Book Exclusive Winchester Vacation Packages

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Winchester flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Valley River Inn

Valley River Inn

3.5 out of 5
Price was CA $1,300, price is now CA $1,020 per person
CA $1,020
per person
Nov 11 - Nov 15
found 7 hours ago
Roundtrip flight included
Montreal (YUL) to Eugene (EUG)
Stay at this 3.5-star family-friendly hotel in Eugene. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the comfy rooms in our reviews. Popular attractions Autzen Stadium and Owen Rose Garden are located nearby.
Home2 Suites by Hilton Eugene Downtown University Area

Home2 Suites by Hilton Eugene Downtown University Area

3 out of 5
Downtown Eugene
Price was CA $1,686, price is now CA $1,371 per person
CA $1,371
per person
Nov 11 - Nov 15
found 7 hours ago
Roundtrip flight included
Montreal (YUL) to Eugene (EUG)
Stay at this 3-star business-friendly hotel in Eugene. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Autzen Stadium and McDonald Theatre are located nearby.
The Florentine Waterfront Hotel

The Florentine Waterfront Hotel

2 out of 5
Price was CA $1,286, price is now CA $1,082 per person
CA $1,082
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Eugene (EUG)
Stay at this hotel in Westlake. Enjoy free WiFi, free parking, and premium bedding. Popular attractions Siltcoos Lake and Jessie M. Honeyman State Park are located nearby.
The 505 Eugene

The 505 Eugene

3 out of 5
Downtown Eugene
Price was CA $1,425, price is now CA $1,201 per person
CA $1,201
per person
Nov 11 - Nov 15
found 7 hours ago
Roundtrip flight included
Montreal (YUL) to Eugene (EUG)
Stay at this 3-star apartment in Eugene. Enjoy free WiFi, free parking, and an in-room coffeemaker. Popular attractions Autzen Stadium and Shelton McMurphey Johnson House are located nearby.
University Inn & Suites

University Inn & Suites

2 out of 5
East University
Price was CA $1,285, price is now CA $1,084 per person
CA $1,084
per person
Nov 11 - Nov 15
found 7 hours ago
Roundtrip flight included
Montreal (YUL) to Eugene (EUG)
Book a stay at this business-friendly motel in Eugene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Autzen Stadium and Matthew Knight Arena are located nearby.

Top Winchester hotels deals

Singing Waters at N. Umpqua

Singing Waters at N. Umpqua

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Stay at this vacation home in Roseburg North. Enjoy a beach locale, laundry facilities, and patios. Popular attractions Winchester Dam and Becker Vineyard are located nearby.
Kitchen
Washer
Riverfront Inn Roseburg

Riverfront Inn Roseburg

2 out of 5
315 W Harvard Ave, Roseburg, OR
Free cancellation
Reserve now, pay when you stay
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Stay at this motel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Stewart Park and Douglas County Museum of History and Natural History are located nearby.
Pool
Breakfast included
Motel 6 Roseburg, OR

Motel 6 Roseburg, OR

2 out of 5
3100 Nw Aviation Dr, Roseburg, OR
Free cancellation
Reserve now, pay when you stay
The price is CA $86 per night
CA $86
CA $95 total
Sep 22 - Sep 23
includes taxes & fees
Stay at this motel in Roseburg. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Umpqua Valley Tennis Center and Stewart Park are located nearby.
Pet-friendly
Parking included
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
Free cancellation
Reserve now, pay when you stay
The price is CA $104 per night
CA $104
CA $114 total
Sep 21 - Sep 22
includes taxes & fees
Book a stay at this business-friendly hotel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Umpqua Valley Tennis Center and Stewart Park are located nearby.
Pool
Breakfast included
Sleep Inn & Suites Roseburg North Near Medical Center

Sleep Inn & Suites Roseburg North Near Medical Center

2.5 out of 5
2855 NW Edenbower Blvd, Roseburg, OR
Free cancellation
Reserve now, pay when you stay
The price is CA $146 per night
CA $146
CA $160 total
Sep 21 - Sep 22
includes taxes & fees
Book a stay at this business-friendly hotel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Umpqua Valley Tennis Center and Stewart Park are located nearby.
Pool
Hot tub
Motel 6 Sutherlin, OR

Motel 6 Sutherlin, OR

2 out of 5
1400 Hospitality Way, Sutherlin, OR
Free cancellation
Reserve now, pay when you stay
The price is CA $70 per night
CA $70
CA $77 total
Sep 23 - Sep 24
includes taxes & fees
Stay at this motel in Sutherlin. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Umpqua Golf Resort and Central Park are located nearby.
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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.

Winchester Vacations

Get your trip off to the best possible start by knowing a thing or two about Winchester before you jet off.

From downtown Roseburg, you'll need to make your way north for 5 miles (8 kilometers) to get to this neighborhood.

Ready to meet some of the locals? 21,000 people live in Roseburg.

Hotels in Winchester

After a long day exploring Winchester, you'll need someplace comfortable to catch up on some sleep. While it's difficult to stay in the center of this neighborhood, it is possible to spend your evenings at one of the 14 properties a quick commute away.

The Holiday Inn Express Roseburg (375 Harvard Blvd) and the Best Western Garden Villa Inn (760 NW Garden Valley Boulevard) are our suggestions for this neighborhood.

Places to visit in Winchester

Ready for some snowboarding? It's one of the best activities in the wider region and a fantastic excuse to spend time in nature. Skiing is one more activity to include on your to-do list.

Where do you fly into for Winchester?

Touching down at Southwest Oregon Regional Airport (OTH)? Winchester is 45 miles (72 kilometers) away. Grab a cup of coffee, secure a ride and you'll be there in no time!

Frequently asked questions

How much are vacation packages to Winchester?
Starting from as low as CA $1,020, hotel and flight packages are an excellent way to stretch your travel budget. Winchester, here you come!
Where can I get the best vacation package deals for Winchester?
Snapping up the perfect package deal to Winchester is a piece of cake with Travelocity. With as many as 400 airlines and 1,000,000 properties all over the globe, you're spoiled for choice when selecting your flights and hotels.
Why should I book my Winchester vacation bundle via Travelocity?
Savings, support and a stress-free booking are just the beginning. Collect lifelong memories and enjoy a fulfilling travel experience knowing you can rely on our team of customer support experts around-the-clock. With the Travelocity Price Match Guarantee, you know you're getting the best deal available.
Can I save money on my Winchester car rental if I bundle it with hotels and flights?
You sure can with our Winchester vacation packages. With one of these, there are lots of ways to make your vacation budget go further. Bundle any two or more car, hotel, flight and tour bookings and see the savings pile up. With a rental car, all the key sights in and around Winchester are just a road trip away.
Which airport is best for Winchester?
Southwest Oregon Regional Airport (OTH), the primary terminal in Winchester, is where you'll stroll through arrivals. You'll find it 72 kilometers west of the center of town.
Where should I stay when visiting Winchester?
Many travelers hit the hay at the Singing Waters at N. Umpqua. It's a great base for your Winchester getaway.

Photos of local treasures

Browse Winchester vacation photos for more inspiration