Winchester Holiday Cottages
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We are delighted to announce that we have been awarded 'Best UK Holiday Cottage/Self Catering Booking Company' at the British Travel Awards.
Your Winchester, Hampshire search returned 27 cottages
- Sleeps4
- Bedrooms2
- PetsYes
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 £792
- Sleeps6
- Bedrooms3
- PetsYes
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 £660
Travel plans can change
Choose our 'Flexible' booking option and cancel by 12 noon on your check-in day to get a refund (exclusions apply).
- Sleeps4
- Bedrooms2
- PetsYes
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 £732
- Sleeps8
- Bedrooms4
- PetsYes
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 £1196
- Sleeps15
- Bedrooms8
- PetsYes
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 £2265
- Sleeps9
- Bedrooms4
- PetsYes
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 £1390
- Sleeps6
- Bedrooms3
- PetsNo
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 £1042
Travel plans can change
Choose our 'Flexible' booking option and cancel by 12 noon on your check-in day to get a refund (exclusions apply).
- Sleeps4
- Bedrooms2
- PetsYes
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 £695
- Sleeps5
- Bedrooms3
- PetsYes
El -Nido is an enchanting pet-friendly lodge in Medstead, Hampshire, boasting a woodburning stove in an open-plan living area and scenic countryside views. Winchester 12.5 miles; Basingstoke 13.5 miles; Guilford 26.2 miles (Ref. 1174277)
- Off-road parking
- Ground floor bedroom
- Dishwasher
7 nights from £643
- Sleeps4
- Bedrooms2
- PetsYes
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 £567
Holiday Park
- Sleeps4
- Bedrooms2
- PetsNo
Forest Holidays Golden Oak cabin is one of 60 cabins dotted among tall beech trees in Blackwood Forest, Hampshire. (Ref. 1147082)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Hot Tub
- Dishwasher
7 nights from £1257
Holiday Park
- 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 £1227
Holiday Park
- 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 £1379
Holiday Park
- 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 £1160
Travel plans can change
Choose our 'Flexible' booking option and cancel by 12 noon on your check-in day to get a refund (exclusions apply).
Holiday Park
- 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 £1004
Holiday Park
- Sleeps6
- Bedrooms3
- PetsYes
Forest Holidays’ Silver Birch cabin is one of 60 cabins surrounded by a 270-hectare beech wood at Blackwood Forest, Hampshire. (Ref. 1146661)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Hot Tub
- Dishwasher
7 nights from £1130
Holiday Park
- 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 £2070
Holiday Park
- 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 £2741
Holiday Park
- 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 £1971
Holiday Park
- 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 £1424
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:
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.