Apartment holiday rentals in Winchester

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Top-rated apartment rentals in Winchester

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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
4.92 out of 5 average rating, 493 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 Whitchurch
4.83 out of 5 average rating, 99 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.

Guest favourite
A spacious living area features a large sectional sofa adorned with yellow cushions. A flat-screen television is mounted on the wall opposite. Natural light floods the room through expansive windows, which provide views of the street outside. A subtle black and white rug complements the modern decor.
Flat in City Centre
4.94 out of 5 average rating, 299 reviews

Large city centre apartment with secure parking

My place is close to all public transport, the city centre, art and culture, right next to the new cinema and restaurant quarter of Town and a short walk to the Mayflower theatre. You’ll love my place because of the neighbourhood, its in the heart of Southampton City Centre and close to lots of the main attractions! My apartment is good for couples, solo adventurers, business travellers and families. This apartment also benefits from secure parking, Wireless internet and a communal garden.

Top guest favourite
Flat in Ventnor
5 out of 5 average rating, 163 reviews

The Ocean Suite, Ventnor Beach (with Sauna)

The ultimate in beachfront living, a perfect romantic escape and popular with many repeat guests. A cedar cabin with panoramic sea views over Ventnor beach, winner of 2025 LUXLife Magazine 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, 1 south facing for sunbathing, the other perfect for an alfresco breakfast in the morning sun. No pets but baby welcome!

Top guest favourite
Flat in Compton
4.98 out of 5 average rating, 301 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
A corner seating area features a wooden table and two folding chairs, positioned near expansive windows that provide unobstructed views of the sea. Soft natural light floods the space, highlighting the light-colored wood paneling and enhancing the coastal ambiance.
Flat in East Wittering
4.94 out of 5 average rating, 170 reviews

Quirky & cool with amazing views to Isle of Wight

Quirky coastal property situated on the beach at Bracklesham Bay. This coastal inspired apartment is light and airy with dramatic sea views across to the Isle of Wight. Close to Chichester harbour and the South Downs and world renowned Goodwood, whether you’re a kite boarder or car enthusiast, this location has it all. Plenty of local restaurants and shops and with great fish and chips on your doorstep, you won’t have to venture far for that seaside experience.

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, 383 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, 161 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, 652 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
A window with multiple panes frames a serene view of the sea, revealing shades of blue and distant sailboats. A basket of fresh fruit sits on a windowsill, while a potted plant adds a touch of greenery to the interior.
Flat in Isle of Wight
4.96 out of 5 average rating, 270 reviews

Seascape - a Luxurious Coastal Escape

**Wightlink Ferry Discount Available Upon Booking** Nestled in a peaceful beachside setting, yet just moments from the Portsmouth-Ryde ferry links and a direct route to London, Seascape offers the ultimate island retreat. Boasting stunning sea views, private beach access via a secluded gate, and a south-facing sun terrace, this luxuriously furnished apartment is perfect for couples or young families seeking relaxation and adventure by the coast.

Top guest favourite
A stunning water view is captured during sunset, with vibrant orange, pink, and purple hues reflected across the calm waters. Silhouetted trees and boats dot the horizon, providing a serene backdrop to the scene.
Flat in Parkstone
5 out of 5 average rating, 107 reviews

Sunset Cabin. Right on the Water's Edge! Stunning!

Welcome to Sunset Cabin! A fabulous one-bedroom waterside garden apartment, backing directly onto the Blue Lagoon and Poole Harbour, overlooking Brownsea Island. A haven for birdlife and stunning sunsets! Peaceful and so close to nature, whilst being centrally located in desirable Lilliput. Enjoy the beautiful view from your bed! Our jetty and slipway, two kayaks and paddleboards are there for you to enjoy the Lagoon and experience the Harbour.

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 $38 SGD per night before taxes and fees

  • Verified guest reviews

    Over 5,130 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

    40 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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