Winchester vacation rentals

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Best Winchester vacation rentals

Most recommended vacation rentals in Winchester

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South Winchester Lodges - Winchester - Bedroom
South Winchester Lodges
Winchester, ENG, United Kingdom
9.2Wonderful(296)
Parking
Free Wi-Fi
Pet friendly
Bull Farm Studios - Winchester - Bedroom
Bull Farm Studios
Winchester, ENG, United Kingdom
8.4Very good(34)
Parking
Free Wi-Fi
Winchester Apartments - Winchester
Winchester Apartments
Winchester, ENG, United Kingdom
7.8Good(934)
Parking
Free Wi-Fi
Bell tent glamping at Marwell Resort - Winchester
Parking
Pet friendly
Watley Farm - Winchester
Watley Farm
Winchester, ENG, United Kingdom
8.2Very good(120)
Parking
Free Wi-Fi
Pet friendly
Idyllic Studio Flat - Winchester
Idyllic Studio Flat
Winchester, ENG, United Kingdom
9.1Wonderful(115)
Parking
Free Wi-Fi
Paddock View - Winchester
Paddock View
Winchester, ENG, United Kingdom
8.8Very good(109)
Parking
Free Wi-Fi
Pet friendly

KAYAK’s insights for vacation rentals in Winchester

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Winchester with confidence.

Which month has the cheapest vacation rental rates in Winchester?

Vacation rentals are cheapest in Winchester in December, with average rates of $85. In comparison, June is the most expensive month, with prices at $316.

What is the cheapest day of the week to book a vacation rental in Winchester?

Wednesday offers the lowest rates in Winchester, with an average nightly price of $72. The highest prices are found on Friday, with average rates at $171.

Good to know

Low season

March

High season

June

Average price (weeknight)

$108

Average price (weekend night)

$133
Cheapest month to stay with an average 40% drop in price.
Most expensive month to stay with an average 127% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's 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 9% 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 The Nestle House (9.8, 24 reviews), The Sky Penthouse (9.8, 48), and City Apartment (9.6, 132), based on ratings and reviews from real travelers.
  • Downtown is the neighborhood in Winchester with the most affordable vacation rental properties (137 properties with an average price of $95 per night). 61, Two Bare Feet, and Settle in Winchester - Stylish Self Check-In Rooms are the most popular rental properties in Downtown.
  • 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 March and December.
  • The cheapest night for renting a vacation home in Winchester is Wednesday. In contrast, the most expensive is Monday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Winchester for 6 days.
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FAQs when booking a vacation home in Winchester

  • 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 apartments, boats, campgrounds, houses, homestays, lodges and villas.

  • 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 18% allowing you to bring your pet along with you.

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

    In the last 72 hours, users have found Winchester vacation rentals for tonight for as low as $135. Search here for similar prices

  • 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.

See more FAQs

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.

Everything you need to know for your stay in Winchester

Winchester vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Winchester. Find cheap vacation homes to rent in Winchester. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Winchester that suits you best.

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