Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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Top guest favorite
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.
Condo in Winchester
4.97 out of 5 average rating, 129 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 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, 387 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, 135 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
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 in Meonstoke
5 out of 5 average rating, 178 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 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
4.95 out of 5 average rating, 699 reviews

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.

Guest favorite
The studio features an elegantly decorated sleeping area with a spacious bed adorned with a colorful bedding. Soft lighting highlights the intricate mirror and chandelier. A comfortable chair sits beside the bed, while large curtains frame the windows, adding to the cozy ambiance.
Condo in Hampshire
4.92 out of 5 average rating, 182 reviews

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 ✅

Top 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, 317 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, 351 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 spacious bedroom features a comfortable king-sized bed with white linens and decorative pillows. Two bedside tables with lamps are positioned on either side. Large windows invite natural light, and the walls are finished in a soft neutral tone, surrounded by a green carpet.
Guesthouse in Colden Common
4.99 out of 5 average rating, 121 reviews

The Limes, Colden Common, Winchester, with parking

This quiet, spacious and comfortable ground floor annexe is situated in a rural village on the south side of Winchester. The Limes, with its own front door, offers a relaxing home from home environment. It is light and airy, set well back from the road, overlooking a lovely garden with views of the countryside. It offers off road parking, 15 minutes from Winchester centre, good size and comfortable double and single bedrooms, with a well equipped kitchen.

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, 178 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 spacious living area features a comfortable sectional sofa with colorful cushions, positioned near large glass doors that open to a vibrant outdoor space. Natural light illuminates the room, highlighting the modern furniture and stylish decor.
Tiny home in Winchester
4.95 out of 5 average rating, 210 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

Top guest favorite
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 in Hampshire
4.93 out of 5 average rating, 174 reviews

Modern Apartment Central Winchester

Situated in the heart of Winchester, this newly refurbished 2-bedroom apartment with its own private entrance and modern décor provides a well thought out space for friends, couples & families. This cosy home provides an excellent upmarket base to explore Winchester. A stone’s throw to the city’s favourite pub, St James Tavern, a warm welcoming traditional pub which serves excellent locally sourced home cooked food.

Popular amenities for Winchester vacation rentals

Quick stats about vacation rentals in Winchester

  • Total rentals

    2.6K properties

  • Nightly prices starting at

    R174 ZAR before taxes and fees

  • Total number of reviews

    113K reviews

  • Family-friendly rentals

    1K properties are a good fit for families

  • Pet-friendly rentals

    570 properties allow pets

  • Rentals with a pool

    40 properties have a pool

Frequently Asked Questions

  • How much does it cost to stay in bed and breakfast rentals in City of Winchester?

    Experience the best of City of Winchester with our bed and breakfast rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Where should I stay in City of Winchester?

    Make yourself at home in City of Winchester by choosing from our most frequently booked neighborhoods. We have over 460 vacation rentals in Netley, over 800 vacation rentals in Freemantle, and over 670 vacation rentals in Botley.

  • Do apartment rentals in City of Winchester have air conditioning?

    Absolutely! We offer over 20 apartment rentals with air conditioning in City of Winchester. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly vacation rentals in City of Winchester?

    Four-legged friends are welcome in City of Winchester. Choose from more than 580 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in City of Winchester?

    Yes! Work meets play with ease at over 1,220 vacation rentals in City of Winchester featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • What are the most popular amenities for Barn Rentals in City of Winchester?

    Enhance your stay in our Barn Rentals with the most popular amenities: over 30 homes with free parking, over 30 homes with a kitchen, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there City of Winchester vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in City of Winchester, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there family-friendly vacation rentals in City of Winchester?

    City of Winchester has more than 1,030 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do barn rentals in City of Winchester have free parking?

    Absolutely! We offer over 30 barn rentals with free parking in City of Winchester. Enjoy a tailored experience with all the comforts you desire.

  • Do chalet rentals in City of Winchester have a kitchen?

    Absolutely! We offer over 10 chalet rentals with a kitchen in City of Winchester. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore

  1. Airbnb
  2. United Kingdom
  3. England
  4. Hampshire
  5. Winchester