Winchester Vacations from $652

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Your Winchester Vacation

Our Winchester vacation packages provide countless opportunities to discover new sights, sounds and experiences. And with all of the travel arrangements worked out, you can relax and enjoy your city adventure without a worry in the world. Can't wait to do some sightseeing but don't know where to begin? Any trip to Winchester should include Quincy Aquatic Center. Stop dreaming and start adventuring. Explore the broad range of options on Expedia today and put your Winchester vacation plans into action!

The Latest Winchester vacation packages

Price found within the past 48 hours. Click for updated prices.
Sleeping Lady Mountain Resort

Sleeping Lady Mountain Resort

2.5 out of 5
Price was $741, price is now $652 per person
$652
per person
Jan 31 - Feb 4
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Wenatchee (EAT)
9.2/10 Wonderful! (294 reviews)
The only thing I wasn’t not fond of was the no TV in the rooms.

Reviewed on Dec 5, 2025

WorldMark Lake Chelan Shores

WorldMark Lake Chelan Shores

3.5 out of 5
Price was $1,218, price is now $982 per person
$982
per person
Jan 15 - Jan 19
found 20 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Wenatchee (EAT)
No reviews
Desert Canyon Golf Resort

Desert Canyon Golf Resort

4 out of 5
Price was $982, price is now $808 per person
$808
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Wenatchee (EAT)
8.4/10 Very Good! (19 reviews)
The staff was amazing. Our room was ready early which meant a lot to us. We were photographing a wedding in Chelan and its always nice to leave our stuff in a room and not in the car. The grounds were beautiful and it was nice to come back after a long day and relax in a wonderful and quiet room. Thank you!

Reviewed on Sep 8, 2025

Weekend Hideout in Leavenworth

Weekend Hideout in Leavenworth

2 out of 5
Price was $1,718, price is now $1,483 per person
$1,483
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Wenatchee (EAT)
10/10 Exceptional! (1 review)
White Water Lodge in Leavenworth

White Water Lodge in Leavenworth

2 out of 5
Price was $1,649, price is now $1,439 per person
$1,439
per person
Jan 31 - Feb 4
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Wenatchee (EAT)
No reviews
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Discover the most popular places to visit in Winchester

The Gorge Amphitheatre

4.5/5(96 reviews)

You can take time to visit The Gorge Amphitheatre during your travels to Quincy. Amble around the area's riverfront or experience its theater scene.

The Gorge Amphitheatre

Cave B Estate Winery

4.5/5(32 reviews)

You can enjoy a tasting or tour at Cave B Estate Winery during your travels to Quincy. Amble around the area's riverfront or experience its theater scene.

Cave B Estate Winery

Quincy Aquatic Center

3.5/5(11 reviews)

Enjoy an outing to Quincy Aquatic Center during your stay in Quincy. Amble around the area's parks or experience its live music.

Quincy Aquatic Center

Winchester Hotel Deals

Holiday Inn Express & Suites George Quincy South by IHG

Holiday Inn Express & Suites George Quincy South by IHG

3 out of 5
224 Bing Ave George WA
Fully refundable
$82 nightly
The price is $91 total per night from Dec 19 to Dec 20
$91 total
Dec 19 - Dec 20
Total with taxes and fees
9/10 Wonderful! (485 reviews)
The check in process was so fast since we did it online first. Nice and clean. Really comfortable bed and pillows.

Reviewed on Nov 20, 2025

Holiday Inn Express & Suites George Quincy South by IHG
Best Western Rama Inn

Best Western Rama Inn

2.5 out of 5
1818 Basin Street SW Ephrata WA
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $116 total per night from Dec 7 to Dec 8
$116 total
Dec 7 - Dec 8
Total with taxes and fees
8.6/10 Excellent! (768 reviews)
Little bit noisy between floors, but overall a good nights stay. Clean an comfy!

Reviewed on Dec 1, 2025

Best Western Rama Inn
Quincy INN and Suites

Quincy INN and Suites

2.5 out of 5
500 F St SW Quincy WA
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $98 total per night from Dec 6 to Dec 7
$98 total
Dec 6 - Dec 7
Total with taxes and fees
8.4/10 Very Good! (204 reviews)
My room was very nice and very clean. The staff was most accommodating. I will certainly stay there again.

Reviewed on Nov 19, 2025

Quincy INN and Suites
See all 201 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
Closest Airport
Pangborn Memorial Airport (EAT)
Top Sights
Beaumont Cellars, Quincy Aquatic Center and Colockum Ridge Golf Course

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Frequently asked questions

How much does a Winchester vacation package cost?
You can snap up a vacation package to this top destination from $652 on Expedia. However, how much your vacation to Winchester costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Winchester?
November, December and January are great times to search for cheap Winchester vacation packages. Traveling in quieter periods means you can typically find better prices on flights and accommodations.
How many days is enough for Winchester?
The ideal length for your Winchester vacation depends on what you'd like to do and see. Typically, a handful of days to a week will give you time to check out all the leading attractions and discover some hidden spots along the way.
How to find the best Winchester package deals?
Use Expedia's handy filters to find some of the best Winchester package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or browse for Winchester package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Winchester vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll usually snag a better deal than booking each component separately. And you'll still get the freedom to create a customized Winchester vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Winchester?
Land amazing discounts by booking your flights in advance with Expedia. If spontaneity 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?
Secure your dream getaway to Winchester with help from our Book Now, Pay Later vacations. No need to save like crazy or wait for the next payday — we've teamed up with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans allow you to split the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's a breeze to stick to your budget and snag great deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.