Winchester Vacations

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Find the Best Winchester Vacation Packages

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 NT$2,308 per night from Jul 13 to Jul 14
NT$2,308
NT$2,608 total
Jul 13 - Jul 14
includes taxes & fees
7.2/10 Good! (776 reviews)
"Not bad"

Reviewed on 2025/6/29

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 NT$1,863 per night from Jul 21 to Jul 22
NT$1,863
NT$2,119 total
Jul 21 - Jul 22
includes taxes & fees
7.2/10 Good! (811 reviews)
"Pool area was very quiet the staff was very helpful and friendly"

Reviewed on 2025/7/11

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 NT$3,797 per night from Jul 13 to Jul 14
NT$3,797
NT$4,290 total
Jul 13 - Jul 14
includes taxes & fees
8.4/10 Very Good! (626 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 2025/7/11

Best Western La Grange Inn & Suites
See all 278 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

Rosemary’s Vineyard & Winery

4.5/5(5 reviews)

You can enjoy a tasting or tour at Rosemary’s Vineyard & Winery during your travels to La Grange. Discover the area's countryside and churches.

Rosemary’s Vineyard & Winery

Lester Park

3.5/5(2 reviews)

After visiting Lester Park, make a plan to see the other sights and activities in La Grange. While you're in the area, wander around the parks.

Lester Park

Fayette County Courthouse

4.5/5(15 reviews)

Fayette County Courthouse is just one of the places to see in La Grange, so why not enjoy the other things to explore during your travels? Amble around the area's parks or visit its churches.

Fayette County Courthouse

Frequently asked questions

How much does a Winchester vacation 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 vacation to Winchester costs.
What are the cheapest months to go to Winchester?
If you're looking to score a cheap Winchester vacation 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 travelers.
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 vacation 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 customize 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 traveling on a weekday, when prices are often lower.
Is it cheaper to book a Winchester vacation as a package?
You can enjoy significant savings on your next Winchester getaway by booking a tailored vacation 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 vacation 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 personalized Winchester vacation package.

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