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Winchester holiday lettings

We found 6,917 holiday rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 46 homes, 16 apartments and other holiday rentals in Winchester that are perfect for your trip. Whether you're travelling with a group or just with your pet, holiday rentals have the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a hot tub. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Find spaces that suit your style

  • Peace of mind
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  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Frequently asked questions

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

The most in-demand types of holiday rentals in Winchester are houses. After something a little different? Vrbo has plenty of options to match the unique needs of our guests, so you'll see holiday properties in loads of shapes and sizes. The perfect home away from home is waiting for you — get yours today.

How much does it cost to rent a holiday rental in Winchester?

A range of things determine what you'll pay for your holiday rental in Winchester, including the time of year, length of stay and property type. However, all of our holiday homes have something in common — excellent value. Just add your travel dates to find your ideal match.

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

The average price for a holiday home close to the beach in Winchester depends on when you'll be there and the size and style of property you're searching for. You can quickly and easily find prices on Vrbo by entering your destination and preferred travel dates. Then make use of the filter tool to pick the number of bedrooms and amenities that you need, like air conditioning, a pool and WiFi.

Are there pet-friendly holiday rentals in Winchester?

Pack a bone and a squeezy toy for the pooch in your life because Winchester has 79 properties that throw out the welcome mat to doggie guests. Let your four-legged friend join in on the family trip at one of our pet-friendly holiday rentals on Vrbo. Simply enter your travel dates and destination, then check our "Pets allowed" filter box.

Can I rent a house with a pool in Winchester?

Mark the "pool" box in our filter tool and pick from 57 houses with private pools in Winchester on Vrbo. Morning soak, afternoon splash or midnight swim? Leisure time is up to you when your holiday property boasts its own swimming pool.

What are popular rental amenities in Winchester?

The most popular rental amenities people are looking for in Winchester include an electric car charging station, nearby museums and a barbecue grill. Whether you're on the road with pals, family or even pets, Vrbo holiday rentals come with the best amenities for starting a new adventure with the people who matter most.

Are there large group holiday rentals in Winchester?

With 12 holiday rentals that can host 10 or more guests in Winchester, there's no need to leave anyone off your guest list. From fun family holidays to events like weddings and birthday parties, Vrbo can help you find a large group rental to suit the occasion.

Are there holiday rentals in Winchester that welcome kids?

Winchester has 73 family-friendly holiday homes. And finding a stay that welcomes kids is easy with our "Properties good for families" filter. On top of having the entire place to yourselves, you'll also get access to amenities and perks like multiple bedrooms, full kitchens and yards.

What are the top attractions for families in Winchester?

Keeping the kids entertained during your stay in Winchester is a snap with these leading family-friendly attractions:

  • LINQ Promenade
  • Shark Reef at Mandalay Bay
  • High Roller

Are there one-bedroom holiday rentals in Winchester?

Yes, you'll find 28 one-bedroom properties in Winchester to pick from. A one-bedroom holiday home is an excellent option if it's just you and your sweetheart or if you're holidaying alone. Add in more privacy, space and convenience than a regular hotel, and you're bound to have a getaway to remember.

Can I find two-bedroom holiday rentals in Winchester?

Winchester has 19 two-bedroom holiday properties to pick from. Go for a holiday home with all the privacy and space you need at a fantastic price on Vrbo.

Are there holiday rentals with WiFi in Winchester?

You'll have a choice of 27 holiday rentals with WiFi in Winchester. If you want to disconnect from the world on your break, but still want to be connected to the web, these properties are just what you need. Narrow your search by applying the WiFi filter on Vrbo.

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