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 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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
Lovely 2BR Cottage Spacious with Garden
A room with a dartboard, a power outlet, a potted plant, and a curtain.

2. 4 Bedrooms - The Family Haven With Parking Near Airport

4 Bedrooms - The Family Haven With Parking Near Airport
3.0 star property
Eastleigh
The price is CA $213
CA $256 total
includes taxes & fees
Nov 1 - Nov 2
4 Bedrooms - The Family Haven 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 $390 total
includes taxes & fees
Oct 20 - Oct 21
Cozy detached bungalow with sunny garden
A living room with a television, wooden cabinet, round coffee table, and a sofa.

4. 4 Bedrooms - The Family Haven | With Parking | Near Airport

4 Bedrooms - The Family Haven | With Parking | Near Airport
Eastleigh
The price is CA $275
CA $315 total
includes taxes & fees
Nov 1 - Nov 2
4 Bedrooms - The Family Haven | With Parking | Near Airport
A coastal walkway with a sandy beach, a wooden fence, and a clear view of the sea.

5. 4-bedroom house in prime location

4-bedroom house in prime location
Hampshire
10.0 out of 10, Exceptional, (2 reviews)
"Had a lovely weekend. Lovely quiet place to stay. X"
United Kingdom
Laura B.
The price is CA $662
CA $1,020 total
includes taxes & fees
Oct 23 - Oct 24
4-bedroom house in prime location
A calm lake with ducks and a swan, a boat docked on the left, and a building in the background.

6. 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 20 - Oct 21
Perfect 2-bedroom house, Albert cottage with WiFi in charming Southampton
A hallway with a wooden door, a mirror, a radiator, and a potted plant.

7. 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 $122
CA $180 total
includes taxes & fees
Oct 31 - Nov 1
Two rooms in a very quiet and clean environment. Central to getting services
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 21 - Oct 22
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 $641
CA $791 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 $336
CA $1,464 total
includes taxes & fees
Oct 19 - Oct 20
A Cozy Magical Retreat at Knightwood Oak
A hotel room with two beds, each with a patterned pillow and a rolled towel on the bed.

11. Long Barn House - Andover

Long Barn House - Andover
Andover
The price is CA $326
CA $651 total
includes taxes & fees
Nov 1 - Nov 2
Long Barn House - Andover
A modern living room with a sofa, a TV mounted on the wall, and a bed in the background.

12. Private Garden Annexe + Parking. Near QA Hospital

Private Garden Annexe + Parking. Near QA Hospital
Wymering
The price is CA $173
CA $173 total
includes taxes & fees
Nov 13 - Nov 14
Private Garden Annexe + Parking. Near QA Hospital
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 $309
CA $415 total
includes taxes & fees
Oct 19 - Oct 20
The Carriage House — Wiltshire Countryside Cottage for up to 6 ppl.
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.

14. 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 $309
CA $430 total
includes taxes & fees
Oct 19 - Oct 20
The Summer House — Unique Hilltop Retreat for up to 4 ppl.
A marina with boats docked along a wooden pier.

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 CA $2,272
CA $2,272 total
includes taxes & fees
Nov 2 - Nov 3
Dairy House - a house that sleeps 16 guests in 7 bedrooms
A hotel room with a bed, yellow curtains, and a window with blinds.

16. 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 19 - Oct 20
Fratton House: Alver Road: Free parking
A pebbled beach with a view of the sea and distant land.

17. 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 hotel room with a wooden bed, white bedding, an orange throw blanket, and a white nightstand with a red vase.

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

Southsea Getaway: Close to Beach & Family Fun!
Southsea
The price is CA $81
CA $81 total
includes taxes & fees
Oct 19 - Oct 20
Southsea Getaway: Close to Beach & Family Fun!
A white building with a curved facade, a central arched entrance, and multiple windows with warm lighting.

19. Gallery - a house that sleeps 18 guests in 5 bedrooms

Gallery - a house that sleeps 18 guests in 5 bedrooms
Gosport
9.4 out of 10, Exceptional, (22 reviews)
"Property is spacious and ideal for a large family group.. Nice stroll in to the town and the ferry"
United Kingdom
Tracey S.
The price is CA $1,622
CA $1,622 total
includes taxes & fees
Nov 2 - Nov 3
Gallery - a house that sleeps 18 guests in 5 bedrooms
A grey door with a mail slot and a number plate indicating '189'.

20. 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 $178
CA $208 total
includes taxes & fees
Oct 22 - Oct 23
Mermaids Rest - newly renovated apartment with shared porch and private entrance
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

Moxy Southampton

Moxy Southampton

10/10 Excellent
"We always come here for our stay before leaving on a cruise out of South Hampton. These folks keep us coming back for helping us out with excellent service (early check ins for example) and will always keep coming back and recommending this place to be THE place to stay while in South Hampton. Also it's location to many restaurants make it a nice place for just that reason. Thank you again for a great stay!"
William 1-night trip
Posted 13 hours ago
Moxy Southampton

Find out more about Winchester

Winchester Vacation Homes information

Number of reviews
63
Accommodation
672 Vacation Homes
Lowest Price
CA $81
Highest Price
CA $2,272

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