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!

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

The Old Meeting Hall, Hampshire

Romantic hideaways in King’s Somborne, near Winchester with 1 bedroom, sleeps 2. Pets welcome. Enclosed Garden / Patio, Pub within 1 mile, Hot Tubs, Short Breaks All Year, Hot Tubs - Private.

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

  • Bungalow
  • Ground Floor Facilities
  • Romantic Getaways
  • Woodburning Stove
  • Decorated at Christmas
  • WiFi
  • Luxury Collection
  • Fishing Nearby/On-site
  • English Country Cottages
  • All En-suite
  • Open Plan
  • Parking - On Site
  • Shower Cubicle
  • Country Cottages
  • Winter Best Sellers
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 Converted carpenter’s studio with hot tub | The Joinery - Acorn Cottages, Owslebury, near Winchester

The Joinery, Hampshire

Large group accommodation in Owslebury, near Winchester with 4 bedrooms, sleeps 8. Pets welcome. Enclosed Garden / Patio, Golf nearby, Pub within 1 mile, Hot Tubs, Short Breaks All Year, Hot Tubs - Private.

Enjoy the walking and cycling routes on the South Downs National Park, and along the way visit nature reserves, historic sites, buildings and museums.

  • Games Room
  • Grouped Properties
  • WiFi
  • South Downs
  • Luxury Collection
  • English Country Cottages
  • Parking - On Site
  • Shower Cubicle
  • Celebration Houses
  • Country Cottages
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Open plan living space | Boxwood - Acorn Cottages, Owslebury, near Winchester

Boxwood, Hampshire

Large cottage to rent in Owslebury, near Winchester with 4 bedrooms, sleeps 8. Pets welcome. Golf nearby, Pub within 1 mile, Hot Tubs, Short Breaks All Year, Hot Tubs - Private.

This carefully converted carpenters studio stands as one of a pair, on the edge of picturesque Owslebury, 7 miles from historic Winchester with its magnificent cathedral.

  • Grouped Properties
  • Decorated at Christmas
  • WiFi
  • South Downs
  • Luxury Collection
  • English Country Cottages
  • Open Plan
  • Parking - On Site
  • Shower Cubicle
  • Celebration Houses
  • Country Cottages
View Property Details
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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.