Winchester Holiday Rentals

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Our top choices for Winchester holiday rentals

10.0 out of 10, Exceptional, (40)
"Amazing!!"
United Kingdom
Maureen S.
The price is NZ$286
includes taxes & fees
8 Jan - 9 Jan
A Restful Studio Near a Creek and Forest - Pets

Cabin in Roseburg

Lil Cedar Lodge
The price is NZ$194
includes taxes & fees
8 Jan - 9 Jan
Lil Cedar Lodge
9.6 out of 10, Exceptional, (13)
"Wonderful environment and very peaceful stay. "
United States
Sarah C.
The price is NZ$272
includes taxes & fees
8 Jan - 9 Jan
Tiny House nestled into the Forest on 160 acre Playground.
9.6 out of 10, Exceptional, (37)
"Nice place, great location."
United States
Gordon
The price is NZ$394
includes taxes & fees
8 Jan - 9 Jan
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
9.8 out of 10, Exceptional, (39)
"Just as advertised! Great house. Would definitely stay there again."
United States
Jake G.
The price is NZ$511
includes taxes & fees
11 Jan - 12 Jan
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun

Holiday Home in Sutherlin

Home Sweet Home
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 NZ$592
includes taxes & fees
27 Jan - 28 Jan
Home Sweet Home
10.0 out of 10, Exceptional, (24)
"Absolutely the most delightful and magical place to stay! Wonderfully gracious hosts! They made our honeymoon stay spectacular and special! James and Gail are fabulous. We had the most incredible breakfast as well. We felt like royalty! "
United States
Rachel S.
The price is NZ$405
includes taxes & fees
7 Feb - 8 Feb
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
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 NZ$623
includes taxes & fees
14 Jan - 15 Jan
The Watusi Place - A Modern Umpqua Valley Getaway
9.6 out of 10, Exceptional, (29)
"Finding the entry to the property was hardest part. Parking was OK. The views and the space was great. Nice central location for many places to visit."
United States
Nicole B.
The price is NZ$341
includes taxes & fees
10 Jan - 11 Jan
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
9.6 out of 10, Exceptional, (52)
"It certainly is adorable, well-kept, well-stocked. We would love to stay here again!"
Canada
Faith S.
The price is NZ$341
includes taxes & fees
7 Feb - 8 Feb
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
9.8 out of 10, Exceptional, (91)
"Thank you so much for the comfy cozy place to stay! "
United States
Kristina C.
The price is NZ$384
includes taxes & fees
8 Jan - 9 Jan
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

Holiday Home in Roseburg

Downtown Stay at the Blue Tiny Twin
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 NZ$312
includes taxes & fees
1 Feb - 2 Feb
Downtown Stay at the Blue Tiny Twin
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 NZ$568
includes taxes & fees
18 Jan - 19 Jan
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
2.0 star property
The price is NZ$320
includes taxes & fees
31 Jan - 1 Feb
Cozy 1-bedroom house in adorable Roseburg with AC
10.0 out of 10, Exceptional, (42)
"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 NZ$311
includes taxes & fees
7 Feb - 8 Feb
Charming, Private Cottage near I-5 and Golf Course.

Holiday Home in Roseburg

Downtown Stay at the Red Tiny Twin!
9.8 out of 10, Exceptional, (21)
"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 NZ$312
includes taxes & fees
7 Feb - 8 Feb
Downtown Stay at the Red Tiny Twin!

Aparthotel in Roseburg

Bell Sister Flats
2.0 star property
The price is NZ$637
includes taxes & fees
20 Jan - 21 Jan
Bell Sister Flats
9.4 out of 10, Exceptional, (19)
"This property was very enjoyable for the children and I enjoyed the kitchen."
United States
Stacy B.
The price is NZ$870
includes taxes & fees
14 Jan - 15 Jan
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
The price is NZ$1,089
includes taxes & fees
23 Jan - 24 Jan
Lone Rock Guest House, 20 acres minutes from the North Umpqua River
2.0 star property
The price is NZ$579
includes taxes & fees
7 Feb - 8 Feb
Private bungalow with AC in charming Roseburg
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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Top Winchester Hotel Reviews

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 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 NZ$194 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?


~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
: This holiday home rental outside of Winchester offers a selection of games, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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.