - part of a collection of 60 nature sensitive cabins. (Ref. 1146624)

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

7 nights from £1220

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A wooden cabin with a deck surrounded by trees in a forest at Blackwood Forest Golden Oak Blackwood Forest
16

Holiday Park

Blackwood Forest, Hampshire, SO21
  • Sleeps6
  • Bedrooms3
  • PetsYes

Surrounded by nature, Forest Holidays Golden Oak cabin is one of 60 cabins in a 270-hectare beech wood at Blackwood Forest, Hampshire. (Ref. 1146568)

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

7 nights from £1350

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A wooded area with two wooden cabins and tall trees at Blackwood Forest Golden Oak Treehouse in Blackwood Forest
18

Holiday Park

Blackwood Forest, Hampshire, SO21
  • Sleeps10
  • Bedrooms5
  • PetsNo

Forest Holidays Golden Oak Treehouse is one of 60 cabins surrounded by a 270-hectare beech wood at Blackwood Forest, Hampshire. (Ref. 1146632)

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

7 nights from £2615

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A wooden cabin surrounded by trees and ferns in a forest at Blackwood Forest Golden Oak Hideaway Blackwood Forest
18

Holiday Park

Blackwood Forest, Hampshire, SO21
  • Sleeps2
  • Bedrooms1
  • PetsNo

Forest Holidays Golden Oak Hideaway cabin at Blackwood Forest, Hampshire, is one of 60 cabins surrounded by a 270-hectare beech wood. (Ref. 1146579)

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

7 nights from £1380

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A wooden house surrounded by tall trees and grass in a forest at Blackwood Forest Golden Oak Blackwood Forest
18

Holiday Park

Blackwood Forest, Hampshire, SO21
  • Sleeps8
  • Bedrooms4
  • PetsNo

Escape to Forest Holidays Golden Oak cabin cocooned by a 270-hectare beech wood in Blackwood Forest - one of 60 nature sensitive cabins in Hampshire. (Ref. 1146612)

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

7 nights from £1955

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A wooden cabin surrounded by tall trees and green plants in a forest at Blackwood Forest Silver Birch Blackwood Forest
16

Holiday Park

Blackwood Forest, Hampshire, SO21
  • Sleeps6
  • Bedrooms3
  • PetsNo

Forest Holidays Silver Birch cabin is surrounded by nature - one of 60 cabins in a 270-hectare beech wood at Blackwood Forest, Hampshire. (Ref. 1146707)

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

7 nights from £1150

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A forest area with tall trees and two wooden cabins surrounded by greenery at Blackwood Forest Golden Oak Treehouse in Blackwood Forest
18

Holiday Park

Blackwood Forest, Hampshire, SO21
  • Sleeps10
  • Bedrooms5
  • PetsYes

Forest Holidays Golden Oak Treehouse at Blackwood Forest, Hampshire, is one of 60 cabins surrounded by a 270-hectare beech wood. (Ref. 1146637)

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

7 nights from £2710

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Map View

Winchester accommodation offers a delightful mix of heritage charm and modern comfort in one of England’s most historic and picturesque cities. With its rich history and easy access to the South Downs, every stay in a Winchester cottage promises both relaxation and inspiration. 

Why Winchester Holidays? 

Choosing Winchester accommodation means stepping into a city which was once the ancient capital of England. Winchester is home to architectural marvels like the majestic Winchester Cathedral and the legendary King Arthur’s Round Table at the Great Hall. 

Beyond its historical past, Winchester is full of stylish shops, award-winning restaurants and a lively arts scene. Just beyond the city limits, the South Downs National Park beckons with its rolling hills and stunning scenic trails. 

Whether you're a culture lover or outdoor enthusiast, Winchester holidays promise a well-rounded and unforgettable getaway. 

Places to Visit from Winchester Cottages 

Staying in a Winchester cottage places you within easy reach of some of England’s most iconic landmarks.

Beyond the city limits, the landscape opens up to the rolling beauty of the South Downs National Park, a haven for walkers, cyclists and nature lovers. Visit the historic village of Chawton, where Jane Austen penned her most beloved novels, or spend a leisurely afternoon at Highclere Castle; better known as Downton Abbey.

For a fun day out with all the family, head to Marwell Zoo, or why not enjoy wine tasting at one of Hampshire’s nearby vineyards if you are heading on a romantic weekend away. Or for a day of exploration, visit the stunning New Forest National Park, with a wide range of walking trails and colourful villages full of fantastic shops and eateries.

From heritage and countryside to food and family days out, Winchester cottages provide the perfect base for exploring it all. 

Other Popular Destinations near Winchester Accommodation: 

Barton-on-Sea

Hayling Island

Portsmouth

Types of Hampshire Holidays 

Head away for a break at Winchester accommodation today! 

Fancy a quick getaway to this county? Explore this range of short breaks in Hampshire. Or why not try something a little different, with a holiday park in Hampshire or these lodges in Hampshire.

Planning on taking your pooch with you? These dog-friendly cottages in Winchester are perfect for finding the right property for you all to enjoy.

Alternatively, browse the full collection of Hampshire cottages. There are also plenty of other city breaks in the UK to choose from.