Holiday rentals in Winchester

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Top-rated holiday rentals in Winchester

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
The exterior of the floating accommodation is illuminated at dusk, highlighting the modern design and large windows. A wooden walkway leads to the entrance, with outdoor seating visible on the private deck. Surrounding buildings can be faintly seen in the background.
Houseboat
4.98 out of 5 average rating, 115 reviews

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

Guest favourite
Three cabins are arranged in a peaceful setting surrounded by greenery. A stone pathway leads to the front of the cabins, marked by wooden posts. Large windows provide views of the exterior landscape, creating a harmonious connection with nature.
Barn
4.97 out of 5 average rating, 405 reviews

Nettlebed Farm Holiday Lets, Barn1 of 3

* From £124 p/n +Airbnb charges Beautiful oak barn set in traditional english countryside. Placed with own access within 15 acres of private woodland and grazing land, away from the main road for peace and tranquility. Guests are able to have privacy for relaxation and enjoy views of horses grazing and the comings and goings of the British wildlife. Just 4 minute drive to the market town of Bishops Waltham or you can join and follow the infamous Pilgrims Trail and walk there in just 30 minutes.

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
4.96 out of 5 average rating, 373 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 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, 453 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
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, 648 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 flint-built hideaway is shown, featuring arched windows and a slate roof. The private garden is surrounded by lush green grass, with a small outdoor table and chairs visible. A tree partially frames the scene, adding to the peaceful atmosphere.
Home
5 out of 5 average rating, 204 reviews

The Piggery: with tennis court and games barn

The Piggery is a secluded flint built hideaway, with lots of period charm, set in the grounds of a manor house. Converted to a high standard it has it’s own private garden, access to the owners tennis court & a large barn with table tennis, table football & pool, wider house grounds including an island, surrounded by the river Meon. Numerous walks direct from The Piggery and a number of local vineyards are nearby. 5/10mins walk away are two super pubs and the very well stocked village shop.

Top guest favourite
Home
4.98 out of 5 average rating, 133 reviews

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.

Guest favourite
The image captures a uniquely designed tiny home with vibrant green and wooden accents. A vintage yellow sports car is positioned prominently in front, while a spacious deck features comfortable seating and potted plants, creating an inviting outdoor area.
Hut
4.98 out of 5 average rating, 308 reviews

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.

Top guest favourite
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
4.92 out of 5 average rating, 406 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.

Guest favourite
An A-frame structure is framed by trees and surrounded by blooming bluebells. Light filters through the open front, illuminating the interior where a seating area is presented. The natural setting offers a serene escape, with vibrant flowers in the foreground enhancing the tranquil scene.
Hut
4.97 out of 5 average rating, 176 reviews

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!

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.
Apartment
4.93 out of 5 average rating, 245 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.

Top guest favourite
The Cottage features a charming exterior with a textured roof and a modern patio area. Surrounded by greenery, a spacious seating arrangement is set on a stone surface, offering a tranquil spot for relaxation. Nearby structures exhibit a contemporary architectural style.
Cottage
4.99 out of 5 average rating, 214 reviews

The Cottage in Compton

Come and enjoy a stay in The Cottage, located in the grounds of our 17th Century converted Barn. Enjoy a unique location on the edge of Winchester with direct access to the countryside. The Cottage has been recently extended and refurbished with everything you will need to make your stay enjoyable. A perfect place for a break to explore all the wonderful things that Winchester has to offer!

Popular amenities for Winchester holiday rentals

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.

Destinations to explore