We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Winchester Self Catering

Revenue impacts this sort order. Learn more

Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
78 rentals in Winchester.
Hang Your Hat - stylish hideaway in Winchester, holiday rental in Winchester
Hang Your Hat - stylish hideaway in Winchester, holiday rental in Winchester
Hang Your Hat - stylish hideaway in Winchester, holiday rental in Winchester

Hang Your Hat - stylish hideaway in Winchester

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
As seen on
HolidayLettings.co.uk logo
Affiliated with FlipKey
The Old Tractor Barn, Crabwood Cottages, holiday rental in Winchester
The Old Tractor Barn, Crabwood Cottages, holiday rental in Winchester
The Old Tractor Barn, Crabwood Cottages, holiday rental in Winchester

The Old Tractor Barn, Crabwood Cottages

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
As seen on
HolidayLettings.co.uk logo
1 Abbotts Court Mews, holiday rental in Winchester
1 Abbotts Court Mews, holiday rental in Winchester
1 Abbotts Court Mews, holiday rental in Winchester

1 Abbotts Court Mews

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
As seen on
HolidayLettings.co.uk logo
Idyllic Hampshire Hideaway - The Orchard Studio, Sparsholt, holiday rental in Winchester
Idyllic Hampshire Hideaway - The Orchard Studio, Sparsholt, holiday rental in Winchester
Idyllic Hampshire Hideaway - The Orchard Studio, Sparsholt, holiday rental in Winchester

Idyllic Hampshire Hideaway - The Orchard Studio, Sparsholt

Private Room
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
HolidayLettings.co.uk logo
The Hayloft, Crabwood Cottages, holiday rental in Winchester
The Hayloft, Crabwood Cottages, holiday rental in Winchester
The Hayloft, Crabwood Cottages, holiday rental in Winchester

The Hayloft, Crabwood Cottages

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
HolidayLettings.co.uk logo
South House Winchester, holiday rental in Winchester
South House Winchester, holiday rental in Winchester
South House Winchester, holiday rental in Winchester

South House Winchester

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
HolidayLettings.co.uk logo
Luxury 3 bedroom Scandinavian Lodge (without hot tub), holiday rental in Winchester
Luxury 3 bedroom Scandinavian Lodge (without hot tub), holiday rental in Winchester
Luxury 3 bedroom Scandinavian Lodge (without hot tub), holiday rental in Winchester

Luxury 3 bedroom Scandinavian Lodge (without hot tub)

Cabin Holiday Rental
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
HolidayLettings.co.uk logo
City Centre Apartment Winchester with parking provided, holiday rental in Winchester
City Centre Apartment Winchester with parking provided, holiday rental in Winchester
City Centre Apartment Winchester with parking provided, holiday rental in Winchester

City Centre Apartment Winchester with parking provided

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
HolidayLettings.co.uk logo
The Down House Cottage, holiday rental in Winchester
The Down House Cottage, holiday rental in Winchester
The Down House Cottage, holiday rental in Winchester

The Down House Cottage

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
HolidayLettings.co.uk logo
Hang Your Hat - The Cottage, holiday rental in Winchester
Hang Your Hat - The Cottage, holiday rental in Winchester
Hang Your Hat - The Cottage, holiday rental in Winchester

Hang Your Hat - The Cottage

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Luxury 2 Bedroom Scandinavian Lodge (without hot tub), holiday rental in Winchester
Luxury 2 Bedroom Scandinavian Lodge (without hot tub), holiday rental in Winchester
Luxury 2 Bedroom Scandinavian Lodge (without hot tub), holiday rental in Winchester

Luxury 2 Bedroom Scandinavian Lodge (without hot tub)

Cabin Holiday Rental
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
HolidayLettings.co.uk logo
Cosy character cottage in central Winchester, holiday rental in Winchester
Cosy character cottage in central Winchester, holiday rental in Winchester
Cosy character cottage in central Winchester, holiday rental in Winchester

Cosy character cottage in central Winchester

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
HolidayLettings.co.uk logo
Stylish House in Winchester with parking for two cars, holiday rental in Winchester
Stylish House in Winchester with parking for two cars, holiday rental in Winchester
Stylish House in Winchester with parking for two cars, holiday rental in Winchester

