Winchester Holidays

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Your Winchester Holiday

When a city adventure is calling your name, answer it with a Winchester holiday package. With all your travel plans worked out before you leave, all you have to do here is focus on having fun. Any trip to Winchester needs a well-designed itinerary. Fill yours with big-name attractions like Melrose Vineyards, Stewart Park and Winchester Dam. Stop daydreaming and start doing. Browse the wide range of options on Expedia today and put your Winchester holiday plans in motion!

Winchester Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
10ºC
Max Temp Summer
27ºC
Top Sights
Wildlife Safari, Melrose Vineyards and Reustle Prayer Rock Vineyards

Our pick of the best Winchester Hotel Deals

Singing Waters at N. Umpqua
Singing Waters at N. Umpqua
Roseburg North, OR
Stay at this holiday home in Roseburg North. Enjoy a beach locale, laundry facilities and patios. Popular attractions Winchester Dam and Becker Vineyard are ...
Stunning!
"Beautifully decorated house! Loved the view of the river in the backyard. So clean and new! No complaints!!"

Reviewed on 10 Jul 2024

Singing Waters at N. Umpqua
Riverfront Inn Roseburg
Riverfront Inn Roseburg
2 out of 5
315 W Harvard Ave, Roseburg, OR
Stay at this motel in Roseburg. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their reviews. Popular ...
8.4/10 Very Good! (1,317 reviews)
"We had a great stay. We stayed there with gkids to go to the wildlife safari. Perfect spot and the staff was so very amazing and kind. Loved our stay."

Reviewed on 29 Jun 2025

Riverfront Inn Roseburg
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
Stay at this business-friendly hotel in Roseburg. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
7.6/10 Good! (1,013 reviews)
"For a basic hotel, and good price this was a very clean hotel"

Reviewed on 29 Jun 2025

Super 8 by Wyndham Roseburg
See all 112 properties in Winchester
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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Winchester travel package cost?
We make it simple to see the world, with Winchester travel packages starting from as little as . You'll have the flexibility to combine your preferred hotels, airlines and car rental. For the ultimate getaway, why not add a couple of tours and activities to your travel itinerary?
If I'm not able to travel, can I cancel my Winchester travel package?
We get it --- life sometimes gets in the way of your plans. If you've booked a Winchester travel package and need to change or cancel it, we can help. We recommend visiting our Customer Service Portal first for information. But generally, if you've taken out your package in the last 24 hours, you may be able to amend or cancel your itinerary free of charge. If it's more than 24 hours, your airline, hotel or car rental company may impose a charge.
How do I get a cheap travel package to Winchester?
Browse and lock in everything in the one place with our Winchester travel packages. We have incredible bargains on hotels, flights and more that'll keep your budget happy and your adventurous side busy. And, with more than 550 airlines and 1,000,000 hotel options all over the world to select from, you have countless opportunities to mix and match your own way.
Does Expedia offer Book Now, Pay Later Winchester holidays?
Your bank balance shouldn't stop you from going on holiday, so Expedia has devised a solution to help. Thanks to our partnership with online lender Klarna, it's easier than ever to book your dream getaway without drying up your savings. Klarna offers flexible payment options at checkout that take the stress out of budgeting for your break. Check out these flexible payment options:

  • Pay monthly holidays: If paying small amounts each month works for you, Klarna can help. Paying in easy monthly instalments will make that dream getaway possible.
  • Pay in instalments holidays: Like the idea of paying off your holiday in multiple transactions? Then check out this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the total upfront) makes it easier to click that "book now" button, consider a low deposit holiday payment plan from Klarna.

Where should I stay in Winchester?
If you'll be checking out Winchester Dam, skip commuting and stay close by. It's one of the top attractions in Winchester.
What are the top hotels in Winchester?
Get your escape off to a fantastic start by locking in a room at Best Western Plus Hood River Inn. It's one of most popular hotels in Winchester. Another leading option is DoubleTree by Hilton Hotel Portland.
How far in advance should I book my Winchester holiday?
Browse Expedia to compare international airfares as early as possible. You can generally purchase a seat up to a year in advance. If you can't find your preferred air carrier, or you've left things to the last moment, don't stress. Low prices to Winchester sometimes emerge just weeks before departure.
What does an Expedia Winchester travel package include?
Flights, hotels and rental cars --- we've got them all. With Expedia, you can shape your Winchester travel package your way. All you have to do is determine exactly what you need. Once you've made your booking, you can add on fun things like activities and tours. The more you bundle, the bigger the savings!
What should I know before booking a Winchester travel package?
Bundling your bookings into a Winchester travel package is the most convenient way to organise your trip. Not only that, you'll save big when you combine your flights, hotels and car rentals. Once you've booked, why not add on an activity or a tour?
Can I choose my airline with a Winchester Expedia travel package?
Yes, the choice is yours. We have access to over 550 airlines globally, so you can customize your Winchester getaway according to your budget and style.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.