Vacation Rentals in City of Winchester

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Our top choices for City of Winchester vacation rentals

Chalet, Garden View | Free WiFi
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 ￥19,272
￥29,455 total
includes taxes & fees
Jan 2 - Jan 3, 2026
The Hugo Stable- Cozy get away
Apartment, Garden View | Free WiFi
The Riley Stable- Cozy Getaway

The Riley Stable- Cozy Getaway

The Riley Stable- Cozy Getaway
2.0 star property
Waterlooville
The price is ￥19,715
￥29,987 total
includes taxes & fees
Dec 26 - Dec 27
The Riley Stable- Cozy Getaway
Apartment, 1 Bedroom, Patio, Garden View | Living area | 42-inch Smart TV with digital channels, Netflix, streaming services
Rudley Ranch

Rudley Ranch

Rudley Ranch
2.5 star property
Waterlooville
The price is ￥22,118
￥32,861 total
includes taxes & fees
Jan 8 - Jan 9, 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 ￥15,166
￥18,536 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Aethelred Annexe - New Build with Full Amenities
Terrace/patio
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 ￥34,124
￥45,078 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Cosy A-Frame cabin nestled in the chalk steams of Hampshire
Interior
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 ￥22,110
￥32,237 total
includes taxes & fees
Dec 28 - Dec 29
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 ￥15,656
￥15,656 total
includes taxes & fees
Jan 2 - Jan 3, 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 ￥18,958
￥22,328 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Garden room, central Winchester
Interior
The Box - Oasis Farm

The Box - Oasis Farm

The Box - Oasis Farm
Fareham
The price is ￥39,812
￥39,812 total
includes taxes & fees
Jan 8 - Jan 9, 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 ￥56,084
￥67,301 total
includes taxes & fees
Dec 31 - Jan 1, 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 ￥84,284
￥101,141 total
includes taxes & fees
Dec 28 - Dec 29
Squirrel's Leap
Interior
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 ￥95,875
￥95,875 total
includes taxes & fees
Jan 24 - Jan 25, 2026
The Stables, Wickham - a barn conversion that sleeps 2 guests in 1 bedroom
4 bedrooms, iron/ironing board, free WiFi
Piping House 4bedroom

Piping House 4bedroom

Piping House 4bedroom
Colden Common
The price is ￥56,242
￥60,244 total
includes taxes & fees
Dec 26 - Dec 27
Piping House 4bedroom
Dining
Piping Green 4Bedroom House

Piping Green 4Bedroom House

Piping Green 4Bedroom House
Colden Common
The price is ￥60,034
￥64,036 total
includes taxes & fees
Dec 26 - Dec 27
Piping Green 4Bedroom House
Dining
The Old Post Office

The Old Post Office

The Old Post Office
Southampton
The price is ￥61,087
￥64,036 total
includes taxes & fees
Jan 8 - Jan 9, 2026
The Old Post Office
Interior
Birdsong Mansion sleeps 12 Twyford Winchester

Birdsong Mansion sleeps 12 Twyford Winchester

Birdsong Mansion sleeps 12 Twyford Winchester
Winchester
The price is ￥210,012
￥212,961 total
includes taxes & fees
Dec 26 - Dec 27
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 ￥165,356
￥168,305 total
includes taxes & fees
Dec 26 - Dec 27
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 ￥20,128
￥20,128 total
includes taxes & fees
Jan 2 - Jan 3, 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 ￥17,802
￥17,802 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Sunday Winchester Wessex Cathedral Hotel | Classic
Outdoor dining
Coppice Hill House

Coppice Hill House

Coppice Hill House
3.0 star property
Southampton
The price is ￥213,399
￥256,079 total
includes taxes & fees
Jan 2 - Jan 3, 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

Macdonald Botley Park Hotel & Spa

Macdonald Botley Park Hotel & Spa

10/10 Excellent
"Very comfortable and clean"
Deji 1-night trip
Posted 4 days ago
Macdonald Botley Park Hotel & Spa

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