Winston Holiday Rentals from €76: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Winston has to offer?

The Watusi Place - A Modern Umpqua Valley Getaway : This highly rated holiday home rental in Winston is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. Another good choice for your trip to Winston is Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen .

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In two weeks

In two months

In three months

In four months

Our top choices for Winston holiday rentals

The Watusi Place - A Modern Umpqua Valley Getaway

Winston

Candace L.

includes taxes & fees

2 Jun - 3 Jun

Lil Cedar Lodge

Roseburg

Zakary S.

includes taxes & fees

28 May - 29 May

Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️

Azalea

Darcy L.

includes taxes & fees

29 May - 30 May

Blissful Solitude Cottage

Douglas County

Matthew O.

includes taxes & fees

1 Jun - 2 Jun

Tiny House nestled into the Forest on 160 acre Playground.

Roseburg

Sarah C.

includes taxes & fees

28 May - 29 May

Country Farm Condo w/kitchen, near 7 Feathers Casino on OR Hwy 5; Dog friendly

Riddle

Brad

includes taxes & fees

18 Jun - 19 Jun

Smart TV, fireplace, books, music library

Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun

Roseburg

Barry W.

includes taxes & fees

1 Jun - 2 Jun

Charming, Private Cottage near I-5 and Golf Course.

Myrtle Creek

Jessica S.

includes taxes & fees

28 May - 29 May

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Top Winston Hotel Reviews

The Lodge at Roseburg

8/10 Good

"Overall it was a nice stay for a quick overnight while on a roadtrip. The bed was comfy and we didn’t hear street noise. It was quiet overall on property. It appears Marriott has bought it out and trying to do some much needed improvements. Breakfast was a little on the colder side but nothing was a deal breaker. Our room door needed some extra lift to close, bathroom still had hairs from previous guests and we found a vape in the room on a shelf. Daughter said the sofa bed was just okay and it had some issues but we managed. "

Riverfront Inn Roseburg

2/10 Terrible

"Absolutely awful experience at the Riverfront Inn in Roseburg. We were exhausted after a long drive and booked this hotel thinking it would be a safe, decent place to stay based on the 8.2/10 rating on Hotels.com. That rating is incredibly misleading. The moment we pulled in, there were cars blocking the entrance and the entire property gave off an unsafe, sketchy feeling. All of the room entrances are outside and the atmosphere honestly felt uncomfortable and unsettling. Check-in took over 30 minutes because staff were dealing with another guest who appeared intoxicated or under the influence and was driving around the property with two young kids in the car. It was disturbing to witness and definitely not something you expect when arriving at a hotel late at night hoping to relax. The hotel also advertises a “better continental breakfast” than nearby hotels, but the breakfast area is basically a tiny counter in the lobby with only four stools to sit on. Very disappointing and misleading. Once we finally got into the room, it was rundown, dirty-feeling, and worst of all — we found bugs in the bed. At that point we just wanted the night to be over. Thankfully this was only a one-night stop on our drive home. Honestly, I would have rather stayed at the Best Western nearby. It looked significantly cleaner, safer, and was somehow cheaper too. Definitely do your research before booking here because this place was nothing like the rating suggests."

Find out more about Winston

Everything you need to know about Winston holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winston holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winston holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winston holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winston. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winston holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winston holiday rentals we have selected for you start as low as €76 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winston rentals

At Expedia, we put the best Winston holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winston rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winston holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winston. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there holiday rentals in Winston?

Yes, there are holiday rentals in Winston close to Wildlife Safari, or you can select a more secluded option if you're looking for a relaxing stay. Winston is known for its restaurants.

What are some of the best holiday rentals that Winston has to offer?

The Watusi Place - A Modern Umpqua Valley Getaway: This highly rated holiday home rental in Winston is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. Another good choice for your trip to Winston is Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen .

How many holiday rentals will I find in Winston?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Winston stay.

What’s there to see and do in Winston?

Family-friendly attractions include Wildlife Safari, whereas South Umpqua River is a spot to enjoy the outdoors. In the wider area, you’ll find Abacela Winery and Stewart Park.

What’s a holiday rental in Winston like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winston. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can provide a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for a small group gathering.

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Our top choices for Winston holiday rentals