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Check prices for these dates

Our top choices for Winchester holiday homes

1. Cosy Annex escape within the South Downs!

Cosy Annex escape within the South Downs!
Upham
9.6 out of 10, Exceptional, (4 reviews)
"Great Annex, calm and peaceful location."
United States
Daniel J.
The price is £99
includes taxes & fees
10 Nov - 11 Nov
Cosy Annex escape within the South Downs!

2. Cozy detached bungalow with sunny garden

Cozy detached bungalow with sunny garden
Southampton
The price is £183
includes taxes & fees
8 Nov - 9 Nov
Cozy detached bungalow with sunny garden

3. Redbridge House | Sleeps 8 | 4 Beds | Parking

Redbridge House | Sleeps 8 | 4 Beds | Parking
Redbridge
The price is £292
includes taxes & fees
8 Nov - 9 Nov
Redbridge House | Sleeps 8 | 4 Beds | Parking

4. Perfect 2-bedroom house, Albert cottage with WiFi in charming Southampton

Perfect 2-bedroom house, Albert cottage with WiFi in charming Southampton
Portswood
10.0 out of 10, Exceptional, (1 review)
"We had a great time, lovely neighborhood, location is easy access to needed items. Marvin is an excellent host. He responds right away with all questions. For a home that is 140 years old it is in excellent shape. Beautifully decorated. Everything we needed was there. Big plus to be on the water. Thank you Marvin!"
United States
Terri M.
The price is £152
includes taxes & fees
8 Nov - 9 Nov
Perfect 2-bedroom house, Albert cottage with WiFi in charming Southampton

5. 3 Bedrooms house ideal for long Stays!

3 Bedrooms house ideal for long Stays!
Southampton
10.0 out of 10, Exceptional, (5 reviews)
"Great location, lovely clean property can recommend."
United Kingdom
Michael R.
The price is £152
includes taxes & fees
29 Nov - 30 Nov
3 Bedrooms house ideal for long Stays!

6. Experience the epitome of English elegance at English Countryside Estate.

Experience the epitome of English elegance at English Countryside Estate.
Lymington
The price is £18,586
includes taxes & fees
8 Nov - 9 Nov
Experience the epitome of English elegance at English Countryside Estate.

7. Beautiful New Forest Hideaway

Beautiful New Forest Hideaway
West Wellow
10.0 out of 10, Exceptional, (2 reviews)
"Lovely cottage!! Clean and had everything you could possibly need!! Our stay was so relaxing we didn’t want to leave and will be back soon !!"
United States
Alena M.
The price is £175
includes taxes & fees
9 Nov - 10 Nov
Beautiful New Forest Hideaway

8. New Forest Retreat | Sauna, Gym, Cinema & Parking

New Forest Retreat | Sauna, Gym, Cinema & Parking
Southampton
10.0 out of 10, Exceptional, (1 review)
"Great stay"
United States
Laela R.
New Forest Retreat | Sauna, Gym, Cinema & Parking

9. Serene 5-bedroom house in Southampton perfect for family getaways

Serene 5-bedroom house in Southampton perfect for family getaways
SOUTHAMPTON
The price is £410
includes taxes & fees
8 Nov - 9 Nov
Serene 5-bedroom house in Southampton perfect for family getaways

10. Blue Sparrow House

Blue Sparrow House
3.0 star property
Portsmouth
10.0 out of 10, Exceptional, (1 review)
The price is £188
includes taxes & fees
8 Nov - 9 Nov
Blue Sparrow House

11. A Cozy Magical Retreat at Knightwood Oak

A Cozy Magical Retreat at Knightwood Oak
Woodlands
The price is £697
includes taxes & fees
8 Nov - 9 Nov
A Cozy Magical Retreat at Knightwood Oak

