Winchester Vacations from $406

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The Latest Winchester vacation packages

Price found within the past 48 hours. Click for updated prices.
Sheraton Austin Georgetown Hotel & Conference Center

Sheraton Austin Georgetown Hotel & Conference Center

4 out of 5
Save 100% on your flight
Price was $639, price is now $406 per person
$406
per person
Jan 30 - Feb 3
found 15 hours ago
Roundtrip flight included
New York (NYC) to Austin (AUS)
9.2/10 Wonderful! (1,001 reviews)
Great property close to downtown area and restaurants. The boiler had an issue and our son took a scolding shower that was scary but management was very responsive and gracious about it. If we go back we would not stay anywhere else.

Reviewed on Nov 30, 2025

Austin Proper Hotel, a Member of Design Hotels

Austin Proper Hotel, a Member of Design Hotels

5 out of 5
Downtown Austin
Save 100% on your flight
Price was $1,085, price is now $635 per person
$635
per person
Feb 7 - Feb 10
found 1 hour ago
Roundtrip non-stop flight included
New York (LGA) to Austin (AUS)
9.2/10 Wonderful! (340 reviews)
Antonio and Giulio !! The best in this hotel

Reviewed on Dec 8, 2025

Sage Hill Inn & Spa

Sage Hill Inn & Spa

4 out of 5
Save 100% on your flight
Price was $1,012, price is now $680 per person
$680
per person
Jan 30 - Feb 3
found 15 hours ago
Roundtrip flight included
New York (NYC) to Austin (AUS)
9/10 Wonderful! (883 reviews)
Excellent service, beautiful grounds. Perfect stay!

Reviewed on Nov 9, 2025

Hilton Garden Inn Austin Downtown

Hilton Garden Inn Austin Downtown

3.5 out of 5
Downtown Austin
Save 100% on your flight
Price was $674, price is now $461 per person
$461
per person
Feb 11 - Feb 15
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Austin (AUS)
7.8/10 Good! (1,008 reviews)
Rachel warmly welcomed us and made sure we were taken care of. She really stands out as a star with customer service.

Reviewed on Dec 6, 2025

Hotel San Jose

Hotel San Jose

4 out of 5
South Congress
Save 100% on your flight
Price was $1,086, price is now $746 per person
$746
per person
Jan 8 - Jan 14
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Austin (AUS)
9.4/10 Exceptional! (247 reviews)
Nice Boutique Hotel- Great Location- Parking Awesome. Courtyard and pool Area are Amazing!! Front Desk Personnel Extremely Helpful!! Booking Again in February for the Marathon.

Reviewed on Dec 3, 2025

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Discover the most popular places to visit in Winchester

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

Kruschel Memorial Park

Kruschel Memorial Park is just one of the places to see in La Grange, so why not enjoy the other things to explore during your travels? Wander the parks or discover the area's countryside.

Kruschel Memorial Park

N.W. Faison House and Museum

You can browse the exhibits at N.W. Faison House and Museum, a museum with a storied past, during your travels to La Grange. Take in the live music and countryside in the area.

N.W. Faison House and Museum

Winchester Hotel Deals

Studio 6 – Giddings, Tx

Studio 6 – Giddings, Tx

2 out of 5
301 Cefco Lane Giddings TX
Fully refundableReserve now, pay when you stay
$67 nightly
The price is $76 total per night from Jan 1 to Jan 2
$76 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
8.6/10 Excellent! (39 reviews)
Caulk around bathtub was coming up. Any movement on the floor above was loud on the floor below. No shampoo in room first night.

Reviewed on Dec 5, 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 Dec 9 to Dec 10
$82 total
Dec 9 - Dec 10
Total with taxes and fees
7.2/10 Good! (850 reviews)
The staff was courteous as usual. Never have any issues with this establishment

Reviewed on Nov 27, 2025

Days Inn by Wyndham Bastrop
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
$71 nightly
The price is $80 total per night from Dec 9 to Dec 10
$80 total
Dec 9 - Dec 10
Total with taxes and fees
7.2/10 Good! (821 reviews)
The rooms were clean beds were great . Only thing better if the air-conditioner would have been on before arrival.

Reviewed on Nov 21, 2025

Super 8 by Wyndham Giddings
See all 284 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.

Find the Best Winchester Vacation Packages

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 $406 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.