Winchester Holidays

Book a Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to NZ$616 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Winchester Holiday

Our pick of the best Winchester Hotel Deals

Super 8 by Wyndham Giddings
Super 8 by Wyndham Giddings
2 out of 5
4002 E Austin St, Hwy 290 E, Giddings, TX
Fully refundableReserve now, pay when you stay
The price is NZ$133 per night from 8 July to 9 July
NZ$133
8 July - 9 July
includes taxes & fees
7.2/10 Good! (773 reviews)
"Not bad"

Reviewed on 29 Jun. 2025

Super 8 by Wyndham Giddings
Days Inn by Wyndham Bastrop
Days Inn by Wyndham Bastrop
2 out of 5
4102 Hwy 71 E, Bastrop, TX
Fully refundableReserve now, pay when you stay
The price is NZ$120 per night from 20 July to 21 July
NZ$120
20 July - 21 July
includes taxes & fees
7.2/10 Good! (807 reviews)
Great! Clean! Will come back.
"Stayed overnight for work. Room was clean. I can see why certain reviews said bugs, but that is only because the lights are bright outside of the room so you have to shut the door quickly or one or two flying critters might sneak in. For the cost you can’t beat it. I will come back next time I am ..."

Reviewed on 3 Jul. 2025

Days Inn by Wyndham Bastrop
Best Western La Grange Inn & Suites
Best Western La Grange Inn & Suites
2.5 out of 5
600 E State Highway 71 Bypass, La Grange, TX
Fully refundableReserve now, pay when you stay
The price is NZ$242 per night from 8 July to 9 July
NZ$242
8 July - 9 July
includes taxes & fees
8.4/10 Very Good! (622 reviews)
"Property was conveniently located, clean and well maintained, and staff was friendly. Room was spacious and microwave and refrigerator were exactly what we needed."

Reviewed on 29 Jun. 2025

Best Western La Grange Inn & Suites
See all 280 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.

Discover the most popular places to visit in Winchester

N.W. Faison House and Museum

You can browse the exhibits at N.W. Faison House and Museum, a museum with a story of its own, during your trip to La Grange. Take in the live music and countryside in the area.

N.W. Faison House and Museum

Frequently asked questions

How much does a Winchester holiday package cost?
You'll find cheap prices on Expedia for your Winchester getaway. However, factors like your choice of hotel, the season and length of stay will determine how much your holiday to Winchester costs.
What are the cheapest months to go to Winchester?
If you're looking to score a cheap Winchester holiday package, consider planning a trip in January, February and May. You'll usually find better rates on flights and hotels during these months --- perfect for budget-conscious travellers.
How many days is enough for Winchester?
With a well-planned itinerary, you can easily hit the main Winchester sights in a few days. But if you want to explore off the beaten track or go on day trips, think about booking your Winchester holiday for longer.
How to find the best Winchester package deals?
Bagging a cheap Winchester package deal is a breeze with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, apply some filters and see what's available. You can customise your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Winchester package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Winchester holiday as a package?
You can enjoy significant savings on your next Winchester getaway by booking a tailored holiday package. Click on the "Package" heading, then enter your travel dates and destination to see the best flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to Winchester?
Land 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 an impromptu Winchester escape.
How to plan a trip to Winchester?

  1. Choose when to get away: Check your diary and pack your bags. Your preferred season and the type of activities available will also help you decide when to visit Winchester.
  2. Set a budget: Factor in costs like flights, transportation and food when calculating how much to save for your trip to Winchester. Then, choose a property that fits your budget, whether that's a wallet-friendly option or a high-end retreat.
  3. Set the duration of your trip: Start by compiling a list of the attractions and activities you want to experience in Winchester. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a personalised Winchester holiday package.

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