12. Dairy House - a house that sleeps 16 guests in 7 bedrooms

Dairy House - a house that sleeps 16 guests in 7 bedrooms
Gosport
9.8 out of 10, Exceptional, (31 reviews)
"House is lovely and was very clean and welcoming. There were issues with a rusty barbecue and a faulty freezer but I'm sure those matters will be resolved for future guests. I was offered recompense for wasted food if appropriate (not necessary).Happy to recommend."
United States
Geraldine C.
The price is £1,226
includes taxes & fees
9 Nov - 10 Nov
Dairy House - a house that sleeps 16 guests in 7 bedrooms

13. Private Garden Annexe + Parking. Near QA Hospital

Private Garden Annexe + Parking. Near QA Hospital
Wymering
The price is £81
includes taxes & fees
12 Nov - 13 Nov
Private Garden Annexe + Parking. Near QA Hospital

14. The Carriage House — Wiltshire Countryside Cottage for up to 6 ppl.

The Carriage House — Wiltshire Countryside Cottage for up to 6 ppl.
Clarendon
The price is £209
includes taxes & fees
15 Nov - 16 Nov
The Carriage House — Wiltshire Countryside Cottage for up to 6 ppl.

15. Open Mind Property- 6BR Home, Hot Tub & Free Parking

Open Mind Property- 6BR Home, Hot Tub & Free Parking
Fareham , PO15 5RS
4.0 out of 10, (1 review)
The price is £310
includes taxes & fees
9 Nov - 10 Nov
Open Mind Property- 6BR Home, Hot Tub & Free Parking

16. Cozy & Self Contained The Garden Annex 306

Cozy & Self Contained The Garden Annex 306
Salisbury
10.0 out of 10, Exceptional, (5 reviews)
"This place was lovely! Incredibly quiet for being in the city."
United States
Dala B.
The price is £87
includes taxes & fees
8 Nov - 9 Nov
Cozy & Self Contained The Garden Annex 306

17. The Summer House — Unique Hilltop Retreat for up to 4 ppl.

The Summer House — Unique Hilltop Retreat for up to 4 ppl.
Salisbury
The price is £222
includes taxes & fees
8 Nov - 9 Nov
The Summer House — Unique Hilltop Retreat for up to 4 ppl.

18. Southsea Getaway: Close to Beach & Family Fun!

Southsea Getaway: Close to Beach & Family Fun!
Southsea
4.0 out of 10, (1 review)
"The location was okay. I stayed for 2 nights and had no WiFi for the duration. Communication with the maintenance guy was ok however he asked me to send emails to the ‘office’ about the internet issue but I had no response from the ‘office’. My bedding had spots of blood on it. All in all…it was not a great experience. Maintenance guy was very apologetic."
United Kingdom
Janet
The price is £40
includes taxes & fees
8 Nov - 9 Nov
Southsea Getaway: Close to Beach & Family Fun!

19. Open Mind Property - 3 Bedroom | Henderson Lodge

Open Mind Property - 3 Bedroom | Henderson Lodge
Southsea
Open Mind Property - 3 Bedroom | Henderson Lodge

20. Fratton House: Alver Road: Free parking

Fratton House: Alver Road: Free parking
Fratton
2.0 out of 10, (1 review)
"The room was clean, however the fan was dirty, blinds were broken. Walking into the property there was an open room full of clutter and mess, immediately in the hallway was what seemed to be a rolled up amount of carpet, and a house a dog that wasn’t disclosed on the listing. Bathroom functionality was poor as the shower dial was practically falling off of the wall and instructions were unclear on how to turn it off, worst bit was the shelf was covered in empty shampoo bottles and what looked to...
United States
Christopher F.
The price is £47
includes taxes & fees
8 Nov - 9 Nov
Fratton House: Alver Road: Free parking
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.

Learn more about Winchester

Medieval majesty awaits at Winchester Cathedral, where centuries of royal history unfold beneath Europe's longest Gothic nave. Explore Jane Austen's final home, then time your visit for the magical Christmas Market or discover distant galaxies at the Science Centre and Planetarium.

A historic building with large windows and pointed arches, surrounded by lush green trees and a grassy area with people sitting and walking.

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