English country holiday cottages to rent

Self-catering holiday cottages to rent near Winchester

Winchester, with a history all the way back to Roman times is perhaps best known for its cathedral, one of the largest in Europe (originally built in 1079) and with the longest nave and overall length of any European Gothic cathedral. It is also home to Winchester College, the oldest public school in the UK still located in its original buildings.

Alongside its history and heritage, Winchester has consistently featured in literature (from Medieval to present) and film over the years, as the birthplace of the fictional Captain Scarlet to Patrick Gale's 2009 book “The Whole Day Through” which was set in the city. It’s a wonderful city as a central hub for the local Hampshire Cottage Holidaymaker. You'll find cottages to suit large and small group accommodation sizes in villages close to Winchester including; Kings Worthy, Owslebury, and Old Alresford - last minute discounts are highlighted!

Romantic break in Owslebury, Winchester with 2 bedrooms, Sleeps 2. Pets welcome. Enclosed Garden/Patio, Golf nearby, Short Breaks All Year.

Super

Exterior | Lower Whiteflood Farm Cottage, Owslebury, Winchester

Lower Whiteflood Farm Cottage, Owslebury, Winchester, Hampshire, SO21 1JN.

Located on a peaceful arable working farm, this cottage offers the ideal base for couples to explore the rolling countryside and glistening coastline of Hampshire.

  • 1 Pet welcome
  • Enclosed Garden/Patio
  • Golf nearby
  • Short Breaks All Year
  • Fuel and Power Included
  • Pets – no charge
  • Rural Location
  • WiFi
  • Bed Linen & Towels Included
  • Washing Machine
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Romantic getaway in King’s Somborne, near Winchester with 1 bedroom, Sleeps 2. Pets welcome. Enclosed Garden/Patio, Pub within 1 mile, Hot Tub, Short Breaks All Year, Hot Tub - Private.

Fabulous

Wonderful, relaxing private hot tub | The Old Meeting Hall, King’s Somborne, near Winchester

The Old Meeting Hall, King’s Somborne, near Winchester, Hampshire, SO20 6NZ.

After a day out exploring the glorious Hampshire countryside, return to The Old Meeting Hall and relax in your own private hot tub.

  • 1 Pet welcome
  • Enclosed Garden/Patio
  • Pub within 1 mile
  • Hot Tub
  • Short Breaks All Year
  • Hot Tub - Private
  • Television
  • WiFi
  • Bed Linen & Towels Included
  • Luxury Collection
  • Washing Machine
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Rental home in Bishop’s Waltham with 3 bedrooms, Sleeps 6. Pub within 1 mile, Short Breaks All Year.

Luxurious

Exterior | The Cart House, Bishop’s Waltham

The Cart House, Bishop’s Waltham, Hampshire, SO32 2LL.

Beautiful spacious barn conversion on the edge of the South Downs National Park near to the picturesque village of Bishop’s Waltham with fabulous views of the adjoining countryside.

  • Pub within 1 mile
  • Short Breaks All Year
  • Dishwasher
  • Fuel and Power Included
  • Highchair
  • Television
  • WiFi
  • Bed Linen & Towels Included
  • Cot Available
  • Luxury Collection
  • Washing Machine
  • Pets – not allowed
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Cottage welcomes dogs in Stockbridge with 2 bedrooms, Sleeps 5. Golf nearby, Pub within 1 mile, Short Breaks All Year.

Good choice!

Exterior | Willow Cottage, Stockbridge

Willow Cottage, Stockbridge, Hampshire, SO20 6HG.

Lovely quaint Victorian cottage in the heart of Stockbridge, famed for its excellent fly-fishing on the River Test that flows through the town.

  • 1 Pet welcome
  • Golf nearby
  • Pub within 1 mile
  • Short Breaks All Year
  • Fuel and Power Included
  • Pets – no charge
  • Television
  • WiFi
  • Bed Linen & Towels Included
  • Washing Machine
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Luxury holiday cottage in Alresford with 3 bedrooms, Sleeps 6. Golf nearby, Pub within 1 mile, Short Breaks All Year.

Fabulous

Living area | Lovington Barn, Alresford

Lovington Barn, Alresford, Hampshire, SO24 0RD.

Escape to the country in this luxury oak framed barn with large suite style bedroom suites and oak framed bi-fold doors opening directly onto the uninterrupted Hampshire countryside -...

  • Golf nearby
  • Pub within 1 mile
  • Short Breaks All Year
  • Dishwasher
  • Fuel and Power Included
  • Rural Location
  • Television
  • WiFi
  • Bed Linen & Towels Included
  • Luxury Collection
  • Washing Machine
  • Pets – not allowed
View Property Details

Exclusive self-catering cottage in Winchester with 2 bedrooms, Sleeps 2 + 2 Children. No pets allowed. Enclosed Garden/Patio, Golf nearby, Pub within 1 mile, Short Breaks All Year.

High standard

Garden and exterior | Mallard Cottage, Winchester

Mallard Cottage, Winchester, Hampshire, SO23 0HX.

Nestled within the charming city of Winchester, this exquisite cottage is the perfect place for couple or a family holiday.

  • Enclosed Garden/Patio
  • Golf nearby
  • Pub within 1 mile
  • Short Breaks All Year
  • Dishwasher
  • Fuel and Power Included
  • Television
  • WiFi
  • Bed Linen & Towels Included
  • Luxury Collection
  • Pets – not allowed
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Uk holiday home in Winchester with 1 bedroom, Sleeps 3. Enclosed Garden/Patio, Short Breaks All Year.

Well equipped

Exterior | Lay Your Hat In Winchester, Winchester

Lay Your Hat In Winchester, Winchester, Hampshire, SO23 7DT.

This delightful cottage oozes charm. It’s full of light in the summer and cosy in the winter. Perfect for two in the heart of the beautiful mediaeval city of Winchester.

  • Enclosed Garden/Patio
  • Short Breaks All Year
  • Dishwasher
  • Fuel and Power Included
  • Highchair
  • Television
  • WiFi
  • Bed Linen & Towels Included
  • Washing Machine
  • Pets – not allowed
View Property Details

Luxury holiday cottage in Winchester with 2 bedrooms, Sleeps 4. Enclosed Garden/Patio, Short Breaks All Year.

Luxurious

Kitchen/diner | Pemberly, Winchester

Pemberly, Winchester, Hampshire, SO23 9JW.

Located on the Jane Austen walking Tour route, this property is set in the picturesque Kingsgate Village and makes you feel like you’ve stepped back in time.

  • Enclosed Garden/Patio
  • Short Breaks All Year
  • Dishwasher
  • Fuel and Power Included
  • WiFi
  • Bed Linen & Towels Included
  • Luxury Collection
  • Washing Machine
  • Pets – not allowed
View Property Details

Staying in Winchester and what to do for holidaymakers

The Winchester Hat Fair, which doesn’t really have much to do with hats at all, is the longest running street theatre, music and comedy festival in the UK, held during the first weekend in July. There is plenty on the historical front to do. In the centre, the Gurkha and Royal Green Jackets Museum are very popular and for those who might want to do something that involves taking in the wonderful restaurants, cafes and shopping along the way, there are numerous historical trails including Tudor, Military, Royal, Winchester Quiz and Walking trails as well as a Wheelchair Visitor trail.