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.
Valley River Inn

Valley River Inn

3.5 out of 5
Price was $631, price is now $503 per person
$503
per person
Feb 13 - Feb 16
found 13 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) 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.
The Florentine Waterfront Hotel

The Florentine Waterfront Hotel

2 out of 5
Price was $974, price is now $761 per person
$761
per person
Feb 11 - Feb 16
found 14 hours ago
Roundtrip non-stop flight included
Oklahoma City (OKC) to Eugene (EUG)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Luggage storage is also provided.
Driftwood Shores Resort And Conference Center

Driftwood Shores Resort And Conference Center

3 out of 5
Price was $803, price is now $691 per person
$691
per person
Feb 11 - Feb 16
found 14 hours ago
Roundtrip non-stop flight included
Oklahoma City (OKC) to Eugene (EUG)
This hotel features an indoor pool and a hot tub. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop, a snack bar/deli, and laundry facilities are also on offer.
Counting Z's

Counting Z's

2 out of 5
Save 100% on your flight
Price was $4,220, price is now $3,721 per person
$3,721
per person
Feb 13 - Feb 16
found 13 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) to Eugene (EUG)
This inn features free WiFi in public areas, laundry facilities, and a virtual front desk.
University Inn & Suites

University Inn & Suites

2 out of 5
East University
Price was $756, price is now $675 per person
$675
per person
Feb 13 - Feb 16
found 13 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) 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.

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.
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
$96 nightly
The price is $106 total per night
$106 total
Dec 14 - Dec 15
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.
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
$66 nightly
The price is $73 total per night
$73 total
Dec 18 - Dec 19
Total with taxes and fees
This hotel 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 24-hour business center. There's an indoor pool on site, and a 24-hour front desk and express check-out are also provided.
Holiday Inn Express Roseburg by IHG

Holiday Inn Express Roseburg by IHG

2.5 out of 5
375 Harvard Blvd Roseburg OR
Free Cancellation
$101 nightly
The price is $111 total per night
$111 total
Dec 28 - Dec 29
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.
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
$81 nightly
The price is $89 total per night
$89 total
Dec 28 - Dec 29
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. 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 on-the-go breakfast and free self parking.
Pool
Hot Tub
Motel 6 Roseburg, OR

Motel 6 Roseburg, OR

2 out of 5
3100 Nw Aviation Dr Roseburg OR
Free Cancellation
$56 nightly
The price is $61 total per night
$61 total
Dec 13 - Dec 14
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.
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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 $503, 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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