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Winchester vacation rentals

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Booking Insights
Recommended by KAYAK

Best Winchester vacation rentals

These are the best prices for Oct 10 - 11.
Second Nature Southampton - Southampton - Lounge
Second Nature Southampton
City Centre
8.7Very good(1834)
Apartment
$174+
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2 bedroom accommodation in Chilworth, near Southampton - Southampton - Living room
2 bedroom accommodation in Chilworth, near Southampton
Southampton, ENG, United Kingdom
9.3Wonderful(23)
Cottage
$136+
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Shirley Apartments, Cozy Studio, 10 Min Drive to City Centre and Cruise Ship Terminals - Southampton - Bedroom
Shirley Apartments, Cozy Studio, 10 Min Drive to City Centre and Cruise Ship Terminals
Redbridge
8.2Very good(105)
Apartment
$140+
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Old Victory House Homestay - Portsmouth - Bathroom
Old Victory House Homestay
Portsmouth, ENG, United Kingdom
6.9Okay(808)
Homestay
$90+
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Orchard Point - Southampton - Bedroom
Orchard Point
City Centre
8.1Very good(52)
Apartment
$201+
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Oxford Street Grand Apartment- Free Even - Southampton - Bedroom
Oxford Street Grand Apartment- Free Even
City Centre
8.7Very good(28)
Apartment
$265+
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Dellside Apartments - Southampton
Dellside Apartments
The Polygon
8.6Very good(30)
Apartment
$317+
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Modern 2BR Retreat in Southampton - Balcony, Free parking & Wifi - Southampton
Modern 2BR Retreat in Southampton - Balcony, Free parking & Wifi
Woolston
9.3Wonderful(3)
House
$534+
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Holly Hill Apartments - Southampton
Holly Hill Apartments
Southampton, ENG, United Kingdom
10Wonderful(78)
Apartment
$122+
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Lakeside: Argosy 3bed house 2bath parking M27 J5 Southampton Airport sleeps 6 - Southampton
Lakeside: Argosy 3bed house 2bath parking M27 J5 Southampton Airport sleeps 6
Southampton, ENG, United Kingdom
9.0Wonderful(2)
House
$472+
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Rabbit's Warren - Southampton
Rabbit's Warren
Southampton, ENG, United Kingdom
9.0Wonderful(4)
House
$633+
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Home accommodation - Southampton
Home accommodation
Millbrook
8.5Very good(371)
Homestay
$73+
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Number 10 service apartment - Danes - Southampton
Number 10 service apartment - Danes
Southampton, ENG, United Kingdom
8.5Very good(98)
Apartment
$130+
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Darwin road guest house room 2 - Southampton
Darwin road guest house room 2
Southampton, ENG, United Kingdom
3.5Poor(54)
Apartment
$45+
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Serene Property Next to Southampton General Hospital - Southampton
Serene Property Next to Southampton General Hospital
Shirley
8.6Very good(93)
Homestay
$80+
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Newly refurbished 1 bed first floor apartment with wifi - Portsmouth
Newly refurbished 1 bed first floor apartment with wifi
Portsmouth, ENG, United Kingdom
8.8Very good(138)
Apartment
$92+
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Booking Insights

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.

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

Sunday offers the lowest rates in Winchester, with an average nightly price of $109. The highest prices are found on Thursday, with average rates at $429.

How early should you book a vacation rental in Winchester?

Book at least 24 days before your stay begins to get the best price for your Winchester vacation rental.

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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

June
July
$305
$432
Cheapest month to stay with an average 77% drop in price.
Most expensive month to stay with an average 68% 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 69% cheaper than hotels on average. Search here to compare prices for all accommodation types in Winchester.
  • The best vacation rental properties in Winchester are Holly Hill Apartments (10.0, 78 reviews), Special seafront apartment (9.6, 81), and St Helens House (9.4, 95), based on ratings and reviews from real travelers.
  • Downtown is the neighborhood in Winchester with the most affordable vacation rental properties (124 properties with an average price of $246 per night). Settle Winchester, 61, and Contemporary apartment in central Winchester 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 June and October.
  • The cheapest night for renting a vacation home in Winchester is Monday. In contrast, the most expensive is Thursday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Winchester for 2 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 $2,100.

  • 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 $8,998.

  • 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, cabins, campgrounds, cottages, houses, homestays, hotels, lodges and luxury tents.

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

    There are many types of properties available for Winchester vacation rentals. If you’re looking for something special, vacation rentals most loved by KAYAK users are Norton Park Hotel and 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 16% 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 $446. Search here for similar prices

  • How much is a vacation rental in Winchester for this weekend?

    In the last 72 hours, users have found Winchester vacation rentals for this weekend for as low as $312 per night. 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.

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.

More options for your stay in Winchester

Complete your trip to Winchester

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