Winchester Vacation Packages
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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!
Top Winchester Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hayward Inn
East University
Price was CA $1,207, price is now CA $1,101 per person
CA $1,101
per person
Jul 7 - Jul 12
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to Eugene (EUG)
9/10 Wonderful! (3,012 reviews)
Room was clean and included breakfast. Location is close to university.
Reviewed on May 21, 2026
Cottage Grove Inn
Price was CA $936, price is now CA $895 per person
CA $895
per person
Jul 7 - Jul 12
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to Eugene (EUG)
8.8/10 Excellent! (1,012 reviews)
Room was exceptionally clean and breakfast was delicous and well presented
Reviewed on May 23, 2026
Valley River Inn
Price was CA $1,355, price is now CA $1,303 per person
CA $1,303
per person
Jul 7 - Jul 12
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to Eugene (EUG)
9.4/10 Exceptional! (1,714 reviews)
Lovely property - convenient access to lots of activities. Great dining and fitness room. Super staff.
Reviewed on May 22, 2026
Home2 Suites by Hilton Eugene Downtown University Area
Downtown Eugene
Price was CA $1,178, price is now CA $1,142 per person
CA $1,142
per person
Jul 7 - Jul 12
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to Eugene (EUG)
8.8/10 Excellent! (978 reviews)
It was warm and cozy. Loved the rooms had tons of storage. I came for a nursing conference so came with lots of stuff. Plus the small kitchen was a huge plus. Comfy beds? Nice linens. Sweet pool! Overall great!
Reviewed on May 18, 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
Super 8 by Wyndham Roseburg
3200 Nw Aviation Dr I-5 Exit # 127 Roseburg OR
Fully refundableReserve now, pay when you stay
The price is CA $110 per night from Jun 7 to Jun 8
CA $110
CA $121 total
Jun 7 - Jun 8
includes taxes & fees
8/10 Very Good! (1,001 reviews)
"Great stop on the rosd"
Reviewed on May 20, 2026
Riverfront Inn Roseburg
315 W Harvard Ave Roseburg OR
Fully refundableReserve now, pay when you stay
The price is CA $141 per night from May 24 to May 25
CA $141
CA $154 total
May 24 - May 25
includes taxes & fees
8.6/10 Excellent! (1,467 reviews)
"Very nice rooms, clean and easy to access. Please put kleenex in rooms though. Love the visual over the river.."
Reviewed on May 20, 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.
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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.
