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
A light-filled living area features a comfortable gray sofa adorned with patterned cushions. A small, cozy armchair sits nearby, and a wooden coffee table is positioned in front. Natural light streams through the window, highlighting a light blue wall and decorative shelf.
Condo in Winchester
4.96 out of 5 average rating, 170 reviews

Spacious central 2 bedroom apartment+ free parking

A spacious family-friendly 2 double/twin bedroom first floor flat located in the lovely Hyde area of central Winchester. Provides easy access to the city centre with all that the city offers. Only 5 minutes stroll to the train station. This apartment is close to all the historical sites and wide variety of restaurants and cafes which you'll enjoy as well as the cathedral and its impressive grounds. Winchester Christmas market and the city's magical atmosphere should be on everybody's calendar.

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 👍

Top guest favorite
A two-story building stands surrounded by lush greenery and blooming rose bushes. A gravel pathway leads to a garage door, while the bright blue sky adds a serene backdrop to the scene. The well-maintained garden enhances the inviting exterior.
Condo in Emery Down
4.98 out of 5 average rating, 404 reviews

Welcoming apartment in the heart of the New Forest

'The Loft' is situated in Emery Down, a beautiful village in the heart of the New Forest where livestock roams free. This welcoming newly refurbished apartment offers a fully equipped kitchen and access to a pretty garden space - perfect for unwinding after a day of exploring. Walking and cycle routes (and a popular pub) can be reached in moments, local amenities are within walking distance in the forest’s capital Lyndhurst and sandy beaches are a short drive away. Private parking is available.

Superhost
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 City Centre
4.76 out of 5 average rating, 233 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 Hampshire
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
A spacious bedroom featuring a kingsize bed with light bedding. A side table with a lamp sits beside the bed, and a light-colored throw is draped across the foot. Natural light enters through a large window adorned with blinds, creating a calm setting.
Condo in Southsea
4.91 out of 5 average rating, 236 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
A living area is depicted with a comfortable sofa, a coffee table, and a television displaying a streaming service. Natural light floods in through multiple glass doors leading to a balcony. A desk is positioned nearby, accompanied by a chair and plants adding to the ambiance.
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
The exterior of Little Bunty Lodge is presented, showcasing a charming single-story structure partially draped in greenery. A pebbled driveway leads to the entrance, framed by well-maintained hedges. The building's rustic roof and windows accent its inviting character amidst a serene natural setting.
Condo in Bashley
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

Guest favorite
A view from above showcases the rooftops of Winchester, surrounded by lush green trees. The historic architecture of buildings can be seen, with a distant glimpse of a notable structure on the horizon, all under a clear blue sky.
Condo in Winchester
4.95 out of 5 average rating, 247 reviews

TOP FLAT CENTRAL ELEGANCE

This unusual apartment, on two levels, perched above Winchester roof tops, has great vistas and is in a very central position in the City. Step outside on to the cosmopolitan and historic high street; department stores, restaurants, coffee shops, museums are all within seconds: Within minutes stroll into the countryside and enjoy the lovely Hampshire scenery.

Top guest favorite
A modern living area features a sleek gray sofa adorned with a light throw blanket. A glass coffee table sits in front, accompanied by a small dining table with two chairs. Colorful wall art enhances the space, while large windows offer views of the surrounding area.
Condo in Gunwharf Quays
4.85 out of 5 average rating, 381 reviews

FAR REACHING HARBOUR VIEWS

Newly renovated One bedroom apartment that is part of Portsmouth Iconic "The Hard". Well proportioned double bedrooms both with built in wardrobes. Views over Portsmouth historic dockyard and as far reaching as the Solent and Isle of White. Located with in 2 minutes walk of Gunwharf Quays and The Hard train and Portsmouth's Historic Dockyard.

Popular amenities for Winchester condo rentals

When is the best time to visit Winchester?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$28,187 GYDG$28,396 GYDG$28,813 GYDG$31,945 GYDG$28,187 GYDG$27,352 GYDG$26,934 GYDG$28,604 GYDG$29,022 GYDG$34,868 GYDG$27,978 GYDG$37,165 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$18,791 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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