Winchester holiday lettings

We found 616 holiday rentals — enter your dates for availability

Discover a selection of 37 homes, 40 apartments and other holiday rentals in Winchester that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday rentals have the best amenities for spending time at your holiday home, such as Wi-Fi and cable TV. Whatever you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • 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

Historical Winchester will entice you

Take a holiday to Winchester and enjoy the area's cathedral, history and museums. Well known for its gardens, monuments and shopping, this welcoming city won't disappoint. Southampton Cruise Terminal and Paultons Family Theme Park - Home of Peppa Pig World are just a couple of the must-see attractions in the area. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Winchester

Are you searching for attractions to visit in the city? Venture out of your cosy holiday rental and experience everything that Winchester has to offer. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Paultons Family Theme Park - Home of Peppa Pig World (13 mi / 21 km)
  • Marwell Zoo (4.8 mi / 7.7 km)
  • The Common (10 mi / 16.1 km)
  • Leisure World (11.8 mi / 18.9 km)
  • New Forest Wildlife Park (14.5 mi / 23.4 km)
  • Thruxton Motorsport Centre (16.3 mi / 26.3 km)

Exploring the gardens and other natural features in Winchester

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Winchester is a great spot to appreciate mother nature. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • New Forest National Park (19.6 mi / 31.5 km)
  • Avington Park (3.3 mi / 5.3 km)
  • Mayflower Park (12 mi / 19.3 km)
  • Calshot Beach (16.9 mi / 27.1 km)
  • Exbury Gardens and Steam Railway (18.3 mi / 29.4 km)
  • Lepe Beach (19.1 mi / 30.8 km)

Transport to and around Winchester

The nearest airport is in Southampton (SOU), located 7.9 mi (12.6 km) from the city centre. If you can't find a flight that's convenient for your trip, you might consider flying into Farnborough (FAB), which is 27.7 mi (44.6 km) away.

If you prefer to travel by train, Winchester Station, Winchester Shawford Station and Winchester Micheldever Station are the main stations that serve the city.

Frequently asked questions

What is the best area to stay in Winchester when booking a holiday rental?
One of the more in-demand neighbourhoods to book a holiday rental in Winchester is Sutton Scotney. Discover your dream stay with Vrbo and experience this area just like a local.
What is the most popular type of holiday rental accommodation in Winchester?
The most desirable types of holiday rentals in Winchester are apartments. After something a little different? Vrbo has a variety of options to match the diverse needs of our guests, so you’ll see holiday properties in lots of sizes and shapes. The ideal fit is waiting for you — get yours today.
How much does it cost to rent a holiday rental in Winchester?
A range of factors influence how much you’ll pay for a holiday rental in Winchester, such as the season, type of property and length of stay. Still, all Vrbo homes have one thing in common — unbeatable value. Simply add your travel dates to find your ideal fit.
How much does it cost to rent a beach house in Winchester?
Prices for beach houses in Winchester vary depending on the style and size of the property and time of year you’re travelling. All you need to do is enter your travel dates into Vrbo and the number of guests to see available options and prices. From there you can use our filters to narrow your search results by ratings, amenities, nearby activities and more.
Are there pet-friendly holiday rentals in Winchester?
With 47 holiday rentals that allow pets, your furry friend can join you on your Winchester getaway. Use our filter tool to browse our pet-friendly holiday rentals and find a stay that’s pawfect on Vrbo.
What are popular rental amenities in Winchester?
The most popular rental amenities people look for in Winchester include tennis, a nearby river and a fireplace. Whether you’re holidaying with family, your besties or even pets, Vrbo holiday properties provide the best amenities for hanging out with the people you cherish the most.
Are there large group holiday rentals in Winchester?
With 11 Winchester holiday rentals that can host five or more people, you can bring a few extra pals or family members along. Whether you’re planning a casual gathering or a birthday party, we’ll help you find a comfortable space to match the occasion.
Are there holiday rentals in Winchester that welcome kids?
Gather your whole family for the adventure of a lifetime in Winchester at one of our 47 family-friendly holiday homes. A lot of these stays come with conveniences that are suitable for getaways with children, including full kitchens, multiple bedrooms and outdoor spaces. Simply check the “Properties good for families” filter box and select your favourite.
What are the top attractions for families in Winchester?
Keep the kids occupied at these top family-friendly attractions in Winchester:

  • Marwell Zoo
  • Winchester Science Centre and Planetarium
  • Great Hall

Are there one-bedroom holiday rentals in Winchester?
Yes, you’ll find 16 one-bedroom properties in Winchester to pick from. A one-bedroom holiday property is a great option if it’s just you and your sweetheart or if you’re travelling alone. Add in more privacy, convenience and space compared to a standard hotel, and you’ve got the makings of an unforgettable getaway.
Can I find two-bedroom holiday rentals in Winchester?
Gather your nearest and dearest and enjoy a relaxing escape in one of the 20 two-bedroom holiday homes Winchester has to offer.
Are there holiday rentals with WiFi in Winchester?
Winchester has 13 holiday rentals with WiFi, so you can stay connected while on holiday. Simply check the “WiFi” box in our handy search filter to find the perfect property. From streaming movie blockbusters to checking emails, these Vrbo homes will keep you online.
How old do you have to be to rent a holiday rental in Winchester?
The age limit can differ across properties on Vrbo, so double-check the rules of the holiday home in Winchester you want. But usually, it’s 16, 18 or 21.
How long can I rent a holiday rental in Winchester for?
It’s up to the Winchester property. To browse available options offering extended stays, simply enter your travel dates and number of people into Vrbo’s search page. You can enjoy having the place to yourself, along with home comforts such as air conditioning, a kitchen and a yard where the kids can run and play. Keep an eye out for long-term stays that offer discounted weekly or monthly prices.

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