City of Winchester holiday rentals

We found 1,591 holiday rentals — enter your dates for availability
Select from 50 houses, 38 apartments and other holiday rentals to find the perfect place for your stay in City of Winchester. Whether you’re travelling with friends, family or even pets, holiday rentals have the amenities that you need and want for your stay, which might include a hot tub and a washer and dryer. You're sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.

Find spaces that suit your style

Find the best place to stay - City of Winchester

Image of Winchester Wessex Hotel by Sunday-Double Room

Winchester Wessex Hotel by Sunday-Double Room

Sleeps 2 · 1 bedroom · 1 bathroom
8.4 out of 10
very good
(104 reviews)
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Top rated rentals - City of Winchester

Image of Second Nature Southampton

Nice place to stay...

9.4 out of 10
exceptional
(1,369 reviews)
.... like a lot of others we were there to join a cruise. The staff were friendly and we greatly enjoyed the breakfast. The view across to the park is nice and this morning we could even see a large cruise ship in the distance! The room was compact but comfortable and being quite new in good condition. It even had an ironing board. Having milk for tea available is a nice touch. We even scored some extra tea bags... Some things we would have liked include tissues and face washers for wiping noses and faces/makeup! YMMV
Christopher
Stayed Aug 2025
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Frequently Asked Questions

What is the best area to stay in City of Winchester when booking a holiday home?

Among the more popular areas for a City of Winchester holiday home is Twyford. When you book your stay with Stayz, you will have the entire place to yourself. So you won't have to share it with anyone except for your group.

What is the most popular type of holiday home accommodation in City of Winchester?

Based on our research, cottages are the most in-demand type of holiday property in City of Winchester. But of course, everyone's idea of an epic stay can differ. Stayz has holiday homes of all sizes, shapes and budgets, so you're sure to discover the best fit for your needs.

How much does it cost to rent a holiday home in City of Winchester?

Property type, length of stay and season are some of the conditions that can influence the price of a holiday home. Simply enter your dates of travel to find the ultimate escape. From cosy cabins to sprawling villas, all Stayz holiday homes offer unbeatable value.

How much does it cost to rent a beach house in City of Winchester?

The average price for a holiday home close to the beach in City of Winchester depends on when you're visiting the area and the size and type of property you want. You can find prices easily and quickly on Stayz by entering your destination and preferred travel dates. Then use the filters to select the number of bedrooms and amenities that you prefer, such as a pool, WiFi and air conditioning.

What are popular home amenities in City of Winchester?

Off-street parking options, a dishwasher and a washing machine are the most popular home amenities in City of Winchester. Whether you're taking to the road as a party of one, with a partner or a bunch of friends, Stayz will help you find a holiday home that suits your style with all the options you need.

Are there large group holiday homes in City of Winchester?

Take your pick of two holiday homes in City of Winchester that can sleep 10 or more guests. Whether you're planning time away with the family or an event like a party, there's plenty of room to get your group together under one roof.

What are the top attractions for families in City of Winchester?

Keeping the kids amused during your City of Winchester holiday is easy with these family-friendly attractions:

  • Marwell Zoo
  • Winchester Christmas Market
  • Winchester Cathedral

Can I find two-bedroom holiday homes in City of Winchester?

City of Winchester has 39 two-bedroom holiday properties to pick from. Experience a holiday home with all the privacy and comfort you need at an attractive price on Stayz.

Are there holiday homes with WiFi in City of Winchester?

You can pick from 26 holiday homes with WiFi in City of Winchester. If you want to disconnect from the world on your trip, but still need to be connected to the internet, these properties are for you. Narrow your search by applying the WiFi filter on Stayz.

How old do you have to be to rent a holiday home in City of Winchester?

The minimum age is generally 16, 18 or 21. It can change from one property to another on Stayz, so look at the rules of your chosen City of Winchester holiday home before making a booking.

How long can I rent a holiday home in City of Winchester for?

The amount of time you can rent a City of Winchester holiday home for varies depending on the property. Just put in your dates of travel to view options offering longer term stays. They feature all you need to make your extended getaway more comfortable like kitchens and yards. Some holiday homes might also offer weekly or monthly discounted prices, so you can have a longer stay for less.

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