Winchester Vacation Rentals from $90: Search Short-Term Rentals

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

Holiday House with Style - Geraldine Retreat : This vacation home rental outside of Winchester is located on a river and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

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Our top choices for Winchester vacation rentals

1. Phoenix Motel

Temuka

Lawrence

$79 nightly

Aug 20 - Aug 21

Total with taxes and fees

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

Waitohi

David A.

$98 nightly

Aug 14 - Aug 15

Total with taxes and fees

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

Pleasant Valley

Anonymous traveler

$121 nightly

Aug 20 - Aug 21

Total with taxes and fees

4. Tui Haven - country escape in Geraldine

Kakahu

Anne B.

$101 nightly

Aug 20 - Aug 21

Total with taxes and fees

Luxury Villa, 3 Bedrooms, Non Smoking | Living area | Flat-screen TV, fireplace, DVD player

5. Coldstream Estate - The Whare

Coldstream

Victoria

$176 nightly

Sep 7 - Sep 8

Total with taxes and fees

6. Coastal Ridge Apartments

Kensington

Sarah

$97 nightly

Aug 9 - Aug 10

Total with taxes and fees

Standard Suite, 1 Bedroom, Non Smoking, Kitchen (apartment 9) | WiFi (surcharge)

7. Blue Dolphin Motel

Maori Hill

Judith

$79 nightly

Sep 3 - Sep 4

Total with taxes and fees

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

Glenwood

Michael W.

$104 nightly

Aug 8 - Aug 9

Total with taxes and fees

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Top Winchester Hotel Reviews

Anchor Motel

10/10 Excellent

"An older motel but well maintained and spotless. Exceptional value for money. We arrived on a cold winter evening and the heater and TV were on to welcome us. We will stay there again."

Phoenix Motel

8/10 Good

"I made a mistake with the booking date, and the host was great at helping me change it. Good location if visiting family in Temuka. Rooms are a bit cold (not unusual for NZ buildings - poor insulation is the norm for older buildings in NZ). The motel provides heaters in each room, which helped. Across the street from Night & Day dairy, good for snacks and supplies. A good option in the small town of Temuka if you dont want to trek from Timaru or Geraldine."

Find out more about Winchester

Everything you need to know about Winchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $90 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Holiday House with Style - Geraldine Retreat: This vacation home rental outside of Winchester is located on a river and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

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. DB Brewery and Caroline Bay Beach 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.

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Check prices for these dates

Our top choices for Winchester vacation rentals

1. Phoenix Motel

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

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

4. Tui Haven - country escape in Geraldine

5. Coldstream Estate - The Whare

6. Coastal Ridge Apartments

7. Blue Dolphin Motel

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

9. River Road Retreat 1 by Tiny Away

10. Field and Fleece Farm Stay by Tiny Away

11. The Huntaway by Tiny Away

12. ‘Jupiter’ Bayview Escape Apartment

13. River Road Retreat 3 by Tiny Away

14. River Road Retreat 2 by Tiny Away

15. River Road Retreat 4 by Tiny Away

16. Jellicoe Retreat - 3 Bedroom House

Find vacation rentals that suit your style

Top Winchester Hotel Reviews

Anchor Motel

Coastal Ridge Apartments

Harbour View Motel

ASURE Scenic Route Motor Lodge

The Sea Breeze

Phoenix Motel

Parklands Motor Lodge Timaru

ASURE Avenue Motor Lodge

Geraldine Motels

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Frequently asked questions

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