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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Top guest favourite
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.
Apartment in Winchester
4.97 out of 5 average rating, 172 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 favourite
The exterior of the barn reveals a charming brick facade, topped with a slate roof. Colorful flowers, including orange and purple blooms, are arranged around a paved patio area, contributing to a serene garden environment. Large windows allow natural light to fill the space.
Barn in New Alresford
4.97 out of 5 average rating, 118 reviews

Self contained annex . In the heart of Alresford

Delightful ,self contained annexed barn with own entrance Sympathetically converted 18th century brick and flint barn with original features situated in the pretty market town of Alresford,Hampshire.Very near to the river Arle with picturesque walks, ducks, swans and all within 5 minutes walk to the centre of town. Ideally situated for The Grange Festival opera Northington and the ancient city of Winchester. N.B. Prices shown now include the Airbnb 15.5% + for their service charge. Plus vat .

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
4.96 out of 5 average rating, 367 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
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, 636 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
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.
Apartment in Compton
5 out of 5 average rating, 127 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 favourite
A triangular-shaped cabin features large glass doors that invite natural light, framed by a wooden facade. A small patio area with a table and two chairs is situated in front, surrounded by neatly trimmed hedges and a lush green landscape.
Hut in Winchester
5 out of 5 average rating, 268 reviews

Nature’s Nook Cosy Couples Woodland Cabin Hursley

Nature's Nook offers guests the perfect rural escape. You will be treated to spectacular views across the Winchester countryside and wildlife right outside your doorstep. Nature's Nook is perfectly located, nestled on the edge of a bluebell woodland with country walks just minutes away and the historical city of Winchester a short drive away. Curl up on the sofa with a book, sit outside by the fire pit, whilst enjoying a drink, or just relax and admire the stunning scenery!

Top guest favourite
The exterior of Stable Cottage is showcased, featuring natural wooden cladding and large windows that allow for ample light. The patio doors reflect the surrounding greenery, while a modern skylight adds an additional element of design to the roofline.
Home in Hampshire
4.98 out of 5 average rating, 124 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.

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 in Hampshire
4.92 out of 5 average rating, 390 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 favourite
A spacious bedroom features a comfortable kingsize bed adorned with decorative pillows. On each side of the bed, bedside lamps provide soft illumination. Framed artwork is displayed on the wall above, while a vintage mirror enhances the light and openness of the space.
Guest house in Exton
4.98 out of 5 average rating, 125 reviews

The Woodshed

The Woodshed is right in the heart of the South Downs National Park, between the villages of Warnford and Exton, a secluded and peaceful space surrounded by a working farm. The Woodshed has a view of Old Winchester Hill that is magic. Activities in the area include biking, hiking, and angling, and three of the best pubs in Hampshire are within a 5 mile radius. As we are a little distance from the main track, I am happy to come and collect guests from Exton if walking.

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 in Ovington
4.97 out of 5 average rating, 165 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!

Top 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.
Flat in Winchester
4.93 out of 5 average rating, 229 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 in Winchester
4.99 out of 5 average rating, 203 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.

Quick stats about holiday rentals in Winchester

  • Total holiday rentals

    Explore 2,660 holiday rentals in Winchester

  • Nightly prices starting at

    Winchester holiday rentals start at $26 SGD per night before taxes and fees

  • Verified guest reviews

    Over 117,650 verified reviews to help you choose

  • Family-friendly holiday rentals

    1,160 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 650 rentals that welcome pets

  • Holiday rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    1,320 properties have a dedicated workspace

  • Wifi availability

    2,560 of Winchester holiday rentals include wifi 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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