Winchester Vacation Home Rentals from CA $81: Search Top Private Vacation Homes for Rent

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Our top choices for Winchester vacation homes

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

A dining area with a wooden table, black chairs, a chandelier, a clock, and a window with curtains.

A pool table with balls, a fireplace, a lamp, and a shelf with decorative items.

A kitchen with light green cabinets, a microwave, a gas stove, and a tiled backsplash.

1. 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 $255

CA $255

CA $306 total

includes taxes & fees

Nov 2 - Nov 3

4 Bedrooms - The Family Haven With Parking Near Airport

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

A kitchen with a gas stove, stainless steel range hood, white cabinets, and a yellow accent wall.

A living room with a sofa, TV, fireplace, and a fan.

A dining area with a table set for four, surrounded by white chairs, under a skylight with a view of greenery outside.

2. Cozy detached bungalow with sunny garden

Cozy detached bungalow with sunny garden

Southampton

The price is CA $247

CA $247

CA $338 total

includes taxes & fees

Oct 13 - Oct 14

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.

A modern staircase with black steps and a glass railing, leading to a lower level.

A compact kitchen with white cabinets, a microwave, a kettle, and a sink.

A kitchen with a gas stove, oven, and a toaster on the countertop.

3. 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)

10/10

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!"

Terri M.

The price is CA $221

CA $221

CA $272 total

includes taxes & fees

Oct 13 - Oct 14

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.

A bedroom with a bed, a window with pink curtains, a wall-mounted picture, and a ceiling light fixture.

A dining area with a wooden table and black chairs, a chandelier, a clock, and a window with curtains.

A dartboard with a bullseye and numbered scoring rings.

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

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

Eastleigh

The price is CA $326

CA $326

CA $372 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.

A hot tub in a backyard with a wooden fence, a hanging chair, and a brick wall.

A modern kitchen with white cabinets, a black countertop, and a wooden floor.

A modern living room with a white sectional sofa, a black coffee table, and a striped side table.

5. 4-bedroom house in prime location

4-bedroom house in prime location

Hampshire

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Had a lovely weekend. Lovely quiet place to stay. X"

Laura B.

The price is CA $537

CA $537

CA $871 total

includes taxes & fees

Oct 18 - Oct 19

4-bedroom house in prime location

A hallway with a wooden door, a mirror, a radiator, and a potted plant.

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

A ceiling with recessed lighting and a mirror.

A bedroom with a bed, a desk, a chair, a television, and a window.

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)

6.0/10

(1 review)

"You get what you pay for"

Tom

The price is CA $132

CA $132

CA $192 total

includes taxes & fees

Nov 5 - Nov 6

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.

A small table with a potted plant, a lamp, and a book, positioned near a window with a view of foliage.

A living room with a sofa, a coffee table, and a radiator.

A bedroom with a sloped ceiling, a bed with a brown quilt, a nightstand with a lamp, and framed pictures on the wall.

7. Beautiful New Forest Hideaway

Beautiful New Forest Hideaway

West Wellow

10.0 out of 10, Exceptional, (2 reviews)

10/10

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 !!"

Alena M.

The price is CA $235

CA $235

CA $330 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.

A modern bedroom with a large bed, a wardrobe, a mirror, and a view of the outdoors.

A modern house with a wooden exterior, large sliding glass doors, a patio with a sofa and table, and a wicker chair.

A wooden staircase with a handrail, a painting on the wall, and a door leading to another room.

8. New Forest Retreat | Sauna, Gym, Cinema & Parking

New Forest Retreat | Sauna, Gym, Cinema & Parking

Southampton

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Great stay"

Laela R.

The price is CA $549

CA $549

CA $700 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.

A modern living room with a sofa, a TV, and a wooden floor. There is a door leading to a bedroom with a bed and a window.

A courtyard with red brick buildings, a cobblestone path, and a street lamp.

A modern living room with a brown leather sofa, a black TV stand, and a wooden dining table.

9. A Cozy Magical Retreat at Knightwood Oak

A Cozy Magical Retreat at Knightwood Oak

Woodlands

The price is CA $325

CA $325

CA $1,451 total

includes taxes & fees

Oct 13 - Oct 14

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.

A living room with a brown leather sofa, teal cushions, a fireplace, and a painting on the wall.

A living room with a brown leather sectional sofa, a single ottoman, and a ceiling light fixture.

A modern kitchen with wooden cabinets, a granite countertop, a built-in oven, and a window providing natural light.

10. Long Barn House - Andover

Long Barn House - Andover

Andover

The price is CA $326

CA $326

CA $652 total

includes taxes & fees

Oct 25 - Oct 26

Long Barn House - Andover

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

A kitchen with a built-in cabinet containing dishes, cups, and storage containers.

A modern kitchen with white cabinets, a microwave, and a washing machine.

