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.
Apartment in Stockbridge
4.89 out of 5 average rating, 173 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
Apartment in Winchester
4.91 out of 5 average rating, 383 reviews

Copper Beech, a secluded two bed apartment

Copper Beech is spacious & modern apartment in a semi-rural location close to Winchester. This apartment has two large king size bedrooms; both with ensuite bathrooms, large lounge/dining area and a well equipped kitchen. One of the bedrooms can sleep up to 4 guests with a daybed (with two full single size beds) plus kingsize bed. Parking is available for two standard-sized vehicles - one blocking in the other. There is a trampoline in a large shared garden for children to play on.

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.
Apartment in Hampshire
4.95 out of 5 average rating, 100 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.

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.
Apartment in Burridge
4.95 out of 5 average rating, 177 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.

Guest favourite
Apartment in Isle of Wight
5 out of 5 average rating, 159 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
Apartment in Compton
4.98 out of 5 average rating, 299 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.
Apartment in Winchester
4.95 out of 5 average rating, 371 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.

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.
Apartment in Medstead
4.91 out of 5 average rating, 152 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.

Guest favourite
Apartment in Froxfield
4.88 out of 5 average rating, 209 reviews

The Studio @ Black Barn, Nr Petersfield.

Newly refurbished, ‘The Studio at Black Barn’ is an open plan self-contained private annexe with own parking right outside its own private entrance and garden. Your accommodation is on the ground floor of a family home, surrounded by countryside near Petersfield. Perfect for 1 or 2 adults to indulge in a relaxing mini break; also ideal for a fleeting overnight work visit and take advantage of the superfast broadband to work from Black Barn.

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.
Apartment in Hampshire
4.92 out of 5 average rating, 196 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.

Guest favourite
The spacious living area is furnished with two comfortable, dark grey sofas, one of which is a pull-out sofa bed. A soft gray rug covers the carpeted floor, complementing the neutral walls. Natural light filters in from a nearby window, and a fireplace adds warmth to the space.
Apartment in Hampshire
4.86 out of 5 average rating, 331 reviews

** Stylish, clean and modern apartment **

Clean, wonderfully modern and ideally located en-suite maisonette within close proximity to the following: * Peppa Pig World / Paultons Park (15 minute drive) * Marwell Zoo (20 mins) * Southampton Airport (5 mins) * Winchester (15 mins) * Southampton Cruise Terminal (20 mins) * The New Forest (20 mins) A great and comfortable apartment with all you need for a relaxing stay.

Guest favourite
A dining table is set for four on a spacious balcony, framed by a view of the river. Two black chairs surround the table, while greenery is visible in the foreground. The tranquil water reflects the sky, enhancing the outdoor dining experience.
Apartment in Portswood
4.86 out of 5 average rating, 200 reviews

Riverside Retreat - Free Parking

Take it easy at this unique and tranquil getaway overlooking the river. Being a stone throw from Southampton central, it’s close enough to be in town within a 5-10 minute car journey but far enough away to slow down. The property offers a large wraparound balcony from master bedroom to lounge diner. Making it a wonderful spot for indoor outdoor living.

Popular amenities for Winchester apartment rentals

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Avg. price$183 NZD$185 NZD$198 NZD$221 NZD$239 NZD$258 NZD$261 NZD$259 NZD$240 NZD$209 NZD$195 NZD$223 NZD
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Quick stats about apartment rentals in Winchester

  • Total holiday rentals

    Explore 70 holiday rentals in Winchester

  • Nightly prices starting at

    Winchester holiday rentals start at $52 NZD 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 and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    70 of Winchester holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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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