Holiday rentals in Winchester

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Top-rated holiday rentals in Winchester

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Guest favourite
A well-appointed room features a spacious bed with plush bedding. Light wood flooring complements the seating area with a circular table and two upholstered chairs. Skylights and decorative lamps provide soft lighting. A mirror adds depth, and a hairdryer is available on the wall.
Guest house
4.91 out of 5 average rating, 139 reviews

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.

Top guest favourite
Two distinct entrances are visible, each framed by elegant archways. A decorative black iron railing separates the front door area from the sidewalk, while light green planters with small shrubs add a touch of greenery to the scene. Large windows allow natural light to fill the interior.
Guest suite
4.97 out of 5 average rating, 417 reviews

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.

Top guest favourite
A quiet street is lined with period houses, showcasing a mix of red brick and white facades. The cobblestone pavement leads past quaint buildings, with clear blue skies overhead. Architectural details include shuttered windows and gabled roofs, creating a charming urban atmosphere.
Townhouse
4.99 out of 5 average rating, 155 reviews

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.

Top guest favourite
The Pigsty features a unique domed structure with a blend of dark and natural wood accents. A small outdoor seating area with a round table and two chairs is positioned at the entrance, surrounded by lush greenery and potted plants.
Hut
4.98 out of 5 average rating, 619 reviews

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.

Top guest favourite
A polished silver bowl filled with ice displays several bottles of champagne. Fresh lilies and elegant candelabras are positioned nearby, adding a touch of sophistication to the setting. The arrangement creates a celebratory atmosphere.
Flat
5 out of 5 average rating, 101 reviews

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.

Top guest favourite
The exterior of the garden flat is showcased, featuring a sloped roof and large glass doors that open to a spacious terrace. A well-manicured lawn surrounds the building, and a dog relaxes peacefully in the grass. Lush greenery and garden beds enhance the inviting outdoor space.
Apartment
5 out of 5 average rating, 112 reviews

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.

Guest favourite
A modern brick exterior presents a spacious home with multiple large windows, providing ample natural light. The entrance features a covered porch, while a gravel driveway leads to the entrance. A separate structure is visible, hinting at added functionality to the property.
Home
4.97 out of 5 average rating, 107 reviews

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.

Top guest favourite
The bedroom features a spacious bed dressed in soft grey bedding, complemented by decorative cushions. Light streams through the window, softened by sheer curtains. A bedside table with literature adds a functional touch, while a wall-mounted mirror enhances the overall brightness.
Home
4.96 out of 5 average rating, 727 reviews

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.

Guest favourite
The studio features an elegantly decorated sleeping area with a spacious bed adorned with a colorful bedding. Soft lighting highlights the intricate mirror and chandelier. A comfortable chair sits beside the bed, while large curtains frame the windows, adding to the cozy ambiance.
Apartment
4.91 out of 5 average rating, 197 reviews

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 ✅

Top guest favourite
A modern cottage exterior is surrounded by lush gardens featuring various flowering plants. The building showcases a mix of wood paneling and large windows, reflecting natural sunlight. A spacious patio area can be seen, providing an inviting space to enjoy the peaceful outdoor setting.
Home
4.98 out of 5 average rating, 111 reviews

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.

Top guest favourite
The lounge area features a comfortable sofa adorned with colorful cushions and a light rug underfoot. A small armchair adds seating options, while natural light filters through the large windows, illuminating the room. A round coffee table rests in the center, enhancing the cozy atmosphere.
Flat
4.95 out of 5 average rating, 380 reviews

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.

Guest favourite
The living room features a light and airy design, showcasing a two-seater sofa and a separate sofa bed. A dining table for four is centered in the space, complemented by a fireplace and a wall-mounted TV. Decorative plants enhance the welcoming atmosphere.
Flat
4.92 out of 5 average rating, 199 reviews

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

When is the best time to visit Winchester?

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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!

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