Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Vacation Rentals in Winchester

Executive Studio | View from room
Coastal Ridge Apartments

Coastal Ridge Apartments

3.5 star property
Kensington
9.6 out of 10, Exceptional, (102)
"Good location for holiday in timaru, close to places we were visiting."
Australia
Michael
The price is ￥16,148
￥18,594 total
includes taxes & fees
Dec 12 - Dec 13
Coastal Ridge Apartments
Garden
Phoenix Motel

Phoenix Motel

4.0 star property
Temuka
9.2 out of 10, Wonderful, (113)
"The place to stay in temuka"
Australia
Steve
The price is ￥13,902
￥16,008 total
includes taxes & fees
Dec 15 - Dec 16
Phoenix Motel
Luxury Villa, 3 Bedrooms, Non Smoking | Living area | Flat-screen TV, fireplace, DVD player
Coldstream Estate - The Whare

Coldstream Estate - The Whare

4.0 star property
Coldstream
10.0 out of 10, Exceptional, (8)
"This is a beautiful property with great character and an interesting history. We were very comfortable as well as charmed by this unique place. "
Australia
Julie
The price is ￥26,981
￥31,153 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Coldstream Estate - The Whare
Property grounds
Country Getaway - Studio room with Ensuite in seven-acre landscaped gardens.

Country Getaway - Studio room with Ensuite in seven-acre landscaped gardens.

Waitohi
10.0 out of 10, Exceptional, (1)
"This was the exact getaway I was looking for. The sleepout was brand new and very tidy. Shower was amzing and the bed very comfy. The owner was so welcoming and friendly. Cannot express how great this stay was! Thank you Gerard and wife (sorry I can't remember your name)"
New Zealand
Daina C.
The price is ￥13,457
￥18,346 total
includes taxes & fees
Dec 29 - Dec 30
Country Getaway - Studio room with Ensuite in seven-acre landscaped gardens.
1 bedroom, WiFi, bed sheets
Barnes Street BNB - Enjoy your stay in lovely private unit.

Barnes Street BNB - Enjoy your stay in lovely private unit.

Glenwood
8.8 out of 10, Excellent, (5)
"We enjoyed our stay."
Australia
Michael W.
The price is ￥11,663
￥16,283 total
includes taxes & fees
Dec 10 - Dec 11
Barnes Street BNB - Enjoy your stay in lovely private unit.
Interior
Entire Self-Contained Unit in Pleasant Valley, Geraldine. Peaceful and private.

Entire Self-Contained Unit in Pleasant Valley, Geraldine. Peaceful and private.

Pleasant Valley
10.0 out of 10, Exceptional, (3)
"Everything was great. A very peaceful spot with a lovely morning chorus from the birds."
New Zealand
Judith L.
Entire Self-Contained Unit in Pleasant Valley, Geraldine. Peaceful and private.
Terrace/patio
The Huntaway by Tiny Away

The Huntaway by Tiny Away

Levels Valley
The price is ￥13,408
￥17,901 total
includes taxes & fees
Dec 11 - Dec 12
The Huntaway by Tiny Away
WiFi, wheelchair access
Blue Dolphin Motel

Blue Dolphin Motel

3.5 star property
Maori Hill
8.0 out of 10, Very Good, (157)
"It was close to town and cosy & warm when we arrived."
Australia
Bridget
The price is ￥11,390
￥14,444 total
includes taxes & fees
Dec 15 - Dec 16
Blue Dolphin Motel
Property grounds
Delightful 1-bed barn with stunning mountain views...

Delightful 1-bed barn with stunning mountain views...

