A large red brick building with a central entrance flanked by columns, a fountain in front, and trees on either side.

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Winchester vacation homes

A room with a dartboard, a power outlet, a potted plant, and a curtain.

1. Eastleigh Luxury Retreat With 4 Bedrooms With Parking Near Airport

Eastleigh Luxury Retreat With 4 Bedrooms With Parking Near Airport
3.0 star property
Eastleigh
The price is ￥29,954
￥35,945 total
includes taxes & fees
Oct 4 - Oct 5
Eastleigh Luxury Retreat With 4 Bedrooms With Parking Near Airport
A dining table set with plates, cutlery, and a glass vase with yellow flowers.

2. 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.
3 Bedrooms house ideal for long Stays!
A bedroom with two single beds, a window with curtains, and a floral wallpaper.

3. Cozy detached bungalow with sunny garden

Cozy detached bungalow with sunny garden
Southampton
The price is ￥28,877
￥38,461 total
includes taxes & fees
Sep 28 - Sep 29
Cozy detached bungalow with sunny garden
A living room with a television, wooden cabinet, round coffee table, and a sofa.

4. Eastleigh Luxury Retreat with 4 Bedrooms | With Parking | Near Airport

Eastleigh Luxury Retreat with 4 Bedrooms | With Parking | Near Airport
Eastleigh
The price is ￥37,085
￥40,419 total
includes taxes & fees
Oct 4 - Oct 5
Eastleigh Luxury Retreat with 4 Bedrooms | With Parking | Near Airport
A calm lake with ducks and a swan, a boat docked on the left, and a building in the background.

5. 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 ￥24,376
￥29,793 total
includes taxes & fees
Sep 29 - Sep 30
Perfect 2-bedroom house, Albert cottage with WiFi in charming Southampton
A paved driveway leading to a wooden gate, a bicycle with a bag, and a shed in a garden setting.

6. Beautiful New Forest Hideaway

Beautiful New Forest Hideaway
West Wellow
10.0 out of 10, Exceptional, (1 review)
"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 ￥25,979
￥36,396 total
includes taxes & fees
Oct 19 - Oct 20
Beautiful New Forest Hideaway
An aerial view of a water park with various play structures and a wooden dock.

7. A Cozy Magical Retreat at Knightwood Oak

A Cozy Magical Retreat at Knightwood Oak
Woodlands
The price is ￥38,815
￥155,126 total
includes taxes & fees
Sep 28 - Sep 29
A Cozy Magical Retreat at Knightwood Oak
A hallway with a wooden door, a mirror, a radiator, and a potted plant.

8. 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 ￥13,126
￥19,470 total
includes taxes & fees
Oct 4 - Oct 5
Two rooms in a very quiet and clean environment. Central to getting services
A modern living room with a sofa, a TV mounted on the wall, and a bed in the background.

9. Private Garden Annexe + Parking. Near QA Hospital

Private Garden Annexe + Parking. Near QA Hospital
Wymering
The price is ￥16,772
￥16,772 total
includes taxes & fees
Oct 5 - Oct 6
Private Garden Annexe + Parking. Near QA Hospital
A hotel room with a bed, a nightstand, a lamp, a window with blinds, and two wall-mounted pictures.

10. Portsmouth House: Free Parking & Family Friendly

Portsmouth House: Free Parking & Family Friendly
Southsea
The price is ￥8,959
￥8,959 total
includes taxes & fees
Sep 29 - Sep 30
Portsmouth House: Free Parking & Family Friendly
A modern living room with a sofa, coffee table, and a view of the kitchen.

11. 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 ￥39,586
￥51,287 total
includes taxes & fees
Sep 29 - Sep 30
The Carriage House — Wiltshire Countryside Cottage for up to 6 ppl.
A cozy room with a wooden door, a brown sofa with white cushions, a white bedside table with a plant, and a large mirror on the wall.

12. La Petite Maison | Southsea Retreat w/ Parking

La Petite Maison | Southsea Retreat w/ Parking
Southsea
8.0 out of 10, Very good, (2 reviews)
"The hosts did a great job with setting up the room for my partner's birthday after I discussed the plan with them, and it looked so magical. The little house is definitely small but perfectly formed, with everything you need, even a small ironing board. The location was really close to the sea and the Canoe Lake Park and only a 10-minute drive to Gunwharf Quays. The TV worked really well, and there was no need to faff around with logging into your own streaming services because the house had its...
United Kingdom
Daisy
The price is ￥16,053
￥25,429 total
includes taxes & fees
Sep 28 - Sep 29
La Petite Maison | Southsea Retreat w/ Parking
A paved pathway leading through a gated entrance with two brick pillars topped with decorative urns, surrounded by lush greenery.

13. The Studio - A cosy studio apartment

The Studio - A cosy studio apartment
Hungerford
10.0 out of 10, Exceptional, (3 reviews)
"Lovely stay would recommend"
United States
Phillip R.
The price is ￥18,751
￥30,002 total
includes taxes & fees
Sep 28 - Sep 29
The Studio - A cosy studio apartment
A modern kitchen with a wooden countertop, a toaster, and a kettle.

14. 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
5 bedroom family home close to Gosport ferry to Portsmouth and the New Forest
A spacious living room with a large sliding glass door leading to a balcony, a white sofa set, a wooden coffee table, and a television mounted on the wall.

15. 4 Bed house | Hill top views | 3 car driveway

4 Bed house | Hill top views | 3 car driveway
Drayton
4 Bed house | Hill top views | 3 car driveway
A bedroom with a sloped ceiling, a heart-shaped wall decoration, a bed with white and dark pillows, and a wooden nightstand with a lamp.

16. 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 ￥41,461
￥54,868 total
includes taxes & fees
Sep 28 - Sep 29
The Summer House — Unique Hilltop Retreat for up to 4 ppl.
A modern dining area with a black and white color scheme, featuring a dining table set with blue plates and glasses, a black vase with dried flowers, and a contemporary light fixture.

17. Open Mind Property - 7 Beds and Free Parking

Open Mind Property - 7 Beds and Free Parking
North End
4.0 out of 10, (1 review)
"2 of the beds in Master bedroom, the legs were broken and unsafe to sleep on. When I complained "
United States
G B.
The price is ￥39,586
￥56,254 total
includes taxes & fees
Oct 2 - Oct 3
Open Mind Property - 7 Beds and Free Parking
A traditional thatched-roof cottage with a wooden door and window, surrounded by dense greenery.

18. Historic studio annexe for two with New Forest on your doorstep

Historic studio annexe for two with New Forest on your doorstep
Burgate
The price is ￥24,939
￥31,189 total
includes taxes & fees
Oct 9 - Oct 10
Historic studio annexe for two with New Forest on your doorstep
A marina with boats docked along a wooden pier.

19. 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 ￥259,709
￥259,709 total
includes taxes & fees
Sep 29 - Sep 30
Dairy House - a house that sleeps 16 guests in 7 bedrooms
A dining area with a table set for four, a sofa in the background, and a plant to the right.

20. Stylish 3 Bedroom Getaway | City Central

Stylish 3 Bedroom Getaway | City Central
Southsea
Stylish 3 Bedroom Getaway | City Central
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 Winchester Hotel Reviews

Holiday Inn Portsmouth by IHG

Holiday Inn Portsmouth by IHG

10/10 Excellent
"Perfect, everything we needed."
Kerry 2-night trip
Posted less than an hour ago
Holiday Inn Portsmouth by IHG

Find out more about Winchester

Winchester Vacation Homes information

Number of reviews
45
Accommodation
684 Vacation Homes
Lowest Price
￥8,959
Highest Price
￥259,709