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.
Royal Inn Eugene

Royal Inn Eugene

2 out of 5
Bethel-Danebo
Price was $904, price is now $790 per person
$790
per person
Sep 17 - Sep 21
found 17 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Eugene (EUG)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.
Downtown Inn

Downtown Inn

2 out of 5
Downtown Eugene
Price was $955, price is now $838 per person
$838
per person
Sep 17 - Sep 21
found 17 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Eugene (EUG)
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.
The 505 Eugene

The 505 Eugene

3 out of 5
Downtown Eugene
Price was $1,406, price is now $1,255 per person
$1,255
per person
Sep 17 - Sep 21
found 17 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Eugene (EUG)
This apartment features a virtual front desk. Take advantage of the free self parking.
The Local Motel & Shops

The Local Motel & Shops

2 out of 5
Downtown Eugene
Price was $1,033, price is now $927 per person
$927
per person
Sep 17 - Sep 21
found 17 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Eugene (EUG)
La Quinta Inn & Suites by Wyndham Springfield

La Quinta Inn & Suites by Wyndham Springfield

3 out of 5
Price was $1,016, price is now $916 per person
$916
per person
Sep 17 - Sep 21
found 17 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Eugene (EUG)
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's a 24-hour gym on site, and a 24-hour front desk and a terrace are also provided.

Top Winchester hotels deals

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
$80 nightly
The price is $88 total per night
$88 total
Sep 9 - Sep 10
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.
Pool
Hot Tub
Riverfront Inn Roseburg

Riverfront Inn Roseburg

2 out of 5
315 W Harvard Ave Roseburg OR
Free Cancellation
Reserve now, pay when you stay
$102 nightly
The price is $111 total per night
$111 total
Sep 1 - Sep 2
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.
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
$119 nightly
The price is $130 total per night
$130 total
Aug 16 - Aug 17
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.
Pool
Hot Tub
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
$112 nightly
The price is $122 total per night
$122 total
Aug 16 - Aug 17
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
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
$144 nightly
The price is $158 total per night
$158 total
Aug 16 - Aug 17
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
Holiday Inn Express And Suites Roseburg North By Ihg

Holiday Inn Express And Suites Roseburg North By Ihg

2.5 out of 5
1530 NW Mulholland Drive Roseburg OR
Free Cancellation
$203 nightly
The price is $222 total per night
$222 total
Aug 21 - Aug 22
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Guests will appreciate free perks like free self parking and WiFi in public areas. Express check-out is also provided.
Pool
Breakfast included
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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 $790, 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.

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