Photo by Michael Uchida

Winchester vacation rentals

We found 6,875 vacation 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 vacation rentals in Winchester that are perfect for your trip. Whether you're traveling with a group or just with your pet, vacation rentals have the amenities you expect for your stay, which might include a fireplace and a washer and dryer. You'll be able to choose a rental for everyone's needs, including places that are non-smoking or accessible.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value
  • A place for everyone
    We stand for diversity, inclusion and families everywhere.
    Learn more

Frequently asked questions

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

The most in-demand types of vacation 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 vacation 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 vacation rental in Winchester?

A range of things determine what you'll pay for your vacation rental in Winchester, including the time of year, length of stay and property type. However, all of our vacation 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 vacation 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 vacation 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 vacation 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 vacation 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 vacation rentals come with the best amenities for starting a new adventure with the people who matter most.

Are there large group vacation rentals in Winchester?

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

Are there vacation rentals in Winchester that welcome kids?

Winchester has 73 family-friendly vacation 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 vacation rentals in Winchester?

Yes, you'll find 28 one-bedroom properties in Winchester to pick from. A one-bedroom vacation home is an excellent option if it's just you and your sweetheart or if you're vacationing 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 vacation rentals in Winchester?

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

Are there vacation rentals with WiFi in Winchester?

You'll have a choice of 27 vacation 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.

More Vacation Rentals ideas

People also search for