Condo vacation rentals in Winchester

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Top-rated condo rentals in Winchester

Guests agree: these condos are highly rated for location, cleanliness, and more.

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Top guest favorite
Condo in Beggarwood
4.99 out of 5 average rating, 175 reviews

Basingstoke, Cosy 2-Bed Apt with private parking

This attractive 2-bedroom ground-floor home-from-home apartment has 2 parking spaces for your use lounge/dining room with comfortable sofa, armchair and table with chairs Fully equipped kitchen internal bathroom featuring a walk-in shower. Double room has, Double bed, and a single room with large 3ft single bed, Our apartment is smart enabled access from M3 Jct 7 and under 5 miles from Central Basingstoke nature parks within walking distance. Complementary beverages, Milk, biscuits, & snacks 👍

Guest favorite
A bright, airy room features a wooden bed positioned against the wall, complemented by potted plants. Light wooden flooring extends across the space, while recessed lighting illuminates the area. Large windows provide natural light, enhancing the minimalist decor with subtle greenery.
Condo in Southampton
4.75 out of 5 average rating, 235 reviews

Cosy and quiet studio on High Street, Southampton

Welcome in our stylish and newly renovated apartment in the heart of Southampton. Just a minute's walk from West Quay. The apartment features kitchen and bathroom, as well as a cozy double bed. Despite its central location, the apartment is quiet, allowing you to relax and unwind after a day of exploring the city. Whether you're in town for business or leisure, our apartment is the perfect base for your stay in Southampton. Just a kind reminder: Our property does not have air conditioning.

Superhost
A cozy living room is furnished with a spacious sectional sofa facing a wall-mounted TV. Large glass doors offer sweeping views of the sky and surrounding area. Green plants add a natural touch, while a sleek wood-burning stove creates a focal point in the inviting space.
Condo in Westbourne
4.85 out of 5 average rating, 187 reviews

The Beach Hytte - Stunning Sea View Penthouse

Enjoy your perfect getaway in this award winning 2 bed penthouse apartment with 180 degree sea views in the heart of the tranquil Alum Chine area of Bournemouth just a few minutes walk from the beach. The property boasts two dining areas, one of which sits on the large balcony with views across Bournemouth beach and a bespoke wood burning stove for the winter nights. The open plan kitchen leads onto a cozy living room where you can enjoy Sky Glass TV entertainment through super fast WiFi.

Guest favorite
The studio features an elegantly decorated sleeping area with a spacious bed adorned with a colorful bedding. Soft lighting highlights the intricate mirror and chandelier. A comfortable chair sits beside the bed, while large curtains frame the windows, adding to the cozy ambiance.
Condo in Winchester
4.91 out of 5 average rating, 209 reviews

Bright Bijou Studio in Central Winchester

A beautiful bright cosy studio apartment on one of the quietest streets in the centre of historic Winchester❤️. The breathtaking cathedral and other must-see sights are all within a flat 10 minute walk. Ideal for short stays or a weekend get-away. Just five minutes walk from train station/city centre, and 10 mins walk from the bus station. * Super-comfy double bed ✅ * Fast WiFi ✅ * Comfortable big chair and table for laptop working ✅ * Wide range of caf/decaf teas and coffees ✅

Guest favorite
The living area features a modern design with a large sectional sofa and a coffee table. A round mirror hangs on the wall, reflecting light, and there is a wall-mounted TV nearby. A small dining table is set for four, complete with plates and glasses.
Condo in Southsea
4.91 out of 5 average rating, 237 reviews

Elegant home, minutes from beach, free parking!

Enjoy a stylish experience at this centrally-located apartment. Walk out of the front door to dozens of cafes, bars and restaurants in one direction and Southsea beach in the other. With a view of Southsea common and the sea close by, this flat is ideal for a seaside staycation. Parking is on-street and parking permits offered cover anumber of neighbouring streets in the KC zone. Parking permits will be provided for the duration of your stay, these allow free on-street parking.

Guest favorite
Condo in Boscombe West
4.91 out of 5 average rating, 214 reviews

Pier View Retreat - Sea Views - With Parking

Tucked away at the top of a period building this completely renovated apartment offers amazing views of the the coast and Boscombe Pier. All new furniture and fittings with a luxurious 2000 spring king size bed to relax in. Motorised blinds allow you wake and enjoy the view without having to leave the bed. A dedicated off road parking space is provided which is rare in this area and the sea front is just a 400 meter walk away.

