Deals on vacations and trips to Winchester

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Winchester flight + hotel vacation packages

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

Hayward Inn

3 out of 5
East University
Price was $986, price is now $812 per person
$812
per person
Sep 11 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Eugene (EUG)
This hotel features an indoor pool and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.
University Inn & Suites

University Inn & Suites

2 out of 5
East University
Price was $1,068, price is now $834 per person
$834
per person
Sep 14 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Eugene (EUG)
This motel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's a seasonal outdoor pool on site, and a 24-hour front desk and a snack bar/deli are also provided.
The Local Motel & Shops

The Local Motel & Shops

2 out of 5
Downtown Eugene
Price was $1,521, price is now $1,215 per person
$1,215
per person
Sep 14 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Eugene (EUG)
The 505 Eugene

The 505 Eugene

3 out of 5
Downtown Eugene
Price was $1,811, price is now $1,447 per person
$1,447
per person
Sep 14 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Eugene (EUG)
This apartment features a virtual front desk. Take advantage of the free self parking.
Best Western Plus Grand Manor Inn

Best Western Plus Grand Manor Inn

2.5 out of 5
Price was $1,309, price is now $1,076 per person
$1,076
per person
Sep 14 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Eugene (EUG)
This hotel features an outdoor pool and a gym. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Dry cleaning and a safe deposit box are also provided.

Top Winchester hotels deals

Singing Waters at N. Umpqua

Singing Waters at N. Umpqua

Roseburg North OR
Get rates
This vacation home featured laundry facilities and barbecue grills.
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
$96 nightly
The price is $105 total per night
$105 total
Jun 28 - Jun 29
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Riverfront Inn Roseburg

Riverfront Inn Roseburg

2 out of 5
315 W Harvard Ave Roseburg OR
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $102 total per night
$102 total
Jun 29 - Jun 30
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. There's an outdoor pool on site, and a 24-hour front desk and a terrace are also provided.
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
$120 nightly
The price is $131 total per night
$131 total
Jun 30 - Jul 1
Total with taxes and fees
A restaurant and a seasonal outdoor pool are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.
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
$86 nightly
The price is $94 total per night
$94 total
Jul 20 - Jul 21
Total with taxes and fees
This hotel features an indoor pool and a hot tub. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.
Best Western Plus Hartford Lodge

Best Western Plus Hartford Lodge

2.5 out of 5
150 Myrtle St Sutherlin OR
Free Cancellation
Reserve now, pay when you stay
$136 nightly
The price is $149 total per night
$149 total
Jun 30 - Jul 1
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the business center and free internet in public areas. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Pet friendly
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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.

Frequently asked questions

How much are vacation packages to Winchester?
Starting from as low as $812, 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 45 mi 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

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