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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.


University Inn & Suites
East University
Price was $512, price is now $371 per person
$371
per person
Jan 28 - Jan 31
found 24 hours ago
Roundtrip flight included
Las Vegas (LAS) to Eugene (EUG)
8/10 Very Good! (1,627 reviews)
The location of this hotel to the University, restaurants and shops was excellent. The property was relatively clean. While the bed was comfortable, the couch in our room had multiple large holes and the towels were nearly threadbare. The worst part though was the fan/heating unit that was mounted on the wall. It would go off approximately every 10 minutes, was loud, and blasted the bed with air making it nearly impossible to sleep.
Reviewed on Nov 2, 2026

Hayward Inn
East University
Price was $945, price is now $718 per person
$718
per person
Jan 14 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Eugene (EUG)
9/10 Wonderful! (3,219 reviews)
I had to carry my luggage up two flights of stairs. The room Smelled of dirty laundry. And the Restaraunt was closed for some unknown reason. However the staff at the front desk were very pleasant.
Reviewed on Nov 2, 2026

Yurtel-Veneta
Price was $524, price is now $410 per person
$410
per person
Jan 28 - Jan 31
found 24 hours ago
Roundtrip flight included
Las Vegas (LAS) to Eugene (EUG)
9.4/10 Exceptional! (3 reviews)
Overall we had a nice, cozy stay at the Yurtel. We needed to book last-minute accomodations for a football game in Eugene and this was a safe, affordable place to stay not absurdly far away. Our yurt was warm and comfortable and the water pressure in the shower was excellent. Our only complaint is the road and neighborhood noise. It should go without saying that you're going to hear outside noise if you're staying in a yurt, but the noise from the nearby highway was quite loud. We also could hear party noise from the neighborhood behind the Yurtel, and apparently folks in Veneta like to set off fireworks for Halloween, so we heard that, too. Thankfully, most of the noise subsided before it was too late and our sleep wasn't disturbed, but it might be nice for the management to include ear plugs in their list of amenities (and maybe eye masks, since early morning light does come in from the skylight at the top of the yurt.) Still, if you're looking for a quirky, affordable place to stay in the area, this would be a good choice.
Reviewed on Nov 2, 2026
Winchester Hotel Deals

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

Riverfront Inn Roseburg
315 W Harvard Ave Roseburg OR
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $95 total per night from Nov 3 to Nov 4
$95 total
Nov 3 - Nov 4
Total with taxes and fees
8.6/10 Excellent! (1,543 reviews)
"I just love the location -this is not fancy but it is clean and has friendly staff-vey low key:)"
Reviewed on Nov 2, 2026

SureStay by Best Western Roseburg
2855 NW Edenbower Blvd Roseburg OR
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $97 total per night from Nov 8 to Nov 9
$97 total
Nov 8 - Nov 9
Total with taxes and fees
8/10 Very Good! (1,001 reviews)
"Clean room and very friendly staff"
Reviewed on Oct 30, 2026
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.



















