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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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51.001148, -1.089678

The Stables at Black Hedges Farmhouse is the perfect antidote to your busy life. The award winning cottage is utterly idyllic and the ideal place to spend a romantic holiday. Located in West Meon in the South Downs National Park - voted the Best Village in Britain by The Times - The Stables is a few minutes' walk from village shops and an award winning pub and there are excellent walks, golf, and horse riding virtually on the doorstep. Tourist board rating: 5 Star Gold

Weekly guide price:
£650 to £950

2  |   1  |   No  |   Enquire  |   Yes

Min nights: 5 (off peak) | 7 (peak)

Preferred arrival day: Friday | 5 Star Gold

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

51.030460, -1.178959

The spacious bedroom with a view onto the an open field has a supering zip link bed with either organic cotton sheets or Irish linen. There's a small double sofa bed on the landing suitable for children under 12. We can provide a travel cot and high chair. There is a log fire with complimentary logs and kindling. There is a down stairs loo and a shower room upstairs.

Weekly guide price:
£819 to £945
Short breaks from £117 per night

2+1  |   1  |   No  |   Yes  |   Yes

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

Preferred arrival day: Flexible

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 guide price:
£980 to £1120
Short breaks from £150 per night

4  |   2  |   No  |   Yes  |   No

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:
£980 to £1400
Short breaks from £190 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:
£1400 to £1540
Short breaks from £200 per night

6  |   3  |   No  |   Yes  |   Yes

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

Preferred arrival day: Flexible

51.060273, -1.375295

The Old Dairy is a converted single storey cottage. It offers an open plan living room, dining room and kitchen which enjoy views of the farm. The small utility room has a tumble dryer and has room to dry wet clothes and boots. The master bedroom boasts an ensuite bathroom with large bath as well as a comfortable kingsize bed and armchair for those wanting to enjoy a peaceful sit down. At the opposite end of the property a wet room with shower can be found, as well as the other two bedrooms, a bunk bed and twin room which has a large wardrobe. The property garden can be accessed through the patio doors which opens out to a small patio area and enclosed garden.  A 10% discount is offered to 2 people just using one bedroon for a full 7 night stay.

Weekly guide price:
£695 to £1150
Short breaks from £128 per night

6  |   3  |   No  |   Yes  |   Yes

Min nights: 3 (off peak) | 7 (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, Favorite 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 center 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:
£630 all year
Short breaks from £110 per night

2  |   1  |   Enquire  |   Enquire  |   Yes

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

Preferred arrival day: Flexible

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 price:
£875 all year
Short breaks from £130 per night

4  |   2  |   2  |   Yes  |   Yes

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

Preferred arrival day: Flexible

51.036820, -1.498988

Stay at Archers Retreat, a beautifully converted medieval barn on Michelmersh Manor Farm near Romsey in Hampshire. This unique holiday cottage sleeps 4 and offers open-plan living with a king-size bed downstairs and a mezzanine double above. Enjoy a wood-burning stove, well-equipped kitchen, and private outdoor seating. Set on a working farm in the scenic Test Valley, with walks from the door and easy access to the New Forest, Winchester, and the River Test. Ideal for couples or older families wanting a peaceful countryside escape with character, history, and access to some of Hampshire’s most loved attractions.

Weekly guide price:
£1330 to £1400
Short breaks from £190 per night

4  |   2  |   No  |   Enquire  |   Yes

Min nights: 2 (off peak) | 3 (peak)

Preferred arrival day: Flexible

51.078440, -1.481354

"The Old Meeting Hall" is a 1 bed holiday Cottage sleeping up to 2 guests in Hampshire. After a day out exploring the glorious Hampshire countryside, return to The Old Meeting Hall and relax in your own private hot tub.. All on the Ground Floor: Open plan living space. Living...

Prices from £152 per night

2  |   1  |   Yes  |   Yes  |   Yes


51.069984, -1.046169

"The Barn" is a 2 bed holiday Cottage sleeping up to 4 guests in Hampshire. Fitted with oak floors and beams, this detached barn conversion lies close to beautiful towns and historic buildings.. 1 step to entrance. Ground Floor: Kitchen/dining room: Oil Aga, Microwave, Fridge,...

