Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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Top guest favorite
A light-filled living area features a comfortable gray sofa adorned with patterned cushions. A small, cozy armchair sits nearby, and a wooden coffee table is positioned in front. Natural light streams through the window, highlighting a light blue wall and decorative shelf.
Condo in Winchester
4.97 out of 5 average rating, 143 reviews

Spacious central 2 bedroom apartment+ free parking

A spacious family-friendly 2 double/twin bedroom first floor flat located in the lovely Hyde area of central Winchester. Provides easy access to the city centre with all that the city offers. Only 5 minutes stroll to the train station. This apartment is close to all the historical sites and wide variety of restaurants and cafes which you'll enjoy as well as the cathedral and its impressive grounds. Winchester Christmas market and the city's magical atmosphere should be on everybody's calendar.

Top guest favorite
The bungalow's exterior features a combination of brick and wood with a textured gabled roof. Flower pots and beds with colorful blooms line the pathway, leading to large windows that allow natural light into the interior.
Bungalow in Eastleigh
4.93 out of 5 average rating, 409 reviews

One bedroom home.

Relax and make yourself at home in this comfortable bungalow with sunny lounge, fully equiped kitchen/diner and bathroom. Situated in a quiet cul-de-sac in the village of Bishopstoke on the outskirts of Eastleigh. The M27 and M3 motorways and Southampton Airport are just a few miles away. The historic City of Winchester is an easy drive. Whether you are on your way to explore the South West, visiting family or friends or just wanting a short break, we offer a convenient home away from home.

Superhost
A rustic cabin with a dark metal roof and timber exterior is surrounded by trees. Smoke gently rises from a chimney. The front porch, featuring large glass doors, leads to a welcoming seating area. A pathway of stepping stones guides the way through the lawn.
Farm stay in Headbourne Worthy
4.98 out of 5 average rating, 342 reviews

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.

Top guest favorite
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 in Hampshire
4.97 out of 5 average rating, 407 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 favorite
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 in Hampshire
4.99 out of 5 average rating, 145 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 favorite
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 in Winchester
4.98 out of 5 average rating, 605 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 favorite
An inviting living area features a curved wooden ceiling and large glass doors that open to a deck. Two reclining chairs are positioned on the outdoor space, complemented by shelves displaying books and decorative items. A round rug adds a cozy touch to the floor.
Cabin in Droxford
5 out of 5 average rating, 107 reviews

Woodrest Cabin, South Downs National Park

Your escape to Woodrest starts with a beautiful walk through ancient woodland to a private and secluded meadow. We have two hand built cabins each set in their own acre of meadow. On arrival you will be met with the most stunning views of the Meon Valley. This unique stay allows you to switch off and enjoy the benefits of being on a family run farm, which has footpaths and woodland for you to explore. The South Downs Way is a short hike away, which leads to a wonderful nature reserve.

Top guest favorite
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 in Hampshire
4.96 out of 5 average rating, 713 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.

Superhost
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.
Condo in Hampshire
4.92 out of 5 average rating, 189 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 favorite
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 in Hampshire
4.98 out of 5 average rating, 103 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.

Guest favorite
A cozy studio bedroom features a spacious bed with white linens and a decorative pillow. Bedside tables with lamps flank each side of the bed. Light wood flooring complements the natural light from the window, while a green plant adds a touch of nature to the space.
Farm stay in Hampshire
4.91 out of 5 average rating, 337 reviews

Room with a view

You’ll love sharing photos of this unique place with your friends. Room with a View is a cosy and bright studio room located in the outskirts of the rural village of Owslebury. Just a 5-mile drive from the medieval city of Winchester, Room with a View is situated in a prime location, perfect for a serene getaway or business stay. Secluded from the busy bustle of the city, yet a swift 10-minute drive, Room with a View is surrounded by acres of fields and beautiful views.

Top guest favorite
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.
Apartment in Winchester
4.95 out of 5 average rating, 366 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.

Popular amenities for Winchester vacation rentals

When is the best time to visit Winchester?

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Frequently Asked Questions

  • What are the best places to stay in City of Winchester?

    Explore accommodations near the historic centre, around the Cathedral Quarter, or in leafy neighborhoods near the river. The city has both characterful homes and family-friendly vacation rentals in quiet residential areas.

  • What are the best things to do in City of Winchester with kids?

    Families often enjoy exploring Winchester Cathedral, interactive exhibits at Winchester City Museum, and walkable green spaces like Abbey Gardens. Seasonal events and local parks are frequently suggested for younger visitors.

