Holiday rentals in Winchester

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Top-rated holiday rentals in Winchester

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Guest favourite
The bungalow's exterior features a combination of brick and wood with a textured gabled roof. Flower pots and beds with colorful blooms line the pathway, leading to large windows that allow natural light into the interior.
Bungalow in Eastleigh
4.93 out of 5 average rating, 408 reviews

One bedroom home.

Relax and make yourself at home in this comfortable bungalow with sunny lounge, fully equiped kitchen/diner and bathroom. Situated in a quiet cul-de-sac in the village of Bishopstoke on the outskirts of Eastleigh. The M27 and M3 motorways and Southampton Airport are just a few miles away. The historic City of Winchester is an easy drive. Whether you are on your way to explore the South West, visiting family or friends or just wanting a short break, we offer a convenient home away from home.

Guest favourite
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.
Guest house in Hampshire
4.91 out of 5 average rating, 129 reviews

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.

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 in Hampshire
4.97 out of 5 average rating, 395 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
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, 141 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 favourite
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, 706 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 favourite
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.
Apartment in Hampshire
4.92 out of 5 average rating, 185 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 ✅

Guest favourite
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
4.97 out of 5 average rating, 161 reviews

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.

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, 330 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
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.
Flat in Winchester
4.95 out of 5 average rating, 358 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 favourite
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, 185 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 favourite
A modern living space is visible through open bi-fold doors, blending indoor and outdoor areas. A sleek seating arrangement is placed outside on a patio, complemented by soft lighting. Inside, a light-filled room showcases a comfortable sofa and dining area, enhancing the welcoming atmosphere.
Tiny home in Winchester
4.95 out of 5 average rating, 222 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 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 Hampshire
4.93 out of 5 average rating, 181 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 holiday rentals

When is the best time to visit Winchester?

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Avg. price$145 SGD$146 SGD$150 SGD$161 SGD$166 SGD$170 SGD$175 SGD$179 SGD$175 SGD$158 SGD$154 SGD$157 SGD
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Frequently Asked Questions

  • How much does it cost to stay in cabin rentals in City of Winchester?

    Experience the best of City of Winchester with our cabin rentals, starting at about $80 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 670 vacation rentals in Botley, over 800 vacation rentals in Freemantle, and over 460 vacation rentals in Netley.

  • 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 570 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 1,180 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 Hotel Rentals in City of Winchester?

    Enhance your stay in our Hotel Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with free parking, 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 1,040 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

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

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

  • Do serviced apartment rentals in City of Winchester have a kitchen?

    Absolutely! We offer over 110 serviced apartment rentals with a kitchen in City of Winchester. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Winchester

  • Total holiday rentals

    Explore 2,560 holiday rentals in Winchester

  • Nightly prices starting at

    Winchester holiday rentals start at $13 SGD per night before taxes and fees

  • Verified guest reviews

    Over 113,310 verified reviews to help you choose

  • Family-friendly holiday rentals

    1,040 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 570 rentals that welcome pets

  • Holiday rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    1,180 properties have a dedicated workspace

  • Wifi availability

    2,420 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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