Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

Our top choices for Winchester vacation rentals

Outdoor dining

River Road Retreat 1 by Tiny Away

River Road Retreat 1 by Tiny Away
Maungati
10.0 out of 10, Exceptional, (2 reviews)
"The place was absolutely beautiful. Far out enough for seclusion, but not too far if you want to find things to do. Very clean and tidy, and the hosts had really good communication :)"
Australia
Alex
The price is ￥11,709
￥17,227 total
includes taxes & fees
Mar 30 - Mar 31
River Road Retreat 1 by Tiny Away
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, (5 reviews)
"Everything was great but best of all, Gerard and Patricia were extremely thoughtful, generous and engaging. Such a beautiful, peaceful and relaxing place to stay!"
United States
Cam
The price is ￥12,424
￥17,233 total
includes taxes & fees
Apr 5 - Apr 6
Country Getaway - Studio room with Ensuite in seven-acre landscaped gardens.
Terrace/patio

Luxury Private Guest Suite with Mountain Views

Luxury Private Guest Suite with Mountain Views
Totara Valley
The price is ￥12,442
￥17,253 total
includes taxes & fees
Apr 1 - Apr 2
Luxury Private Guest Suite with Mountain Views
Interior

Field and Fleece Farm Stay by Tiny Away

Field and Fleece Farm Stay by Tiny Away
Levels Valley
The price is ￥17,610
￥23,142 total
includes taxes & fees
Mar 31 - Apr 1
Field and Fleece Farm Stay by Tiny Away
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, (9 reviews)
"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 ￥31,610
￥36,351 total
includes taxes & fees
Apr 20 - Apr 21
Coldstream Estate - The Whare
Exterior

Coastal Ridge Apartments

Coastal Ridge Apartments
3.5 star property
Kensington
9.6 out of 10, Exceptional, (104 reviews)
"Very friendly staff, clean room, easy parking, good location."
Australia
YING
The price is ￥15,866
￥18,453 total
includes taxes & fees
Apr 18 - Apr 19
Coastal Ridge Apartments
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
8.8 out of 10, Excellent, (6 reviews)
"Delightful peaceful location a few minutes'drive from the good facilities in the rural town of Geraldine. The property is well equipped, comfortable and has its own entrance to the rear of the main house. "
United Kingdom
Ian
The price is ￥16,121
￥21,488 total
includes taxes & fees
Apr 9 - Apr 10
Entire Self-Contained Unit in Pleasant Valley, Geraldine. Peaceful and private.
Garden

Phoenix Motel

Phoenix Motel
4.0 star property
Temuka
9.2 out of 10, Wonderful, (118 reviews)
"Nice, flexible host. "
United States
Duncan
The price is ￥13,254
￥15,439 total
includes taxes & fees
Apr 11 - Apr 12
Phoenix Motel
Standard Suite, 1 Bedroom, Non Smoking, Kitchen (apartment 9) | WiFi, wheelchair access

Blue Dolphin Motel

Blue Dolphin Motel
3.5 star property
Maori Hill
8.0 out of 10, Very Good, (168 reviews)
"Clean and tidy great location great hosts "
Australia
Judith
The price is ￥11,135
￥14,187 total
includes taxes & fees
Apr 3 - Apr 4
Blue Dolphin Motel
Property grounds

River Road Retreat 3 by Tiny Away

River Road Retreat 3 by Tiny Away
Maungati
The price is ￥14,706
￥20,238 total
includes taxes & fees
Mar 29 - Mar 30
River Road Retreat 3 by Tiny Away
1 bedroom, bed sheets

River Road Retreat 4 by Tiny Away

River Road Retreat 4 by Tiny Away
Maungati
The price is ￥14,687
￥20,212 total
includes taxes & fees
Mar 30 - Mar 31
River Road Retreat 4 by Tiny Away
Interior

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 review)
"Good"
New Zealand
Chaman L.
The price is ￥5,067
￥10,152 total
includes taxes & fees
Apr 13 - Apr 14
Green Hayes Estate Rentals - R4 Magnolia House in a quiet country setting
Exterior detail

The Huntaway by Tiny Away

The Huntaway by Tiny Away
Levels Valley
The price is ￥17,517
￥23,035 total
includes taxes & fees
Mar 31 - Apr 1
The Huntaway by Tiny Away
Beach nearby

‘Jupiter’ Bayview Escape Apartment

‘Jupiter’ Bayview Escape Apartment
Timaru Central
9.4 out of 10, Exceptional, (3 reviews)
"The host was very friendly and accommodating! The location was great and the home very comfortable."
Canada
Sally S.
The price is ￥36,812
￥65,479 total
includes taxes & fees
Mar 30 - Mar 31
‘Jupiter’ Bayview Escape Apartment
Exterior

Tui Haven - country escape in Geraldine

Tui Haven - country escape in Geraldine
Kakahu
Tui Haven - country escape in Geraldine
Outdoor dining

River Road Retreat 2 by Tiny Away

River Road Retreat 2 by Tiny Away
Maungati
The price is ￥13,564
￥19,089 total
includes taxes & fees
Mar 29 - Mar 30
River Road Retreat 2 by Tiny Away
Interior

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 ￥5,988
￥12,378 total
includes taxes & fees
Apr 13 - Apr 14
R1Quiet country setting close to Ski Fields, Levels Raceway and Fonterra factory
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 ￥5,067
￥11,530 total
includes taxes & fees
Apr 14 - Apr 15
Green Hayes Estate Rentals- Magnolia House Room 3
Interior

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 ￥5,067
￥11,318 total
includes taxes & fees
Apr 13 - Apr 14
R2Quiet country setting close to ski fields, Levels Raceway and Fonterra factory
Interior

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 ￥5,067
￥11,530 total
includes taxes & fees
Apr 23 - Apr 24
Green Hayes Estate Rentals - R5 Magnolia House in quiet peaceful country setting
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

Aaron Court Motel

Aaron Court Motel

6/10 Okay
"Room are dated, handy to town and beach"
Alexander 2-night trip
Posted 14 hours ago
Aaron Court Motel

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

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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?

Spacious, modern, centrally located house.: This vacation home rental outside of Winchester has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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 Washdyke Lagoon Wildlife Refuge. Ashbury Park 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.