Holiday Homes in Winchester

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Find holiday rentals that suit your style

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 NZ$242
includes taxes & fees
12 Nov - 13 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 NZ$486
includes taxes & fees
16 Nov - 17 Nov
Cozy detached bungalow with sunny garden

3. 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 NZ$370
includes taxes & fees
29 Nov - 30 Nov
3 Bedrooms house ideal for long Stays!

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 NZ$370
includes taxes & fees
12 Nov - 13 Nov
Perfect 2-bedroom house, Albert cottage with WiFi in charming Southampton

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

Redbridge House | Sleeps 8 | 4 Beds | Parking
Redbridge
The price is NZ$773
includes taxes & fees
13 Nov - 14 Nov
Redbridge House | Sleeps 8 | 4 Beds | Parking

6. Two rooms in a very quiet and clean environment. Central to getting services

Two rooms in a very quiet and clean environment. Central to getting services
Southampton
6.0 out of 10, (1 review)
"You get what you pay for"
Canada
Tom
The price is NZ$209
includes taxes & fees
20 Nov - 21 Nov
Two rooms in a very quiet and clean environment. Central to getting services

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 NZ$417
includes taxes & fees
15 Nov - 16 Nov
Beautiful New Forest Hideaway

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

Serene 5-bedroom house in Southampton perfect for family getaways
SOUTHAMPTON
The price is NZ$952
includes taxes & fees
11 Dec - 12 Dec
Serene 5-bedroom house in Southampton perfect for family getaways

9. A Cozy Magical Retreat at Knightwood Oak

A Cozy Magical Retreat at Knightwood Oak
Woodlands
A Cozy Magical Retreat at Knightwood Oak

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

Experience the epitome of English elegance at English Countryside Estate.
Lymington
The price is NZ$43,713
includes taxes & fees
12 Nov - 13 Nov
Experience the epitome of English elegance at English Countryside Estate.

11. Blue Sparrow House

Blue Sparrow House
3.0 star property
Portsmouth
10.0 out of 10, Exceptional, (1 review)
The price is NZ$406
includes taxes & fees
6 Dec - 7 Dec
Blue Sparrow House

12. 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)
Open Mind Property- 6BR Home, Hot Tub & Free Parking

13. Private Garden Annexe + Parking. Near QA Hospital

Private Garden Annexe + Parking. Near QA Hospital
Wymering
The price is NZ$192
includes taxes & fees
12 Nov - 13 Nov
Private Garden Annexe + Parking. Near QA Hospital

14. Portsmouth Townhouse with Superfast Wifi & Free Parking

Portsmouth Townhouse with Superfast Wifi & Free Parking
Fratton
2.0 out of 10, (1 review)
"Main light did not work, and in the dark, I had to move the bed to access a dangerous wall socket for the bedside light. There was nowhere to put clothes, items or a desk to use and no chair and no space for this anyway. Better if the small double bed was swopped for a single to allow a desk & chair to be put in. The steep and shallow stairs were a safety hazard, so be careful. And the TV didn't allow access to Freeview! There was no crockery or cutlery to use despite advertising a well-equipped...
United Kingdom
Stephen John
The price is NZ$95
includes taxes & fees
12 Nov - 13 Nov
Portsmouth Townhouse with Superfast Wifi & Free Parking

15. 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 NZ$2,925
includes taxes & fees
12 Nov - 13 Nov
Dairy House - a house that sleeps 16 guests in 7 bedrooms

16. 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 NZ$499
includes taxes & fees
12 Nov - 13 Nov
The Carriage House — Wiltshire Countryside Cottage for up to 6 ppl.

17. 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 NZ$190
includes taxes & fees
23 Nov - 24 Nov
Cozy & Self Contained The Garden Annex 306

18. Mermaids Rest - newly renovated apartment with shared porch and private entrance

Mermaids Rest - newly renovated apartment with shared porch and private entrance
Copnor
The price is NZ$249
includes taxes & fees
19 Nov - 20 Nov
Mermaids Rest - newly renovated apartment with shared porch and private entrance

19. 5 bedroom family home close to Gosport ferry to Portsmouth and the New Forest

5 bedroom family home close to Gosport ferry to Portsmouth and the New Forest
Gosport
The price is NZ$440
includes taxes & fees
12 Dec - 13 Dec
5 bedroom family home close to Gosport ferry to Portsmouth and the New Forest

20. 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 NZ$545
includes taxes & fees
15 Nov - 16 Nov
The Summer House — Unique Hilltop Retreat for up to 4 ppl.
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.

Explore a world of travel with Expedia