Holiday Homes in Winchester
Canterbury
New Zealand
Holiday Homes
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Holiday Homes in Winchester

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your current months are November, 2026 and December, 2026.

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Our top choices for Winchester holiday homes

A living room with a sofa, pillows, and a vase of flowers.

A spacious living room with a fireplace, a wooden dining table, and a bookshelf filled with books.

A kitchen with wooden floors, white cabinetry, and a dining area with a table and chairs.

A striped bean bag chair on a patio with a brick building in the background.

1. Coldstream Estate - The Whare

Coldstream Estate - The Whare

4.0 star property

Coldstream

10.0 out of 10, Exceptional, (11 reviews)

10/10

Exceptional

(11 reviews)

"What a charming place! This place was more than I hoped. Beautiful styled while allowing for comfort. The surrounds are stunning and the home is delightful. I will be recommending this to friends who need a relaxing stop to recharge. We didn’t want to leave!!"

Jenny

The price is NZ$409

NZ$409

includes taxes & fees

19 Nov - 20 Nov

Coldstream Estate - The Whare

A glass-enclosed shower area with a marble wall, a towel rack, and a curtain.

A bedroom with two beds, a window with a view of greenery, a patterned carpet, and a wooden bench.

A building with a flat roof, a satellite dish, and a front porch with steps leading to a door. There are picnic tables in the foreground.

A compact kitchen with white cabinets, a stove, and a refrigerator.

2. R2Quiet country setting close to ski fields, Levels Raceway and Fonterra factory

R2Quiet country setting close to ski fields, Levels Raceway and Fonterra factory

Temuka

The price is NZ$130

NZ$130

includes taxes & fees

7 Dec - 8 Dec

R2Quiet country setting close to ski fields, Levels Raceway and Fonterra factory

A modern kitchen with a central island, wooden flooring, and a dining area with a long table and chairs.

A garden with a stone pathway leading up a slope, surrounded by various shrubs and trees.

A modern kitchen with white cabinetry, a large island with stools, a black refrigerator, and a patterned backsplash.

A modern house with solar panels, large windows, and a wooden deck.

3. Spacious home and tranquil garden close to village

Spacious home and tranquil garden close to village

Geraldine

The price is NZ$505

NZ$505

includes taxes & fees

12 Nov - 13 Nov

Spacious home and tranquil garden close to village

A modern building with a wooden exterior and large glass windows.

A modern kitchen with a dining area, a view through a window, and a kitchen counter with a microwave.

A bedroom with a bed, a TV, and a view of the outdoors.

A modern, single-story cabin with large glass doors and windows, a wooden deck, and a small outdoor seating area.

4. River Road Retreat 1 by Tiny Away

River Road Retreat 1 by Tiny Away

Maungati

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Perfect accommodation for a stay in the area. Modern conveniences, comfortable bed, lovely rural views. I really enjoyed my stay. "

Trish K.

The price is NZ$181

NZ$181

includes taxes & fees

15 Nov - 16 Nov

River Road Retreat 1 by Tiny Away

A hot tub in a wooden barrel with a view of a house and garden.

A modern kitchen with a central island, stainless steel appliances, and a large window.

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

A white barn with a covered porch, surrounded by a well-maintained lawn and various shrubs.

5. Lady G | Villa & Guesthouse | Hot Tub | Guests 14+

Lady G | Villa & Guesthouse | Hot Tub | Guests 14+

Geraldine

The price is NZ$486

NZ$486

includes taxes & fees

24 Nov - 25 Nov

Lady G | Villa & Guesthouse | Hot Tub | Guests 14+

A bedroom with a bed, a dresser, a window, and a mural of dolphins.

A living room with a wooden floor, a brick fireplace, a green kitchen area, and a dining area with stools.

A two-story house with a red roof, a front porch, and a green front yard.

A living room with a wooden staircase, a patterned sofa, a clock, and a framed picture on the wall.

6. Large 4-Bedroom Home with Dual Living & short Walk to Beach/Town

Large 4-Bedroom Home with Dual Living & short Walk to Beach/Town

West End

The price is NZ$432

NZ$432

includes taxes & fees

15 Nov - 16 Nov

Large 4-Bedroom Home with Dual Living & short Walk to Beach/Town

A well-maintained lawn with a trampoline, a small shed, and a fenced area.

