
Holiday rentals in Winchester
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Top-rated holiday rentals in Winchester
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Central, Quiet & Self-Contained
Incredibly central location. Only 150m from Cathedral & 200m to High St. Quiet: Set back from the street, double glazing, detached building. King size bed with luxury mattress & topper, hypoallergenic duvet & pillows, Egyptian cotton bedlinen and fluffy towels. Work space. Reading & soft lighting. Well Equipped: Tea & Coffee Facilities, Mini Fridge, TV (Netflix only) Iron+Board, Hairdryer, Toiletries & Fan. Secure parking subject to availability £20per night. NB. Access via external staircase.

Own Front Door
Welcome to the beautiful city of Winchester! I have self contained central accommodation comprising of a double bedroom with en-suite shower room, a lounge with fridge/tea/coffee making facilities and your own private front door accessed from the street at ground level. The accommodation has been part of a massive renovation of the main house, now fully completed. Dating from the 1850’s it still retains a Victorian feel with high ceilings and sash windows. It is a lovely light, airy space.

St Michael's Hall, City Centre
St Michael's Hall is a unique, newly renovated church hall in the heart of the historic city centre. A stone's throw from the Cathedral, College, buzzy high street and water meadows, it's the perfect base to explore everything Winchester and the surrounding area has to offer. Each bedroom has its own bathroom, meaning it's as suitable for two couples as it is for a romantic city break or four friends. One on-street parking permit is available, while the train station is a short walk away.

The Pigsty
The Pigsty is Winchester's first luxury woodland hideaway, with beautiful views of Vale Farm. Less than 2.5 miles from the historic centre of Winchester, this peaceful retreat is perfect for those looking to visit the city, or escape for some peace. The Pigsty’s domed design with wooden interior has a roll top bath, cosy open plan living space and decking area to enjoy dinner with sunset views. Just a few minutes walk from the famous Clarendon Way, and a 30 minute walk to the city centre.

The Sky Penthouse, City Centre Luxury
Positioned right in the heart of charming historic Winchester The Sky Penthouse offers luxury modern comfortable 5 star accommodation . Private parking for one car . Positioned an easy level 300 meter walk from the main High Street within the City Centre , 400 meters from Winchester Cathedral and 500 meters from Winchester train station. Great location with a garden. Guests can choose the bed configuration of both the double bedrooms, either 6ft wide super king luxury beds or single beds.

Beautiful stylish Garden flat 8 mins to Winchester
Unique and stylish, this very comfortable and relaxing space offers the peacefulness of countryside whilst being a stones throw from the beautiful city of Winchester - a very short drive or a beautiful walk away. You get the best of both worlds with the city's pubs, restaurants, cafes and historic sights close at hand as well as river walks by the Itchen & beautiful countryside straight from your door. Excellent transport links to London, M3, Southampton Airport and the New Forest.

Annex for couple or solo stay.
The Beehive, is a separate building with private access. It's part of our home in Headbourne Worthy and set in a peaceful semi-rural retreat. It is perfect for solo visitors or couples but not suitable for young children. We have lovely views, with great access to the rural footpaths and only a 15-20 minute walk to Winchester. It is a bright and airy space, with modern features and neutral décor. We are a 5 minute drive from the City of Winchester and mainline train station to London.

Central Winchester 1 Bedroom Home with own parking
Welcome to your lovely detached one bedroom home in a quiet leafy private road on the edge of St Giles Hill - just above medieval Winchester and on the edge of beautiful the South Downs Way. Your self-contained home includes parking on the drive, a stylish double bedroom, shower room, living area (with full double-width sofa bed) incorpoating a full kitchen/washing machine. Its an easy 10 minute downhill stroll across the park (lovely for a sunset picnic) to historic Winchester.

Bright Bijou Studio in Central Winchester
A beautiful bright cosy studio apartment on one of the quietest streets in the centre of historic Winchester❤️. The breathtaking cathedral and other must-see sights are all within a flat 10 minute walk. Ideal for short stays or a weekend get-away. Just five minutes walk from train station/city centre, and 10 mins walk from the bus station. * Super-comfy double bed ✅ * Fast WiFi ✅ * Comfortable big chair and table for laptop working ✅ * Wide range of caf/decaf teas and coffees ✅

Stable Cottage Beauworth Southdowns Hampshire
Welcome to Stable Cottage, your idyllic getaway. Our newly built cottage is designed to the highest standard for your comfort and enjoyment. The cozy atmosphere is enhanced by super-insulated walls and a log-burning stove that keep you warm during colder months. In summer, the sliding patio doors let in sunshine and stunning views of the Hampshire countryside. Stay connected with super-fast fibre broadband and a Smart TV. Your stay at Stable Cottage will be unforgettable.

Central Winchester garden flat, permit parking
Winchester City Centre- Bijou, charming, characterful, homely, warm and cosy self contained one bedroom flat with free permit parking and luxuriously large bath tub with shower, private garden with patio for alfresco dining. Fully equipped galley kitchen for self - catering. Only a five minute level walk to the central High Street and Cathedral, with the world famous Christmas Market through November and December. Less than ten minutes walk from the Railway Station.

