Winchester Vacations from $438

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The Latest Winchester vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Austin NW - Lakeway by IHG

Holiday Inn Express & Suites Austin NW - Lakeway by IHG

3 out of 5
Save 100% on your flight
Price was $624, price is now $438 per person
$438
per person
Nov 11 - Nov 17
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Austin (AUS)
8/10 Very Good! (1,003 reviews)
Hotel was very convenient to all areas

Reviewed on Sep 29, 2025

Club Wyndham Austin

Club Wyndham Austin

3 out of 5
Downtown Austin
Save 100% on your flight
Price was $1,336, price is now $928 per person
$928
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Austin (AUS)
8.6/10 Excellent! (440 reviews)
The property was pretty good overall. The one on Clearwater beach has more amenities and larger public areas but probably just a different overall plan.

Reviewed on Sep 25, 2025

Hilton Garden Inn Austin Downtown

Hilton Garden Inn Austin Downtown

3.5 out of 5
Downtown Austin
Price was $683, price is now $483 per person
$483
per person
Nov 21 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Austin (AUS)
7.8/10 Good! (1,006 reviews)
Signage for entrance was hard to see.

Reviewed on Oct 1, 2025

Omni Barton Creek Resort & Spa Austin

Omni Barton Creek Resort & Spa Austin

5 out of 5
Barton Creek
Save 100% on your flight
Price was $1,428, price is now $1,019 per person
$1,019
per person
Nov 25 - Dec 1
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Austin (AUS)
9.2/10 Wonderful! (826 reviews)
It was great to get away.

Reviewed on Sep 24, 2025

Fairmont Austin Gold Experience

Fairmont Austin Gold Experience

5 out of 5
Downtown Austin
Save 100% on your flight
Price was $1,170, price is now $851 per person
$851
per person
Nov 21 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Austin (AUS)
9.6/10 Exceptional! (644 reviews)
Wonderful staff and great location for the UT football game.

Reviewed on Sep 28, 2025

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Discover the most popular places to visit in Winchester

Lester Park

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

The Bugle Boy

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

The Bugle Boy

Jersey Barnyard

Enjoy an outing to Jersey Barnyard during your stay in La Grange. While you're in the area, stroll along the riverfront.

Jersey Barnyard

Winchester Hotel Deals

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
$136 nightly
The price is $154 total per night from Nov 2 to Nov 3
$154 total
Nov 2 - Nov 3
Total with taxes and fees
8.4/10 Very Good! (637 reviews)
"Friendly staff - comfortable rooms"

Reviewed on Aug 26, 2025

Best Western La Grange Inn & Suites
Studio 6 – Giddings, Tx

Studio 6 – Giddings, Tx

2 out of 5
301 Cefco Lane, Giddings, TX
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $113 total per night from Oct 19 to Oct 20
$113 total
Oct 19 - Oct 20
Total with taxes and fees
9.6/10 Exceptional! (4 reviews)
"Clean"

Reviewed on Sep 11, 2025

Studio 6 – Giddings, Tx
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
$72 nightly
The price is $82 total per night from Oct 5 to Oct 6
$82 total
Oct 5 - Oct 6
Total with taxes and fees
7.2/10 Good! (834 reviews)
"It was a lil dated but worked"

Reviewed on Sep 25, 2025

Days Inn by Wyndham Bastrop
See all 289 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.

Winchester Essential Information

Language
English
Currency
U.S dollars
Top Sights
Rohan Meadery, Texas Quilt Museum and Fayette Heritage Museum and Library

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Frequently asked questions

How much does a Winchester vacation package cost?
You'll find cheap prices from $438 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?
You can typically find lower prices and greater availability in July, November and December. Browse our cheap Winchester vacation packages and you could score some great off-season discounts.
How many days is enough for Winchester?
With a well-planned itinerary, you can easily tick off the most popular Winchester sights in a handful of days. But if you'd like to discover hidden spots or take day trips, consider 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.
Does Expedia offer Book Now, Pay Later Winchester vacation packages?
If you're anything like us, you love traveling but don't love the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your Winchester vacation over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.