Default HTG hotel image

Winchester Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Winchester holiday rentals

A modern two-story house with a blue exterior, a front porch, and a wooden picnic table.

1. Phoenix Motel

Phoenix Motel
4.0 star property
Temuka
9.2 out of 10, Wonderful, (122 reviews)
"Great place to stay and being opposite a ‘Night-&-Day store was a bonus.will definitely stay there again."
Australia
Lawrence
The price is HK$717
HK$825 total
includes taxes & fees
22 Oct - 23 Oct
Phoenix Motel
A garden pathway with lush greenery and flowering plants.

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

Country Getaway - Studio room with Ensuite in seven-acre landscaped gardens.
Waitohi
9.8 out of 10, Exceptional, (6 reviews)
"A great all round experience in a country setting, great hosts, breakfast, bed and knowledge "
Australia
David A.
The price is HK$595
HK$826 total
includes taxes & fees
19 Oct - 20 Oct
Country Getaway - Studio room with Ensuite in seven-acre landscaped gardens.
A coastal building with balconies, labeled "COASTAL RIDGE TIMARU LUXURY ACCOMMODATION."

3. Coastal Ridge Apartments

Coastal Ridge Apartments
3.5 star property
Kensington
9.6 out of 10, Exceptional, (113 reviews)
"One of the bests stays I’ve experienced, ticks all the boxes and then some.. thank you !"
Australia
Sarah
The price is HK$886
HK$1,019 total
includes taxes & fees
6 Nov - 7 Nov
Coastal Ridge Apartments
A small, single-story house with a porch, a satellite dish, and a gravel driveway.

4. Tui Haven - country escape in Geraldine

Tui Haven - country escape in Geraldine
Kakahu
10.0 out of 10, Exceptional, (2 reviews)
"The cottage was lovely really comortable bed. Free range eggs for breakfast. Deicious..0"
New Zealand
Anne B.
The price is HK$573
HK$851 total
includes taxes & fees
25 Oct - 26 Oct
Tui Haven - country escape in Geraldine
A living room with a sofa, pillows, and a vase of flowers.

5. Coldstream Estate - The Whare

Coldstream Estate - The Whare
4.0 star property
Coldstream
10.0 out of 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!!"
Australia
Jenny
The price is HK$1,501
HK$1,726 total
includes taxes & fees
19 Oct - 20 Oct
Coldstream Estate - The Whare
A bedroom with a bed, bedside table, and a window.

6. Field and Fleece Farm Stay by Tiny Away

Field and Fleece Farm Stay by Tiny Away
Levels Valley
The price is HK$691
HK$957 total
includes taxes & fees
19 Oct - 20 Oct
Field and Fleece Farm Stay by Tiny Away
A modern building with a wooden exterior and large glass windows.

7. River Road Retreat 1 by Tiny Away

River Road Retreat 1 by Tiny Away
Maungati
10.0 out of 10, Exceptional, (2 reviews)
"Perfect accommodation for a stay in the area. Modern conveniences, comfortable bed, lovely rural views. I really enjoyed my stay. "
United States
Trish K.
The price is HK$540
HK$806 total
includes taxes & fees
18 Oct - 19 Oct
River Road Retreat 1 by Tiny Away
A wooden shelf with wine bottles and glasses, a coffee maker, and a vase.

8. Lady Gs Guesthouse | Gorgeous escape for 2

Lady Gs Guesthouse | Gorgeous escape for 2
Geraldine
The price is HK$1,171
HK$1,510 total
includes taxes & fees
18 Oct - 19 Oct
Lady Gs Guesthouse | Gorgeous escape for 2
A modern living room with a grey sofa, a television, and a coffee table. There is a dining area in the background with a table and chairs.

9. 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 reviews)
"We enjoyed our stay."
Australia
Michael W.
The price is HK$706
HK$953 total
includes taxes & fees
1 Nov - 2 Nov
Barnes Street BNB - Enjoy your stay in lovely private unit.
A well-maintained lawn with a trampoline, a small shed, and a fenced area.

