
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.

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.

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.

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.

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.

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.

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.

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.

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 ✅

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!

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.

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.

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
Weekly condo rentals

City Centre Riverside Apartment

Top-floor retreat with views & free parking

Fulflood View

Fab central self contained studio, just like home

Central Chic 3bd, Cosy in Great Location

Detached Studio in Chandlers Ford with Parking

Cosy 1-Bed Escape with Free Parking (At Hem)

"Fabulous Location" Central Winchester Apartment
Pet-friendly condo rentals

2BR | Poole Centre | Beaches&Shops | Pet friendly

2 Bed Apartment, WI-FI, 5 min Walk to the Beach

Modern town apartment 2 mins from water.

Cloud 9..Beautiful Entire Flat in East Wittering

Station Location

Attractive annexe in stunning rural location

Large one bedroom flat in Central Farnham

Alma Court Retreat Freshwater IOW
Condo rentals with a pool

Beautiful 3-bed flat by the sea with use of pool

Bright, spacious annexe in beautiful Pewsey Vale.

Apartment 12

Flat 10 Pelican House

The Palms Apartment 16 with Balcony

Apartment 11

The Palms, Apartment 2

2-BR Penthouse Apt. close to Beach with Pool*.
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$22,795 GYD | G$24,469 GYD | G$25,096 GYD | G$25,932 GYD | G$26,142 GYD | G$27,396 GYD | G$28,024 GYD | G$28,651 GYD | G$28,651 GYD | G$25,305 GYD | G$25,096 GYD | G$24,259 GYD |
| Avg. temp | 5°C | 5°C | 7°C | 9°C | 12°C | 15°C | 17°C | 17°C | 15°C | 11°C | 8°C | 5°C |
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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- New Forest National Park
- Paultons Park Home of Peppa Pig World
- University of Oxford
- Goodwood Motor Circuit
- Stonehenge
- Windsor Castle
- Hampton Court Palace
- Boscombe Beach
- Highclere Castle
- Winchester Cathedral
- Twickenham Stadium
- Chessington World of Adventures Resort
- Kimmeridge Bay
- Thorpe Park Resort
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- Goodwood Racecourse
- Highcliffe Beach
- Worthing Pier
- West Wittering Beach
- The Tank Museum
- Wentworth Golf Club
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