
Holiday rentals in Winchester
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Top-rated holiday rentals in Winchester
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Rivers stays with hot tub
Our unique river stay offers a one-of-a-kind experience, combining modern comfort & nature. This charming space features panoramic windows that invite the soothing sounds of the flowing water and stunning views of the surroundings right into your living area. Enjoy your morning on the private deck while watching the sunrise, or unwind in the evening with a glass of wine as you listen to the gentle rustle of leaves. Perfect for couples, solo adventurers, or anyone looking to reconnect with nature

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.

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.

New Barn
A self-contained studio flat on the first floor of an oak-framed barn in the heart of Owslebury village, a stone’s throw from The Ship pub. It has a kitchen and dining area, bathroom with shower, and a living space with a large double, or twin beds. The kitchen includes a two-ringed hob, fridge, combi-microwave,kettle, coffee machine and toaster. There is off-road private parking just outside the property. EV charger - 22kW type 2 - available on request (extra charge for electricity used).

Stable Cottage Beauworth Southdowns Hampshire
Nestled within the South Downs National Park, this charming countryside escape offers uninterrupted views across open fields where sheep graze. Wake up to breathtaking bedroom views, explore the surrounding countryside and historic Winchester, and in the winter, cosy up beside the crackling log burner. Thoughtfully equipped for families with babies and children, as well as couples seeking a peaceful getaway, it’s the perfect retreat to unwind and enjoy Hampshire’s beautiful landscape.

The Hangar - countryside views, seclusion & peace.
The Farley Hangar is a peaceful space with far reaching views of Hampshire's woodlands and the Isle of Wight. Located on our family farm and private airstrip in the Test Valley. Winchester, Romsey and Stockbridge are just 20 mins away. On the doorstep of numerous cycle routes and footpaths including the Claredon Way (Sals-Win). King size bed & full-size bath with rain shower. From your private deck with log burner you will see various wildlife species and watch the stars at night.

Lotus Car Spa & Horse Hut
Yes, that is a hot tub in a Lotus Elan! On the outskirts of Medstead village, in the corner of a field where shire horses once roamed, you’ll find a tiny home like no other. Once hauled to and fro for Polo and Shire shows, The Horse Hut has been lovingly transformed into a luxury holiday stay—while maintaining its horsey heritage. Whether you're soaking in the Lotus Spa or sitting back on the verandah, take in the beautiful vista of the Hampshire countryside and Hattingley Valley.

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.

The Glade at Ladyhill Vineyard near Winchester
Nestled on the edge of an ancient wood in South Downs National Park and with fantastic views over Ladyhill Vineyard and the Hampshire countryside The Glade has a cosy A-Frame to grab a good night sleep, a separate shower room with flushable loo to keep you fresh and a kitchen equip-for-easy glamping. Relax and admire the views, BBQ on the fire pit, spot deer and hare or stroll down the river Itchen to The Bush gastro pub. You’ll return home totally refreshed!

Luxury Cabin with Outdoor Bath, Sauna & Fireplace
Set on the edge of the South Downs National Park, this luxurious cedar cabin offers complete privacy, stillness and refined comfort. Soak beneath the stars in your private outdoor bathtub, unwind in your exclusive sauna, or rest beside the indoor wood burner fireplace. Designed by a fellow traveller for deep rest and reconnection, every detail is intentional — inviting calm, closeness to nature and a quiet sense of renewal that lingers long after you leave.

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
Other great holiday rentals in Winchester

Nettlebed Farm Holiday Lets, Barn1 of 3

The Treehouse at Barrow Hill Barns

Artist studio with outdoor bath and field views

Pretty self contained annexe

The Piggery: with tennis court and games barn

Stunning studio, 5 minute walk to South Downs Way

Barn on The South Downs Way, Dogs Welcome

The Woodshed
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.
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- Stonehenge
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