Winchester Holiday Rentals

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Holiday Rentals in Winchester

Singing Waters at N. Umpqua
Stereo
Singing Waters at N. Umpqua
10.0 out of 10, Exceptional, (4)
"We so enjoyed out time in the home. Sat outside ever night and enjoyed the view and hearing the river. Only drawback was sprinklers coming on as we were walking down to see the river at 8 pm. Other than that it wa one of our favorite places to stay. We will be back"
Singing Waters at N. Umpqua
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
2 bedrooms, desk, iron/ironing board, travel cot
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
9.8 out of 10, Exceptional, (53)
"This is a cute property! It is decorated with a 60s vibe and has a fun record player, which brought back memories for me. We were Goldilocks trying to find the right beds at first. If you are like us, here’s a help. The bed that shares a wall with the living room is a more solid bed the firmest of all, the other bed is very soft and less stable, the couch is ok for naps but they offer a blow up that worked well if the soft bed is too soft. Items for to use for the oven would be helpful....
The price is AU$341
includes taxes & fees
28 July - 29 July
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Heavenly Bungalow, Entire Home!
Exterior
Heavenly Bungalow, Entire Home!
10.0 out of 10, Exceptional, (22)
"This house had the cutest character which made for a fantastic stay."
Heavenly Bungalow, Entire Home!
Firewater Lodge Cabin Experience
Terrace/patio
Firewater Lodge Cabin Experience
10.0 out of 10, Exceptional, (35)
"What a wonderful place to get away and enjoy life. Stunning log cabin with so many features. Beautiful backyard that we spent a lot of time in. Firepit was awesome as well as the grills. Everything so clean and so comfortable and perfect hosts who were always available for questions. We will be back again and again, as long as it is available. Highly recommended. Thank you to Jon and your siblings for making this available. Very impressive cabin."
Firewater Lodge Cabin Experience
Sophisticated Bungalow, Sparkling clean!
Fridge, microwave, oven, stovetop
Sophisticated Bungalow, Sparkling clean!
10.0 out of 10, Exceptional, (50)
"Pictures did not do it justice. Well put together, tidy, GREAT location, and nice layout. Next time in area, this is going to be our #1 choice. Was perfect."
Sophisticated Bungalow, Sparkling clean!
Just off I-5, RV available on secluded lot. 2 livestock stalls. Close to town.
Property grounds
Just off I-5, RV available on secluded lot. 2 livestock stalls. Close to town.
10.0 out of 10, Exceptional, (3)
"Stayed here while figuring out my living situation during the sale of my place. Doug was so helpful and kind. I love the setting, watching cows graze while drinking coffee in the morning. Bed is comfortable. Very quiet. If you like a little solitude while RV'ing, you should enjoy it here."
Just off I-5, RV available on secluded lot. 2 livestock stalls. Close to town.
Historic Lodge across the street from the Umpqua River
Private kitchen
Historic Lodge across the street from the Umpqua River
9.8 out of 10, Exceptional, (20)
"The room has all the amenities we needed to be comfortable. The location was beautiful. The hosts were very friendly and welcoming. Staying here was the perfect way to wrap up our vacation. Thank you!"
The price is AU$224
includes taxes & fees
28 June - 29 June
Historic Lodge across the street from the Umpqua River
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
Property grounds
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
9.6 out of 10, Exceptional, (27)
"Clean, comfy, great neighborhood. Missed having thermostat to control temp. Very loud furnace came on at night, waking us up every time. It was comfortable without the blast furnace. We opened window to stay cool at night."
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
The Watusi Place - A Modern Umpqua Valley Getaway
Terrace/patio
The Watusi Place - A Modern Umpqua Valley Getaway
10.0 out of 10, Exceptional, (31)
"Everything was great‼️"
The price is AU$651
includes taxes & fees
10 July - 11 July
The Watusi Place - A Modern Umpqua Valley Getaway
Lost World Lodge - Your Jurassic Park Vacation Rental
TV, table football, stereo
Lost World Lodge - Your Jurassic Park Vacation Rental
9.0 out of 10, Wonderful, (2)
"Loved the Lost World theme of the apartment. It was super clean, spacious, and great location. The KOA park is the cleanest park I've seen and we love the drive in movie theater."
