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Winchester Cathedral, Winchester, Hampshire
Winchester Cathedral, Winchester, Hampshire

Self Catering Holiday Cottages in Winchester

The historic city of Winchester is right on the edge of the South Downs National Park in Hampshire, known for being the original capital of England.
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51.090651, -1.226788

Beautifully presented throughout, Park Farm Cottages offers 5 Star luxury self-catering amongst the scenic beauty of the Hampshire countryside. Sitting on the edge of the South Downs National Park, guests can enjoy peace and tranquility with the River Itchen opposite adding to the charm. Park Farm Cottages is close to the city of Winchester and a popular choice with large groups sleeping up to ten guests who want to holiday or celebrate together. Tourist board rating: 5 Star Gold

Weekly price:
Please enquire with owner

10+2  |   3  |   1  |   Yes  |   Yes

Min nights: Enquire

Preferred arrival day: Friday | 5 Star Gold

51.090651, -1.226788

Perfect for couples and small families, West Cottage sleeps three guests and offers 5 Star self-catering in a beautifully peaceful part of Hampshire on the outskirts of the South Downs National Park. Close to Winchester, this fabulous architect-designed eco-build holiday home sits opposite the River Itchen and offers all the right ingredients for a relaxing break. Tourist board rating: 5 Star Gold

Weekly guide price:
£404 to £624

3  |   2  |   1  |   Yes  |   Yes

Min nights: Enquire

Preferred arrival day: Friday | 5 Star Gold

51.090651, -1.226788

An award winning single storey 5 Star holiday home situated in Hampshire on the edge of the South Downs National Park, near Winchester. East Cottage enjoys a wonderful tranquil position opposite the River Itchen and is ideal for a relaxing break. Tourist board rating: 5 Star Gold

Weekly guide price:
£736 to £1248

7  |   3  |   1  |   Yes  |   Yes

Min nights: Enquire

Preferred arrival day: Friday | 5 Star Gold

51.036820, -1.498988

There's nothing rustic about this well-appointed Shepherd Hut. Set in a field with gorgeous views, the holiday cottage is two modern timber and corrugated metal huts sleeping four people in two bedrooms with electricity, running water and a proper bathroom. Shepherd Hut is on the family-run Michelmersh Farm, where the owners raise dairy cows, sheep and keep horses and chickens. It's an idyllic location only a few miles from Romsey and within easy reach of the New Forest and South Downs National Parks, the Hampshire coast, Stonehenge, Winchester and Salisbury. Shepherd Hut is romantic for couples and fun for families. 

Weekly price:
£1120 all year

4  |   2  |   No  |   Yes  |   No

Min nights: 2

Preferred arrival day: Flexible

51.036820, -1.498988

Enjoy a farm holiday in this lovely holiday cottage on Michlemersh Manor Farm near Romsey. Foxglove Cottage sleeps four people in two double bedrooms and is welcoming and comfortable for couples or families. The farm has roots going back to 1205. The current owners raise dairy cows and sheep, and it's a great way to introduce children to the delights of country life. There are excellent footpaths and cycling routes nearby. Days out can include exploring the New Forest National Park, shopping and sightseeing in Salisbury and Winchester, visiting Stonehenge, or sunning yourself on Hampshire beaches like Milford-on-Sea. 

Weekly price:
£840 all year
Short breaks from £120 per night

4  |   2  |   Enquire  |   Yes  |   Yes

Min nights: 2 (off peak) | 2 (peak)

Preferred arrival day: Flexible

51.036820, -1.498988

Enjoy a self-catering farm holiday within reach of the New Forest National Park, Southampton, Winchester and Salisbury at Bluebells on family-run Michelmersh Manor Farm. There are some beautiful footpaths and cycle routes nearby, as well as golf, fishing and horse riding.

Weekly guide price:
£539 to £1135
Short breaks from £160 per night

6  |   3  |   2  |   Yes  |   Yes

Min nights: 2 (off peak) | 2 (peak)

Preferred arrival day: Flexible

51.036820, -1.498988

This elegant wing of a listed property dates back to medieval times, although the standard of self catering accommodation is firmly in the 21st-Century! It is part of a working farm and enjoys rural views of fields and farmland from the house and a private garden. Located close to Romsey in Hampshire, the Manor is ideal for families who can easily explore Salisbury, Winchester and the New Forest National Park as well as the south coast and sites such as Stonehenge.

