Condo vacation rentals in Winchester

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Top-rated condo rentals in Winchester

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Top guest favorite
The entrance features a light blue door with decorative glass panels, accompanied by a welcoming doormat. Vibrant pink flowers are arranged in pots alongside lush greenery, creating a bright and inviting entrance.
Condo in Hamble-le-Rice
4.93 out of 5 average rating, 191 reviews

Walking, watersports or relax in lovely Hamble

A cosy apartment with private entrance and private parking directly outside. Tastfully furnished,ideal for a couple or solo guest. A short stroll from Hamble harbour with a great choice of pubs,cafe's,bars and restuartants.Explore Hamble's 55 acre coastal heath or enjoy a short beach walk to nearby Royal Victoria Country Park.Sailing and waterborn activies in the harbour.Attractions HMS Victory, shopping,dining and entertainment at Gunwharf Quays just a 30 min drive away. 150Mbs guest Fast Wifi.

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
4.97 out of 5 average rating, 144 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
The open-plan living area showcases modern furnishings with floor-to-ceiling windows, allowing natural light to fill the space. A cozy dining table is set for two, complemented by a plush sofa and a stylish rug, creating a welcoming atmosphere for relaxation.
Condo in Hampshire
4.93 out of 5 average rating, 299 reviews

The Perch, a touch of luxury in the New Forest

The Perch is situated in the center of Lyndhurst, considered by many to be ‘the heart of the New Forest’. With floor-to-ceiling windows you will have views across the rooftops to the open forest and up and down the bustling & busy High Street below. Furnished and equipped to a very high standard, it is the perfect pad for up to two adults. Step out of The Perch and you are immediately surrounded by coffee-shops, restaurants, pubs and boutique shops. Sorry no babies, children or pets allowed.

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
4.97 out of 5 average rating, 375 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.

Guest favorite
A well-lit bedroom features a cozy double bed with neutral bedding. Two windows allow natural light to brighten the space. A small table and chairs are arranged beside a decorative plant. Minimalist wall art complements the warm wooden flooring.
Condo in City Centre
4.78 out of 5 average rating, 203 reviews

Stylish flat on High Street close to ship terminal

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.

Top guest favorite
The exterior of the garden flat is showcased, featuring a sloped roof and large glass doors that open to a spacious terrace. A well-manicured lawn surrounds the building, and a dog relaxes peacefully in the grass. Lush greenery and garden beds enhance the inviting outdoor space.
Condo in Compton
5 out of 5 average rating, 103 reviews

Beautiful stylish Garden flat 8 mins to Winchester

Unique and stylish, this very comfortable and relaxing space offers the peacefulness of countryside whilst being a stones throw from the beautiful city of Winchester - a very short drive or a beautiful walk away. You get the best of both worlds with the city's pubs, restaurants, cafes and historic sights close at hand as well as river walks by the Itchen & beautiful countryside straight from your door. Excellent transport links to London, M3, Southampton Airport and the New Forest.

Guest favorite
A cozy living area features a dark gray sectional sofa adorned with patterned cushions. Two small white tables are positioned in front, with a bottle of wine and a glass displayed. Natural light fills the space through a window, highlighting a geometric-patterned rug.
Condo in Portsmouth
4.89 out of 5 average rating, 104 reviews

Cozy apartment in Southsea with parking.

This newly furnished one bedroom flat is located a stone's throw from the beach right in the heart of Southsea. A big advantage is the private parking space directly in front of the house. The flat is just meters away from the best bars and restaurants the city has to offer, not to mention the Kings Theatre. The most beautiful beach in Southsea is a 10 minute walk away. The train station is a 10 minute walk to the other side. This flat will allow you to fully enjoy your stay in Southsea.

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
4.92 out of 5 average rating, 190 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 well-lit bedroom features a spacious bed with soft bedding and two bedside lamps for additional light. A dresser sits opposite the bed, adorned with a small plant. A window provides natural light and is complemented by a large mirror on the wall.
Condo in City Centre
4.87 out of 5 average rating, 201 reviews

Next to theatre, close to port and free parking!

At less than 400 yards from Southampton Central Train Station, you will be a short walk / taxi ride from everything the city has to offer. 1 guaranteed free parking space. Boasting 2 bedrooms, one with a double bed, one with a single and a living space complete with sofa bed, will comfortably sleep 4 people. Make yourselves at home in the kitchen, equipped with all essential cooking appliances, or explore the bars and restaurants of the town. Recommendations can be given!

Top guest favorite
A modern studio space features a comfortable sofa and a round dining table. Large glass doors open to a patio, leading to a grassy area with trees visible in the background. Natural light fills the room through sheer curtains.
Condo in Wiltshire
4.97 out of 5 average rating, 197 reviews

River View: Peaceful, private studio in Salisbury

River View is a modern, peaceful studio just a 2 minute drive from Salisbury Station and a 25 minute level walk from the city centre. It is the perfect base for visiting all that Salisbury and the surrounding area has to offer. Large, scenic windows give plenty of light and views to a long garden, with woodland and river beyond. With your own front door you will be able to come and go as you wish. We have plenty of secure, gated off road parking for car and cycles.

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 Hampshire
4.93 out of 5 average rating, 213 reviews

Coach House Flat in South Downs National Park.

Newly available after a break, our lovely flat has been renovated and is ready for you to enjoy and 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
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, 219 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

Popular amenities for Winchester condo rentals

When is the best time to visit Winchester?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$22,795 GYDG$24,469 GYDG$25,096 GYDG$25,932 GYDG$26,142 GYDG$27,396 GYDG$28,024 GYDG$28,651 GYDG$28,651 GYDG$25,305 GYDG$25,096 GYDG$24,259 GYD
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Quick stats about condo rentals in Winchester

  • Total vacation rentals

    Explore 170 vacation rentals in Winchester

  • Nightly prices starting at

    Winchester vacation rentals start at G$6,274 GYD per night before taxes and fees

  • Verified guest reviews

    Over 8,540 verified reviews to help you choose

  • Family-friendly vacation rentals

    80 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    120 properties have a dedicated workspace

  • Wi-Fi availability

    170 of Winchester vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winchester rentals

  • 4.7 Average rating

    Winchester stays receive an average rating of 4.7 out of 5 from guests

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