
Holiday houses in Winchester
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Top-rated holiday rentals in Winchester
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A Unique Farm Retreat
There’s something magical about The Granary. Set in acres of farmland with spectacular sunrises and sunsets, The Granary brims with rustic charm. A dreamy hideaway with an outdoor copper bath and wood fired hot tub. An idyllic get-away-from-it-all yet only 3 miles to historic Winchester. Soak amid hot water, steam and fresh air surrounded by nature and birdsong, enjoy magnificent sunsets from the ‘Sundowner’ or cosy up toasting marshmallows over the fire pit - a perfect escape to unwind.

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.

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.

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 ✅

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.

The Hidden house in Winchester
The Hidden House is a slice of modern luxury tucked away in the heart of Winchester. Detached and private, this space is perfectly placed for exploring Winchester and all it has to offer. Our guests also love hiding away and making use of the big TV setup and Hotel Chocolat Velvetiser! Don't take our word for it - check out our reviews. Winchester High Street/The Cathedral - 10 min walk Winchester Train Station - 5 min walk

Stable Apartment with Hot Tub near Winchester
Newly renovated apartment with copper bath and hot tub in a converted stable 3 miles from Winchester. An en-suite bunk room is available on request for an extra fee. The well-equipped kitchen has a table seating six, alongside a boot room/utility, and sitting room with flame effect fire. Guests have access to the owner’s pool (May to September) and tennis court. Private hot tub and fenced garden with outdoor furniture.

Modern Apartment Central Winchester
Situated in the heart of Winchester, this newly refurbished 2-bedroom apartment with its own private entrance and modern décor provides a well thought out space for friends, couples & families. This cosy home provides an excellent upmarket base to explore Winchester. A stone’s throw to the city’s favourite pub, St James Tavern, a warm welcoming traditional pub which serves excellent locally sourced home cooked food.

The Cottage in Compton
Come and enjoy a stay in The Cottage, located in the grounds of our 17th Century converted Barn. Enjoy a unique location on the edge of Winchester with direct access to the countryside. The Cottage has been recently extended and refurbished with everything you will need to make your stay enjoyable. A perfect place for a break to explore all the wonderful things that Winchester has to offer!

The Annexe-central Winchester
The annexe is a cosy oasis hidden in the heart of central Winchester. It’s a completely private en-suite bedroom in a quiet leafy cul-de-sac. The theatre and many of Winchester’s best restaurants are right on your doorstep. The train station and High Street are a 5 minute walk away. 5 minutes in the other direction and you can be in Winnall Moors nature reserve.

Mews townhouse Winchester station.
Two bedroom, two bathroom high specification town house. Set back from Stockbridge Road in a quiet mews, across the road is the car park entrance of Winchester station, it's only a 3 minute walk from the house to the platforms. Comfortably sleeps 4 (maximum 7). Enjoy a well equipped kitchen, balcony, wifi, garage parking.
Popular amenities for Winchester holiday rentals
Stay near Winchester's top sights
Other great holiday rentals in Winchester

Weaver's Cottage

Central Winchester apartment with parking

Fab central self contained studio, just like home

Room with a view

Studio in Abbots Worthy

Stable Cottage Beauworth Southdowns Hampshire

Luxury 2BR apartment + parking central Winchester

Central, Quiet & Self-Contained
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $233 NZD | $228 NZD | $244 NZD | $266 NZD | $269 NZD | $271 NZD | $281 NZD | $293 NZD | $299 NZD | $289 NZD | $276 NZD | $298 NZD |
| 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 $33 NZD 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 and kid-friendly amenities

Pet-friendly accommodation
Find 70 rentals that welcome pets

Rentals with dedicated workspaces
130 properties have a dedicated workspace

Wi-Fi availability
310 of Winchester holiday rentals include Wi-Fi 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
- Paultons Park Home of Peppa Pig World
- University of Oxford
- Goodwood Motor Circuit
- Bracklesham Bay
- Stonehenge
- Windsor Castle
- Hampton Court Palace
- Highclere Castle
- Lower Mill Estate
- Boscombe Beach
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- Winchester Cathedral
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