A spacious living room with a leather sofa, a glass coffee table, and a dining area with wooden chairs.

A bedroom with a bed, a desk, a chair, a fan, and a view of the outdoors.

A modern kitchen with stainless steel appliances, patterned backsplash, and wooden flooring.

7. Find your stay peaceful and comfortable with luxury. Kids friendly

Find your stay peaceful and comfortable with luxury. Kids friendly

Scarborough

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"Wow 5 stars from us everything was better than the photos and booking this place was super easy and I had to change the dates, and they made it so easy for us to change without any drama, thank again."

susan c.

The price is NZ$328

NZ$328

includes taxes & fees

17 Nov - 18 Nov

Find your stay peaceful and comfortable with luxury. Kids friendly

A modern living room with a sliding glass door leading to a balcony, a black refrigerator, and a dark-colored sofa.

A hallway with a wooden floor, a black bookshelf, a hanging plant, and a chandelier.

A modern living room with a sofa, a dining table with chairs, a bench, and a large window with a view of trees and a house.

A dining area with a wooden table, cushioned benches, and a decorative wall clock.

8. Prime Spot Stay - Entire guest suite

Prime Spot Stay - Entire guest suite

Waimataitai

The price is NZ$391

NZ$391

includes taxes & fees

15 Nov - 16 Nov

Prime Spot Stay - Entire guest suite

A modern, single-story building with large windows, a wooden deck, and a white chair.

A modern building with a sign indicating it is managed by Tiny Away.

A compact kitchen with a wooden table and chairs, a microwave, and a window overlooking a garden.

A bedroom with a bed, a floral pillow, and a window with a view of a field.

9. River Road Retreat 3 by Tiny Away

River Road Retreat 3 by Tiny Away

Maungati

The price is NZ$200

NZ$200

includes taxes & fees

15 Nov - 16 Nov

River Road Retreat 3 by Tiny Away

A modern cabin with a wooden exterior, a sliding glass door entrance, a small dining area with a table and chairs, and a bench outside.

A neatly made bed with checkered pillows, a bedside table with a book, and a window with blinds.

A small, modern cabin with a wooden exterior and a glass door leading to an interior with a bed, a table, and a chair.

A compact kitchen with a microwave, sink, and a dining area with a table and chairs.

10. River Road Retreat 2 by Tiny Away

River Road Retreat 2 by Tiny Away

Maungati

The price is NZ$200

NZ$200

includes taxes & fees

15 Nov - 16 Nov

River Road Retreat 2 by Tiny Away

A modern bedroom with a bed, bedside tables, a built-in microwave, and a large window.

An outdoor seating area with a table and chairs, overlooking a grassy field and hills.

A room with a wooden table and chairs, a window with a view, and a wall-mounted clothes rack.

A view through a window of a rural landscape with fields and hills.

11. River Road Retreat 4 by Tiny Away

River Road Retreat 4 by Tiny Away

Maungati

The price is NZ$200

NZ$200

includes taxes & fees

15 Nov - 16 Nov

River Road Retreat 4 by Tiny Away

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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Temuka Holidays
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Geraldine Vintage Car and Machinery Museum
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Geraldine Observatory
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Talbot Forest Scenic Reserve
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Holiday Homes in Winchester

Change your mind

Treat yourself

Be picky

Find holiday rentals that suit your style

Check prices for these dates

Our top choices for Winchester holiday homes

1. Coldstream Estate - The Whare

2. R2Quiet country setting close to ski fields, Levels Raceway and Fonterra factory

3. Spacious home and tranquil garden close to village

4. River Road Retreat 1 by Tiny Away

5. Lady G | Villa & Guesthouse | Hot Tub | Guests 14+

6. Large 4-Bedroom Home with Dual Living & short Walk to Beach/Town

7. Find your stay peaceful and comfortable with luxury. Kids friendly

8. Prime Spot Stay - Entire guest suite

9. River Road Retreat 3 by Tiny Away

10. River Road Retreat 2 by Tiny Away

11. River Road Retreat 4 by Tiny Away

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