Winchester Vacations from $638

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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.
Valueinn Motel

Valueinn Motel

2 out of 5
Bethel-Danebo
Save 100% on your flight
Price was $837, price is now $638 per person
$638
per person
Jun 17 - Jun 21
found 22 hours ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Eugene (EUG)
7.2/10 Good! (782 reviews)
Clean, convenient and very friendly staff! Also very quiet which we appreciated.

Reviewed on Apr 5, 2026

Valley River Inn

Valley River Inn

3.5 out of 5
Save 100% on your flight
Price was $1,154, price is now $851 per person
$851
per person
Jun 17 - Jun 21
found 22 hours ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Eugene (EUG)
9.4/10 Exceptional! (1,548 reviews)
The AC was strong and worked well and the room was very clean.

Reviewed on Apr 12, 2026

The 505 Eugene

The 505 Eugene

3 out of 5
Downtown Eugene
Save 100% on your flight
Price was $1,394, price is now $1,044 per person
$1,044
per person
Jun 17 - Jun 21
found 22 hours ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Eugene (EUG)
9.2/10 Wonderful! (50 reviews)
This little place was perfect. Great location. Close to food, shopping, and was super quiet. It was comfortable and clean. Would definitely stay again!

Reviewed on Mar 22, 2026

The Local Motel & Shops

The Local Motel & Shops

2 out of 5
Downtown Eugene
Save 100% on your flight
Price was $1,293, price is now $971 per person
$971
per person
Jun 17 - Jun 21
found 22 hours ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Eugene (EUG)
8.8/10 Excellent! (114 reviews)
Very clean! Will definitely stay here again!

Reviewed on Feb 23, 2026

Campbell House Inn

Campbell House Inn

3 out of 5
Downtown Eugene
Save 100% on your flight
Price was $935, price is now $711 per person
$711
per person
Jun 17 - Jun 21
found 22 hours ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Eugene (EUG)
9.6/10 Exceptional! (1,001 reviews)
Breakfast was delicious. The grounds were beautiful. It is a cozy place to relax and unwind.

Reviewed on Apr 11, 2026

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Winchester Hotel Deals

Singing Waters at N. Umpqua

Singing Waters at N. Umpqua

Roseburg North OR
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
The Lodge at Roseburg

The Lodge at Roseburg

2.5 out of 5
375 Harvard Blvd Roseburg OR
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $139 total per night from Apr 17 to Apr 18
$139 total
Apr 17 - Apr 18
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
Check in was easy. Room was clean and large, with a balcony overlooking the river, including 2 chairs and a small table. It was too cool to use it much, but would be very nice when warmer. Shower had great pressure. Only difficulty we had was our key didn't work when we returned each day, so we had ...

Reviewed on Apr 7, 2026

The Lodge at Roseburg
Riverfront Inn Roseburg

Riverfront Inn Roseburg

2 out of 5
315 W Harvard Ave Roseburg OR
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $100 total per night from Apr 14 to Apr 15
$100 total
Apr 14 - Apr 15
Total with taxes and fees
8.6/10 Excellent! (1,451 reviews)
My room was clean, and comfy. Everything was like it should have been. I liked their outdoor area by the river. I didn't realize that there were rooms facing the river with balconies. I was cold and rainy when i was there, so I didn't get to check out much.

Reviewed on Apr 11, 2026

Riverfront Inn Roseburg
See all 117 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 $638 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.