Holiday Rentals in City of Winchester

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Top Cities in City of Winchester

Our top choices for City of Winchester holiday rentals

Cabin in Waterlooville

The Hugo Stable- Cozy get away
2.0 star property
The price is €164
includes taxes & fees
31 Dec - 1 Jan 2026
The Hugo Stable- Cozy get away

Cabin in Waterlooville

The Riley Stable- Cozy Getaway
2.0 star property
The price is €164
includes taxes & fees
31 Dec - 1 Jan 2026
The Riley Stable- Cozy Getaway

Cabin in Waterlooville

Rudley Ranch
2.5 star property
The price is €179
includes taxes & fees
5 Jan - 6 Jan 2026
Rudley Ranch
2.0 star property
10.0 out of 10, Exceptional, (1)
"Had a lovely stay at the Aethelred Annexe! Great amenities and an incredibly generous host. It felt very warm and cozy and the bed was super comfy. Great location for a quick drive/ bus into the city centre. Would absolutely recommend."
United States
Andrea W.
The price is €105
includes taxes & fees
4 Jan - 5 Jan 2026
Aethelred Annexe - New Build with Full Amenities
9.4 out of 10, Exceptional, (3)
"Lovely cabin and outside kitchen plus garden. It's my second stay and I enjoyed my stay. Love the garden kitchen,. It's very pretty and relaxing ."
United Kingdom
Nicola H.
The price is €252
includes taxes & fees
5 Jan - 6 Jan 2026
Cosy A-Frame cabin nestled in the chalk steams of Hampshire
2.0 star property
The price is €180
includes taxes & fees
28 Dec - 29 Dec
Beautiful Hampshire at Mulberry Barn Annexe
The price is €85
includes taxes & fees
2 Jan - 3 Jan 2026
Sunday Winchester Wessex Cathedral Hotel | Compact

Apartment in Winchester

Garden room, central Winchester
The price is €126
includes taxes & fees
14 Jan - 15 Jan 2026
Garden room, central Winchester

Cottage in Fareham

The Box - Oasis Farm
The price is €217
includes taxes & fees
4 Jan - 5 Jan 2026
The Box - Oasis Farm
5.0 star property
The price is €365
includes taxes & fees
31 Dec - 1 Jan 2026
Peaceful Elevated Residential Area - Walk to City

Cottage in Winchester

Squirrel's Leap
3.0 star property
The price is €550
includes taxes & fees
2 Jan - 3 Jan 2026
Squirrel's Leap
9.8 out of 10, Exceptional, (10)
"Fabulous place to stay."
United States
CHRISTOPHER S.
The price is €521
includes taxes & fees
13 Jan - 14 Jan 2026
The Stables, Wickham - a barn conversion that sleeps 2 guests in 1 bedroom

Holiday Home in Colden Common

Piping House 4bedroom
The price is €328
includes taxes & fees
31 Dec - 1 Jan 2026
Piping House 4bedroom

Holiday Home in Colden Common

Piping Green 4Bedroom House
The price is €348
includes taxes & fees
31 Dec - 1 Jan 2026
Piping Green 4Bedroom House
The price is €348
includes taxes & fees
31 Dec - 1 Jan 2026
A 2 bedroom apartment in the heart of beautiful Bishops Waltham!
The price is €1,158
includes taxes & fees
31 Dec - 1 Jan 2026
Birdsong Mansion sleeps 12 Twyford Winchester

Holiday Home in Winchester

Birdsong House
10.0 out of 10, Exceptional, (1)
"We had a wonderful stay at Birdsong house. The owner was always available and the house was so cozy and comfortable! Thank you"
United Kingdom
Judith D.
The price is €915
includes taxes & fees
31 Dec - 1 Jan 2026
Birdsong House
The price is €109
includes taxes & fees
2 Jan - 3 Jan 2026
Sunday Winchester Wessex Cathedral Hotel | Twin
6.0 out of 10, (1)
"Carpets and sofa in room were noticeably stained. Otherwise the view was great, bed was comfortable and clean. Staff were very helpful and professional "
Canada
Cathy
The price is €97
includes taxes & fees
2 Jan - 3 Jan 2026
Sunday Winchester Wessex Cathedral Hotel | Classic

Cottage in Southampton

Coppice Hill House
3.0 star property
The price is €1,392
includes taxes & fees
3 Jan - 4 Jan 2026
Coppice Hill House
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top City of Winchester Hotel Reviews

Find out more about City of Winchester

Holiday Homes in City of Winchester

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