Winchester Vacations from $2,541

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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.
Blue Elk Inn

Blue Elk Inn

2.5 out of 5
Price was $2,688, price is now $2,541 per person
$2,541
per person
Apr 13 - Apr 18
found 14 hours ago
Roundtrip flight included
Honolulu (HNL) to Wenatchee (EAT)
9.6/10 Exceptional! (1,002 reviews)
Lovely quaint place to stay. Hot tub was qarm, no jets. We still enjoyed it. Hot showers, very clean and comfy rooms with a valcony. Breakfast with lots of varieows and good. We definately enjoyed our visit and will come back.

Reviewed on Feb 10, 2026

Rockwell Retreat 4 Bedroom Home by NW Comfy Cabins by RedAwning

Rockwell Retreat 4 Bedroom Home by NW Comfy Cabins by RedAwning

3 out of 5
Downtown Leavenworth
Price was $4,359, price is now $4,124 per person
$4,124
per person
Apr 13 - Apr 18
found 14 hours ago
Roundtrip flight included
Honolulu (HNL) to Wenatchee (EAT)
No reviews
Alpine Acres Lodge 3 Bedroom Home by NW Comfy Cabins by RedAwning

Alpine Acres Lodge 3 Bedroom Home by NW Comfy Cabins by RedAwning

3.5 out of 5
Price was $4,158, price is now $3,936 per person
$3,936
per person
Apr 13 - Apr 18
found 14 hours ago
Roundtrip flight included
Honolulu (HNL) to Wenatchee (EAT)
No reviews
Riverwood Lodge 5 Bedroom Home by NW Comfy Cabins by RedAwning

Riverwood Lodge 5 Bedroom Home by NW Comfy Cabins by RedAwning

2 out of 5
Price was $4,134, price is now $3,915 per person
$3,915
per person
Apr 13 - Apr 18
found 14 hours ago
Roundtrip flight included
Honolulu (HNL) to Wenatchee (EAT)
No reviews
Icicle Village Resort

Icicle Village Resort

3.5 out of 5
Price was $2,801, price is now $2,657 per person
$2,657
per person
Apr 13 - Apr 18
found 14 hours ago
Roundtrip flight included
Honolulu (HNL) to Wenatchee (EAT)
9.4/10 Exceptional! (1,392 reviews)
The room was spotless. Love that the room also had a comfortable chair and 2 chairs at the table for comfortable seating. The bed was very comfortable.

Reviewed on Feb 17, 2026

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Discover the most popular places to visit in Winchester

Tremendous venue for an outdoor concert! Easy camping a 30 minute walk away. This was Dead & Company June 29, 2018. #lifeatexpedia

The Gorge Amphitheatre

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

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

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

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
$92 nightly
The price is $102 total per night from Feb 21 to Feb 22
$102 total
Feb 21 - Feb 22
Total with taxes and fees
8.6/10 Excellent! (786 reviews)
Nice staff

Reviewed on Feb 14, 2026

Best Western Rama Inn
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
$103 nightly
The price is $114 total per night from Feb 21 to Feb 22
$114 total
Feb 21 - Feb 22
Total with taxes and fees
9/10 Wonderful! (504 reviews)
Room was spacious and the bed is very comfortable! The bathroom is small, and very few shelves to place toiletry bags.

Reviewed on Feb 18, 2026

Holiday Inn Express & Suites George Quincy South by IHG
Knights Inn Quincy

Knights Inn Quincy

1.5 out of 5
710 10th Ave SW Quincy WA
Fully refundableReserve now, pay when you stay
$59 nightly
The price is $65 total per night from Feb 20 to Feb 21
$65 total
Feb 20 - Feb 21
Total with taxes and fees
6.8/10 (294 reviews)
Room was slightly dirty as well as if it was cleaned well why were there still a pair of pants in the closet on the ground. If the room was cleaned correctly wouldn’t t those of been found. Wouldn’t stay there again!

Reviewed on Feb 16, 2026

Knights Inn Quincy
See all 230 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 $2,541 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.