Winchester Vacations from $424

Book a Hotel + Flight or Car together to unlock savings

Your Winchester Vacation

When a city adventure is calling your name, answer it with a Winchester vacation package. With all your travel plans worked out before you leave, all you have to do here is focus on having fun. Any trip to Winchester needs a well-designed itinerary. Fill yours with big-name attractions like Melrose Vineyards, Stewart Park and Winchester Dam. Stop daydreaming and start doing. Browse the wide range of options on Expedia today and put your Winchester vacation plans in motion!

The Latest Winchester vacation packages

Price found within the past 48 hours. Click for updated prices.
Campus Inn & Suites Eugene Downtown

Campus Inn & Suites Eugene Downtown

2 out of 5
Downtown Eugene
Price was $534, price is now $424 per person
$424
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Eugene (EUG)
8/10 Very Good! (1,010 reviews)
Carson said the room was beautiful.

Reviewed on Oct 7, 2025

Graduate by Hilton Eugene

Graduate by Hilton Eugene

4 out of 5
Downtown Eugene
Save 100% on your flight
Price was $838, price is now $595 per person
$595
per person
Nov 14 - Nov 17
found 16 hours ago
Roundtrip non-stop flight included
Burbank (BUR) to Eugene (EUG)
9/10 Wonderful! (1,027 reviews)
Valley River Inn

Valley River Inn

3.5 out of 5
Price was $971, price is now $723 per person
$723
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Eugene (EUG)
9.2/10 Wonderful! (841 reviews)
Dry nice, would recommend

Reviewed on Oct 8, 2025

University Inn & Suites

University Inn & Suites

2 out of 5
East University
Price was $686, price is now $523 per person
$523
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Eugene (EUG)
8/10 Very Good! (1,414 reviews)
We loved the proximity to the university and where my daughter’s apartment is located.

Reviewed on Oct 4, 2025

Hayward Inn

Hayward Inn

3 out of 5
East University
Price was $583, price is now $462 per person
$462
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Eugene (EUG)
8.8/10 Excellent! (2,876 reviews)
Staff was very friendly. Everything was clean and they served an exceptional breakfast

Reviewed on Oct 6, 2025

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Winchester Hotel Deals

Riverfront Inn Roseburg

Riverfront Inn Roseburg

2 out of 5
315 W Harvard Ave, Roseburg, OR
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $111 total per night from Nov 1 to Nov 2
$111 total
Nov 1 - Nov 2
Total with taxes and fees
8.4/10 Very Good! (1,406 reviews)
"River view, nice staff, balconies and a riverwalk!"

Reviewed on Oct 6, 2025

Riverfront Inn Roseburg
Motel 6 Sutherlin, OR

Motel 6 Sutherlin, OR

2 out of 5
1400 Hospitality Way, Sutherlin, OR
Fully refundable
$58 nightly
The price is $64 total per night from Oct 20 to Oct 21
$64 total
Oct 20 - Oct 21
Total with taxes and fees
7.4/10 Good! (1,000 reviews)
"Very basic place as indicated by the price. No toiletries besides a couple of small bar soap s. Just needed a place to crash for a few hours so it was fine."

Reviewed on Oct 2, 2025

Motel 6 Sutherlin, OR
Holiday Inn Express Roseburg by IHG

Holiday Inn Express Roseburg by IHG

2.5 out of 5
375 Harvard Blvd, Roseburg, OR
Fully refundable
$127 nightly
The price is $139 total per night from Nov 7 to Nov 8
$139 total
Nov 7 - Nov 8
Total with taxes and fees
8.8/10 Excellent! (1,001 reviews)
"Carpet was extremely dirty, rooms are very outdated, behind the night stand was a little trash, but staff was friendly and it was safe, close to freeway and the parking was very convenient. View to the lake was pleasant. Beds were very comfortable and clean at least and in the bathroom even though ..."

Reviewed on Oct 4, 2025

Holiday Inn Express Roseburg by IHG
See all 116 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
Max Temp Winter
50ºF
Max Temp Summer
80ºF
Top Sights
Wildlife Safari, Reustle Prayer Rock Vineyards and HillCrest Winery and Distillery

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Frequently asked questions

How much does a Winchester vacation package cost?
You can grab a vacation package to this destination from $424 on Expedia. But how much your vacation to Winchester costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Winchester?
If you'd like to score a cheap Winchester vacation package, consider traveling in October, November and December. You'll generally find better prices on flights and accommodations during these quieter months — perfect for a budget-friendly getaway.
How many days is enough for Winchester?
The ideal duration of your Winchester vacation depends on what you'd like to do and see. Generally, a handful of days to a week will give you plenty of time to hit all the main sights and discover some hidden spots along the way.
How to find the best Winchester package deals?
Begin your search for a Winchester package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Guest rating," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Winchester package deal right away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Winchester adventure off to a flying start.
Is it cheaper to book a Winchester vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking hotels and flights individually. Better still, you can personalize your Winchester escape to fit your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Winchester?
If you have your Winchester vacation dates locked in, book as early as you can to snap up some awesome deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are great for impromptu escapes.
Does Expedia offer Book Now, Pay Later Winchester vacation packages?
If you're anything like us, you love exploring new places but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the overall cost of your Winchester trip over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up cheap 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.