Stylish House in Winchester with parking for two cars

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
HolidayLettings.co.uk logo
Contemporary apartment in central Winchester, holiday rental in Winchester
Contemporary apartment in central Winchester, holiday rental in Winchester
Contemporary apartment in central Winchester, holiday rental in Winchester

Contemporary apartment in central Winchester

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
South House offers high comfort self-catering accommodation for up to 6 people,, holiday rental in Winchester
South House offers high comfort self-catering accommodation for up to 6 people,, holiday rental in Winchester
South House offers high comfort self-catering accommodation for up to 6 people,, holiday rental in Winchester

South House offers high comfort self-catering accommodation for up to 6 people,

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Charming 3 bed Thatched Cottage in Rural Village near Stockbridge Winchester, holiday rental in Winchester
Charming 3 bed Thatched Cottage in Rural Village near Stockbridge Winchester, holiday rental in Winchester
Charming 3 bed Thatched Cottage in Rural Village near Stockbridge Winchester, holiday rental in Winchester

Charming 3 bed Thatched Cottage in Rural Village near Stockbridge Winchester

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
HolidayLettings.co.uk logo
Luxury 2 Bedroom Scandinavian Lodge with HOT TUB, holiday rental in Winchester
Luxury 2 Bedroom Scandinavian Lodge with HOT TUB, holiday rental in Winchester
Luxury 2 Bedroom Scandinavian Lodge with HOT TUB, holiday rental in Winchester

Luxury 2 Bedroom Scandinavian Lodge with HOT TUB

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
HolidayLettings.co.uk logo
Charming period cottage quietly located in the centre of Winchester, holiday rental in Winchester
Charming period cottage quietly located in the centre of Winchester, holiday rental in Winchester
Charming period cottage quietly located in the centre of Winchester, holiday rental in Winchester

Charming period cottage quietly located in the centre of Winchester

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Luxury 3 Bedroom, Scandinavian Lodge with HOT TUB , holiday rental in Winchester
Luxury 3 Bedroom, Scandinavian Lodge with HOT TUB , holiday rental in Winchester
Luxury 3 Bedroom, Scandinavian Lodge with HOT TUB , holiday rental in Winchester

Luxury 3 Bedroom, Scandinavian Lodge with HOT TUB

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
HolidayLettings.co.uk logo
Beautiful Apartment in Centre of Winchester with Parking, holiday rental in Winchester
Beautiful Apartment in Centre of Winchester with Parking, holiday rental in Winchester
Beautiful Apartment in Centre of Winchester with Parking, holiday rental in Winchester

Beautiful Apartment in Centre of Winchester with Parking

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
The Loft Winchester., holiday rental in Winchester
The Loft Winchester., holiday rental in Winchester
The Loft Winchester., holiday rental in Winchester

The Loft Winchester.

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Gorgeous Apartment in the heart of Winchester, holiday rental in Winchester
Gorgeous Apartment in the heart of Winchester, holiday rental in Winchester
Gorgeous Apartment in the heart of Winchester, holiday rental in Winchester

Gorgeous Apartment in the heart of Winchester

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Very Stylish contemporary house within the Centre of Winchester, holiday rental in Winchester
Very Stylish contemporary house within the Centre of Winchester, holiday rental in Winchester
Very Stylish contemporary house within the Centre of Winchester, holiday rental in Winchester

Very Stylish contemporary house within the Centre of Winchester

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
City Centre Home With Private Off Road Parking, holiday rental in Winchester
City Centre Home With Private Off Road Parking, holiday rental in Winchester
City Centre Home With Private Off Road Parking, holiday rental in Winchester

City Centre Home With Private Off Road Parking

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
HolidayLettings.co.uk logo
South House - In the centre of Winchester, holiday rental in Winchester
South House - In the centre of Winchester, holiday rental in Winchester
South House - In the centre of Winchester, holiday rental in Winchester

