Winchester Vacations from $426

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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.
Graduate by Hilton Eugene

Graduate by Hilton Eugene

4 out of 5
Downtown Eugene
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Eugene (EUG)
8.8/10 Excellent! (1,000 reviews)
Parking is not included! Plan an extra $22.oo a day

Reviewed on Aug 11, 2025

Counting Z's

Counting Z's

2 out of 5
Save 100% on your flight
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Eugene (EUG)
7.8/10 Good! (141 reviews)
Keep exending my stay bc it feels so homey and relaxing

Reviewed on Jul 27, 2025

Valley River Inn

Valley River Inn

3.5 out of 5
Save 100% on your flight
per person
Sep 25 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Eugene (EUG)
9.2/10 Wonderful! (612 reviews)
Very nice place for family to stay. However they said they did not honor Expedia awards perks.

Reviewed on Aug 12, 2025

Maverick Hotel Eugene Near University, Ascend Hotel Collection

Maverick Hotel Eugene Near University, Ascend Hotel Collection

2 out of 5
East University
Save 100% on your flight
per person
Sep 25 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Eugene (EUG)
8.6/10 Excellent! (538 reviews)
great location for campus visits + track events

Reviewed on Aug 9, 2025

Courtesy Inn Eugene Downtown

Courtesy Inn Eugene Downtown

2 out of 5
Downtown Eugene
Save 100% on your flight
per person
Sep 25 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Eugene (EUG)
8.2/10 Very Good! (1,003 reviews)
Issues with staff being at the front desk. Waited 10 minutes before showed up to check in. Called and they didn’t even answer the phone. Happened several times not only with me but others. Disappointed. Room was set alcove with no light. Was given option of another room however the couch stunk!

Reviewed on Aug 12, 2025

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Winchester Hotel Deals

Singing Waters at N. Umpqua

Singing Waters at N. Umpqua

Roseburg North
10/10 Exceptional! (5 reviews)
Family Reunion
"This house was perfect for our annual family reunion about a mile past this house. We had our family all together and really enjoyed being close to family here. The house has a wonderful kitchen and great layout. We did not cook there as we had most of our family meals at farm up the road. I would ..."

Reviewed on Jul 13, 2025

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Singing Waters at N. Umpqua
Riverfront Inn Roseburg

Riverfront Inn Roseburg

2 out of 5
315 W Harvard Ave, Roseburg, OR
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $116 total per night from Sep 1 to Sep 2
$116 total
Sep 1 - Sep 2
Total includes taxes and fees
8.4/10 Very Good! (1,360 reviews)
"The check-in staff is so great here! Beds are always comfortable & clean, and I like the grassy sitting area by the river. Cleanliness in the rest of the room seems to be hit or miss (squished bugs on a wall, debris in the upholstered chair, dust all over the side-table, etc.) and during my last ..."

Reviewed on Aug 9, 2025

Riverfront Inn Roseburg
Sleep Inn & Suites Roseburg North Near Medical Center

Sleep Inn & Suites Roseburg North Near Medical Center

2.5 out of 5
2855 NW Edenbower Blvd, Roseburg, OR
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $116 total per night from Aug 31 to Sep 1
$116 total
Aug 31 - Sep 1
Total includes taxes and fees
8/10 Very Good! (1,008 reviews)
"Amazing staff! Hotel used to be a smoking hotel."

Reviewed on Aug 11, 2025

Sleep Inn & Suites Roseburg North Near Medical Center
See all 112 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 grab a vacation package to this destination from $426 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.