Holiday Rentals Winchester from £86: Find Short-Term Rentals & Holiday Accommodations

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

Private Umpqua River Retreat w/ 2 King Suites & Patio : This holiday home rental outside of Winchester is located on a river, and has a patio, a garden 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.

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Our top choices for Winchester holiday rentals

1. <br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

Roseburg

Sharon K.

includes taxes & fees

16 Sept - 17 Sept

2. Lil Cedar Lodge

Roseburg

Zakary S.

includes taxes & fees

17 Sept - 18 Sept

3. Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~

Roseburg

Nicole B.

includes taxes & fees

4 Oct - 5 Oct

4. Downtown Stay at the Red Tiny Twin!

Roseburg

Sue S.

includes taxes & fees

17 Sept - 18 Sept

5. The Urban Boho Charmer with Private Backyard, BBQ & Hammock

Roseburg

Gordon

includes taxes & fees

18 Sept - 19 Sept

Smart TV, fireplace, books, music library

"Bell Sister Flats is amazing - so gorgeous, warm and inviting. We loved being on Main Street and walking to coffee, dinner, drinks. So much attention to detail and such comfort provided from the bed to the sheets to the towels and love seat and, oh the shower! Terry and Paul were wonderful hosts, so attentive and generous. Loved that they promoted the local community with goods and services in the flat. Loved our stay!"

Tara T.

includes taxes & fees

19 Sept - 20 Sept

Deluxe Apartment, City View | Private kitchen

12. Bell Sister Flats

Roseburg

Daniel

includes taxes & fees

16 Sept - 17 Sept

13. The Watusi Place - A Modern Umpqua Valley Getaway

Winston

Pamela M.

includes taxes & fees

20 Sept - 21 Sept

14. Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants

Roseburg

includes taxes & fees

15 Sept - 16 Sept

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

Myrtle Creek

Suzy

includes taxes & fees

20 Sept - 21 Sept

16. Elk Meadow Hideaway LLC Minutes away Worlds apart

Myrtle Creek

includes taxes & fees

5 Oct - 6 Oct

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Top Winchester Hotel Reviews

Riverfront Inn Roseburg

10/10 Excellent

"This was a very nice hotel. Room was very clean, bed comfortable and balcony with a nice view was enjoyable."

SureStay by Best Western Roseburg

10/10 Excellent

"Let's be fair here about the four star rating - they were renovating some of the rooms and unfortunately the elevator was being fixed. As someone that needed the elevator, it was irritating. The hotel didn't know in advance that I would need it; there wasn't any notation. What is important is that they prepared a first floor room for my husband and me for the early morning. The front desk staff had been very professional and understanding. I really liked this hotel. Our room was clean and the beds were comfortable. I will definitely stay here again when I am travelling through Oregon. It was safe, the parking was convenient, and close to everything."

Find out more about Winchester

Everything you need to know about Winchester 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 Winchester 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 Winchester holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. 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 Winchester 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 Winchester holiday rentals we have selected for you start as low as £86 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester 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 Winchester 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 Winchester 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 Winchester. 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

Can I find a holiday rental in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay. Winchester is known for its restaurants.

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

Private Umpqua River Retreat w/ 2 King Suites & Patio: This holiday home rental outside of Winchester is located on a river, and has a patio, a garden 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.

What’s there to see and do in Winchester?

While exploring the area, visit family-friendly sights like Wildlife Safari, or get outside and enjoy nature at North Umpqua River. Winchester Dam and Stewart Park are a couple of places you'll find in the wider area.

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals offer extras like kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for a family trip.

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Our top choices for Winchester holiday rentals