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, 190 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, 134 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.

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
4.94 out of 5 average rating, 293 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
4.98 out of 5 average rating, 370 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
4.76 out of 5 average rating, 188 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
A bright living area features a navy sofa and two wooden chairs positioned around a small dining table. A television on a white media console faces the seating area. Natural light filters through the large window, dressed with dark curtains.
Condo in Dorset
4.97 out of 5 average rating, 108 reviews

Private annex, driveway parking Wi-fi + TV Sports.

Churchill Annex is in Parkstone. 3 mins walk to Waitrose & 3 mins by car to John Lewis; & 100+ shops on Ashley Road; 5 mins drive to sandy beaches of Branksome + Sandbanks, with miles of golden sand. A private annex1st floor of the hosts home. It is a home away from home. Sorry, no pets + no smoking. Benefits from own entrance, separate kitchen, lounge, bedroom + bathroom. Access via a self check-in key-lock box. 50 inchtv + TNT Sports + SKY Sports . Great for a weekend, week or month

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, 184 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 ✅

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.

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, 213 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
The living room showcases a large foam-filled sofa positioned in front of a wall-mounted 65" Smart 4K TV. Natural light floods the space through the nearby windows, highlighting the contemporary decor. A balcony offers river views, enhancing the overall atmosphere.
Condo in St Mary's
4.91 out of 5 average rating, 155 reviews

New Upscale Contemporary Apartment - River Views

Experience modern luxury at this new contemporary riverfront apartment with breathtaking panoramic river views to enjoy. The large apartment features two generously sized bedrooms and bathrooms, guaranteeing your utmost comfort. Revel in the convenience of a walk-in wardrobe, while secure underground parking and gated access offer peace of mind. Your path to an upscale getaway begins here.

Guest favorite
A comfortable living area features a dark sofa paired with a patterned armchair. A glass-top coffee table sits on a decorative area rug, complemented by a colorful vase. Natural light enters through the curtains, illuminating the space and highlighting the wall art.
Condo in Ocean Village
4.9 out of 5 average rating, 106 reviews

Elegant Apartment on the Marina in Ocean Village

Discover seaside serenity in our charming Ocean Village retreat. This cozy Airbnb invites you to unwind in Southampton's premier waterfront community. Enjoy Marina views, a private balcony, and modern amenities. Steps from the marina and restaurants, this stylish getaway ensures a perfect blend of relaxation and coastal adventure. Book now for an unforgettable stay by the sea!

Guest favorite
The exterior of a red-brick house and an annex is visible, surrounded by landscaped grounds. A gravel driveway leads to the entrance, framed by well-maintained greenery including shrubs and trees. Bright sunlight illuminates the scene, enhancing the inviting atmosphere of the spacious property.
Condo in Hampshire
4.91 out of 5 average rating, 293 reviews

Comfortable detached annex for 2

Detached, comfortable and self-contained annex for one person or a couple, in quiet surroundings with parking. Light, modern and airy. Easy reach of historic and natural beauty. Andover station 1.5 miles, London 1hr by train. Easy access A303/M3. I use this as a workspace and spare space for family when they visit, but also rent it out on Airbnb from time to time.

Popular amenities for Winchester condo rentals

When is the best time to visit Winchester?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$25,070 GYDG$24,653 GYDG$26,115 GYDG$31,965 GYDG$28,204 GYDG$27,369 GYDG$26,951 GYDG$28,622 GYDG$29,040 GYDG$27,160 GYDG$27,369 GYDG$30,085 GYD
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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$16,714 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,730 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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