Winchester Vacations from $358

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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.
Valley River Inn

Valley River Inn

3.5 out of 5
Price was $541, price is now $358 per person
$358
per person
Jan 8 - Jan 12
found 19 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Eugene (EUG)
9.2/10 Wonderful! (989 reviews)
All pet rooms should be in one area.

Reviewed on Oct 20, 2025

Graduate by Hilton Eugene

Graduate by Hilton Eugene

4 out of 5
Downtown Eugene
Price was $652, price is now $464 per person
$464
per person
Jan 8 - Jan 12
found 19 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Eugene (EUG)
9/10 Wonderful! (1,026 reviews)
Was fine, the decor was a little unusual but it is a college town.

Reviewed on Oct 20, 2025

Counting Z's

Counting Z's

2 out of 5
Price was $563, price is now $432 per person
$432
per person
Jan 8 - Jan 12
found 19 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Eugene (EUG)
7.8/10 Good! (160 reviews)
Great staff!! Working the establishment, there. Good thing I got a beard, cuz I can't stop blushing. The hospitality there is unbelievable. Great people, great place, great price, walking distance from downtown

Reviewed on Sep 6, 2025

University Inn & Suites

University Inn & Suites

2 out of 5
East University
Price was $495, price is now $383 per person
$383
per person
Jan 8 - Jan 12
found 19 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Eugene (EUG)
8/10 Very Good! (1,446 reviews)
Easy check in and out property

Reviewed on Oct 20, 2025

River House Inn, a Baymont by Wyndham

River House Inn, a Baymont by Wyndham

2 out of 5
Price was $620, price is now $480 per person
$480
per person
Jan 8 - Jan 12
found 22 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Eugene (EUG)
8.6/10 Excellent! (1,012 reviews)
The property is aged. Our shower had old holes in the wall where the old curtain used to hang. No attempt to cover/repair it. Also floors are thin, could hear people upstairs walking around at 2am. Beds were comfortable & loved the deck overlooking the river. Staff was super nice & very helpful which is what made me score this a 4. Very walkable to a great coffee place, restaurants & shopping along the river.

Reviewed on Oct 18, 2025

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Winchester Hotel Deals

Singing Waters at N. Umpqua

Singing Waters at N. Umpqua

Roseburg North
10/10 Exceptional! (9 reviews)
The pictures are exactly how you will find this home. The remodel is first class, the river view amazing. A native of Roseburg, our family stayed here while visiting family. Very peaceful..hosts were very responsive.

Reviewed on Sep 12, 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
$100 nightly
The price is $110 total per night from Nov 21 to Nov 22
$110 total
Nov 21 - Nov 22
Total with taxes and fees
8.4/10 Very Good! (1,428 reviews)
Great little Inn with a view of the River. Convientily located close to almost everything...

Reviewed on Oct 20, 2025

Riverfront Inn Roseburg
Motel 6 Roseburg, OR

Motel 6 Roseburg, OR

2 out of 5
3100 Nw Aviation Dr, Roseburg, OR
Fully refundable
$58 nightly
The price is $64 total per night from Nov 2 to Nov 3
$64 total
Nov 2 - Nov 3
Total with taxes and fees
7.4/10 Good! (1,006 reviews)
Watching the planes take off and land from the airport next door love watching the planes taking off from there

Reviewed on Oct 15, 2025

Motel 6 Roseburg, OR
See all 119 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
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 $358 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.