
Winchester Vacations from $426
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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.




Maverick Hotel Eugene Near University, Ascend Hotel Collection
East University
Save 100% on your flight
per person
Sep 25 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Eugene (EUG)
8.6/10 Excellent! (538 reviews)
great location for campus visits + track events
Reviewed on Aug 9, 2025

Courtesy Inn Eugene Downtown
Downtown Eugene
Save 100% on your flight
per person
Sep 25 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Eugene (EUG)
8.2/10 Very Good! (1,003 reviews)
Issues with staff being at the front desk. Waited 10 minutes before showed up to check in. Called and they didn’t even answer the phone. Happened several times not only with me but others. Disappointed. Room was set alcove with no light. Was given option of another room however the couch stunk!
Reviewed on Aug 12, 2025
Winchester Hotel Deals

Singing Waters at N. Umpqua
Roseburg North
10/10 Exceptional! (5 reviews)
Family Reunion
"This house was perfect for our annual family reunion about a mile past this house. We had our family all together and really enjoyed being close to family here. The house has a wonderful kitchen and great layout. We did not cook there as we had most of our family meals at farm up the road. I would ..."
Reviewed on Jul 13, 2025

Riverfront Inn Roseburg
315 W Harvard Ave, Roseburg, OR
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $116 total per night from Sep 1 to Sep 2
$116 total
Sep 1 - Sep 2
Total includes taxes and fees
8.4/10 Very Good! (1,360 reviews)
"The check-in staff is so great here! Beds are always comfortable & clean, and I like the grassy sitting area by the river. Cleanliness in the rest of the room seems to be hit or miss (squished bugs on a wall, debris in the upholstered chair, dust all over the side-table, etc.) and during my last ..."
Reviewed on Aug 9, 2025

Sleep Inn & Suites Roseburg North Near Medical Center
2855 NW Edenbower Blvd, Roseburg, OR
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $116 total per night from Aug 31 to Sep 1
$116 total
Aug 31 - Sep 1
Total includes taxes and fees
8/10 Very Good! (1,008 reviews)
"Amazing staff! Hotel used to be a smoking hotel."
Reviewed on Aug 11, 2025
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.