Guest favorite
Condo in Southampton
4.91 out of 5 average rating, 107 reviews

Top-floor retreat with views & free parking

Step into a stylish top-floor flat with stunning skyline views, private balcony and secure parking. Just 10–15 mins to the city centre, 15–20 mins to the cruise terminal and 1.6 miles from Southampton airport with fast M27/M3 access. Nearby buses and e-bikes make exploring easy. Bright, modern and peaceful, it’s the perfect base - whether you’re here for Southampton, a cruise, or adventures across Hampshire.

Guest favorite
Condo in New Milton
4.89 out of 5 average rating, 243 reviews

Luxurious Apartment in New Forest National Park

Little Bunty Lodge is ideal for a romantic getaway or a peaceful solo retreat, this luxurious studio offers comfort and style. A great base to explore the beautiful New Forest, with ponies and deer roaming free, as well as the stunning local beaches. Barton beach 3 miles Avon beach 6.5 miles Lymington 7.5 miles Christchurch 7 miles Bournemouth 14 miles Southampton with West Quay shopping complex 18.5 miles

Top guest favorite
A charming flat, built above a garage, features a stone facade adorned with climbing greenery. Surrounding it, a small garden showcases vibrant flowers, with a well-maintained lawn and lush shrubbery enhancing the peaceful outdoor setting.
Condo in Liss
4.94 out of 5 average rating, 236 reviews

Coach House Flat in South Downs National Park.

Our lovely flat has been recently renovated and is ready for you to enjoy. Since January 2026 it also has a brand new washing machine. It is a self contained flat built above our garage in the building that used to be the old Coach House. Set in a quiet location on the northern edge of the South Downs National Park it is well placed for walking, many local attractions, and the lovely town of Petersfield.

Guest favorite
A wide view of a landscape features a variety of trees, displaying lush green foliage. The sky is clear, allowing bright sunlight to illuminate the scene. The hills in the distance create a peaceful backdrop, enhancing the natural beauty of the surroundings.
Condo in Winchester
4.83 out of 5 average rating, 104 reviews

Lovely 1 Bedroom 1 Bathroom Self Contained Space

Take a break and unwind at this peaceful space on top of St Giles Hill in Winchester. Only a 10 min walk into town, to enjoy all that Winchester has to offer. The property is a self contained garden property with stunning views towards the South Downs and St Catherines Hill. The property has a double bedroom and bathroom for guests to enjoy.

Superhost
Condo in Gunwharf Quays
4.8 out of 5 average rating, 134 reviews

The Solent Suite

Newly renovated One bedroom apartment that is part of Portsmouth Iconic "The Hard". Views over Portsmouth historic dockyard and as far reaching as the Solent and Isle of Wight. Located with in 2 minutes walk of Gunwharf Quays and The Hard train and Portsmouth's Historic Dockyard. Parking included with stay!

Guest favorite
A small dining area is situated by a window, featuring a round table surrounded by two modern chairs. The view beyond showcases Windsor Castle, framed by elegant curtains that complement the architecture.
Condo in Windsor
4.97 out of 5 average rating, 238 reviews

Stunning 1Bd with Castle View

Beautifully appointed and recently refurbished one bed apartment (45sqm) with Castle Views in Park Street Windsor just 100m from the Long Walk. Great access to the heart of Windsor, close to Central and Eton Riverside Stations. Great kitchen, wifi and TV.

Popular amenities for Winchester condo rentals

When is the best time to visit Winchester?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$28,242 GYDG$28,451 GYDG$28,869 GYDG$32,007 GYDG$28,242 GYDG$27,405 GYDG$26,987 GYDG$28,660 GYDG$29,079 GYDG$34,936 GYDG$28,033 GYDG$37,237 GYD
Avg. temp5°C5°C7°C9°C12°C15°C17°C17°C15°C11°C8°C5°C

Quick stats about condo rentals in Winchester

  • Total vacation rentals

    Explore 20 vacation rentals in Winchester

  • Nightly prices starting at

    Winchester vacation rentals start at G$18,828 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,920 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Winchester vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winchester rentals

  • 4.9 Average rating

    Winchester stays are highly rated by guests—averaging 4.9 out of 5!

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