Winchester Holidays from NZ$1,999

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The Latest Winchester Holiday Deals

Price found within the past 48 hours. Click for updated prices.
The LEEF Hotel

The LEEF Hotel

2 out of 5
Citrus Grove
per person
12 Sept - 19 Sept
found 22 hours ago
Return direct flight included
Auckland (AKL) to Los Angeles (LAX)
8.6/10 Excellent! (55 reviews)
Great safe and quiet location. Perfect place if going to the Rose Bowl.

Reviewed on 23 Jun. 2025

Hotel Maya

Hotel Maya

4 out of 5
per person
12 Sept - 19 Sept
found 22 hours ago
Return direct flight included
Auckland (AKL) to Long Beach (LGB)
8.2/10 Very Good! (1,698 reviews)
Great views, big room, comfortable bed. The room was clean. There were some strings coming out of the sofa bed, but just need to be cut a bit. The drinks at Fuego downstairs are delish. Overall, we had a great birthday stay.

Reviewed on 25 Jun. 2025

Level Los Angeles Downtown - South Olive

Level Los Angeles Downtown - South Olive

4.5 out of 5
Downtown Los Angeles
per person
12 Sept - 19 Sept
found 22 hours ago
Return direct flight included
Auckland (AKL) to Los Angeles (LAX)
8.4/10 Very Good! (1,052 reviews)
Exterior looks great, entrance staff is not friendly, inside is looks good but need a care more about furniture

Reviewed on 25 Jun. 2025

Beverly Laurel Hotel at West Hollywood

Beverly Laurel Hotel at West Hollywood

3 out of 5
Beverly Grove
per person
12 Sept - 19 Sept
found 22 hours ago
Return direct flight included
Auckland (AKL) to Los Angeles (LAX)
8.2/10 Very Good! (1,006 reviews)
Great experience great location and service! Huge shoutout to Marlo! He made our experience much better and easier checking in and out, valet service was incredible room service is super nice

Reviewed on 26 Jun. 2025

The Kinney - Venice Beach

The Kinney - Venice Beach

3 out of 5
per person
12 Sept - 19 Sept
found 22 hours ago
Return direct flight included
Auckland (AKL) to Los Angeles (LAX)
8.8/10 Excellent! (1,001 reviews)
Great spot by the beach pool and clean rooms nice staff

Reviewed on 18 Jun. 2025

Winchester Holiday

Our pick of the best Winchester Hotel Deals

Pala Casino Spa And Resort
Pala Casino Spa And Resort
4 out of 5
11154 Highway 76, Pala, CA
Fully refundableReserve now, pay when you stay
The price is NZ$267 per night from 1 July to 2 July
NZ$267
1 July - 2 July
includes taxes & fees
8.6/10 Excellent! (3,445 reviews)
"Rooms were really nice. Super clean. Pool was amazing. Staff was great!"

Reviewed on 24 Jun. 2025

Pala Casino Spa And Resort
Motel 6 Temecula, CA - Historic Old Town
Motel 6 Temecula, CA - Historic Old Town
2 out of 5
41900 Moreno Rd, Temecula, CA
Fully refundableReserve now, pay when you stay
The price is NZ$111 per night from 2 July to 3 July
NZ$111
2 July - 3 July
includes taxes & fees
8/10 Very Good! (1,595 reviews)
"Great location to Old Town. No noise issues. Dog-friendly. Comfy bed. Reasonably priced. Had a slight concern about cleanliness since I found a single long hair hanging from one of the rolled towels. But I would stay here again."

Reviewed on 23 Jun. 2025

Motel 6 Temecula, CA - Historic Old Town
Pala Mesa Golf Resort
Pala Mesa Golf Resort
3.5 out of 5
2001 Old Highway 395, Fallbrook, CA
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (519 reviews)
"I want to give a huge thank you to Mackey at Palo Mesa Golf Resort for going above and beyond to accommodate me. I had to stay at another hotel the night before and was worried about the gap between check-out and check-in, but Mackey made sure there was a smooth transition. He responded quickly and ..."

Reviewed on 23 Jun. 2025

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Pala Mesa Golf Resort
See all 1,515 properties in Winchester
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.

Frequently asked questions

How much does a Winchester holiday package cost?
You'll find cheap prices from NZ$1,999 on Expedia for your Winchester getaway. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your holiday to Winchester costs.
What are the cheapest months to go to Winchester?
February, September and December are the best times to search for cheap Winchester holiday packages. Opting to travel in quieter periods means you'll typically find reduced prices on flights and accommodation.
How many days is enough for Winchester?
With a well-organised itinerary, you can easily tick off the main Winchester sights in a few days. But if you prefer to discover lesser-known spots or take day trips, consider booking your Winchester holiday for longer.
How to find the best Winchester package deals?
Use Expedia's handy filters to help you find some of the best Winchester package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or search for Winchester package deals in the off-season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your holiday package as early as possible.
Is it cheaper to book a Winchester holiday as a package?
An Expedia holiday package could land you great savings when compared to arranging stays and flights separately. Better still, you can customise your Winchester getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a holiday package to Winchester?
Enjoy amazing discounts by reserving your flights in advance with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Winchester trip.
How to plan a trip to Winchester?

  1. Pick the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to go to Winchester.
  2. Budget wisely: Besides the cost of your hotel, you'll need to factor in other expenses too. These include food, flights and transportation. Also, set aside some extra funds for unexpected costs that may crop up during your trip to Winchester.
  3. Set the duration of your trip: Start by making a list of all the activities and attractions you want to experience in Winchester. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your accommodation and airfare: Once you've settled on your travel dates and duration, lock in the right Winchester holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.