Winchester Holiday Rentals

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Holiday Rentals in Winchester

Apartment in Winston

2.0 star property
10.0 out of 10, Exceptional, (1)
"The views are out of this world! The horses on property are gorgeous! This truly felt like a vacation within a vacation (drove that way for the wildlife safari park). We plan to come back again! Property owner is a sweetheart! "
United States
Charles B.
The price is AU$184
includes taxes & fees
5 Dec - 6 Dec
the Bunkhouse coyote- Private Studio Retreat Room

Holiday Home in Roseburg

10.0 out of 10, Exceptional, (40)
"Great place! The only thing I’d change is some blackout curtains if folks wanted to sleep in! Otherwise everything was amazing, Very sweet host and not to mention the beautiful property! "
United Kingdom
Hunter S.
The price is AU$280
includes taxes & fees
12 Dec - 13 Dec
A Restful Studio Near a Creek and Forest - Pets

Holiday Home in Roseburg

10.0 out of 10, Exceptional, (24)
"My parents stayed here for our son's graduation. They were very impressed with the hosts and warm welcome they received"
United States
SharonLee S.
The price is AU$375
includes taxes & fees
4 Dec - 5 Dec
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!

Apartment in Roseburg

2.0 star property
10.0 out of 10, Exceptional, (3)
"Terry's place was such a treat! The apartment exceeded so many of our expectations and was perfect for our mini vacation. Wonderful features and amenities. Beautiful finishes, linens and furnishings. Super responsive host. We look forward to our next stay!"
United States
CARISSA F.
The price is AU$514
includes taxes & fees
5 Dec - 6 Dec
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants

Cabin in Roseburg

The price is AU$175
includes taxes & fees
5 Dec - 6 Dec
Lil Cedar Lodge

Holiday Home in Roseburg

9.8 out of 10, Exceptional, (90)
"Cute decor, great location and easy to get to. It was a good fit for our weekend stay. "
United States
Sandra C.
The price is AU$343
includes taxes & fees
4 Dec - 5 Dec
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

Holiday Home in Roseburg North

9.4 out of 10, Exceptional, (18)
"This property was very enjoyable for the children and I enjoyed the kitchen."
United States
Stacy B.
The price is AU$692
includes taxes & fees
4 Dec - 5 Dec
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

Holiday Home in Roseburg

9.6 out of 10, Exceptional, (36)
"Nice place, great location."
United States
Gordon
The price is AU$354
includes taxes & fees
28 Dec - 29 Dec
The Urban Boho Charmer with Private Backyard, BBQ & Hammock

Holiday Home in Roseburg

9.6 out of 10, Exceptional, (19)
"It was a perfect place for us to stay for a short trip to visit family with our two little dogs."
United States
Rochelle S.
The price is AU$281
includes taxes & fees
5 Dec - 6 Dec
Red Tiny Twins, Downtown Eco & Pet Friendly Stay

Holiday Home in Winston

10.0 out of 10, Exceptional, (47)
"The house was amazing! Easy to get in, clean and well stocked. Definitely recommend to anyone looking for a nice place."
United States
Amy H.
The price is AU$595
includes taxes & fees
30 Dec - 31 Dec
The Watusi Place - A Modern Umpqua Valley Getaway

Holiday Home in Roseburg

9.6 out of 10, Exceptional, (13)
"Just as described, clean & comfortable loft bed. Owner great with communication & so nice. Would stay again "
United States
Lucinda H.
The price is AU$244
includes taxes & fees
4 Dec - 5 Dec
Tiny House nestled into the Forest on 160 acre Playground.

Holiday Home in Glide

2.0 star property
The price is AU$794
includes taxes & fees
26 Dec - 27 Dec
Lone Rock Guest House, 20 acres minutes from the North Umpqua River

Holiday Home in Roseburg

9.8 out of 10, Exceptional, (37)
"Just as advertised! Great house. Would definitely stay there again."
United States
Jake G.
The price is AU$445
includes taxes & fees
14 Dec - 15 Dec
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun

Holiday Home in Sutherlin

8.6 out of 10, Excellent, (10)
"We really enjoyed our stay! There are super comfortable beds, comfortable couch, fantastic washing machine, nice front porch and clean kitchen! The host was communicative and friendly ! Would for sure recommend and will stay there again on our next trip! "
United States
A T.
The price is AU$237
includes taxes & fees
6 Dec - 7 Dec
Home Sweet Home

Holiday Home in Roseburg

9.4 out of 10, Exceptional, (19)
"Just the right size and location for a wine country getaway weekend. Had everything we needed, and more. Will not hesitate to book again next trip, if it's available."
United States
John L.
The price is AU$279
includes taxes & fees
4 Dec - 5 Dec
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

Cottage in Myrtle Creek

10.0 out of 10, Exceptional, (41)
"This is the second time I have stayed here, both times with my dog. The place is convenient, quiet, clean, comfortable, and with great touches and landscaping outside. Wonderful place."
United States
Carter L.
The price is AU$278
includes taxes & fees
2 Jan - 3 Jan 2026
Charming, Private Cottage near I-5 and Golf Course.

Holiday Home in Roseburg

2.0 star property
The price is AU$530
includes taxes & fees
2 Jan - 3 Jan 2026
Private bungalow with AC in charming Roseburg

Aparthotel in Roseburg

2.0 star property
The price is AU$554
includes taxes & fees
6 Dec - 7 Dec
Bell Sister Flats

Apartment in Roseburg

2.0 star property
The price is AU$182
includes taxes & fees
2 Jan - 3 Jan 2026
Bunkhouse Bear Room -Private Studio Retreat

Holiday Home in Roseburg

9.6 out of 10, Exceptional, (51)
"It certainly is adorable, well-kept, well-stocked. We would love to stay here again!"
Canada
Faith S.
The price is AU$359
includes taxes & fees
4 Dec - 5 Dec
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
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.

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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, 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 favourite 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 depend 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 AU$175 per night. Entering your travel dates in the search wizard might find you 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?

River Vista Vacation Homes: This holiday home rental outside of Winchester is located on a river, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a coffee maker.

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. Melrose Vineyards and Reustle Prayer Rock 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.