Apartment holiday rentals in Winchester

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Top-rated apartment rentals in Winchester

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Top guest favourite
The kitchen features modern cabinetry with a dark countertop and stainless steel backsplash. A glass vase with fresh flowers adds a touch of nature. A patterned towel hangs from the oven, complementing the bright green wall behind, creating a functional cooking space.
Flat
4.9 out of 5 average rating, 298 reviews

Southsea - Welcoming Seaside Apartment

Situated just off the beachfront and within walking distance of Southsea's shops and restaurants .There is a frequent bus service to Gunwharf and the Historic Dockyard right outside the door. The apartment is of one bedroom with a comfy king size bed, a fully equipped kitchen, bathroom and a separate lounge with balcony. There is an allocated parking space in front of the building for you. Also, check out our new listing 'Period Seaside Apartment' in the same building full of character & charm

Top guest favourite
A cozy lounge area features a brown sofa adorned with plaid cushions, complemented by a wooden dining table set for meals. Natural light enters through a large window with a view of greenery, enhancing the peaceful atmosphere.
Flat
4.98 out of 5 average rating, 192 reviews

Bursledon Peewit Hill, Home from Home

Modern, fully equipped one bedroom annexe with bathroom,kitchen and lounge area. TV in the bedroom and lounge. Use of garden space weather permitting. Close to the M27 and Bursledon train station is 5 minutes drive away. Approx 5 miles from Southampton City centre and about 10 minutes from Hamble. Motorway access to South coast cities such as Bournemouth, Portsmouth and shopping in West Quay Southampton ,Gunwharf Quays in Portsmouth. Also 20 mins away from Southampton docks for cruise ships

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, 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
Flat
4.91 out of 5 average rating, 390 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.

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, 181 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
Flat
5 out of 5 average rating, 162 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!

Guest favourite
Flat
4.95 out of 5 average rating, 168 reviews

Coast Beachfront GF 6 guests dog friendly aptment

Coast built in 2020, located on Southbourne clifftop, 7 miles of award winning Blue Flag sandy beaches; stretching from Hengistbury Head to Sandbanks. It’s a stone’s throw from Southbourne’s high street bustling with a selection cafés, restaurants and pubs that are dog friendly. Only a 15 minute drive to the New Forest and walking distance to Bournemouth beach. Coast features an enclosed garden which offers magnificent sea and coastal views and so does the master bedroom.

Top guest favourite
Flat
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
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, 380 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
4.92 out of 5 average rating, 160 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
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
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.

Top guest favourite
Flat
4.88 out of 5 average rating, 216 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.

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 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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