- Estate Lodge
- Riverside Retreat
- Bonnie Brae
- Heartview Cottage
- Paisley Cottage
- The Damson Barn
- Buxton Farmhouse
- The Foaling Box at Lanhill
- Walnut Coach House
- Blossom Cottage
- Donne Cottage
- Frankel
- Amberley House
- Hill View Cottage
- Nature’s Nest
- Priory West Gate
- The Luxury Barn
- Tinkers Folly
- Whispering Leaves
- The Partridge
- Ermine
- Silver Crescent House
- Plum Cottage
- Loch Ness Mansion
- Darcy Hall
- Windermere Retreat
- The Highland Croft
- The Barns at Ampneyfield
- Mariner’s Cottage
- The Milking Parlour
Luxury Cottages in Winchester
- Sleeps 14 in seven bedrooms
- Private hot tub included
- Eight modern bathrooms throughout
- Near Winchester and South Downs
- Pet-friendly Hampshire countryside property
Luxury Cottages in Winchester & Prestige Holiday Homes to Rent
Searching for a luxury cottage in Winchester? Whether you want a romantic retreat for two, a stylish family escape or an elegant home for a special occasion, we have a wide choice of prestige holiday cottages here to suit every taste and budget.
Our luxury cottages are the perfect base for memorable breaks of all kinds — romantic weekends, honeymoons, milestone birthdays, anniversaries and special-occasion celebrations. Browse cottages with private hot tubs, swimming pools, sea views and designer interiors — all in Uk.
Many of our prestige holiday homes feature private grounds, log burners, premium kitchens, home cinemas, spa facilities and WiFi throughout. From characterful farmhouses to luxury barn conversions, find your perfect luxury holiday cottage and make your escape one to remember.
Popular searches
- Luxury cottages with hot tubs
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- Five-star self-catering
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Holiday cottages in Winchester, Hampshire
Plan Your Winchester Luxury Escape
Everything your group needs for a brilliant Winchester break — live weather, tide times, days out, walks, pubs & restaurants, beaches, EV charging, shops and how to get around Hampshire.
Local Weather
Open-MeteoPlanning a holiday in Hampshire? Keep an eye on the local forecast before you set off. Whether you're heading for the Hampshire coast or exploring inland, here's the weather and a five-day outlook to help you make the most of your stay.
Tide Times — Hampshire Coast
Environment AgencyThe Hampshire coastline is one of the finest in England, and knowing the tides makes all the difference for beach days, coastal walks and watersports. These readings from the nearest Hampshire tide gauge show whether the water is rising or falling.
Days Out Nearby
Geoapify PlacesFrom historic castles to family attractions and nature reserves, Hampshire is packed with brilliant days out. These are real places to visit near your Hampshire holiday cottage.
The Absentee Pig by Julian Trevelyan
Landmark · Winchester
The Square, Winchester, SO23 9BL, United Kingdom
Curle's Passage
Attraction · Winchester
Cathedral Close, Winchester, SO23 9LS, United Kingdom
Rousseau
Landmark · Winchester
The Square, Winchester, SO23 9BL, United Kingdom
County War Memorial
Landmark · Winchester
Cathedral Close, Winchester, SO23 9LS, United Kingdom
Rhythm Colour by Sonia Delaunay
Landmark · Winchester
The Square, Winchester, SO23 9BL, United Kingdom
Regatta at Cowes and Landscape at Villerville by Raoul Dufy
Landmark · Winchester
The Square, Winchester, SO23 9BL, United Kingdom
Troupe de Eglantine by Henri de Toulouse-Lautrec
Landmark · Winchester
The Square, Winchester, SO23 9BL, United Kingdom
Peter Blake
Landmark · Winchester
The Square, Winchester, SO23 9BL, United Kingdom
Treble Clef by Joseph Albers
Landmark · Winchester
The Square, Winchester, SO23 9BL, United Kingdom
Golconde by René Magritte
Landmark · Winchester
The Square, Winchester, SO23 9ES, United Kingdom
Walking Routes
OSM OverpassThere's no better way to explore Hampshire than on foot. From gentle coastal strolls to woodland trails, these are real waymarked footpaths and named routes near your cottage.
