Winchester Holiday Rentals from €112: Search Short-Term Rentals

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.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Winchester holiday rentals

A modern house with a stone pathway leading to the entrance, surrounded by various plants and a large planter.

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

Roseburg

Nicole B.

includes taxes & fees

18 Oct - 19 Oct

A modern living room with a white sofa, a patterned rug, and a flat-screen TV mounted on the wall.

2. Cozy & Comfortable 2-bedroom home

Roseburg

includes taxes & fees

18 Oct - 19 Oct

A small, single-story house with a green door, white trim, and a small porch.

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

Roseburg

Gordon

includes taxes & fees

26 Oct - 27 Oct

A house with a covered porch, a seating area with a sofa and armchair, and a small table.

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

Roseburg

Cindan G.

includes taxes & fees

19 Oct - 20 Oct

A small house with a porch and string lights.

5. Downtown Stay at the Red Tiny Twin!

Roseburg

Sue S.

includes taxes & fees

18 Oct - 19 Oct

A wooden cabin named 'Lil Cedar Lodge' with a metal roof, two windows, and a small porch with a chair and table.

6. Lil Cedar Lodge

Roseburg

Zakary S.

includes taxes & fees

4 Nov - 5 Nov

A wooden cabin with a deck, outdoor seating, and a pathway lit by ground lights.

7. Tiny House nestled into the Forest on 160 acre Playground.

Roseburg

kimberley

includes taxes & fees

4 Nov - 5 Nov

A wooden deck with a white railing, a potted plant, and a table.

8. Luxury, Full Service Bed and Breakfast - you are the only guest in our home!

Roseburg

"Our hosts, James and Gail, are so lovely. They really care about their guests experience and I felt they truly cared about our experience. It’s a gorgeous home that they have decorated meticulously, and made so comfortable for guests to enjoy. The bed was super comfy and the room cozy. The bedding and towels were soft and top notch. They didn’t skimp on anything. Gail is a great cook and provided homemade food, snacks, and drinks. Some items came from her garden. James is a master with sound and...

Susan

includes taxes & fees

1 Nov - 2 Nov

A modern kitchen with stainless steel appliances, a wooden dining table, and a tufted ottoman.

9. Bell Sister Flats

Roseburg

Daniel

includes taxes & fees

21 Oct - 22 Oct

A living room with a sofa, a coffee table, a fireplace, a TV, and a painting on the wall.

10. Home Sweet Home

Sutherlin

Barbara S.

includes taxes & fees

19 Oct - 20 Oct

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

Roseburg

"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

21 Oct - 22 Oct

A spacious living area with a wooden dining table, black chairs, a ceiling fan, and a television displaying a beach scene.

12. The Watusi Place - A Modern Umpqua Valley Getaway

Winston

Jessica M.

includes taxes & fees

19 Oct - 20 Oct

A storefront with a black awning displaying the names 'Bell Sister Flats' and 'Paul L Bentley Architect A.I.A. P.C.' with contact numbers and a door marked '615'.

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

Roseburg

includes taxes & fees

21 Oct - 22 Oct

A compact kitchen with a microwave, coffee maker, and a cabinet labeled 'UMPQUA VALLEY'.

14. Elk Meadow Hideaway LLC Minutes away Worlds apart

Myrtle Creek

includes taxes & fees

18 Oct - 19 Oct

A wooden pathway leading to a covered area with a view of a mountainous landscape.

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

Myrtle Creek

Darla S.

includes taxes & fees

25 Oct - 26 Oct

A modern house with a gravel driveway, large windows, and a view of a forest.

16. Lone Rock Guest House, 20 acres minutes from the North Umpqua River

Glide

"I have stayed at probably 100 rental houses in my life - this is hands down my favorite and was best suited for my outdoor boys. There are endless things to do on the property and you are in the center of an outdoor adventure town with lakes, rivers, hikes, waterfalls, fishing and more. It was private, clean, well stocked, comfortable and high quality - and the host was responsive, welcoming and helpful. Thank you for the memories. I hope we can come back for an even longer stay next time."

Secret L.

includes taxes & fees

19 Oct - 20 Oct

View all properties

Find holiday rentals that suit your style

Apartments

Private holiday homes

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Winchester Hotel Reviews

Umpqua Valley Hotel

10/10 Excellent

"The staff were helpful and gave suggestions. Breakfast was served and good. Alittle bit of everything to choose. Easy access to find. I would recommend it"

Best Western Garden Villa Inn

8/10 Good

"Staff was excellent, helpful & very friendly. Ice machine was out in the parking lot away from the hotel. Breakfast was delicious. The one negative we had was there was not a cable guide for the TV. Unfortunately, I forgot to request a first floor room due to my mobility issues. When we got to the hotel there were only second floor room available with no elevator. The staff transfered us to a first floor room the next morning. They gave us a room with a raised toilet & extra safety bars, which I appreciated. We will be staying there again."

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 €112 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. Stewart Park and Melrose Vineyards 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.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winchester holiday rentals