Winchester vacation rentals

Mon 5/6
Tue 5/7

Search hundreds of travel sites at once for vacation home deals in Winchester

...and more

Let KAYAK do the searching

Save on your next stay

Search and compare hundreds of travel sites at once for vacation rentals in Winchester

We’re completely free to use – no hidden charges or fees

Best Winchester vacation rentals

Most recommended vacation rentals in Winchester

Show all
Two Bare Feet - Winchester - Living room
Two Bare Feet
9.3 Wonderful
$149+
$149+
Parking
Free Wi-Fi
South Winchester Lodges - Winchester - Bedroom
South Winchester Lodges
9.3 Wonderful
$392+
$392+
Parking
Free Wi-Fi
Pet friendly
Station Rooms
7.9 Good
$95+
$95+
Free Wi-Fi
Pet friendly
Bull Farm Studios
8.5 Very good
$77+
$77+
Parking
Free Wi-Fi
61
7.5 Good
$73+
$73+
Free Wi-Fi
Winchester Apartments
8.1 Very good
$129+
$129+
Parking
Free Wi-Fi
Paddock View
8.4 Very good
$127+
$127+
Parking
Free Wi-Fi
Pet friendly

Good to know

Low season

October

High season

November

Average price (weeknight)

$151

Average price (weekend night)

$266
Cheapest month to stay with an average 56% drop in price.
Most expensive month to stay with an average 84% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

When to book a vacation rental in Winchester

Price per night / rental. Prices are not fixed and may vary with time.
Average nightly price per month
Average nightly price

Top tips for finding Winchester vacation rental deals

  • History lovers will find themselves close to some of the major attractions if they look for Winchester holiday rentals that are in the city centre. For example Two Bare Feet is located only a short distance from Winchester Cathedral, a medieval Anglican building with a Norman Crypt.
  • If you want to travel to other nearby locations, you should look for Winchester holiday rentals that are close to the station. For example, Station Room is located near to Winchester Train Station. From here, you can get to cities like Southampton and London with ease.
  • Food lovers wanting to enjoy some of the best restaurants should look for Winchester holiday rentals that are located in the centre of the city, where many of the top eateries are. For instance The Loft Winchester is only a short walk from many popular establishments.
  • If you want to practise your swing whilst you’re on holiday you should look for Winchester holiday homes that are to the north of the city, where some of the best golf courses are. For example, Specious Apt. Winchester is only a short drive to Winchester Golf Academy.
  • Football lovers should look for accommodation that’s near to Southampton, where some leading clubs are based. For example Superb Brand New Southampton City Apartments is only a short walk from St Mary’s Stadium, where Southampton Football Club play.
  • Vacation rentals in Winchester are around 51% more expensive than hotels on average. Search here to compare prices for all accommodation types in Winchester.
  • The best vacation rental properties in Winchester are Hang Your Hat (9.8, 103 reviews), The Sky Penthouse (9.8, 40), and 4 Bed City House with Private Garden and Parking (9.7, 33), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Winchester, you should consider visiting during the low season. The cheapest vacation homes in Winchester can be found in October and March.
  • The cheapest night for renting a vacation home in Winchester is Saturday. In contrast, the most expensive is Friday.
  • Book your Winchester vacation rental more than 90 days before your stay begins to get the best price.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Winchester for 4 days.

FAQs when booking a vacation home in Winchester

  • How much is a vacation rental for a week in Winchester?

    The average price for a weekly Winchester vacation rental found by KAYAK users in the last 2 weeks is $2,492.

  • How much is a vacation rental for a month in Winchester?

    The average price for a monthly Winchester vacation rental found by KAYAK users in the last 2 weeks is $10,681.

  • What types of vacation rentals are available in Winchester?

    There are loads of different property types that you can make your vacation home in Winchester. You’ll find lodges, apartments, houses, cottages and homestays.

  • What are some of the most-loved vacation rentals available in Winchester?

    If you’re looking for something special, the vacation rental most loved by KAYAK users is South Winchester Lodges.

  • Are there any pet-friendly vacation rentals in Winchester?

    There are a number of dog and pet-friendly Winchester vacation rentals, with around 19% allowing you to bring your pet along with you.

  • How much is a vacation rental in Winchester?

    KAYAK users have found vacation rentals in Winchester for as cheap as $77 in the last 3 days. The average price is $356.

  • How can I find vacation rentals near me in Winchester?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

  • Where is best to stay for parking?

    If you want to hire a car in Winchester, or should you plan to hire one upon arrival, you should search for holiday rentals that provide parking. For instance The Barrel Room offers free parking to its guests. The parking is also private, so you will have peace of mind that your car is safe.

  • What are the benefits of having a kitchen in a rental property?

    Having a self-catered facility provides you with the freedom to eat in when you please, which is helpful if you’re travelling on a budget. For example Mulberry Barn - Self Contained – offers facilities like an oven and a stove top, so you can cook as much as you like. There are also supermarkets only a short drive away, where you can get fresh ingredients for each day.

  • Where is best to stay to be close to the airport?

    For those that have an early flight to catch, or if you’re in Winchester on business, it’s a good idea to stay close to the terminal building. For instance, The Elizabeth House Apartment is about an 11min drive from Southampton Airport (SOU). It’s also around a 21min drive to Winchester, so it’s conveniently situated.

  • Are there rentals that are suitable for disabled guests?

    If you’re disabled or have mobility limitations then you should look for holiday homes that are accessible. For instance Lodge at Solent has disabled access and an entire unit that is located on the ground floor. This room is also wheelchair accessible. Inside the room there is a roll-in shower, shower chair, lowered sink and toilet with grab rails for your convenience.

Where to stay in Winchester?

Our map will help you find the perfect place to stay in Winchester by showing you the exact location of each vacation rental.