A covered outdoor area with a window, a brick floor, and a wooden fence.

11. Private Garden Annexe + Parking. Near QA Hospital

Private Garden Annexe + Parking. Near QA Hospital

Wymering

The price is CA $152

CA $152

CA $152 total

includes taxes & fees

Oct 15 - Oct 16

Private Garden Annexe + Parking. Near QA Hospital

A grey door with a mail slot and a number plate indicating '189'.

A bedroom with two beds, each with a different patterned bedspread, a bedside table with a lamp, and a mirror on the wall.

A green sofa with multiple pillows and a blanket, a wooden chair, and a patterned wall.

A white door with a small window and a peephole.

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 $178

CA $178

CA $209 total

includes taxes & fees

Oct 13 - Oct 14

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.

A bedroom with a large bed, a nightstand, a lamp, a chair, and a skylight.

An outdoor patio with a round table, chairs, and a large umbrella.

A staircase with a wooden handrail and a landing area with framed pictures on the wall.

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 $309

CA $415 total

includes taxes & fees

Oct 18 - Oct 19

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.

A cozy living room with a wooden ceiling, a staircase, a fireplace, and a television.

A two-story house with a covered patio and a stone deck.

A modern living room with a sofa, coffee table, and a kitchen area in the background.

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 $332

CA $332

CA $454 total

includes taxes & fees

Oct 13 - Oct 14

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

A modern kitchen with a wooden countertop, a toaster, and a kettle.

A living room with a grey sofa, wooden coffee table, and a TV stand with a basket.

A wooden cabin with a pitched roof, a butterfly cutout on the door, and a window with shutters.

A backyard with a wooden deck, a grassy lawn, and a glass door leading to a patio area.

15. 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 $302

CA $302

CA $453 total

includes taxes & fees

Nov 1 - Nov 2

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

A marina with boats docked along a wooden pier.

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

A bedroom with two beds, a skylight, a bedside table with a mirror, and a wooden cabinet.

A two-story brick house with a gabled roof, a front door, and two windows on the upper floor.

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)

9.8/10

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."

Geraldine C.

The price is CA $2,275

CA $2,275

CA $2,275 total

includes taxes & fees

Nov 2 - Nov 3

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

A pebbled beach with a view of the sea and distant land.

A living room with a fireplace, a television, and a sofa.

A neatly arranged bedroom with a bed, bedside lamps, a small table, a decorative vase, and a painting on the wall.

A coastal walkway with benches, a cafe, and a view of the sea.

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

The price is CA $301

CA $301

CA $525 total

includes taxes & fees

Oct 13 - Oct 14

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

A hotel room with a bed, a flat-screen TV mounted on the wall, a window with blinds, and a green pendant light.

A neatly made bed with a green and white duvet, a world map on the wall, and a motivational quote.

A modern bathroom with a glass-enclosed shower, a white sink, and a toilet.

A modern bedroom with a bed, a desk, a chair, a TV, and a window with blinds.

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

Southsea Getaway: Close to Beach & Family Fun!

Southsea

4.0 out of 10, (1 review)

4.0/10

(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."

Janet

The price is CA $81

CA $81

CA $81 total

includes taxes & fees

Oct 13 - Oct 14

Southsea Getaway: Close to Beach & Family Fun!

A bedroom with a bed, a white ladder, a shelf with items, a painting on the wall, and a window with curtains.

A bathroom with a white bathtub, a towel rack, a potted plant, and a shower area.

A bedroom with a bed, curtains, a nightstand, a plant, and a window.

A bedroom with a bed, a nightstand, a mirror, and a window with curtains.

19. Alver Road House: Hot Tub, Free Parking & Family Friendly

Alver Road House: Hot Tub, Free Parking & Family Friendly

Fratton

The price is CA $92

CA $92

CA $92 total

includes taxes & fees

Nov 1 - Nov 2

Alver Road House: Hot Tub, Free Parking & Family Friendly

A bedroom with a large bed, a nightstand, and a lamp.

A bedroom with a sloped ceiling, a bed with white bedding, two bedside lamps, and a wooden nightstand with drawers.

A brick wall with a sign reading "No. 16a Coach House" and a white building in the background.

A pathway through a garden with purple flowers and trees.

20. Coach House - a house that sleeps 8 guests in 4 bedrooms

Coach House - a house that sleeps 8 guests in 4 bedrooms

Gosport

9.4 out of 10, Exceptional, (3 reviews)

9.4/10

Exceptional

(3 reviews)

"Peaceful and spacious house with all rooms en suite affording individual privacy when required. Ideally located on bus routes to all attractions. "

CHRISTOPHER W.

The price is CA $1,495

CA $1,495

CA $1,495 total

includes taxes & fees

Oct 19 - Oct 20

Coach House - a house that sleeps 8 guests in 4 bedrooms

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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