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.
Courtesy Inn Eugene Downtown

Courtesy Inn Eugene Downtown

2 out of 5
Downtown Eugene
per person
Aug 15 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Eugene (EUG)
8.2/10 Very Good! (1,006 reviews)
What a wonderful hotel! Delightful staff, comfy beds, ample pillows, clean rooms & bath w lg tub, quiet, lovely hanging flower baskets, fresh paint & more. Free parking & continental breakfast. Not a lot of flash or big corporate hype, it's a welcoming, safe property with ample tv options & charm. The owners care about this property & it shows. So glad we found it! Definitely will return.

Reviewed on Jul. 13, 2025

Valley River Inn

Valley River Inn

3.5 out of 5
per person
Aug 15 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Eugene (EUG)
9.2/10 Wonderful! (453 reviews)
Sweetwater Restaurant on property was excellent. View of river while eating was beautiful.Staff very friendly! Pool was excellent! Loved the balcony in our room!

Reviewed on Jul. 15, 2025

La Quinta Inn & Suites by Wyndham Springfield

La Quinta Inn & Suites by Wyndham Springfield

3 out of 5
per person
Aug 15 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Eugene (EUG)
9.2/10 Wonderful! (1,119 reviews)
It was a bummer the elevator was broken this trip..

Reviewed on Jul. 14, 2025

Graduate by Hilton Eugene

Graduate by Hilton Eugene

4 out of 5
Downtown Eugene
per person
Aug 15 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Eugene (EUG)
9/10 Wonderful! (1,001 reviews)
Beautiful property. Great restaurant and on-site entertainment for all ages. Love the decor- there are Ducks everywhere. Located within walking distance to many other restaurants. Safe area. We organized staff who are very welcoming and helpful. We will stay here again.

Reviewed on Jul. 10, 2025

Hayward Inn

Hayward Inn

3 out of 5
East University
per person
Aug 15 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Eugene (EUG)
8.8/10 Excellent! (2,826 reviews)
The hotel is good location. Room is spacious and comfortable as well. We also love customer service and staff was great

Reviewed on Jul. 15, 2025

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Winchester Hotel Deals

Singing Waters at N. Umpqua

Singing Waters at N. Umpqua

Roseburg North
Stunning!
"Beautifully decorated house! Loved the view of the river in the backyard. So clean and new! No complaints!!"

Reviewed on Jul. 10, 2024

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Singing Waters at N. Umpqua
Riverfront Inn Roseburg

Riverfront Inn Roseburg

2 out of 5
315 W Harvard Ave, Roseburg, OR
Fully refundableReserve now, pay when you stay
The price is CA $153 per night from Jul 17 to Jul 18
CA $153
CA $167 total
Jul 17 - Jul 18
includes taxes & fees
8.4/10 Very Good! (1,325 reviews)
Room with a View
"It was great for our dog walking. The grounds were pleasant with the river view and the lawn. Room was good breakfast was good."

Reviewed on Jul. 12, 2025

Riverfront Inn Roseburg
Super 8 by Wyndham Roseburg

Super 8 by Wyndham Roseburg

2.5 out of 5
3200 Nw Aviation Dr I-5 Exit # 127, Roseburg, OR
Fully refundableReserve now, pay when you stay
The price is CA $96 per night from Aug 11 to Aug 12
CA $96
CA $105 total
Aug 11 - Aug 12
includes taxes & fees
7.8/10 Good! (1,012 reviews)
"Good for the price"

Reviewed on Jul. 14, 2025

Super 8 by Wyndham Roseburg
See all 114 properties in Winchester
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

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Family Vacations

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Frequently asked questions

How much does a Winchester vacation package cost?
You can pick up a vacation package to this popular destination from CA $894 on Expedia. But how much your vacation to Winchester costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Winchester?
January, February and November are great times to search for cheap Winchester vacation packages. Choosing to travel in less busy periods means you'll typically find better prices on flights and accommodations.
How many days is enough for Winchester?
Usually, a handful of days is great for a Winchester vacation. With a detailed itinerary, you can go to all the top sights like Douglas County Museum of History and Natural History, as well as discover some hidden treasures along the way.
How to find the best Winchester package deals?
Use Expedia's handy filters to find some unbeatable Winchester package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Winchester package deals in the off-season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Winchester vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging hotels and flights separately. Better still, you can tailor your Winchester escape to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Winchester?
If you have your Winchester vacation dates finalized, book as early as you can to score some fantastic deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Winchester?

  1. Choose when to get away: Check your calendar and pack your bags. Your preferred time of year and the activities on offer will also help you decide when to escape to Winchester.
  2. Work out your budget: Make sure you have enough money to pay for everything from transportation and food to flights and activities. Your accommodations will likely be the biggest expense during your trip to Winchester.
  3. Work out your trip length: Think about how long you want to spend discovering Winchester. Plan your itinerary so you can get to all the attractions and activities you're interested in at a comfortable pace.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to choose a Winchester vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.