Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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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, 410 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.

Guest favorite
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, 346 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, 408 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, 148 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, 606 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
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.
Condo in Compton
5 out of 5 average rating, 103 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.

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, 715 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.

Top guest favorite
A charming brick and flint building is surrounded by neatly trimmed bushes and a well-maintained garden. Two wooden chairs and a small table are set outside, inviting guests to enjoy the tranquil rural setting under clear skies.
Guesthouse in Winchester
4.97 out of 5 average rating, 550 reviews

Idyllic Hideaway Ham Green Cottage near Winchester

The Orchard Studio at Ham Green Cottage is a pretty brick and flint building tucked away in a corner of our truly English country garden. You are completely private. We are family-friendly and you can expect a comfortable stay and warm welcome. We are in a village close to the historic city of Winchester, however our setting is completely rural and quiet. We have a fantastic village pub or there are lots of places to chose from in Winchester itself - the best of both worlds!

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, 341 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, 368 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.

Top guest favorite
A modern studio layout is displayed, featuring a kitchenette with a microwave, oven, and fridge. Bright yellow accents enhance the design. A small dining area with two barstools is positioned near a flat-screen TV. Natural light fills the space through a window with a light-filtering blind.
Guest suite in Hampshire
4.97 out of 5 average rating, 188 reviews

Pretty self contained annexe

Pretty, self contained annexe with its own entrance, located between the historic city of Winchester & Southampton and on the doorstep of the New Forest National Park. Great travel links - M3/M27, Southampton Airport & Southampton Parkway station. Studio comprises double bed, kitchen with oven, hob, fridge & microwave. Breakfast bar, which doubles as a workspace, shower room and shared use of patio and garden. We also have a young, bouncy dog!

Top guest favorite
A modern living space is visible through open bi-fold doors, blending indoor and outdoor areas. A sleek seating arrangement is placed outside on a patio, complemented by soft lighting. Inside, a light-filled room showcases a comfortable sofa and dining area, enhancing the welcoming atmosphere.
Tiny home in Winchester
4.95 out of 5 average rating, 234 reviews

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

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 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 vacation rentals in Winchester

  • Total vacation rentals

    Explore 310 vacation rentals in Winchester

  • Nightly prices starting at

    Winchester vacation rentals start at ﺩ.ﺇ73 per night before taxes and fees

  • Verified guest reviews

    Over 18,110 verified reviews to help you choose

  • Family-friendly vacation rentals

    150 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 70 rentals that welcome pets

  • Rentals with dedicated workspaces

    130 properties have a dedicated workspace

  • Wi-Fi availability

    300 of Winchester vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Winchester rentals

  • 4.7 Average rating

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

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