10. 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, (3 reviews)
"Great high end accomodation that we were very happy with."
New Zealand
Ryan P.
The price is HK$691
HK$1,584 total
includes taxes & fees
28 Oct - 29 Oct
Find your stay peaceful and comfortable with luxury. Kids friendly
A bathroom with a wooden vanity, a glass shower enclosure, and a hand dryer.

11. The Huntaway by Tiny Away

The Huntaway by Tiny Away
Levels Valley
The price is HK$994
HK$1,259 total
includes taxes & fees
30 Oct - 31 Oct
The Huntaway by Tiny Away
A wooden shelf with wine bottles and glasses, a coffee maker, and a vase.

12. Lady Geraldine’s Guesthouse | Sleeps 2 Boutique

Lady Geraldine’s Guesthouse | Sleeps 2 Boutique
Geraldine
The price is HK$1,171
HK$1,514 total
includes taxes & fees
26 Oct - 27 Oct
Lady Geraldine’s Guesthouse | Sleeps 2 Boutique
A kitchen with wooden cabinets, a white refrigerator, a microwave, and a stove.

13. Suite Caroline 2 Bedroom apartment

Suite Caroline 2 Bedroom apartment
Maori Hill
The price is HK$1,258
HK$1,447 total
includes taxes & fees
30 Oct - 31 Oct
Suite Caroline 2 Bedroom apartment
A two-story house with a red roof, a front porch, and a green front yard.

14. 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 HK$1,278
HK$1,968 total
includes taxes & fees
15 Nov - 16 Nov
Large 4-Bedroom Home with Dual Living & short Walk to Beach/Town
A modern living room with a flat-screen TV mounted on the wall, a sliding door, and two potted plants.

15. Prime Spot Stay - Entire guest suite

Prime Spot Stay - Entire guest suite
Waimataitai
The price is HK$1,357
HK$1,715 total
includes taxes & fees
1 Nov - 2 Nov
Prime Spot Stay - Entire guest suite
A modern, single-story building with large windows, a wooden deck, and a white chair.

16. River Road Retreat 3 by Tiny Away

River Road Retreat 3 by Tiny Away
Maungati
The price is HK$626
HK$892 total
includes taxes & fees
18 Oct - 19 Oct
River Road Retreat 3 by Tiny Away
A modern bedroom with a bed, bedside tables, a built-in microwave, and a large window.

17. River Road Retreat 4 by Tiny Away

River Road Retreat 4 by Tiny Away
Maungati
The price is HK$626
HK$892 total
includes taxes & fees
18 Oct - 19 Oct
River Road Retreat 4 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.

18. River Road Retreat 2 by Tiny Away

River Road Retreat 2 by Tiny Away
Maungati
The price is HK$626
HK$892 total
includes taxes & fees
18 Oct - 19 Oct
River Road Retreat 2 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Bay Viaduct Motor Lodge

Bay Viaduct Motor Lodge

10/10 Excellent
"Great place, very welcoming. Reception gave a map to help us plan our trip south the next day which was very useful. Oh, and within walking distance of penguin nesting across the park."
Stephen 1-night trip
Posted 4 days ago
Bay Viaduct Motor Lodge

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:

  • View our selection of featured holiday rentals in Winchester
  • Use the map to find apartments and other holiday homes in the Winchester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winchester while they last

Look no further and take a look at our great range of rental properties in Winchester!

Frequently asked questions

Can I find a holiday rental in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay. Winchester is known for its cafés and spas. Make sure you have time to check out the gardens while you're in the area.

What are some of the best holiday rentals that Winchester has to offer?

Coldstream Estate - The Whare: This holiday home rental outside of Winchester is located near the beach, and has a fireplace, a terrace and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a private garden 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. Timaru Lighthouse and Caroline Bay Beach are a couple of places you'll find in the wider area.

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from public hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for family trips.