Prices from £230 per night

4  |   2  |   Yes  |   Yes  |   Yes


51.066865, -1.590807

"Downs View Dairy" is a 5 bed holiday Cottage sleeping up to 11 guests in Wiltshire. This rural village comes with a shop and a pub with a skittle alley and serving food. The city of Salisbury is nearby with its fine architecture including its cathedral, as well as a wide range of high-quality amenities to make the most of....

Prices from £593 per night

11  |   5  |   Yes  |   Yes  |   Yes


50.986329, -1.580250

"Pinns Farm Bungalow" is a 2 bed holiday Cottage sleeping up to 4 guests in Hampshire. This delightful detached farm cottage offers a rural retreat of complete peace and privacy. Step out of the door and you are in a large sunny garden that is encouraged to act as a wildlife haven for both animal and plant life...

Prices from £220 per night

4  |   2  |   Yes  |   Yes  |   Yes


51.035949, -1.586143

"The Bike Shed" is a 1 bed holiday Cottage sleeping up to 2 guests in Hampshire. A quaint village resting amid the countryside of Hampshire. West Tytherley is a tranquil holiday spot boasting a useful convenience store and a charming old pub with a skittle alley and serving delicious food. The surrounding area is a paradise...

Prices from £134 per night

2  |   1  |   No  |   Yes  |   Yes


50.954907, -1.212219

"1 Bed" is a 1 bed holiday Apartment sleeping up to 2 guests in Southampton. Bishop's Waltham, a lovely little medieval market town is nestled at the source of the River Hamble, right on the edge of South Downs National Park. The town enjoys plenty of pleasantries with traditional shopping, pub lunches and a visit to...

Prices from £146 per night

2  |   1  |   Yes  |   Yes  |   Yes


51.059670, -1.574917

"Oaklands Farm - Cottage 5" is a 1 bed holiday Cottage sleeping up to 2 guests in Wiltshire. Cottage 5 at Oaklands Farm is nestled in the village of East Tytherley, sitting in the beautiful Test Valley. Perfect for couples, the annexe is situated within the owners’ grounds of Oaklands Farm.. All on the Ground Floor:...

Prices from £222 per night

2  |   1  |   Yes  |   Yes  |   Yes


51.059670, -1.574917

"Cottage 3 - UK46609" is a 1 bed holiday Cottage sleeping up to 2 guests in Wiltshire. Cottage 3 at Oaklands Farm is nestled in the village of East Tytherley, sitting in the beautiful Test Valley. Perfect for couples, the annexe is situated within the owners’ grounds of Oaklands Farm. All on the Ground Floor:...

Prices from £167 per night

2  |   1  |   Yes  |   Yes  |   Yes


51.059670, -1.574917

"Cottage 1 - UK46611" is a 1 bed holiday Cottage sleeping up to 2 guests in Wiltshire. Cottage 1 is a one bedroom studio apartment in an old converted barn, located on Oaklands Farm and even has its own airstrip and shared tennis courts.. All on the Ground Floor: Open plan living...

Prices from £157 per night

2  |   1  |   Yes  |   Yes  |   Yes


51.059670, -1.574917

"Cottage 2 - UK46612" is a 1 bed holiday Cottage sleeping up to 2 guests in Wiltshire. Cottage 2 is a one bedroom studio apartment in an old converted barn, located on Oaklands Farm and even has its own airstrip and shared tennis courts.. All on the Ground Floor: Open plan living...

Prices from £215 per night

2  |   1  |   Yes  |   Yes  |   Yes


50.998000, -1.586594

"Dairy Farm" is a 2 bed holiday Cottage sleeping up to 3 guests in Hampshire. The Dairy Farm is a beautiful 16th century thatched cottage set within the picturesque village of Sherfield English in the Test Valley.. 2 steps to entrance. Ground Floor: Living/dining room: Freeview Smart...

Prices from £225 per night

3  |   2  |   Yes  |   Yes  |   Yes


50.908850, -1.417973

"Cosy Southampton Apartment" is a 1 bed holiday Apartment sleeping up to 4 guests in Southampton. Sitting just south-west of where the River Itchen and the River Test meet, Southampton is a beautiful and lively port city offering a fantastic setting for any holiday in the UK. With a wide selection of pubs, bars and restaurants, as well as a...

Prices from £159 per night

4  |   1  |   Yes  |   Yes  |   Yes


51.206867, -1.476583

"4 Eastgate - UK34281" is a 1 bed holiday Cottage sleeping up to 4 guests in Hampshire. We love this property! With so much to see and places to explore right on the doorstep, this property is perfect for business or leisure travellers.. 1 step to entrance. All on the First Floor: Open plan living...

