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.
Quality Inn & Suites Springfield - Eugene North
Price was CA $2,086, price is now CA $1,740 per person
CA $1,740
per person
Jul 3 - Jul 10
found 20 hours ago
Roundtrip flight included
Moncton (YQM) to Eugene (EUG)
7.8/10 Good! (1,000 reviews)
Needed 2 rooms, one dog friendly. Check in was 3pm we arrived at 6pm and one room was not ready. It was a short drive so we were not tired, went to dinner and the room was ready.if you get a dog friendly room you only pay extra if you have a dog. Rooms were clean though outdated. The beds were clean and comfortable. Staff was friendly and helpful. Gave my son a 1pm late checkout which was very helpful for the time line we needed. Only negative to me was the room not being ready, it could be a big problem if you wanted to check in at check-in time. For the money a good place.
Reviewed on Apr 1, 2026
Valley River Inn
Price was CA $2,750, price is now CA $2,039 per person
CA $2,039
per person
Jul 3 - Jul 10
found 20 hours ago
Roundtrip flight included
Moncton (YQM) to Eugene (EUG)
9.4/10 Exceptional! (1,548 reviews)
Was a great property, right on Wilamette River. Only downside was no continental breakfast. There a nice restaurant on site that was great.
Reviewed on Apr 13, 2026
Hayward Inn
East University
Price was CA $2,854, price is now CA $2,308 per person
CA $2,308
per person
Jul 3 - Jul 10
found 20 hours ago
Roundtrip flight included
Moncton (YQM) to Eugene (EUG)
9/10 Wonderful! (2,951 reviews)
Stopped late while passing through. Ok place, didn’t realize the buildings are spread far out and parking was limited. Probably wouldn’t stay again but was ok for just the night
Reviewed on Apr 12, 2026
The 505 Eugene
Downtown Eugene
Price was CA $2,749, price is now CA $2,249 per person
CA $2,249
per person
Jul 3 - Jul 10
found 20 hours ago
Roundtrip flight included
Moncton (YQM) 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
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
The Lodge at Roseburg
375 Harvard Blvd Roseburg OR
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from Apr 26 to Apr 27
CA $175
CA $192 total
Apr 26 - Apr 27
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
Rooms are dated though a renovation is planned and will bring much needed updates to the building. Very convenient location, friendly staff who were personable and went above & beyond to assist with room location and storing luggage. Hotel and rooms were very clean despite their age.
Reviewed on Apr 12, 2026
Riverfront Inn Roseburg
315 W Harvard Ave Roseburg OR
Fully refundableReserve now, pay when you stay
The price is CA $124 per night from Apr 14 to Apr 15
CA $124
CA $136 total
Apr 14 - Apr 15
includes taxes & 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
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.