  • What are some of the best things to do in City of Winchester?

    Explore the historic Winchester Cathedral, wander the Great Hall, and stroll through guided walks along the River Itchen. Locally rooted shops, museums, and green spaces are often recommended.

  • How is the weather in City of Winchester?

    Winchester has cool, wetter winters averaging 35–47°F (2–8°C), with milder, comfortably warm summers near 54–72°F (12–22°C). Rainfall is spread through the year, so packing layers and a waterproof jacket is useful.

  • When is the best time to visit City of Winchester?

    Late spring through early fall is often recommended for milder temperatures, blooming gardens, and outdoor events. Winter brings festive decorations, while autumn features colorful foliage along city walks.

  • What are the best places to visit in City of Winchester?

    The city has historic attractions such as Winchester Cathedral and the Great Hall, plus tranquil spaces like Abbey Gardens. The City Museum and riverside walks are frequently suggested by visitors.

  • What are some hiking trails in City of Winchester?

    Winchester has scenic paths along the River Itchen and through St. Catherine's Hill, often recommended for gentle hikes or panoramic views. The city is also a starting point for longer routes like the South Downs Way.

  • What are some family activities we can do in City of Winchester?

    Families can explore hands-on exhibits at Winchester City Museum, picnic in Abbey Gardens, or follow historic-themed treasure trails around the city centre. Parks and seasonal events make the city welcoming for all ages.

  • What are some of the best day trip ideas from City of Winchester?

    Popular day trips include historic sites in Salisbury, nature reserves in the South Downs, and local villages known for their markets. The surrounding Hampshire countryside has gardens and walking trails frequently suggested by locals.

  • Are there any pet friendly accommodations available in City of Winchester?

    Winchester has pet-friendly vacation rentals, with many hosts welcoming pets in residential neighborhoods near parks and green spaces. The city’s walking paths and gardens appeal to those traveling with animals.

  • What are some local tips for visiting City of Winchester?

    Arrive early for quieter walks at the Cathedral or city markets, and explore side streets for independent shops and cafes. Check seasonal events before you go, and wear comfortable shoes for cobblestone paths.

  • What is City of Winchester known for?

    Winchester is known for its medieval history, including Winchester Cathedral and the Great Hall with King Arthur’s legendary Round Table. The city has a tradition of locally rooted markets and cultural heritage.

  • What are the best hidden gems to explore in City of Winchester?

    Consider exploring St. Catherine’s Hill for panoramic views, tucked-away water meadows along the River Itchen, or art at local galleries. Independent bookshops and historic pubs add character around quieter lanes.

  • What are the best foods to try in City of Winchester?

    Winchester has traditional English pies, locally sourced cheeses, and seasonal produce often found at city markets. Artisan bakeries and cafes serve specialties like Hampshire watercress soup and homemade cakes.

  • What should I bring for a trip to City of Winchester?

    Pack weather-appropriate layers, comfortable walking shoes, and a waterproof jacket since conditions can be changeable. An umbrella, reusable water bottle, and camera are useful for exploring city sites and parks.

  • What is the nightlife in City of Winchester like?

    Nightlife in Winchester has cosy pubs, wine bars, and occasional live music venues around the city centre. Some historic pubs host quiz nights or storytelling events, with a relaxed, welcoming atmosphere.

  • What are the most popular events or festivals in City of Winchester?

    Winchester is known for its festive Christmas market, seasonal food festivals, and annual literary events often held around the Cathedral and city centre. Cultural celebrations mark spring and summer weekends.

  • Are there family friendly vacation rentals in City of Winchester?

    Winchester has family-friendly vacation rentals in neighborhoods near parks, schools, and city attractions. Many hosts provide amenities for children, with easy access to local green spaces and playgrounds.

Quick stats about vacation rentals in Winchester

  • Total vacation rentals

    Explore 2,560 vacation rentals in Winchester

  • Nightly prices starting at

    Winchester vacation rentals start at ﺩ.ﺇ37 per night before taxes and fees

  • Verified guest reviews

    Over 113,310 verified reviews to help you choose

  • Family-friendly vacation rentals

    1,040 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 570 rentals that welcome pets

  • Vacation rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    1,180 properties have a dedicated workspace

  • Wi-Fi availability

    2,420 of Winchester vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winchester rentals

  • 4.7 Average rating

    Winchester stays receive an average rating of 4.7 out of 5 from guests

Destinations to explore

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