
Vacation rentals in Winchester
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Top-rated vacation rentals in Winchester
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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.

One bedroom home.
Relax and make yourself at home in this comfortable bungalow with sunny lounge, fully equiped kitchen/diner and bathroom. Situated in a quiet cul-de-sac in the village of Bishopstoke on the outskirts of Eastleigh. The M27 and M3 motorways and Southampton Airport are just a few miles away. The historic City of Winchester is an easy drive. Whether you are on your way to explore the South West, visiting family or friends or just wanting a short break, we offer a convenient home away from home.

Central, Quiet & Self-Contained
Incredibly central location. Only 150m from Cathedral & 200m to High St. Quiet: Set back from the street, double glazing, detached building. King size bed with luxury mattress & topper, hypoallergenic duvet & pillows, Egyptian cotton bedlinen and fluffy towels. Work space. Reading & soft lighting. Well Equipped: Tea & Coffee Facilities, Mini Fridge, TV (Netflix only) Iron+Board, Hairdryer, Toiletries & Fan. Secure parking subject to availability £20per night. NB. Access via external staircase.

A Unique Farm Retreat
There’s something magical about The Granary. Set in acres of farmland with spectacular sunrises and sunsets, The Granary brims with rustic charm. A dreamy hideaway with an outdoor copper bath and wood fired hot tub. An idyllic get-away-from-it-all yet only 3 miles to historic Winchester. Soak amid hot water, steam and fresh air surrounded by nature and birdsong, enjoy magnificent sunsets from the ‘Sundowner’ or cosy up toasting marshmallows over the fire pit - a perfect escape to unwind.

Own Front Door
Welcome to the beautiful city of Winchester! I have self contained central accommodation comprising of a double bedroom with en-suite shower room, a lounge with fridge/tea/coffee making facilities and your own private front door accessed from the street at ground level. The accommodation has been part of a massive renovation of the main house, now fully completed. Dating from the 1850’s it still retains a Victorian feel with high ceilings and sash windows. It is a lovely light, airy space.

St Michael's Hall, City Centre
St Michael's Hall is a unique, newly renovated church hall in the heart of the historic city centre. A stone's throw from the Cathedral, College, buzzy high street and water meadows, it's the perfect base to explore everything Winchester and the surrounding area has to offer. Each bedroom has its own bathroom, meaning it's as suitable for two couples as it is for a romantic city break or four friends. One on-street parking permit is available, while the train station is a short walk away.

Beautiful garden house, edge of town & South Downs
Beautiful self-contained lodge in the glorious garden of a Georgian Country House. Five minutes walk to the small market town of Bishops Waltham, with shops, restaurants and pubs. Surrounded by stunning countryside, on the edge of the South Downs, with wonderful walks from the house. Open plan kitchen-dining area & lounge, 2 bedrooms and a bathroom upstairs plus separate downstairs shower room. Sunny patio area with table and chairs & Weber bbq, perfect for watching the sun go down.

Quiet Winchester One Bedroom Home with own parking
Welcome to your lovely detached one bedroom home in a quiet leafy private road on the edge of St Giles Hill - just above medieval Winchester and on the edge of beautiful the South Downs Way. Your self-contained home includes parking on the drive, a stylish double bedroom, shower room, living area (with full double-width sofa bed) incorpoating a full kitchen/washing machine. Its an easy 10 minute downhill stroll across the park (lovely for a sunset picnic) to historic Winchester.

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 ✅

Room with a view
You’ll love sharing photos of this unique place with your friends. Room with a View is a cosy and bright studio room located in the outskirts of the rural village of Owslebury. Just a 5-mile drive from the medieval city of Winchester, Room with a View is situated in a prime location, perfect for a serene getaway or business stay. Secluded from the busy bustle of the city, yet a swift 10-minute drive, Room with a View is surrounded by acres of fields and beautiful views.

Central Winchester garden flat, permit parking
Winchester City Centre- Bijou, charming, characterful, homely, warm and cosy self contained one bedroom flat with free permit parking and luxuriously large bath tub with shower, private garden with patio for alfresco dining. Fully equipped galley kitchen for self - catering. Only a five minute level walk to the central High Street and Cathedral, with the world famous Christmas Market through November and December. Less than ten minutes walk from the Railway Station.

Pretty self contained annexe
Pretty, self contained annexe with its own entrance, located between the historic city of Winchester & Southampton and on the doorstep of the New Forest National Park. Great travel links - M3/M27, Southampton Airport & Southampton Parkway station. Studio comprises double bed, kitchen with oven, hob, fridge & microwave. Breakfast bar, which doubles as a workspace, shower room and shared use of patio and garden. We also have a young, bouncy dog!
Popular amenities for Winchester vacation rentals
Other great vacation rentals in Winchester

Cosy 1Bed Flat

Private garden room, free permit parking

A new detached Studio Annexe

The Sky Penthouse, City Centre Luxury

New Modern Studio in Chandlers Ford with Parking

Beautifully presented stylish Garden flat

One bedroom cottage escape

Luxury 2BR apartment + parking central Winchester
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$23,222 GYD | G$23,432 GYD | G$24,059 GYD | G$25,733 GYD | G$26,570 GYD | G$27,197 GYD | G$28,034 GYD | G$28,662 GYD | G$28,034 GYD | G$25,314 GYD | G$24,687 GYD | G$25,105 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 |
Frequently Asked Questions
How much does it cost to stay in cabin rentals in City of Winchester?
Experience the best of City of Winchester with our cabin rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Where should I stay in City of Winchester?
Make yourself at home in City of Winchester by choosing from our most frequently booked neighborhoods. We have over 670 vacation rentals in Botley, over 800 vacation rentals in Freemantle, and over 460 vacation rentals in Netley.
Do apartment rentals in City of Winchester have air conditioning?
Absolutely! We offer over 20 apartment rentals with air conditioning in City of Winchester. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in City of Winchester?
Four-legged friends are welcome in City of Winchester. Choose from more than 570 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in City of Winchester?
Yes! Work meets play with ease at over 1,180 vacation rentals in City of Winchester featuring dedicated workspaces. Stay connected and productive in your home away from home.
What are the most popular amenities for Hotel Rentals in City of Winchester?
Enhance your stay in our Hotel Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there City of Winchester vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in City of Winchester, available on Airbnb. Make a splash and soak up the sun in style!
Are there family-friendly vacation rentals in City of Winchester?
City of Winchester has more than 1,040 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do hotel rentals in City of Winchester have free parking?
Absolutely! We offer over 10 hotel rentals with free parking in City of Winchester. Enjoy a tailored experience with all the comforts you desire.
Do serviced apartment rentals in City of Winchester have a kitchen?
Absolutely! We offer over 110 serviced apartment rentals with a kitchen in City of Winchester. Enjoy a tailored experience with all the comforts you desire.
Quick stats about vacation rentals in Winchester

Total vacation rentals
Explore 2,560 vacation rentals in Winchester

Nightly prices starting at
Winchester vacation rentals start at G$2,092 GYD per night before taxes and fees

Verified guest reviews
Over 113,310 verified reviews to help you choose

Family-friendly vacation rentals
1,040 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 570 rentals that welcome pets

Vacation rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
1,180 properties have a dedicated workspace

Wi-Fi availability
2,420 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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