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

Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Winchester vacation homes

A modern kitchen with a central island, pendant lights, and a dining area with a table and chairs.

1. Lovely 2BR Cottage Spacious with Garden

Lovely 2BR Cottage Spacious with Garden
Winchester City Center
8.0 out of 10, Very good, (2 reviews)
"The property was excellent for location in Winchester and was very clean. The ‘garden’ is a small area of decking. "
United Kingdom
barbara
The price is CA $317
CA $595 total
includes taxes & fees
Oct 9 - Oct 10
Lovely 2BR Cottage Spacious with Garden
A room with a dartboard, a power outlet, a potted plant, and a curtain.

2. 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 CA $255
CA $306 total
includes taxes & fees
Nov 2 - Nov 3
Eastleigh Luxury Retreat With 4 Bedrooms With Parking Near Airport
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 CA $290
CA $386 total
includes taxes & fees
Oct 12 - Oct 13
Cozy detached bungalow with sunny garden
A calm lake with ducks and a swan, a boat docked on the left, and a building in the background.

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 CA $220
CA $271 total
includes taxes & fees
Oct 14 - Oct 15
Perfect 2-bedroom house, Albert cottage with WiFi in charming Southampton
A living room with a television, wooden cabinet, round coffee table, and a sofa.

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

Eastleigh Luxury Retreat with 4 Bedrooms | With Parking | Near Airport
Eastleigh
The price is CA $326
CA $371 total
includes taxes & fees
Nov 1 - Nov 2
Eastleigh Luxury Retreat with 4 Bedrooms | With Parking | Near Airport
A hallway with a wooden door, a mirror, a radiator, and a potted plant.

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 CA $132
CA $191 total
includes taxes & fees
Nov 6 - Nov 7
Two rooms in a very quiet and clean environment. Central to getting services
A living room with a fireplace, a mounted TV displaying "NETFLIX," and a bookshelf.

7. Spacious and Comfy 2 Bed Southampton Home Sleep 5

Spacious and Comfy 2 Bed Southampton Home Sleep 5
Bevois Valley
The price is CA $336
CA $383 total
includes taxes & fees
Oct 29 - Oct 30
Spacious and Comfy 2 Bed Southampton Home Sleep 5
A paved driveway leading to a wooden gate, a bicycle with a bag, and a shed in a garden setting.

8. 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 CA $235
CA $329 total
includes taxes & fees
Oct 13 - Oct 14
Beautiful New Forest Hideaway
A dining area with a table set for four, surrounded by chairs, with large windows and potted plants.

9. 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.
The price is CA $605
CA $756 total
includes taxes & fees
Nov 1 - Nov 2
New Forest Retreat | Sauna, Gym, Cinema & Parking
An aerial view of a water park with various play structures and a wooden dock.

10. A Cozy Magical Retreat at Knightwood Oak

A Cozy Magical Retreat at Knightwood Oak
Woodlands
The price is CA $405
CA $1,534 total
includes taxes & fees
Oct 9 - Oct 10
A Cozy Magical Retreat at Knightwood Oak
A modern living room with a sofa, a TV mounted on the wall, and a bed in the background.

11. Private Garden Annexe + Parking. Near QA Hospital

Private Garden Annexe + Parking. Near QA Hospital
Wymering
The price is CA $152
CA $152 total
includes taxes & fees
Oct 14 - Oct 15
Private Garden Annexe + Parking. Near QA Hospital
A modern kitchen with white cabinets, a grey backsplash, and a built-in microwave.

12. 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 CA $161
CA $191 total
includes taxes & fees
Oct 14 - Oct 15
Mermaids Rest - newly renovated apartment with shared porch and private entrance
A modern living room with a sofa, coffee table, and a view of the kitchen.

13. 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 CA $336
CA $442 total
includes taxes & fees
Oct 11 - Oct 12
The Carriage House — Wiltshire Countryside Cottage for up to 6 ppl.
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
The price is CA $301
CA $450 total
includes taxes & fees
Nov 6 - Nov 7
5 bedroom family home close to Gosport ferry to Portsmouth and the New Forest
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.

15. 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 CA $372
CA $493 total
includes taxes & fees
Oct 11 - Oct 12
The Summer House — Unique Hilltop Retreat for up to 4 ppl.
A marina with boats docked along a wooden pier.

16. 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 CA $2,271
CA $2,271 total
includes taxes & fees
Nov 3 - Nov 4
Dairy House - a house that sleeps 16 guests in 7 bedrooms
A hotel room with a bed, yellow curtains, and a window with blinds.

17. 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 CA $92
CA $92 total
includes taxes & fees
Oct 9 - Oct 10
Fratton House: Alver Road: Free parking
A hotel room with a bed, a flat-screen TV mounted on the wall, a window with blinds, and a green pendant light.

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 CA $81
CA $81 total
includes taxes & fees
Oct 14 - Oct 15
Southsea Getaway: Close to Beach & Family Fun!
A pebbled beach with a view of the sea and distant land.

19. spacious home with pool table, 3 bedrooms, 2 minutes drive from seafront

spacious home with pool table, 3 bedrooms, 2 minutes drive from seafront
Gosport
spacious home with pool table, 3 bedrooms, 2 minutes drive from seafront
A wooden arbor with pink blossoms, a brick pathway, and a house with a blue roof in the background.

20. Cozy & Self Contained The Garden Annex 306

Cozy & Self Contained The Garden Annex 306
Salisbury
10.0 out of 10, Exceptional, (4 reviews)
"This place was lovely! Incredibly quiet for being in the city."
United States
Dala B.
The price is CA $160
CA $190 total
includes taxes & fees
Nov 3 - Nov 4
Cozy & Self Contained The Garden Annex 306
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

Meon Valley Hotel, Spa & Golf

Meon Valley Hotel, Spa & Golf

8/10 Good
"Everything was as it was advertised, a little run down but the ground were stunning and the staff were great! The Greek lady on the evening shift was exceptionally hospitable! If we find ourselves back in Southampton we’ll be staying here"
Sarah 2-night trip
Posted 1 hour ago
Meon Valley Hotel, Spa & Golf

Find out more about Winchester

Winchester Vacation Homes information

Number of reviews
44
Accommodation
672 Vacation Homes
Lowest Price
CA $81
Highest Price
CA $2,271

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