Apartment holiday rentals in Winchester

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Top-rated apartment rentals in Winchester

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Top guest favourite
The exterior of a thatched cottage is shown, characterized by its traditional roof and whitewashed walls. Lush greenery surrounds the entrance, featuring flower beds and trees. A gravel driveway leads up to the cottage, complementing the tranquil ambiance of its rural setting.
Flat in Stockbridge
4.9 out of 5 average rating, 183 reviews

Little Trout, Nether Wallop: an oasis of calm

Little Trout is the annex to a 17th century thatched cottage. A one-bedroom flat with fully equipped kitchen, large shower and comfortable sitting room, it is perfect for a trip to West Hampshire and the Test Valley. You will find an oasis of calm in a busy world where you can relax in comfort after an active day visiting the many sites of historic interest or admiring our beautiful local scenery. Almost all our guests have told us that the bed is the most comfortable they have ever slept in!

Guest favourite
Flat in Isle of Wight
4.99 out of 5 average rating, 166 reviews

The Ocean Suite, Ventnor Beach (with Sauna)

Laid back beachfront living at its best, a romantic escape - popular with many repeat guests. A cedar cabin with panoramic sea views over Ventnor beach, winner 2025 LUXLife Awards, Best Coastal Retreat, South England. 52 sq metres and open plan, with bi-fold windows/doors creating a beautiful space of just you and the ocean. With 2 private balconies, one south facing for sunbathing, the second with a private sauna, combine with a swim in the sea just a few steps away. No pets but baby welcome!

Top guest favourite
A bedroom features a four-poster bed with sheer drapes, dressed in crisp white linens and a textured blue blanket. Skylights illuminate the room, complemented by dark blue walls and a contrasting light carpet. A wooden desk and colorful artwork add to the welcoming ambiance.
Flat in Winchester
4.93 out of 5 average rating, 498 reviews

Treetops, Awesome 3 Bedroom Flat in Winchester

Treetops is a spacious, lovely & private first floor three bedroom flat. There is everything that you could need for a comfortable stay. The well-equipped flat has its own entrance, a lounge/diner kitchen, hall, 3 bedrooms & 3 bathrooms. It can sleep up to 8 people. Treetops is in a beautiful environment approximately a mile from the centre of Winchester and the train station. Shops, takeaways & a restaurant are only a 5-minute walk away. There is on-site off-road parking available.

Top guest favourite
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.
Flat in Winchester
5 out of 5 average rating, 101 reviews

The Sky Penthouse, City Centre Luxury

Positioned right in the heart of charming historic Winchester The Sky Penthouse offers luxury modern comfortable 5 star accommodation . Private parking for one car . Positioned an easy level 300 meter walk from the main High Street within the City Centre , 400 meters from Winchester Cathedral and 500 meters from Winchester train station. Great location with a garden. Guests can choose the bed configuration of both the double bedrooms, either 6ft wide super king luxury beds or single beds.

Guest favourite
The exterior of a charming two-story building is adorned with greenery, featuring brick and flint walls. A well-maintained stone pathway leads to the entrance, which is framed by lush plants. Bright sunlight illuminates the scene under a clear blue sky.
Flat in Hampshire
4.83 out of 5 average rating, 104 reviews

Apartment, Whitchurch,Hants, inc E.V charging

Newly refurbished ground floor flat, located in the center of Whitchurch ,Hampshire. EV charger (type 2, 3.5 KW). Complementary charging is included. Within walking distance to bus stop and train station (mainline to London Waterloo). Walking distance to Whitchurch Silk Mill. Bombay Sapphire distillery is 2 miles away. Clock barn wedding venue 2.7 mile. Carfest 5 miles Highclere castle 7.5 miles The flat includes a new oven with induction hob, microwave, smart TV, iron and a hairdryer.

Top guest favourite
A charming brick cottage is surrounded by lush greenery and flowering plants. Two flower boxes adorn the front windows. A small table and chairs are positioned near the entrance, providing an inviting outdoor space. A gravel path leads to the cottage entrance.
Flat in Hampshire
4.95 out of 5 average rating, 101 reviews

Coachmans Cottage

Coachman’s Cottage is a converted Coach house and Harness room originally built in 1860. It is next door to the owner’s home. Southampton water is a short walk away, and the New Forest lies to the north. There are many local attractions near by including Exbury Gardens and the National Motor Museum at Beaulieu. The property is all on one level. Hythe is just over a mile away. There is a washing machine and tumble dryer available for guests in an adjacent building. Pub 200 mtrs walk away.

Top guest favourite
Flat in Winchester
4.91 out of 5 average rating, 317 reviews

The Loft with free off road parking

A self-contained studio by apartment with kitchen facilities, double bed, sofa and TV. En-suite toilet and shower room. Free off street parking on the doorstep. Situated 5-10 minutes walk from Winchester's historic city centre and even closer to the widely renowned Black Boy pub. Within 150 metres of the South Downs Way. Just a few minutes walk from the Winchester Sports Centre. The apartment is accessed via an external staircase and so may not suit those with mobility issues.

Top guest favourite
Flat in Compton
4.98 out of 5 average rating, 303 reviews

The Annexe at Longacre, near Winchester

The Annexe is a bright and airy self contained house separate from our home. The accomodation is over two floors with wonderful views out to the Hampshire countryside. We are on a quiet private country road 2 miles from the vibrant city of Winchester, 6 miles from Southampton Airport and 3 miles from IBM Hursley. Excellent transport links to London (1 hour from Shawford Station) and to Southampton. We live in the main house. Follow us on Instagram @longacreannexe

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, 388 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 spacious grassy area is seen from a small balcony, framed by greenery and trees. A playground structure and garden shed are visible in the background, while the sky displays soft, overcast lighting enhancing the serene countryside atmosphere.
Flat in Medstead
4.92 out of 5 average rating, 165 reviews

A Discreet Hampshire Downs Retreat for Quiet Stays

Set within the rolling Hampshire Downs, this thoughtfully designed annexe offers rare privacy, calm and refined simplicity. Evenings invite slow living beside your wood burner, while mornings begin beneath the luxury outdoor hot-water shower, immersed in countryside stillness. Designed as I like to travel myself, every detail is intentional, understated and quietly indulgent — a discreet retreat for guests who value space, quality and uninterrupted rest.

Top guest favourite
The kitchen features modern cabinetry with a wood countertop, including a gas stove and a microwave. Natural light floods in through expansive windows, illuminating the open living space which contains a dining table and comfortable seating. A TV is mounted on the wall.
Flat in Arundel
4.95 out of 5 average rating, 659 reviews

Spacious Flat in Central Arundel

A light stylish apartment in a listed building with an outdoor terrace and views over the town. It is situated on the main High Street directly across the road from Arundel Castle. The location is central a step away from restaurants cafes, bars, bistros, lido and beautiful walks. The accommodation is good for couples, solo adventurers and business travellers. THERE ARE JUST OVER 2 OUTSIDE STAIRCASES SO THE APARTMENT IS NOT SUITABLE FOR ALL- SPORRY.

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, 207 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.

Popular amenities for Winchester apartment rentals

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Quick stats about flat rentals in Winchester

  • Total holiday rentals

    Explore 70 holiday rentals in Winchester

  • Nightly prices starting at

    Winchester holiday rentals start at £22 per night before taxes and fees

  • Verified guest reviews

    Over 4,820 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    70 of Winchester holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Winchester rentals

  • 4.6 Average rating

    Winchester stays receive an average rating of 4.6 out of 5 from guests

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