Timaru
9.8 out of 10, Exceptional, (24)
"Views and friendly hosts"
Australia
debra
The price is ￥53,828
￥69,169 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Delightful 1-bed barn with stunning mountain views...
1 bedroom, bed sheets
River Road Retreat 1 by Tiny Away

River Road Retreat 1 by Tiny Away

Maungati
The price is ￥13,408
￥18,801 total
includes taxes & fees
Dec 10 - Dec 11
River Road Retreat 1 by Tiny Away
Microwave, oven, stovetop
Green Hayes Estate Rentals - R4 Magnolia House in a quiet country setting

Green Hayes Estate Rentals - R4 Magnolia House in a quiet country setting

Temuka
10.0 out of 10, Exceptional, (1)
"Good"
New Zealand
Chaman L.
The price is ￥4,755
￥9,680 total
includes taxes & fees
Dec 10 - Dec 11
Green Hayes Estate Rentals - R4 Magnolia House in a quiet country setting
1 bedroom, bed sheets
River Road Retreat 4 by Tiny Away

River Road Retreat 4 by Tiny Away

Maungati
The price is ￥15,574
￥20,967 total
includes taxes & fees
Dec 10 - Dec 11
River Road Retreat 4 by Tiny Away
Terrace/patio
Field and Fleece Farm Stay by Tiny Away

Field and Fleece Farm Stay by Tiny Away

2.0 star property
Levels Valley
The price is ￥13,408
￥17,903 total
includes taxes & fees
Dec 10 - Dec 11
Field and Fleece Farm Stay by Tiny Away
Property grounds
River Road Retreat 3 by Tiny Away

River Road Retreat 3 by Tiny Away

Maungati
The price is ￥15,574
￥20,967 total
includes taxes & fees
Dec 10 - Dec 11
River Road Retreat 3 by Tiny Away
Outdoor dining
River Road Retreat 2 by Tiny Away

River Road Retreat 2 by Tiny Away

Maungati
The price is ￥15,574
￥20,967 total
includes taxes & fees
Dec 10 - Dec 11
River Road Retreat 2 by Tiny Away
1 bedroom, free WiFi, bed sheets, wheelchair access
Green Hayes Estate Rentals- Magnolia House Room 3

Green Hayes Estate Rentals- Magnolia House Room 3

Temuka
The price is ￥4,755
￥11,022 total
includes taxes & fees
Dec 10 - Dec 11
Green Hayes Estate Rentals- Magnolia House Room 3
Microwave, oven, stovetop
R1Quiet country setting close to Ski Fields, Levels Raceway and Fonterra factory

R1Quiet country setting close to Ski Fields, Levels Raceway and Fonterra factory

Temuka
The price is ￥4,306
￥10,299 total
includes taxes & fees
Dec 10 - Dec 11
R1Quiet country setting close to Ski Fields, Levels Raceway and Fonterra factory
Oven, stovetop
Green Hayes Estate Rentals - R5 Magnolia House in quiet peaceful country setting

Green Hayes Estate Rentals - R5 Magnolia House in quiet peaceful country setting

Temuka
The price is ￥4,755
￥11,022 total
includes taxes & fees
Dec 10 - Dec 11
Green Hayes Estate Rentals - R5 Magnolia House in quiet peaceful country setting
Microwave, oven, stovetop
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 ￥4,755
￥10,816 total
includes taxes & fees
Dec 10 - Dec 11
R2Quiet country setting close to ski fields, Levels Raceway and Fonterra factory
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

Bay Viaduct Motor Lodge

Bay Viaduct Motor Lodge

10/10 Excellent
"Room was large, clean and well equipped. The staff were extremely helpful. Was slightly noisy at night with the proximity to State Highway 1 and you could occasionally hear the large trucks going by, but generally quiet."
Ian 3-night trip
Posted 7 days ago
Bay Viaduct Motor Lodge

Find out more about Winchester

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Frequently asked questions

Can I find a vacation rental in Winchester?

Yes, we give you a choice of vacation rentals near popular local attractions in Winchester, or you can select a more secluded option if you're looking for relaxation. Winchester is known for its cafes and spas. Make sure you have time to check out the gardens while you're in the area.

What are some of the best vacation home rentals in Winchester?

Coldstream Estate - The Whare: This vacation home rental outside Winchester is located near the beach and has a fireplace, a terrace, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a full-sized fridge, a dishwasher, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a private yard and a library.

What’s there to see and do in Winchester?

Explore the area and family-friendly sights such as Geraldine Observatory, or get out into nature at a spot like Ashbury Park. Geraldine Historical Society Museum and Timaru Lighthouse are a couple of places you'll find in the larger area.

What’s a vacation rental in Winchester like?

Vacation rentals are private properties you can stay in for a long or short time in Winchester. Vacation rentals provide amenities like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for families.