Book Exclusive Winchester Vacation Packages

Choose one or more items to build your trip:

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
per person
Mar. 24 - Mar. 28
found 2 hours ago
Roundtrip flight included
Vancouver (YVR) to Eugene (EUG)
Stay at this 3.5-star family-friendly hotel in Eugene. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the comfy rooms in our reviews. Popular attractions Owen Rose Garden and Valley River Center Mall are located nearby.
Florence Lighthouse Inn

Florence Lighthouse Inn

2.5 out of 5
per person
Mar. 9 - Mar. 14
found 24 hours ago
Roundtrip flight included
Toronto (YYZ) to Eugene (EUG)
Stay at this motel in Florence. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff 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
per person
Mar. 9 - Mar. 14
found 24 hours ago
Roundtrip flight included
Toronto (YYZ) 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.
Travelodge by Wyndham Florence

Travelodge by Wyndham Florence

2.5 out of 5
per person
Mar. 9 - Mar. 14
found 24 hours ago
Roundtrip flight included
Toronto (YYZ) 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.
Driftwood Shores Resort And Conference Center

Driftwood Shores Resort And Conference Center

3 out of 5
per person
Mar. 9 - Mar. 14
found 24 hours ago
Roundtrip flight included
Toronto (YYZ) to Eugene (EUG)
Stay at this 3-star beach hotel in Florence. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Heceta Beach and North Jetty Beach are located nearby.

Top Winchester hotels deals

Singing Waters at N. Umpqua

Singing Waters at N. Umpqua

Get rates
Stay at this vacation home in Roseburg North. Enjoy a beach locale, balconies, and an in-room coffeemaker. 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
The price is CA $135 per night
CA $135
CA $148 total
includes taxes & fees
1 Feb - 2 Feb
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
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 $116 per night
CA $116
CA $127 total
includes taxes & fees
4 Feb - 5 Feb
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 Stewart Park and Douglas County Museum of History and Natural History are located nearby.
Pool
Hot tub
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 $104 per night
CA $104
CA $114 total
includes taxes & fees
15 Feb - 16 Feb
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 Stewart Park and Winchester Dam are located nearby.
Pool
Hot tub
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 $92 per night
CA $92
CA $101 total
includes taxes & fees
22 Feb - 23 Feb
Book a stay at this business-friendly hotel in Roseburg. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Stewart Park and Douglas County Museum of History and Natural History are located nearby.
Pool
Hot tub
Hampton Inn & Suites Roseburg

Hampton Inn & Suites Roseburg

2.5 out of 5
1620 Nw Mulholland Dr, Roseburg, OR
Free cancellation
Reserve now, pay when you stay
The price is CA $216 per night
CA $216
CA $236 total
includes taxes & fees
16 Feb - 17 Feb
Stay at this 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 Stewart Park and Douglas County Museum of History and Natural History are located nearby.
Pool
Breakfast included
Don't see what you're looking for?
See all available properties in Winchester
View all properties
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 $664, 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