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.
Graduate by Hilton Eugene
Downtown Eugene
Price was CA $918, price is now CA $836 per person
CA $836
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEA) to Eugene (EUG)
9/10 Wonderful! (1,017 reviews)
Front desk was great, room - shower was dirty and had hair in the drain.
No shower gel, was empty when I got to the room
Reviewed on Feb 21, 2026
Campbell House Inn
Downtown Eugene
Price was CA $1,332, price is now CA $1,201 per person
CA $1,201
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Charleston (CRW) to Eugene (EUG)
9.6/10 Exceptional! (1,001 reviews)
Room was spotless, staff was friendly & efficient. Breakfast was wonderful, especially the cinnamon scones. Very relaxing stay.
Reviewed on Feb 23, 2026
Downtown Inn
Downtown Eugene
Price was CA $1,137, price is now CA $1,031 per person
CA $1,031
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Charleston (CRW) to Eugene (EUG)
9/10 Wonderful! (826 reviews)
This place had everything we needed for our one night stay. It was clean and felt safe enough. We were able to walk to the Hult center and find plenty of options to eat dinner nearby.
Reviewed on Jan 5, 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
Holiday Inn Express Roseburg by IHG
375 Harvard Blvd Roseburg OR
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Mar 5 to Mar 6
CA $135
CA $148 total
Mar 5 - Mar 6
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
Convenient location. Clean room. Gorgeous view from balcony. Good breakfast.
Reviewed on Feb 25, 2026
SureStay by Best Western Roseburg
2855 NW Edenbower Blvd Roseburg OR
Fully refundableReserve now, pay when you stay
The price is CA $98 per night from Mar 1 to Mar 2
CA $98
CA $108 total
Mar 1 - Mar 2
includes taxes & fees
8/10 Very Good! (1,007 reviews)
Nice staff, clean room, nice breakfast. Not fancy but perfectly suitable for a quick stay.
Reviewed on Feb 23, 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.