Weekly guide price:
£585 to £1499
Short breaks from £160 per night

6  |   3  |   No  |   Yes  |   Yes

Min nights: 2 (off peak) | 2 (peak)

Preferred arrival day: Flexible

51.057878, -1.650399

A delightful stylish holiday retreat for two in a wonderfully tranquil area deep within Bentley Woods where rare butterflies and fallow deer can be seen under the giant oaks. Sitting on the Hampshire/Wiltshire borders, this is a walkers and cyclists paradise and Little Farley is only a short drive from the New Forest National Park.

Weekly guide price:
£395 to £780

2  |   1  |   2  |   No  |   Yes

Min nights: 3 (off peak) | 4 (peak)

Preferred arrival day: Friday

51.062832, -1.609156

Sitting in an acre of grounds, this well presented holiday home is perfect for families, friends and pet owners. Located on the Wiltshire/Hampshire border in the village of West Tytherley with good pub within walking distance, there are a multitude of attractions within easy reach including Salisbury, The New Forest, Winchester and Stonehenge. Whether you want to simply relax or explore, this welcoming cottage is an excellent choice.

Weekly guide price:
£425 to £795

4  |   2  |   2  |   Yes  |   Yes

Min nights: Enquire

Preferred arrival day: Flexible

51.057878, -1.650399

A fabulous country chic holiday retreat for up to six guests in a magical spot within an oasis of calm on the Hampshire/Wiltshire borders. Perfect for escaping away from it all, Farley Lodge sits within Bentley Woods, a haven for wildlife with superb opportunities for cyclists and walkers. Whether you want to simply relax or explore Hampshire and its many attractions including the New Forest National Park, Farley Lodge is a welcoming retreat to enjoy a taste of country life.

Weekly guide price:
£430 to £1650

6  |   3  |   2  |   Yes  |   Yes

Min nights: 3 (off peak) | 4 (peak)

Preferred arrival day: Friday

50.932291, -1.200856

The South Downs and the New Forest are both fantastic places for a holiday so where better to stay than between them in the Meon Valley, within easy reach of beautiful forests, favourite attractions and excellent amenities. Kiss Cottage is a quiet, one-bedroom property at the end of a private drive and within walking distance of the centre of Waltham Chase. There are lovely walks, traffic-free cycling routes and opportunities to play golf and horse ride close by, while Portsmouth, Salisbury, Chichester and the Solent are all only a short drive away.

Weekly price:
£455 all year
Short breaks from £65 per night

2  |   1  |   Enquire  |   Enquire  |   Yes

Min nights: 5 (off peak) | 5 (peak)

Preferred arrival day: Flexible

The historic city of Winchester is right on the edge of the South Downs National Park in Hampshire, known for being the original capital of England. For recommendations of how to fill your time when you visit, read on.

Where to Go in Winchester

Winchester Cathedral is a sightseeing highlight for tourists visiting the city. Built on the site of the original 7th-century Old Minster, the huge building dates back to the 11th century and has plenty of beautiful examples of historic architecture, as well as a famous collection of bronze statues.

The ruins of Wolvesey Castle is another top tourist spot, owned by the English Heritage organisation. What was once the chief residence of the Bishop of Winchester is now a free site that is great to explore on your own or with the help of an audio guide, with a nearby path taking you to another historic site in the city, Catherine's Hill.

To complete the recommendations of where to go in Winchester, the National Trust property Winchester City Mill offers brilliant insight into a working mill that is still in use today. There are flour milling and baking demonstrations available, activities for children and then the mill site is home to one of the UK’s only urban otter populations.

What to Do in Winchester

A top activity for those visiting Winchester is to visit the Military Museums in Peninsular Barracks. There are six different venues each dedicated to a topic related to military history which are all a great place to learn more about a wide range of events from across history and see the memorabilia from them.

If you’re a fan of Downton Abbey then you can visit the location the popular television programme was filmed in just over 20 miles out of Winchester. Highclere Castle is set in an 18th-century park and is beautifully decorated with furniture from across the centuries, providing a great place to visit for an excursion out of the city.

For a more modern attraction, the Winchester Science Centre & Planetarium is a firm favourite for families coming to visit the city. There are lots of brilliant interactive exhibits, along with the Uk’s largest planetarium that hosts a range of interesting daily shows.

Best Time to Visit Winchester

Winchester is a large city that is best explored on foot, so the best time of year to visit is when the chance of rain is low and the temperature is pleasantly warm. The spring and summer seasons in the UK between March and August are your best chance for warm and dry weather, with tourist activity peaking in Winchester in July and August.