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 $437, price is now $365 per person
$365
per person
Nov 22 - Nov 24
found 20 hours ago
Roundtrip non-stop flight included
Burbank (BUR) 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.
Valley River Inn

Valley River Inn

3.5 out of 5
Price was $679, price is now $518 per person
$518
per person
Nov 22 - Nov 24
found 20 hours ago
Roundtrip non-stop flight included
Burbank (BUR) to Eugene (EUG)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Families will appreciate the children's pool and picnic area. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi.
Graduate by Hilton Eugene

Graduate by Hilton Eugene

4 out of 5
Downtown Eugene
Price was $593, price is now $471 per person
$471
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip flight included
Burbank (BUR) to Eugene (EUG)
This hotel features an indoor pool, A 24-hour gym, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. There's a bar/lounge on site, and a 24-hour front desk and wedding services are also provided.
Counting Z's

Counting Z's

2 out of 5
Price was $572, price is now $473 per person
$473
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip flight included
Burbank (BUR) to Eugene (EUG)
This inn features free WiFi in public areas, laundry facilities, and a virtual front desk.
The 505 Eugene

The 505 Eugene

3 out of 5
Downtown Eugene
Price was $666, price is now $561 per person
$561
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip flight included
Burbank (BUR) to Eugene (EUG)
This apartment features a virtual front desk. Take advantage of the free self parking.

Top Winchester hotels deals

Singing Waters at N. Umpqua

Singing Waters at N. Umpqua

Get rates
This vacation home featured laundry facilities and barbecue grills.
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
$101 nightly
The price is $111 total per night
$111 total
Nov 4 - Nov 5
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
Motel 6 Roseburg, OR

Motel 6 Roseburg, OR

2 out of 5
3100 Nw Aviation Dr, Roseburg, OR
Free Cancellation
$58 nightly
The price is $64 total per night
$64 total
Nov 2 - Nov 3
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A snack bar/deli and laundry facilities are also provided.
Pet friendly
Parking included
Motel 6 Sutherlin, OR

Motel 6 Sutherlin, OR

2 out of 5
1400 Hospitality Way, Sutherlin, OR
Free Cancellation
$58 nightly
The price is $64 total per night
$64 total
Nov 2 - Nov 3
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Express check-out, a computer station, and laundry facilities are also on offer.
Pet friendly
Parking included
Holiday Inn Express Roseburg by IHG

Holiday Inn Express Roseburg by IHG

2.5 out of 5
375 Harvard Blvd, Roseburg, OR
Free Cancellation
$126 nightly
The price is $138 total per night
$138 total
Nov 22 - Nov 23
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Rosewood Inn and Suites

Rosewood Inn and Suites

2.5 out of 5
790 NW Garden Valley Blvd, Roseburg, OR
Free Cancellation
Reserve now, pay when you stay
$62 nightly
The price is $68 total per night
$68 total
Oct 26 - Oct 27
Total with taxes and fees
An outdoor pool is featured at this motel, along with free self parking. Guests will appreciate free perks like self-serve breakfast and WiFi in public areas. There's a picnic area and multilingual staff can provide around-the-clock assistance.
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 $365, 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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