South Downs Way
National trail · Winchester → Eastbourne
Allan King Way
Regional route
Clarendon Way
Regional route · Winchester to Salisbury
Itchen Way
Regional route
Monarch's Way
Regional route · approximate route of Charles II's escape
Pilgrims' Trail
Regional route
St James' Way
Regional route · Reading Abbey (Church of St James) → Southampton (Town Quay)
St Swithun's Way
Regional route · Winchester → Farnham
Three Castles Path
Regional route
Keble Way
Waymarked route
Kingfisher Trail
Local route
Otter Trail
Local route
EV Charging Points
Open Charge MapTravelling to Hampshire in an electric vehicle? Many of our cottages offer EV charging, and there's a growing network of public chargers across the county. These are real charging points near your Hampshire stay.
The Brooks Shopping Centre
2 points · up to 7 kW
Winchester, SO23 8QY
ICUEVE900606
1 point · up to 11 kW
Winchester, SO23 9EF
St. Thomas Apartments
9 points · up to 4 kW
Winchester, SO23 9EH
WCC St Peters Car Park
2 points · up to 22 kW
Winchester, SO23 7DD
Park Avenue - Lighting Column 3
1 point · up to 3.7 kW
Winchester, SO23 8DJ
Durngate 2
2 points · up to 22 kW
Winchester, SO23 8DX
Park Avenue
1 point · up to 22 kW
Winchester, SO23 8DL
Hyde Abbey Road - Lighting Column 3
1 point · up to 3.7 kW
Winchester, SO23 7DA
Hyde Abbey Road - Lighting Column 5
1 point · up to 3.7 kW
Winchester, SO23 7DA
King Alfred Terrace - Lighting Column 1
1 point · up to 3.7 kW
Winchester, SO23 7DE
King Alfred Terrace - Lighting Column 2
1 point · up to 3.7 kW
Winchester, SO23 7DE
6 Alswitha Terrace, King Alfred Pl
1 point · up to 3.7 kW
Winchester, SO23 7DQ
Getting Around
GeoapifyGetting to and around Hampshire is easy once you know your options. From the nearest railway stations to local buses, here's how to reach your Hampshire holiday cottage and explore the area.
Winchester Station
Nearest railway station
Shawford Station
Nearest railway station
Chandler's Ford Station
Nearest railway station
Pubs & Restaurants
GeoapifyWhether you're after a proper country pub or a good meal out, Hampshire has plenty to offer. These are real venues near your cottage.
Bakers Arms
Winchester
The William Walker
Winchester
The Stables
Winchester
Starbucks
Winchester
The Dispensary Kitchen
Winchester
Republic of Pizza & Desserts
Winchester
Costa
Winchester
The Eclipse Inn
Winchester
Pitcher & Piano
Winchester
Cathedral Refectory
Winchester
Cafe Monde
Winchester
Maison Blanc
Winchester
Supermarkets & Shops
GeoapifyStocking up for your stay in Hampshire? Here are the nearest supermarkets and convenience stores to your cottage.
Tesco Express
Winchester SO23 9AS
Sainsbury's
Winchester SO23 8AQ
Winchester Mini-Market
Winchester SO23 9BQ
The Co-operative Food
Winchester SO23 8SD
SU Shop
Winchester SO22 4NR
Londis
Winchester SO23 9PS
One Stop
Winchester SO23 0NY
Stanmore News Food & Wine
Winchester SO22 4AE
Tesco Extra
Winchester SO23 7RS
Useful Info
GeoapifyGood to know before your stay in Hampshire — nearest hospitals and A&E departments.
Royal Hampshire County Hospital
Winchester
Sarum Road Hospital (BMI)
Winchester