Apartment holiday rentals in Winchester

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Top-rated apartment rentals in Winchester

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Guest favourite
Flat
4.99 out of 5 average rating, 170 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
The garden is arranged with tables and chairs under umbrellas, surrounded by vibrant flowers and greenery. A lantern is placed on one table, while an assortment of seating options, including recliners, offer inviting spots for relaxation. The area appears tranquil and well-maintained.
Flat
4.96 out of 5 average rating, 568 reviews

* Spacious Flat * Quiet&Clean * Everything Close *

🎩The "Top Hat" apartment. Very clean, large self-contained, by the green expanse of Southsea Common & the seafront. A breath of fresh air! Take a quiet early morning stroll without the tourists. Although shops, bars & restaurants are only a stone's throw away, the area feels peaceful and secluded. Very private. Smart TV's with Xbox. Come & enjoy fabulous Southsea. Your adventure is ready & waiting. All it needs now is you! Host on site if needed. 🚘12hr/24hr street parking permits £5/£10 each.

Guest favourite
A charming wooden annexe is depicted, featuring a sloped roof and multiple windows. The exterior is set against a backdrop of lush greenery and a clear blue sky. A gravel pathway leads to the entrance, framed by shrubbery and garden elements.
Flat
4.92 out of 5 average rating, 254 reviews

Ellerslie Lodge Annexe private, cosy. Free parking

Nestled in the slopes of Portsdown Hill, a welcoming "countryside" retreat, whether relaxing or business. This private first floor annex has everything you need. A 5 minute drive from M27 . Included a Hospitality Pack. Free parking for one car, on private driveway covered by CCTV. Easy access to M27, M3, A3, QA, Hospital, Fort Nelson, Historic Dockyard. Near local businesses and Trafalgar Wharf. Fully equipped kitchenette with hotplate .Shower room and comfy double bed . Free Wi-fi

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
4.93 out of 5 average rating, 503 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
5 out of 5 average rating, 105 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
4.83 out of 5 average rating, 109 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
The exterior of a single-story annexe features a light-colored facade with multiple windows and a prominent front door. A brick wall surrounds the garden area, enhancing the entrance. The property includes a driveway with a parked car, framed by greenery on either side.
Flat
4.95 out of 5 average rating, 194 reviews

Exceptional room and study area.

This is the majority of a furnished annexe (no kitchen) located in Burridge , which is half-way between Portsmouth and Southampton. About a mile away from both Swanwick Marina and Park Gate village, Swanwick train station is 15 minute walk. With it's own entrance comprising of main bedroom/sitting area, separate study area and separate shower room. There is space to park a car off the road. A convenient base to visit Winchester, Portsmouth, Southampton and The New Forest. Self check in.

Top guest favourite
A two-story cottage is showcased with a slate roof and traditional architectural elements. The exterior features wooden garage doors and a well-maintained garden hedge. A cobblestone driveway leads up to the entrance, framed by a backdrop of clear blue skies.
Flat
4.99 out of 5 average rating, 247 reviews

Little Greatfield is a character 2 bedroom cottage

Unique situation this detached cottage, with an EV charger, is within the Greatfield estate and has beautiful private gardens within a parkland setting. There is a private security gate for access. We are a short walk (5 mins) from Bucklers Hard village and Beaulieu River, where you will find the Master Builders hotel and pub, the Marina and the Maritime Museum. For the hotel restaurant advance booking is recommended. There is a lovely riverside walk to Beaulieu village ( 2.5 miles ).

Top guest favourite
Flat
4.98 out of 5 average rating, 308 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
4.94 out of 5 average rating, 178 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
4.95 out of 5 average rating, 396 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
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
4.95 out of 5 average rating, 676 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.

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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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