Winchester Holidays

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    Better together

    Save up to S$134 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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    Plan, book, and manage your trip all in one place

Top hotels in Winchester

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 S$114 per night from 24 Jul to 25 Jul
S$114
24 Jul - 25 Jul
includes taxes & fees
7.2/10 Good! (780 reviews)
"Not bad"

Reviewed on 29 Jun, 2025

Super 8 by Wyndham Giddings
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 S$188 per night from 28 Jul to 29 Jul
S$188
28 Jul - 29 Jul
includes taxes & fees
8.4/10 Very Good! (630 reviews)
"Room and bathroom was clean. No funky smells. Staff was friendly, courteous, and helpful. Breakfast was good as well. No complaints. Will stay there again."

Reviewed on 11 Jul, 2025

Best Western La Grange Inn & Suites
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 S$93 per night from 24 Jul to 25 Jul
S$93
24 Jul - 25 Jul
includes taxes & fees
7.2/10 Good! (816 reviews)
Budget friendly clean accomodation
"Somewhat older but updated budget hotel. Quite clean and staff very helpful. Second stay there"

Reviewed on 15 Jul, 2025

Days Inn by Wyndham Bastrop
See all 274 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.

Popular places to visit

Texas Quilt Museum

You can spend an afternoon exploring the galleries in Texas Quilt Museum during your travels in La Grange. While you're in the area, wander around the parks.

Texas Quilt 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.