Holiday rentals in City of Winchester

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Top-rated holiday rentals in City of Winchester

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

Guest favourite
Bungalow in Eastleigh
One bedroom home.
Relax and make yourself at home in this comfortable bungalow with sunny lounge, fully equiped kitchen/diner and bathroom. Situated in a quiet cul-de-sac in the village of Bishopstoke on the outskirts of Eastleigh. The M27 and M3 motorways and Southampton Airport are just a few miles away. The historic City of Winchester is an easy drive. Whether you are on your way to explore the South West, visiting family or friends or just wanting a short break, we offer a convenient home away from home.
6–13 Sep
$92 SGD per night
4.94 out of 5 average rating, 373 reviews
Guest favourite
Guest house in Hampshire
Beautiful Self Contained Annex in South Downs NP
This brick and flint barn has been converted to a smart modern annex separate to our house. Set in the beautiful village of Meonstoke in the heart of the Meon Valley and the South Downs National Park. Ideal for visitors wanting a little luxury at the end of a day of outdoor pursuits. A really comfortable bed with blackout blinds and ensuite shower room. A spacious living area, with kitchen, dining area & log burning stove. Free wifi. Coffee (Nespresso machine) and tea, bread and jams included.
5–12 May
$112 SGD per night
4.92 out of 5 average rating, 170 reviews
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

Popular amenities for City of Winchester holiday rentals

Stay near City of Winchester's top sights

Marwell Zoo176 locals recommend
Westquay Shopping Centre61 locals recommend
Southampton Common52 locals recommend
Mayflower Theatre91 locals recommend
St Mary's Stadium19 locals recommend
Royal Victoria Country Park49 locals recommend

Other great holiday rentals in City of Winchester

Guest favourite
Flat in Staple Gardens
No.1 The Old Printworks, Winchester
30 Jul – 6 Aug
$210 SGD per night
4.95 out of 5 average rating, 151 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
Guest house in New Alresford
17th century cottage Georgian town
26 Apr – 3 May
$162 SGD per night
4.93 out of 5 average rating, 238 reviews
Guest favourite
Guest house in Shawford
Spacious one bed annex, Shawford, Winchester
1–8 Sep
$119 SGD per night
4.83 out of 5 average rating, 165 reviews
Guest favourite
Guest suite in Hampshire
The Annexe-central Winchester
25 Jun – 2 Jul
$103 SGD per night
4.87 out of 5 average rating, 209 reviews
Guest favourite
Farm stay in Hampshire
Room with a view
9–16 Nov
$94 SGD per night
4.9 out of 5 average rating, 140 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
Loft in Charlecote
Beautiful Apartment in Centre of Winchester
15–22 Aug
$230 SGD per night
4.92 out of 5 average rating, 157 reviews
Guest favourite
Hut in Winchester
The Pigsty
1–8 Oct
$273 SGD per night
4.97 out of 5 average rating, 452 reviews
Guest favourite
Guest house in Winchester
Idyllic Hideaway Ham Green Cottage near Winchester
14–21 Feb
$178 SGD per night
4.97 out of 5 average rating, 456 reviews
Guest favourite
Flat in Compton
The Annexe at Longacre, near Winchester
10–17 Feb
$142 SGD per night
4.98 out of 5 average rating, 223 reviews

Quick stats about holiday rentals in City of Winchester

Total rentals

2.3K properties

Rentals with dedicated workspaces

1.1K properties have a dedicated workspace

Rentals with a pool

40 properties have a pool

Pet-friendly rentals

510 properties allow pets

Family-friendly rentals

870 properties are a good fit for families

Total number of reviews

89K reviews

Destinations to explore

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