Winchester Vacation Home Rentals from CA $75: Search Top Private Vacation Homes for Rent

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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Our top choices for Winchester vacation homes

1. Cosy Annex escape within the South Downs!

Upham

Daniel J.

CA $190 total

includes taxes & fees

Nov 3 - Nov 4

A neatly made bed with a leaf-patterned bedspread, two bedside lamps, a painting of vintage cars, and a window with curtains.

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

Redbridge

CA $561 total

includes taxes & fees

Oct 31 - Nov 1

A bedroom with two single beds, a window with curtains, and a floral wallpaper.

3. Cozy detached bungalow with sunny garden

Southampton

CA $375 total

includes taxes & fees

Nov 2 - Nov 3

A room with a bed, a television, a small table with a kettle, a chair, and a window with blinds.

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

Southampton

Tom

CA $174 total

includes taxes & fees

Oct 31 - Nov 1

A calm waterfront with a boat docked, a swan, and ducks swimming. There is a round table and a chair in the foreground.

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

Portswood

Terri M.

CA $272 total

includes taxes & fees

Nov 9 - Nov 10

A coastal house with a stone pathway leading to the entrance, situated by the sea with a sailboat in the background.

6. Beautiful New Forest Hideaway

West Wellow

Alena M.

CA $326 total

includes taxes & fees

Nov 3 - Nov 4

A modern kitchen with grey cabinets, a built-in oven, and a stainless steel range hood.

7. A Cozy Magical Retreat at Knightwood Oak

Woodlands

A modern living room with a sofa, a TV mounted on the wall, and a bed in the background.

8. Private Garden Annexe + Parking. Near QA Hospital

Wymering

CA $150 total

includes taxes & fees

Nov 6 - Nov 7

A brick building with a dark wooden door, two windows, and a bench in front.

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

Clarendon

CA $390 total

includes taxes & fees

Nov 15 - Nov 16

A dining table set with yellow napkins, clear glassware, and a bowl of fruit.

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

Gosport

Geraldine C.

CA $2,285 total

includes taxes & fees

Nov 9 - Nov 10

A spacious living area with a high ceiling, wooden beams, a large TV, and a dining area with a table and chairs.

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

Salisbury

CA $422 total

includes taxes & fees

Nov 8 - Nov 9

A modern bedroom with a bed, pillows, a cityscape painting, and a hanging light fixture.

12. Fawcett House: Southsea Gem with Kitchen & Free parking

Southsea

""I did not stay at this property due to a total failure of service and severe health hazards. Upon arrival, no staff were present and the room was already occupied by two other guests due to a double-booking. The property was in a severe state of disrepair: the door was detached from its hinges, the walls were unwashed, and the bedding had significant biological stains and unwashed pillowcases. Furthermore, there was a heavy, pervasive odor of tobacco smoke. As a diagnosed COPD patient, this...

Keith

CA $76 total

includes taxes & fees

Nov 1 - Nov 2

A white building with a curved facade, a central arched entrance, and multiple windows with warm lighting.

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

Gosport

Tracey S.

CA $1,604 total

includes taxes & fees

Nov 9 - Nov 10

A hotel room with a bed, yellow curtains, and a window with blinds.

14. Fratton House: Alver Road: Free parking

Fratton

"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...

Christopher F.

CA $91 total

includes taxes & fees

Oct 30 - Oct 31

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

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

Southsea

CA $75 total

includes taxes & fees

Oct 30 - Oct 31

A living room with a brown leather sofa, a wooden coffee table, a beige armchair, and a brown leather armchair.

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

Gosport

CA $478 total

includes taxes & fees

Nov 16 - Nov 17

A hot tub in a room with large windows, a wooden deck, and a small heater.

17. Bury Villa - sleeping 18 guests

Gosport

Sarah N.

CA $2,050 total

includes taxes & fees

Nov 2 - Nov 3

A modern living room with a grey sofa, a washing machine, and a TV mounted on the wall.

18. Cosy Portsmouth House: Free Parking & Kitchen

Southsea

CA $95 total

includes taxes & fees

Oct 30 - Oct 31

A spacious living room with a large TV, comfortable seating, and large windows offering views of the outside.

19. The Deck House, Isle of Wight

Gurnard

CA $1,420 total

includes taxes & fees

Nov 2 - Nov 3

A traditional brick house with a steeply pitched roof, multiple windows, and a large front door.

20. Elegant Hampshire Countryside Stay, Petersfield

Petersfield

Alice B.

CA $1,931 total

includes taxes & fees

Nov 1 - Nov 2

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Top Winchester Hotel Reviews

New Place

10/10 Excellent

"Stayed for 3 nights and thoroughly enjoyed our stay. Room as advertised, clean and well appointed, the breakfasts were great, and although we only dined on one evening, that meal was lovely too. The meals are served in grand old dining rooms that make you feel special before you even start. Every member of staff we encountered were friendly, polite and efficient. A great break away."

Holiday Inn Portsmouth by IHG

8/10 Good

"The room was spacious and clean. The staff were cheerful and helpful. The pool was a bonus and supplied towels. The breakfast was plentiful and varied and of a good quality. Unfortunately the all day menu let it down as food was luke warm at most, overcooked at times and not all items were available. You also had to ask for kids menu and the pricing was not clear. Would we return, yes as the pros outweighed the cons."

Find out more about Winchester

Winchester Vacation Homes information

Number of reviews	80
Accommodation	672 Vacation Homes
Lowest Price	CA $75
Highest Price	CA $2,285

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Winchester Vacation Rentals

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winchester vacation homes

1. Cosy Annex escape within the South Downs!

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

3. Cozy detached bungalow with sunny garden

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