Winchester Holidays from NZ$2,132

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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
20 Sept - 27 Sept
found 1 day ago
Return direct flight included
Auckland (AKL) to Los Angeles (LAX)
8.6/10 Excellent! (115 reviews)
Loved it!! Would definitely recommend this place.

Reviewed on 10 Aug. 2025

Fairmont Century Plaza Gold Experience

Fairmont Century Plaza Gold Experience

5 out of 5
Century City
Save 100% on your flight
per person
20 Sept - 27 Sept
found 1 day ago
Return direct flight included
Auckland (AKL) to Los Angeles (LAX)
9.8/10 Exceptional! (113 reviews)
This property was beautifully renovated. I visited with my teen daughter and felt very safe in the hotel and surrounding area. This hotel is very centrally located so if you are looking to hit up many sites in LA this is a great spot. Quiet and a little off the beaten path but definitely walkable to shopping (Century City) and Beverly Hills area. We booked the Gold level and it was great, They had a separate concierge lounge that you can get small breakfast items/appetizers/snacks and grab water/soda on the go. Bella (the other staff as well in the Gold level) were super friendly and helpful. Would definitely recommend!

Reviewed on 1 Aug. 2025

Glendale Hotel

Glendale Hotel

2.5 out of 5
Somerset
per person
20 Sept - 27 Sept
found 11 hours ago
Return direct flight included
Auckland (AKL) to Los Angeles (LAX)
8.4/10 Very Good! (2,650 reviews)
It was our first time staying here and the virtual checkin was different but it was quick and easy. I have never had to pay extra for parking but i would stay here again.

Reviewed on 10 Aug. 2025

The Pierside Santa Monica

The Pierside Santa Monica

4 out of 5
Downtown Santa Monica
per person
20 Sept - 27 Sept
found 1 day ago
Return direct flight included
Auckland (AKL) to Los Angeles (LAX)
8.8/10 Excellent! (1,336 reviews)
Good food bed confort internet good

Reviewed on 11 Aug. 2025

Hollywood Inn Suites Hotel

Hollywood Inn Suites Hotel

2.5 out of 5
West Athens
per person
20 Sept - 27 Sept
found 11 hours ago
Return direct flight included
Auckland (AKL) to Los Angeles (LAX)
8.2/10 Very Good! (1,510 reviews)
Hotel itself was very nice, surrounding area was not

Reviewed on 9 Aug. 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
8.6/10 Excellent! (3,712 reviews)
"Had a great time. Live music, good drinks and food. Rooms are amazing and so comfy."

Reviewed on 10 Aug. 2025

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Pala Casino Spa And Resort
South Coast Winery Resort and Spa

South Coast Winery Resort and Spa

4 out of 5
34843 Rancho California Rd, Temecula, CA
Fully refundableReserve now, pay when you stay
The price is NZ$404 per night from 19 Aug to 20 Aug
NZ$404
19 Aug - 20 Aug
includes taxes & fees
8.8/10 Excellent! (1,010 reviews)
"Quiet"

Reviewed on 9 Aug. 2025

South Coast Winery Resort and Spa
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! (610 reviews)
"Hotel restaurant food was great. Beds were comfortable and temperature/ AC inside hotel rooms worked well. Rooms are in separate buildings far away from the lobby, and are not easily walkable with the construction. Pool was closed."

Reviewed on 9 Aug. 2025

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Pala Mesa Golf Resort
See all 1,511 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$2,132 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.