Stylish Apartment • Central Winchester
Situated in the heart of Winchester, this newly refurbished two-bedroom apartment with its own private entrance offers a stylish and comfortable stay for couples, friends and families. Modern décor and thoughtful design create a cosy space to relax after exploring the city’s historic streets, shops and cathedral. You’re just steps from the popular St James Tavern, a welcoming traditional pub serving excellent locally sourced food.
Popular amenities for Winchester holiday rentals
Stay near Winchester's top sights
Other great holiday rentals in Winchester

Central Winchester, Maximalist, Victorian House

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Private garden room, free permit parking

Stunning House in Central Winchester

Grove Place, Winchester (2 parking spaces)

Fab central self contained studio, just like home

The Bowie is a David Bowie themed Smart Home + EV

Luxury 2BR apartment + parking central Winchester
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £104 | £102 | £109 | £119 | £120 | £121 | £126 | £131 | £134 | £129 | £123 | £133 |
| Avg. temp | 5°C | 5°C | 7°C | 9°C | 12°C | 15°C | 17°C | 17°C | 15°C | 11°C | 8°C | 5°C |
Frequently Asked Questions
What are the best places to stay in Winchester?
Winchester has a mix of accommodation options around the historic city centre, near the railway station, and just outside in residential neighborhoods. Many visitors choose areas that provide easy access to the Cathedral, local restaurants, museums, and small shops.
What are the best things to do in Winchester with kids?
Families can explore Winchester Science Centre, wander the historic streets, or visit riverside parks for outdoor play. The Great Hall, home to the legendary Round Table, is also frequently suggested for curious young visitors.
What are some of the best things to do in Winchester?
Explore Winchester Cathedral, stroll along the River Itchen, and visit the Great Hall to learn about local legends. Markets, galleries, and walking trails give a taste of the city's vibrant community.
How is the weather in Winchester?
Winchester experiences cool, damp winters averaging 35–47°F (2–8°C), and mild summers near 54–72°F (12–22°C). It is a good idea to pack layers and a light waterproof jacket throughout the year.
When is the best time to visit Winchester?
Late spring through early autumn is often recommended for milder temperatures and outdoor activities. Seasonal festivals and historic sites draw visitors year-round, but gardens and walking routes are especially lively in warmer months.
What are the best places to visit in Winchester?
Winchester has the acclaimed Winchester Cathedral, the Great Hall with its medieval history, and riverside walks along the Itchen. City museums and markets around the centre are frequently suggested for visitors.
What are some hiking trails in Winchester?
The South Downs Way passes near Winchester and has scenic countryside paths suitable for walking. Riverside trails along the Itchen and routes through nearby nature reserves also attract hikers and families.
What are some family activities we can do in Winchester?
Families enjoy interactive exhibits at Winchester Science Centre, picnics in Abbey Gardens, and the city's historic walking tours. The Great Hall and parks around the centre are local favourites for a relaxed outing.
What are some of the best day trip ideas from Winchester?
Travellers often take day trips to the New Forest for woodland walks, Salisbury and its cathedral, or tour nearby villages known for local produce and markets. Coastal spots around Hampshire also appeal to visitors.
Are there any pet friendly accommodations available in Winchester?
Winchester has pet-friendly stays, especially in neighbourhoods near parks and walking trails. Many hosts welcome dogs, making it easy to enjoy outdoor spaces together.
What are some local tips for visiting Winchester?
Try exploring early in the day for fewer crowds at popular sites like Winchester Cathedral. Local markets and independent cafes are scattered throughout the centre, and walking shoes help on cobbled and uneven streets.
What is Winchester known for?
Winchester is known for its rich medieval history, impressive Cathedral, and connections to legends such as King Arthur’s Round Table. The city also has a reputation for vibrant markets and lively community events.
What are the best hidden gems to explore in Winchester?
Seek out Wolvesey Castle, the quiet grounds of St. John’s Almshouses, and the water meadows just beyond the city centre for peaceful walks. Independent bookshops and small art galleries are also worth exploring.
What are the best foods to try in Winchester?
Local menus frequently suggest Hampshire watercress, artisan cheeses, and seasonal game dishes. Independent bakeries feature British pastries, and area pubs often serve classics like fish and chips.
What should I bring for a trip to Winchester?
Bring comfortable walking shoes for cobbled streets and local trails, a waterproof jacket for changeable weather, and layers to accommodate cool mornings and warmer afternoons. A camera is handy for historic architecture and scenic views.
What is the nightlife in Winchester like?
Winchester’s nightlife features relaxed pubs, live music venues, and wine bars around the centre. Many spots celebrate local brews and host evening events in historic settings.
What are the most popular events or festivals in Winchester?
Winchester has recurring events such as the Winchester Christmas Market, a well-attended food festival in summer, and seasonal literary celebrations. The city’s calendar often features music, arts, and outdoor gatherings.
Are there family friendly vacation rentals in Winchester?
Family-friendly rentals are found across Winchester, particularly near the city centre and parks. Many hosts provide amenities for young guests, making it easy to relax after days spent exploring historic and outdoor attractions.
Quick stats about holiday rentals in Winchester

Total holiday rentals
Explore 310 holiday rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at £15 per night before taxes and fees

Verified guest reviews
Over 19,150 verified reviews to help you choose

Family-friendly holiday rentals
150 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 70 rentals that welcome pets

Rentals with dedicated workspaces
130 properties have a dedicated workspace

Wifi availability
310 of Winchester holiday rentals include wifi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Winchester rentals

4.8 Average rating
Winchester stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
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- New Forest National Park
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- University of Oxford
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- Stonehenge
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- Windsor Castle
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