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Winchester flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Travelodge by Wyndham Florence

Travelodge by Wyndham Florence

2.5 out of 5
Price was CA $1,342, price is now CA $1,293 per person
CA $1,293
per person
Mar 15 - Mar 21
found 12 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Eugene (EUG)
Stay at this hotel in Florence. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siuslaw Pioneer Museum and Historic Old Town Florence are located nearby.
Quality Inn Florence

Quality Inn Florence

2.5 out of 5
Price was CA $1,445, price is now CA $1,338 per person
CA $1,338
per person
Mar 15 - Mar 21
found 12 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Eugene (EUG)
Book a stay at this business-friendly hotel in Florence. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Sandpines Golf Course and Three Rivers Casino are located nearby.
River House Inn, a Baymont by Wyndham

River House Inn, a Baymont by Wyndham

2 out of 5
Price was CA $1,620, price is now CA $1,534 per person
CA $1,534
per person
Mar 15 - Mar 21
found 12 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Eugene (EUG)
Book a stay at this business-friendly motel in Florence. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Historic Old Town Florence and Siuslaw Pioneer Museum are located nearby.
Super 8 by Wyndham Florence OR

Super 8 by Wyndham Florence OR

2.5 out of 5
Price was CA $1,588, price is now CA $1,505 per person
CA $1,505
per person
Mar 15 - Mar 21
found 12 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Eugene (EUG)
Stay at this motel in Florence. 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 Historic Old Town Florence and Siuslaw Pioneer Museum are located nearby.
Best Western Pier Point Inn

Best Western Pier Point Inn

2.5 out of 5
Price was CA $1,721, price is now CA $1,676 per person
CA $1,676
per person
Mar 15 - Mar 21
found 12 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Eugene (EUG)
Book a stay at this business-friendly hotel in Florence. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Suislaw River Bridge and Historic Old Town Florence are located nearby.

Top Winchester hotels deals

Singing Waters at N. Umpqua

Singing Waters at N. Umpqua

Roseburg North OR
Get rates
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
Get rates
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
Best Western Garden Villa Inn

Best Western Garden Villa Inn

2.5 out of 5
760 NW Garden Valley Boulevard Roseburg OR
Free cancellation
Reserve now, pay when you stay
The price is CA $120 per night
CA $120
CA $132 total
Feb 26 - Feb 27
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
Hot tub
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 $82 per night
CA $82
CA $90 total
Feb 15 - Feb 16
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
SureStay by Best Western Roseburg

SureStay by Best Western Roseburg

2.5 out of 5
2855 NW Edenbower Blvd Roseburg OR
Free cancellation
Reserve now, pay when you stay
The price is CA $115 per night
CA $115
CA $126 total
Feb 3 - Feb 4
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
Breakfast included
Comfort Inn Roseburg

Comfort Inn Roseburg

2.5 out of 5
1539 NW Mullholland Drive Roseburg OR
Free cancellation
Reserve now, pay when you stay
The price is CA $118 per night
CA $118
CA $129 total
Feb 15 - Feb 16
includes taxes & fees
Book a stay at this golf 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
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See all available properties in Winchester
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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 $1,293, 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