South House - In the centre of Winchester

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
HolidayLettings.co.uk logo
Affiliated with FlipKey
Beautiful and Cosy Apartment in the centre of Winchester, holiday rental in Winchester
Beautiful and Cosy Apartment in the centre of Winchester, holiday rental in Winchester
Beautiful and Cosy Apartment in the centre of Winchester, holiday rental in Winchester

Beautiful and Cosy Apartment in the centre of Winchester

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Right in the heart of Winchester with Castle View, holiday rental in Winchester
Right in the heart of Winchester with Castle View, holiday rental in Winchester
Right in the heart of Winchester with Castle View, holiday rental in Winchester

Right in the heart of Winchester with Castle View

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Peaceful elevated residential area - walk to city, holiday rental in Winchester
Peaceful elevated residential area - walk to city, holiday rental in Winchester
Peaceful elevated residential area - walk to city, holiday rental in Winchester

Peaceful elevated residential area - walk to city

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
No. 79 Tower Street ~ Rapunzel on Tower, holiday rental in Winchester
No. 79 Tower Street ~ Rapunzel on Tower, holiday rental in Winchester
No. 79 Tower Street ~ Rapunzel on Tower, holiday rental in Winchester

No. 79 Tower Street ~ Rapunzel on Tower

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
The Sky Penthouse, City Centre Luxury, holiday rental in Winchester
The Sky Penthouse, City Centre Luxury, holiday rental in Winchester
The Sky Penthouse, City Centre Luxury, holiday rental in Winchester

The Sky Penthouse, City Centre Luxury

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Entire City centre home, exclusive use,  off street private parking, holiday rental in Winchester
Entire City centre home, exclusive use,  off street private parking, holiday rental in Winchester
Entire City centre home, exclusive use,  off street private parking, holiday rental in Winchester

Entire City centre home, exclusive use, off street private parking

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
3 Bedroom, Luxury Scandinavian Lodge, set in woodland, holiday rental in Winchester
3 Bedroom, Luxury Scandinavian Lodge, set in woodland, holiday rental in Winchester
3 Bedroom, Luxury Scandinavian Lodge, set in woodland, holiday rental in Winchester

3 Bedroom, Luxury Scandinavian Lodge, set in woodland

Cabin Holiday Rental
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
HolidayLettings.co.uk logo
Designer's House perfectly, quiet, close to centre, holiday rental in Winchester
Designer's House perfectly, quiet, close to centre, holiday rental in Winchester
Designer's House perfectly, quiet, close to centre, holiday rental in Winchester

Designer's House perfectly, quiet, close to centre

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
No. 81 Tower Street ~ Designers Townhouse, holiday rental in Winchester
No. 81 Tower Street ~ Designers Townhouse, holiday rental in Winchester
No. 81 Tower Street ~ Designers Townhouse, holiday rental in Winchester

No. 81 Tower Street ~ Designers Townhouse

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
As seen on
HolidayLettings.co.uk logo
Meed, holiday rental in Winchester
Meed, holiday rental in Winchester
Meed, holiday rental in Winchester

Meed

Condo/Apartment
0 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
As seen on
HolidayLettings.co.uk logo
2 Bedroom, Luxury Scandinavian Lodge set in woodland, holiday rental in Winchester
2 Bedroom, Luxury Scandinavian Lodge set in woodland, holiday rental in Winchester
2 Bedroom, Luxury Scandinavian Lodge set in woodland, holiday rental in Winchester

2 Bedroom, Luxury Scandinavian Lodge set in woodland

Cabin Holiday Rental
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
HolidayLettings.co.uk logo
Unique Home in the Heart of Winchester Centre, holiday rental in Winchester
Unique Home in the Heart of Winchester Centre, holiday rental in Winchester
Unique Home in the Heart of Winchester Centre, holiday rental in Winchester

Unique Home in the Heart of Winchester Centre

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
HolidayLettings.co.uk logo
Affiliated with FlipKey
Immaculate 4-Bed House in Winchester Free Parking, holiday rental in Winchester
Immaculate 4-Bed House in Winchester Free Parking, holiday rental in Winchester
Immaculate 4-Bed House in Winchester Free Parking, holiday rental in Winchester

