Holiday rentals in Winchester

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Top-rated holiday rentals in Winchester

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Farm stay in Headbourne Worthy
A Unique Farm Retreat
There’s something magical about The Granary. Set in acres of farmland with spectacular sunrises and sunsets, The Granary brims with rustic charm. A dreamy hideaway with an outdoor copper bath and wood fired hot tub. An idyllic get-away-from-it-all yet only 3 miles to historic Winchester. Soak amid hot water, steam and fresh air surrounded by nature and birdsong, enjoy magnificent sunsets from the ‘Sundowner’ or cosy up toasting marshmallows over the fire pit - a perfect escape to unwind.
30 Sep – 7 Oct
$302 SGD per night
5.0 out of 5 average rating, 224 reviews
Guest favourite
Flat in Hampshire
Romantic, artist’s flat, superb central location.
Romantic, bow-fronted, ground floor Regency property with lots of character. Well-appointed but down to earth. Directly opposite the famous King Alfred's statue in the centre of town: 1 minute walk to the river, 1 minute to city centre shops, 3 mins to Winchester Cathedral, 15 mins to train station. Kitchen opens into small pretty garden, then onto quiet cul-de sac for parking (permit provided- parking in the cul-de-sac not guaranteed but there are plenty of streets within the permit zones).
13–20 Jun
$194 SGD per night
4.95 out of 5 average rating, 170 reviews
Guest favourite
Apartment in Hampshire
Lovely 1 bedroom apartment with private parking
Lovely 1st floor 1 bedroom apartment with private entrance and secure free parking. Only 200m from the railway station and a 10 minute walk to the City centre. Immaculately decorated throughout. A fully equipped kitchen with welcome pack. 200Mbit WiFi. SmartTV. Gas central heating. King size bed with 100% cotton duvet cover. The pillows and duvet are duck feather and down. A selection of white fluffy towels. Iron, ironing board and hairdryer. 100m from coffee shops and a pizza restaurant.
2–9 Jun
$188 SGD per night
4.96 out of 5 average rating, 105 reviews

Popular amenities for Winchester holiday rentals

Stay near Winchester's top sights

The Great Hall55 locals recommend
Sainsbury's7 locals recommend
Winchester Christmas Market11 locals recommend
St Catherine's Hill55 locals recommend
Theatre Royal Winchester41 locals recommend
The Old Vine21 locals recommend

Other great holiday rentals in Winchester

Guest favourite
Guest house in Sparsholt
Rural retreat very near Winchester
1–8 Jun
$151 SGD per night
4.96 out of 5 average rating, 455 reviews
Guest favourite
Guest house in Winchester
Water Meadows Lodge beside Winchester South Downs
5–12 Nov
$124 SGD per night
4.95 out of 5 average rating, 260 reviews
Guest favourite
Cottage in Hampshire
Cosy country cottage with chalk stream charm
9–16 Jul
$216 SGD per night
5.0 out of 5 average rating, 169 reviews
Guest favourite
Home in Winchester
Martyr Worthy Home with a View
7–14 Nov
$199 SGD per night
4.99 out of 5 average rating, 241 reviews
Guest favourite
Guest suite in Ovington
Luxury annexe near the River Itchen & Alresford
13–20 May
$125 SGD per night
4.98 out of 5 average rating, 127 reviews
Guest favourite
Hut in Winchester
Nature’s Nook Cosy Couples Woodland Cabin Hursley
9–16 Apr
$240 SGD per night
5.0 out of 5 average rating, 151 reviews
Guest favourite
Flat in Winchester
City Apartment
28 Jul – 4 Aug
$232 SGD per night
4.99 out of 5 average rating, 116 reviews
Guest favourite
Guest house in Hampshire
The Lodge Winchester
6–13 Aug
$200 SGD per night
4.97 out of 5 average rating, 145 reviews
Guest favourite
Apartment in Hampshire
Spacious Central Winchester 1 Bedroom Flat
30 Dec – 6 Jan
$130 SGD per night
5.0 out of 5 average rating, 26 reviews
Guest favourite
Flat in Hampshire
Flat in central Winchester
30 Aug – 6 Sep
$150 SGD per night
4.86 out of 5 average rating, 22 reviews
Guest favourite
Apartment in Hampshire
Bright Bijou Studio in Central Winchester
8–15 Jun
$153 SGD per night
4.93 out of 5 average rating, 89 reviews
Guest favourite
Townhouse in Hampshire
St Michael's Hall, City Centre
24–31 Oct
$257 SGD per night
4.98 out of 5 average rating, 64 reviews

Quick stats about holiday rentals in Winchester

Total rentals

310 properties

Wifi availability

300 properties include access to wifi

Rentals with dedicated workspaces

120 properties have a dedicated workspace

Pet-friendly rentals

80 properties allow pets

Family-friendly rentals

150 properties are a good fit for families

Total number of reviews

16K reviews

Destinations to explore

  1. Airbnb
  2. United Kingdom
  3. England
  4. Hampshire
  5. Winchester