Vacation rentals in Winchester

4.94 out of 5 average rating, 277 reviews

A comfortable living area is anchored by a soft blue sofa adorned with light green cushions. A small black table sits in front, while a bookshelf filled with various books stands in the background. Sliding glass doors allow natural light and outdoor views.

Guest suite in Hampshire

The Oaks, Twyford Moors, South Downs National Park

There is WIFI and a large dining table to work at. There is a fully equipped kitchen. The bed is a Superking. The Oaks is annexed to our house, so we are available to answer any queries, give guidance on places to visit and dine and usually we will be available to show you the property in person. Twyford Moors is an area of outstanding natural beauty in the South Downs National Park. The River Itchen, a famous chalk stream, is close by. This is also Jane Austen country—visit her home at Chawton, and Winchester Cathedral, where she's buried. There are beautiful riverside walks including a 2hr walk into the heart of Winchester along the water meadows and by St Catherine's Hill. There are country pubs and excellent restaurants available locally and 15 mins drive away in Winchester There is parking for one car under cover in the car port but also room in the drive for a second vehicle . There are some beautiful walks along the River Itchen nearby. The outdoor terrace area to The Oaks is not enclosed and young children would need to be observed when outside. We have two, small friendly dogs that may visit your terraced area as it is not enclosed.

4.93 out of 5 average rating, 105 reviews

A well-appointed room features a spacious bed with plush bedding. Light wood flooring complements the seating area with a circular table and two upholstered chairs. Skylights and decorative lamps provide soft lighting. A mirror adds depth, and a hairdryer is available on the wall.

Guesthouse in Hampshire

Central, Quiet & Self-Contained

Incredibly central location. Only 150m from Cathedral & 200m to High St. Quiet: Set back from the street, double glazing, detached building. King size bed with luxury mattress & topper, hypoallergenic duvet & pillows, Egyptian cotton bedlinen and fluffy towels. Work space. Reading & soft lighting. Well Equipped: Tea & Coffee Facilities, Mini Fridge, TV (Netflix only) Iron+Board, Hairdryer, Toiletries & Fan. Secure parking subject to availability £20per night. NB. Access via external staircase.

4.97 out of 5 average rating, 379 reviews

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

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.

4.99 out of 5 average rating, 133 reviews

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

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.

4.94 out of 5 average rating, 173 reviews

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

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 ✅

4.91 out of 5 average rating, 297 reviews

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

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.

4.99 out of 5 average rating, 101 reviews

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.

Guesthouse in Hampshire

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.

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.

4.95 out of 5 average rating, 340 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.

Guesthouse in Colden Common

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.

4.99 out of 5 average rating, 118 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.

4.97 out of 5 average rating, 172 reviews

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

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!

4.95 out of 5 average rating, 203 reviews

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

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

4.92 out of 5 average rating, 166 reviews

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

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.

Vacation rentals for every style

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Apartments

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Winchester vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Winchester's top sights

Marwell Zoo248 locals recommend

Winchester Cathedral319 locals recommend

Southampton Airport50 locals recommend

Other great vacation rentals in Winchester

A large window features multiple panes, providing a view of the lush greenery outside. The soft fabric valance frames the window, while light colors of the bed linens in the foreground complement the serene setting beyond.

4.89 out of 5 average rating, 19 reviews

Beautiful & Spacious Retreat in Winchester

4.91 out of 5 average rating, 55 reviews

A private outdoor seating area features two green chairs positioned beneath a wooden pergola. Soft lighting from hanging bulbs illuminates the space, which is surrounded by a variety of plants including ivy. A gravel path leads through the charming garden setting.

Guesthouse in Hampshire

Private garden room, free permit parking

Superhost

A welcoming living area features a large wooden dining table adorned with a bowl of fruit. Comfortable black sofas provide seating, while a modern TV is mounted on the wall. A decorative fireplace and artwork add character to the space.

Apartment in Hampshire

4.65 out of 5 average rating, 20 reviews

Historic Winchester Apartment

4.99 out of 5 average rating, 68 reviews

The open-plan living area features a light-colored sofa accented with cushions, a round coffee table, and a decorative plant by the window. Soft natural light enters through the large window, illuminating the warm wood flooring and minimalist decor.

Condo in Winchester

The Print Rooms, Old Printworks, Winchester

Superhost

A sitting area is highlighted by a spacious sofa with decorative cushions and natural light streaming in from plantation-shuttered windows. A small dining table with chairs is positioned nearby, complemented by a framed abstract art piece on the wall.

4.68 out of 5 average rating, 112 reviews

Central Winchester apartment with parking

A polished silver bowl filled with ice displays several bottles of champagne. Fresh lilies and elegant candelabras are positioned nearby, adding a touch of sophistication to the setting. The arrangement creates a celebratory atmosphere.

5 out of 5 average rating, 95 reviews

The Sky Penthouse, City Centre Luxury

4.98 out of 5 average rating, 88 reviews

A modern cottage exterior is surrounded by lush gardens featuring various flowering plants. The building showcases a mix of wood paneling and large windows, reflecting natural sunlight. A spacious patio area can be seen, providing an inviting space to enjoy the peaceful outdoor setting.

Home in Hampshire

Stable Cottage Beauworth Southdowns Hampshire