Immaculate 4-Bed House in Winchester Free Parking

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
HolidayLettings.co.uk logo
Affiliated with FlipKey
Winchester Cottage Opposite Famous Organic FarmShop - 3 Bedrooms & Garden Office, holiday rental in Winchester
Winchester Cottage Opposite Famous Organic FarmShop - 3 Bedrooms & Garden Office, holiday rental in Winchester
Winchester Cottage Opposite Famous Organic FarmShop - 3 Bedrooms & Garden Office, holiday rental in Winchester

Winchester Cottage Opposite Famous Organic FarmShop - 3 Bedrooms & Garden Office

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
As seen on
HolidayLettings.co.uk logo
Affiliated with FlipKey
Winchester Retreat, holiday rental in Winchester
Winchester Retreat, holiday rental in Winchester
Winchester Retreat, holiday rental in Winchester

Winchester Retreat

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
As seen on
HolidayLettings.co.uk logo
Affiliated with FlipKey
No. 5 Winchester - No. 5 Winchester is a stunning one bedroom mews cottage with, holiday rental in Winchester
No. 5 Winchester - No. 5 Winchester is a stunning one bedroom mews cottage with, holiday rental in Winchester
No. 5 Winchester - No. 5 Winchester is a stunning one bedroom mews cottage with, holiday rental in Winchester

No. 5 Winchester - No. 5 Winchester is a stunning one bedroom mews cottage with

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
HolidayLettings.co.uk logo
A unique property rental in historical Winchester, holiday rental in Winchester
A unique property rental in historical Winchester, holiday rental in Winchester
A unique property rental in historical Winchester, holiday rental in Winchester

A unique property rental in historical Winchester

Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
3 bedroom, Scandinavian Log Cabin, Winchester, holiday rental in Winchester
3 bedroom, Scandinavian Log Cabin, Winchester, holiday rental in Winchester
3 bedroom, Scandinavian Log Cabin, Winchester, holiday rental in Winchester

3 bedroom, Scandinavian Log Cabin, Winchester

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
31 Queens Road Rental - Self-contained Apartment, holiday rental in Winchester
31 Queens Road Rental - Self-contained Apartment, holiday rental in Winchester
31 Queens Road Rental - Self-contained Apartment, holiday rental in Winchester

31 Queens Road Rental - Self-contained Apartment

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Westgate Cottage in the heart of Winchester, holiday rental in Winchester
Westgate Cottage in the heart of Winchester, holiday rental in Winchester
Westgate Cottage in the heart of Winchester, holiday rental in Winchester

Westgate Cottage in the heart of Winchester

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
★The Jewel Of Central Winchester★, holiday rental in Winchester
★The Jewel Of Central Winchester★, holiday rental in Winchester
★The Jewel Of Central Winchester★, holiday rental in Winchester

★The Jewel Of Central Winchester★

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
1 bed Boscobel Apartments free parking, holiday rental in Winchester
1 bed Boscobel Apartments free parking, holiday rental in Winchester
1 bed Boscobel Apartments free parking, holiday rental in Winchester

1 bed Boscobel Apartments free parking

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Escape to Boscobel: Enjoy a Cosy 1 Bed Apartment with Free Parking, holiday rental in Winchester
Escape to Boscobel: Enjoy a Cosy 1 Bed Apartment with Free Parking, holiday rental in Winchester
Escape to Boscobel: Enjoy a Cosy 1 Bed Apartment with Free Parking, holiday rental in Winchester

Escape to Boscobel: Enjoy a Cosy 1 Bed Apartment with Free Parking

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
The Nestle House City Centre Luxury, holiday rental in Winchester
The Nestle House City Centre Luxury, holiday rental in Winchester
The Nestle House City Centre Luxury, holiday rental in Winchester

The Nestle House City Centre Luxury

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
2 bedroom accommodation in Winchester, holiday rental in Winchester
2 bedroom accommodation in Winchester, holiday rental in Winchester
2 bedroom accommodation in Winchester, holiday rental in Winchester

2 bedroom accommodation in Winchester

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Showing results 1-50 of 78
Frequently Asked Questions about Winchester