Prices from £269 per night

4  |   1  |   No  |   Yes  |   Yes


51.043500, -1.345552

"The Old Cook House" is a 2 bed holiday Cottage sleeping up to 4 guests in Hampshire. The Old Cook House is an ex-army property which has been renovated over the years to provide living accommodation.. 2 steps to entrance. All on the Ground Floor: Living room: Smart...

Prices from £239 per night

4  |   2  |   Yes  |   Yes  |   Yes


51.059670, -1.574917

"Oaklands Farm - Cottage 4" is a 2 bed holiday Cottage sleeping up to 4 guests in Wiltshire. Cottage 4 at Oaklands Farm is nestled in the village of East Tytherley, sitting in the beautiful Test Valley. Perfect for couples, this studio apartment is situated within the owners’ grounds of Oaklands Farm.. All on the Ground Floor:...

Prices from £165 per night

4  |   2  |   Yes  |   Yes  |   Yes


51.206867, -1.476583

"6 Eastgate -UK34289" is a 1 bed holiday Cottage sleeping up to 4 guests in Hampshire. This apartment is perfectly located to explore the vibrant historic town of Andover and the natural beauty of the North Wessex Downs. 1 step to entrance. All on the First Floor: Open plan living...

Prices from £269 per night

4  |   1  |   No  |   Yes  |   Yes


51.039504, -1.613496

"The Dunnit@Manor Farm" is a 3 bed holiday Cottage sleeping up to 6 guests in Wiltshire. West Tytherley is a charming village located in Hampshire's countryside. In addition to a helpful convenience shop and a wonderful old pub with a skittle alley and delicious meals, West Tytherley is a peaceful holiday destination. Outdoor...

Prices from £412 per night

6  |   3  |   No  |   Yes  |   Yes


51.095432, -1.562988

"3 Bed Cottage in Stockbridge" is a 3 bed holiday Cottage sleeping up to 6 guests in Hampshire. Additional information and rules. Please enquire if you wish to bring more than 1 dog - 3 bedrooms – 2 super-king-size and 1 twin room - 1 bathroom with bath, walk-in shower, and WC, plus 1 additional downstairs WC - Electric...

Prices from £467 per night

6  |   3  |   No  |   Yes  |   No


51.177600, -1.397400

"4 Bed Cottage in Winchester" is a 4 bed holiday Cottage sleeping up to 8 guests in Hampshire. Additional information and rules. Please enquire if you wish to bring more than 1 dog - 4 bedrooms, 1 king-size, 2 doubles and 1 double with sofa bed - 2 bathrooms, 1 family bathroom, 1 en-suite and 1 separate WC - 2 wood...

Prices from £724 per night

8  |   4  |   No  |   Yes  |   No


51.219070, -1.469856

"Caulder Court" is a 3 bed holiday Cottage sleeping up to 8 guests in Hampshire. A great choice for larger families or groups of friends as a base to explore Hampshire and the wider area.. 2 steps to entrance. Ground Floor: Living room: Freeview TV, Patio Doors Leading To...

Prices from £499 per night

8  |   3  |   Yes  |   Yes  |   Yes


51.073011, -1.312023

"The Dacha" is a 2 bed holiday Cottage sleeping up to 4 guests in Hampshire. Nestled in the heart of Hampshire lies Winchester, a city steeped in history and home to a wealth of attractions that will leave you in awe. Marvel at the grandeur of the Great Hall, home to the legendary Round Table, and lose yourself in the...

Prices from £156 per night

4  |   2  |   No  |   Yes  |   Yes


50.969672, -1.358486

"Luxury rooms at Leigh Road" is a 1 bed holiday BandB sleeping up to 1 guests in Hampshire.

Prices from £70 per night

1  |   1  |   No  |   Yes  |   Yes


51.070616, -1.298614

"Student Only Riverside Way in Winchester" is a 1 bed holiday Apartment sleeping up to 1 guests in Hampshire.

Prices from £43 per night

1  |   1  |   No  |   Yes  |   Yes


50.911648, -1.199971

"Royal Swan, Ashley Manor - B&B" is a 1 bed holiday BandB sleeping up to 1 guests in Hampshire.

Prices from £129 per night

1  |   1  |   No  |   Yes  |   No


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.