
Vacation rentals in Winchester
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Top-rated vacation rentals in Winchester
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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.

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.

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.

Quiet Winchester One 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 ✅

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!

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.

Entire House Central Winchester 2bed private patio
In the heart of historic Winchester, Wykeham Cottage provides a perfect base for exploring the city. On beautiful St Swithun Street, overlooking the Cathedral wall, the cottage has a south-facing, private patio and an on-street parking permit for one car. Fabulous restaurants, markets, pubs, shops and riverside walks are all minutes away on foot, as are the ruins of Wolvesey Castle, Winchester College and the medieval church St Swithun-upon-Kingsgate.

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!

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
Winchester apartment rentals

Exceptional room and study area.

Seascape - a Luxurious Coastal Escape

*Stunning River Views*, modern in great location

The Annexe @ Mandalay Lodge

Newly Refurbished Spacious Flat : Highclere

The Annexe at Longacre, near Winchester

Little Trout, Nether Wallop: an oasis of calm

City Apartment
Winchester house rentals

Orchard Barn Spa, exclusively for you, New Forest

Homely and Comfortable in a quiet location

Romantic 17th Century Paper Mill on The Meon River

Spacious and Stylish Home in Heart of Top Village

Historic town centre riverside hideaway

Lovely Coach House

Stride’s Barn

Sea-facing coastal holiday home near New Forest
Other great vacation rentals in Winchester

The Barn @ North Lodge -Soho Farmhouse-esque Cabin

The Hayloft - Rural retreat very near Winchester

Oak Framed Barn with Tennis Court

Room with a view

Nature’s Nook Cosy Couples Woodland Cabin Hursley

Mews townhouse Winchester station.

Beautiful guest suite in rural Hampshire

Central, Quiet & Self-Contained
Quick stats about vacation rentals in Winchester
Total rentals
310 properties
Nightly prices starting at
R348 ZAR before taxes and fees
Total number of reviews
18K reviews
Family-friendly rentals
150 properties are a good fit for families
Pet-friendly rentals
70 properties allow pets
Rentals with dedicated workspaces
130 properties have a dedicated workspace
Frequently Asked Questions
How is the weather in Winchester?
Winchester experiences a temperate maritime climate with mild winters and warm summers. Average highs in summer are around 70°F (21°C), while in winter, temperatures hover around 45°F (7°C). Rainfall is distributed fairly evenly throughout the year.
What are some of the best things to do in Winchester?
Take a walk through the vibrant Winchester Farmers Market, visit Winchester Science Centre for interactive exhibits, or explore Winchester College, one of the oldest schools in the country. For a touch of culture, visit the Theatre Royal Winchester for a performance.
What is the best time of year to visit Winchester?
Many visitors explore Winchester from June to August when there's plenty of sunshine and the Winchester Hat Fair, a free outdoor arts festival, enlivens the city. Another popular time is during the Winchester Christmas Market in late November to December.
What are the best places to stay in Winchester?
The city centre, with its proximity to historical sites and vibrant eateries, is a favourite amongst visitors. St. Cross, known for its peaceful ambiance, and Hyde, within walking distance of the city centre, are also popular. For a rural retreat, consider the surrounding Hampshire countryside.
What are the best places to visit in Winchester?
Winchester Cathedral, one of the largest cathedrals in Europe, is often recommended. Other frequently suggested places include Winchester City Mill, a working watermill, and the Great Hall, home to King Arthur's Round Table. For history lovers, the Winchester City Museum is a must.
What are some hiking trails in Winchester?
Explore the South Downs Way, a long-distance footpath spanning 100 miles (160 km), or the shorter but equally enjoyable St. Catherine's Hill, offering spectacular views of the city. Alternatively, immerse yourself in the natural beauty of the Itchen Navigation Heritage Trail, a serene walk along the Itchen River.
What are some family activities to do in Winchester?
Families can enjoy a fun-filled day at Marwell Zoo, home to hundreds of exotic and endangered animals, or learn about the natural world at Winchester Science Centre. The interactive Winchester City Museum and the Military Museums are also popular with families.
What are some of the best day trip ideas in Winchester?
Consider a day trip to the ancient Stonehenge, located about 40 miles (64 km) from Winchester. Another frequently suggested trip is to the beautiful New Forest National Park, just 23 miles (37 km) away. The historic city of Bath, known for its Roman-built baths, is also within reach at 54 miles (87 km).
Are there vacation rentals with a dedicated workspace in Winchester?
Yes! Work meets play with ease at over 140 vacation rentals in Winchester featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Winchester?
Four-legged friends are welcome in Winchester. Choose from more than 70 vacation rentals for guests traveling with pets.
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- New Forest national park
- Bournemouth Beach
- Paultons Park Home of Peppa Pig World
- Oxford University
- Goodwood Motor Circuit
- Stonehenge
- Boscombe Beach
- Hampton Court Palace
- Windsor Castle
- Lower Mill Estate
- Chessington World of Adventures Resort
- West Wittering Beach
- Kimmeridge Bay
- Winchester Cathedral
- Thorpe Park Resort
- Highclere Castle
- Southbourne Beach
- Goodwood Racecourse
- Arundel Castle
- Highcliffe Beach
- The Tank Museum
- Wentworth Golf Club
- RHS Garden Wisley
- Worthing Pier