Vacation rentals in City of Winchester

4.96 out of 5 average rating, 109 reviews

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

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.

The kitchen features modern cabinetry in neutral tones, with a spacious island and wooden dining table. Appliances include a stainless steel refrigerator, microwave, and coffee maker. Soft lighting enhances the ambiance, while a brick arch over the stove adds a touch of character.

4.98 out of 5 average rating, 104 reviews

Stylish Victorian villa in Winchester

Stylish Victorian semi-detached villa in the highly sought after area of Fulflood. Off-street parking and a few minutes walk from the station with fast trains to London and the South Coast. 10 minutes walk into central Winchester with shops, eateries and the cathedral. Finished and equipped to a high standard it is the perfect base for a stay in Winchester and the surrounding countryside. Local amenities including pub, coffee shops, deli, takeaways and convenience store within 2 minutes walk.

4.99 out of 5 average rating, 126 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.

4.98 out of 5 average rating, 566 reviews

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

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.

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.

4.96 out of 5 average rating, 670 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.

4.94 out of 5 average rating, 169 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 ✅

4.83 out of 5 average rating, 458 reviews

A pathway leads to a secluded studio nestled within a leafy garden. The entrance features wooden decking and large glass doors that provide a view into the cozy interior. Surrounding greenery adds to the privacy of the space.

Tiny home in Winchester

Cosy rural hideaway, Hursley, near Winchester

Fantastic rural retreat! Gorgeous cosy space, very private with own secluded garden. Everything that you need for a relaxing break. Five miles from both Winchester and Romsey, a fifteen minute walk to the lovely village of Hursley with its two pubs and great walks! Perfect for IBM Hursley, Peppa Pig World/Paultons Park, the New Forest (25 minutes) and beaches (40 minutes). You can be in Southampton with cinemas, bowling, shopping etc in 20 minutes. A great exploring base!

4.97 out of 5 average rating, 155 reviews

A spacious studio annex features a king-size bed with a light blanket, a comfortable sofa, and a wooden coffee table. Natural light enters through a window, highlighting the simple white walls and wooden flooring. A dresser and rack add functional decor to the room.

Guest suite in Ovington

Luxury annexe near the River Itchen & Alresford

Beautifully decorated studio annex in the village of Ovington - a lovely rural spot yet a short drive from Winchester and walkable to Alresford. Light and airy space - king size bed, sofa, TV, chest drawers and table & chairs. There is a small kitchenette (small fridge, kettle, toaster, microwave, cafetiere, crockery, glassware and cutlery). Fresh towels, tea, coffee and biscuits are ready for you on your arrival. An iron, cot and high chair can be arranged on request.

4.95 out of 5 average rating, 328 reviews

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

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.

A balcony features two white, ornate chairs paired with a small round table. Potted plants of various sizes embellish the area. A lush green tree and neighboring buildings are visible in the background, set against a clear blue sky.

4.88 out of 5 average rating, 300 reviews

City Centre Riverside Gem With Parking.

An amazing two bedroom period cottage that is superbly located for all of Winchester's amenities, adjacent to the city mill and just a few steps away from the High Street. The cottage offers city living in a delightful tucked away location backing onto the River Itchen and only seconds from all the city centre has to offer. The house suits all needs, a romantic weekend, a South Downs Way stop over, family break and equally a business trip.

4.92 out of 5 average rating, 150 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.

4.99 out of 5 average rating, 150 reviews

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

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!

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Popular amenities for City of Winchester vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near City of Winchester's top sights

Marwell Zoo64 locals recommend

Winchester Cathedral110 locals recommend

Southampton Airport10 locals recommend

Other great vacation rentals in City of Winchester

A spacious living area is presented with two comfortable sofas, adorned with decorative cushions. A wooden coffee table sits in the center, complemented by a flat-screen television mounted on the wall. Natural light filters in through small windows, highlighting the soft carpeted flooring.

4.9 out of 5 average rating, 41 reviews

South Downs Comfy Getaway

5 out of 5 average rating, 22 reviews

A loft studio with a spacious bed covered in a blue patterned duvet. Skylights allow natural light to fill the room. A seating area is visible with a cozy couch, and the kitchen area includes basic appliances. Soft rugs enhance the wooden floor.

Guest suite in West End

Farmhouse Loft Studio

4.92 out of 5 average rating, 279 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

5 out of 5 average rating, 166 reviews

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

The Piggery: with tennis court and games barn

5 out of 5 average rating, 6 reviews

A cozy corner of the bedroom is displayed, featuring a decorative heart-shaped pillow on a spacious bed. A softly glowing bedside lamp sits on a small nightstand, alongside a simple clock. Fresh, white bedding complements the light and airy atmosphere.

Apartment in Winchester

Bright & Cosy Flat in Winchester, near Cathedral

The kitchen features modern cabinetry with a mix of light and dark colors, complemented by wooden accents. A central island with bar stools provides a gathering space. Natural light floods the area, highlighting the sleek design and open layout connecting to the dining space.

4.9 out of 5 average rating, 10 reviews

In the heart of old Winchester

Farm stay in Headbourne Worthy

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.

4.98 out of 5 average rating, 319 reviews

A Unique Farm Retreat