Holiday Rentals in City of Winchester

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Top Cities in City of Winchester

Southampton showing heritage elements, a castle and heritage architecture
Holiday RentalsHoliday Rentals

Southampton

Southampton

Our top choices for City of Winchester holiday rentals

Chalet, Garden View
The Hugo Stable- Cozy get away

The Hugo Stable- Cozy get away

The Hugo Stable- Cozy get away
2.0 star property
Waterlooville
The price is €164
includes taxes & fees
31 Dec - 1 Jan 2026
The Hugo Stable- Cozy get away
Apartment, Garden View
The Riley Stable- Cozy Getaway

The Riley Stable- Cozy Getaway

The Riley Stable- Cozy Getaway
2.0 star property
Waterlooville
The price is €164
includes taxes & fees
31 Dec - 1 Jan 2026
The Riley Stable- Cozy Getaway
Apartment, 1 Bedroom, Patio, Garden View | Living area
Rudley Ranch

Rudley Ranch

Rudley Ranch
2.5 star property
Waterlooville
The price is €179
includes taxes & fees
5 Jan - 6 Jan 2026
Rudley Ranch
Interior
Aethelred Annexe - New Build with Full Amenities

Aethelred Annexe - New Build with Full Amenities

Aethelred Annexe - New Build with Full Amenities
2.0 star property
Winchester
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
2 bedrooms, WiFi, bed sheets
Cosy A-Frame cabin nestled in the chalk steams of Hampshire

Cosy A-Frame cabin nestled in the chalk steams of Hampshire

Cosy A-Frame cabin nestled in the chalk steams of Hampshire
Winchester
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
Private kitchen
Beautiful Hampshire at Mulberry Barn Annexe

Beautiful Hampshire at Mulberry Barn Annexe

Beautiful Hampshire at Mulberry Barn Annexe
2.0 star property
Micheldever
The price is €180
includes taxes & fees
28 Dec - 29 Dec
Beautiful Hampshire at Mulberry Barn Annexe
Interior
Sunday Winchester Wessex Cathedral Hotel | Compact

Sunday Winchester Wessex Cathedral Hotel | Compact

Sunday Winchester Wessex Cathedral Hotel | Compact
Southampton
The price is €85
includes taxes & fees
2 Jan - 3 Jan 2026
Sunday Winchester Wessex Cathedral Hotel | Compact
1 bedroom, iron/ironing board, WiFi, bed sheets
Garden room, central Winchester

Garden room, central Winchester

Garden room, central Winchester
Winchester
The price is €126
includes taxes & fees
14 Jan - 15 Jan 2026
Garden room, central Winchester
Private kitchen
The Box - Oasis Farm

The Box - Oasis Farm

The Box - Oasis Farm
Fareham
The price is €217
includes taxes & fees
4 Jan - 5 Jan 2026
The Box - Oasis Farm
House (3 Bedrooms) | Terrace/patio
Peaceful Elevated Residential Area - Walk to City

Peaceful Elevated Residential Area - Walk to City

Peaceful Elevated Residential Area - Walk to City
5.0 star property
Winchester
The price is €365
includes taxes & fees
31 Dec - 1 Jan 2026
Peaceful Elevated Residential Area - Walk to City
Dining
Squirrel's Leap

Squirrel's Leap

Squirrel's Leap
3.0 star property
Winchester
The price is €550
includes taxes & fees
2 Jan - 3 Jan 2026
Squirrel's Leap
Fridge, microwave, oven, stovetop
The Stables, Wickham - a barn conversion that sleeps 2 guests in 1 bedroom

The Stables, Wickham - a barn conversion that sleeps 2 guests in 1 bedroom

The Stables, Wickham - a barn conversion that sleeps 2 guests in 1 bedroom
Shedfield
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
Smart TV
Piping House 4bedroom

Piping House 4bedroom

Piping House 4bedroom
Colden Common
The price is €328
includes taxes & fees
31 Dec - 1 Jan 2026
Piping House 4bedroom
Private kitchen
Piping Green 4Bedroom House

Piping Green 4Bedroom House

Piping Green 4Bedroom House
Colden Common
The price is €348
includes taxes & fees
31 Dec - 1 Jan 2026
Piping Green 4Bedroom House
2 bedrooms, desk, iron/ironing board, free WiFi
A 2 bedroom apartment in the heart of beautiful Bishops Waltham!

A 2 bedroom apartment in the heart of beautiful Bishops Waltham!

A 2 bedroom apartment in the heart of beautiful Bishops Waltham!
Southampton
The price is €348
includes taxes & fees
31 Dec - 1 Jan 2026
A 2 bedroom apartment in the heart of beautiful Bishops Waltham!
Interior
Birdsong Mansion sleeps 12 Twyford Winchester

Birdsong Mansion sleeps 12 Twyford Winchester

Birdsong Mansion sleeps 12 Twyford Winchester
Winchester
The price is €1,158
includes taxes & fees
31 Dec - 1 Jan 2026
Birdsong Mansion sleeps 12 Twyford Winchester
Interior
Birdsong House

Birdsong House

Birdsong House
Winchester
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
Interior
Sunday Winchester Wessex Cathedral Hotel | Twin

Sunday Winchester Wessex Cathedral Hotel | Twin

Sunday Winchester Wessex Cathedral Hotel | Twin
Winchester
The price is €109
includes taxes & fees
2 Jan - 3 Jan 2026
Sunday Winchester Wessex Cathedral Hotel | Twin
Interior
Sunday Winchester Wessex Cathedral Hotel | Classic

Sunday Winchester Wessex Cathedral Hotel | Classic

Sunday Winchester Wessex Cathedral Hotel | Classic
Winchester
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
Outdoor spa tub
Coppice Hill House

Coppice Hill House

Coppice Hill House
3.0 star property
Southampton
The price is €1,392
includes taxes & fees
2 Jan - 3 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

Meon Valley Hotel, Golf & Country Club

Meon Valley Hotel, Golf & Country Club

10/10 Excellent
"Good, quiet and clean room."
Lynn 2-night trip
Posted 1 day ago
Meon Valley Hotel, Golf & Country Club

Find out more about City of Winchester

Holiday Homes in City of Winchester

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