Winchester Vacations from $503

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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.
WorldMark Chelan - Lake House

WorldMark Chelan - Lake House

4 out of 5
Price was $609, price is now $503 per person
$503
per person
Nov 14 - Nov 17
found 5 hours ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Wenatchee (EAT)
8.8/10 Excellent! (41 reviews)
The personnel were excellent, kind, helpful and friendly. The hotel was very clean and had all that we needed. It was walkable, close to everything. We appreciated the warm pool this time of year and the game room. Thank you! We'll be back.

Reviewed on Apr 3, 2025

WorldMark Leavenworth

WorldMark Leavenworth

3 out of 5
Price was $1,194, price is now $841 per person
$841
per person
Nov 14 - Nov 17
found 5 hours ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Wenatchee (EAT)
10/10 Exceptional! (8 reviews)
Complimentary popcorn, hot chocolate, coffee, and DVDs... plus gifted us a mug, chocolates, and rose for my wife's birthday!

Reviewed on Mar 7, 2025

LOGE Leavenworth - Downtown

LOGE Leavenworth - Downtown

3 out of 5
Downtown Leavenworth
Price was $1,158, price is now $942 per person
$942
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Wenatchee (EAT)
9.2/10 Wonderful! (1,008 reviews)
The location of the hotel is great! It is right in downtown so it’s a easy walk if you want to grab a bite to eat or shop.

Reviewed on Aug 26, 2025

Desert Canyon Golf Resort

Desert Canyon Golf Resort

4 out of 5
Price was $1,030, price is now $848 per person
$848
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Wenatchee (EAT)
8.4/10 Very Good! (16 reviews)
Far from civilization. So come with what you need and you should have a good time!

Reviewed on Aug 5, 2025

Quincy INN and Suites

Quincy INN and Suites

2.5 out of 5
Price was $920, price is now $777 per person
$777
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Wenatchee (EAT)
8.6/10 Excellent! (185 reviews)
Very friendly and helpful staff

Reviewed on Aug 25, 2025

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Discover the most popular places to visit in Winchester

The Gorge Amphitheatre

4.5/5(96 reviews)

The Gorge Amphitheatre is one of the more well-known attractions to visit during your trip 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

Beaumont Cellars

You can enjoy a tasting or tour at Beaumont Cellars during your travels to Quincy. Stroll along the riverfront or experience the area's live music.

Beaumont Cellars

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
$116 nightly
The price is $128 total per night from Sep 1 to Sep 2
$128 total
Sep 1 - Sep 2
Total with taxes and fees
Holiday Inn Express & Suites George Quincy South by IHG
Soap Lake Natural Spa & Resort

Soap Lake Natural Spa & Resort

3.5 out of 5
236 Main Avenue East, Soap Lake, WA
Fully refundableReserve now, pay when you stay
$133 nightly
The price is $147 total per night from Sep 28 to Sep 29
$147 total
Sep 28 - Sep 29
Total with taxes and fees
Soap Lake Natural Spa & Resort
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
$108 nightly
The price is $119 total per night from Sep 1 to Sep 2
$119 total
Sep 1 - Sep 2
Total with taxes and fees
8.4/10 Very Good! (174 reviews)
"Very friendly and helpful staff"

Reviewed on Aug 25, 2025

Quincy INN and Suites
See all 170 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.

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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 $503 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.