Lost World Lodge - Your Jurassic Park Vacation Rental
Family-Friendly Winston Vacation Rental w/ Deck!
Fridge, microwave, stovetop, dishwasher
Family-Friendly Winston Vacation Rental w/ Deck!
10.0 out of 10, Exceptional, (5)
"The property is very nice with a good view. Very well supplied with all necessary items for cooking and meals. Ease of working with hostess."
Family-Friendly Winston Vacation Rental w/ Deck!
Charming Historical lodge across from Umpqua river
Private kitchen
Charming Historical lodge across from Umpqua river
9.4 out of 10, Exceptional, (19)
"A wonderful place to stay highly recommended, and will go there again when we visit Glide."
The price is AU$263
includes taxes & fees
28 June - 29 June
Charming Historical lodge across from Umpqua river
The Bucket List Retreat
Property grounds
The Bucket List Retreat
9.6 out of 10, Exceptional, (24)
"Comfy beds, great location to our activity, accommodating owner who went out of their way to send us something we left behind. Would definitely stay a this property again."
The Bucket List Retreat
A Restful Studio Near a Creek and Forest - Pets
Property grounds
A Restful Studio Near a Creek and Forest - Pets
10.0 out of 10, Exceptional, (12)
"A small, all-contained unit. It is modern, clean, and quiet. Easy checkin and checkout process. Pleasant, responsive host. It's a beautiful property. A little out of the way but not too far of a drive to town. They don't mind pups and actually make the pups comfortable as well. We'll be back."
The price is AU$298
includes taxes & fees
2 July - 3 July
A Restful Studio Near a Creek and Forest - Pets
The Rad Pad - 80s themed Tiny House
Property grounds
The Rad Pad - 80s themed Tiny House
10.0 out of 10, Exceptional, (3)
"What a fun place to stay in Sutherlin while traveling on Interstate 5. The decor is exactly as pictured and was a great trip down memory lane. The house is spotless, well-stocked, and very comfortable. The check-in process was easy, and it also was very easy to communicate with Jim. Thank you!"
The Rad Pad - 80s themed Tiny House
Xenia House-Roseburg Retreat with a View!
Terrace/patio
Xenia House-Roseburg Retreat with a View!
10.0 out of 10, Exceptional, (5)
"Lovely house and great host. Would happily stay again!"
Xenia House-Roseburg Retreat with a View!
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Property grounds
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
9.8 out of 10, Exceptional, (16)
"Nice"
The price is AU$352
includes taxes & fees
2 July - 3 July
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Tiny House nestled into the Forest on 160 acre Playground.
Property grounds
Tiny House nestled into the Forest on 160 acre Playground.
8.0 out of 10, Very good, (2)
"We had a wonderful stay! The tiny house is new, clean, and more spacious than you might expect! You feel totally removed from town but in reality aren't that far to go grab some wine or groceries. Sure, there isn't a stove or microwave but you can do a lot with a toaster oven and a hot plate! Make sure to check out Lighthouse Bakery- so delicious. Our favorite part was cuddling up in the reclining couch and sipping wine and reading, listening to the wildlife. We hope to return soon!"
The price is AU$261
includes taxes & fees
9 July - 10 July
Tiny House nestled into the Forest on 160 acre Playground.
Quiet and Comfy (Zip Tye Ranch)
TV
Quiet and Comfy (Zip Tye Ranch)
9.0 out of 10, Wonderful, (24)
"Very clean property, comfortable beds, and well stocked with fresh linens/towels/etc. Owners were get with effortless check in, wifi directions, and checking with us in through the app. Downsides were very minor but include no doors on the bedrooms just a curtain, bathroom sink kept backing up, and the sliding door blinds and lock didnt work well."
Quiet and Comfy (Zip Tye Ranch)
Monroe River House. Luxury. Private Beach. Prime Location. Family Friendly
Fridge, microwave, oven, stovetop
Monroe River House. Luxury. Private Beach. Prime Location. Family Friendly
10.0 out of 10, Exceptional, (3)
"Great house with a wonderful backyard. Would definitely stay here again."
Monroe River House. Luxury. Private Beach. Prime Location. Family Friendly
Don't see what you're looking for?
See all available properties in Winchester
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.

Other types of properties in Winchester you may be interested in

Singing Waters at N. Umpqua
Stereo
Singing Waters at N. Umpqua
10.0 out of 10, Exceptional, (4)
"We so enjoyed out time in the home. Sat outside ever night and enjoyed the view and hearing the river. Only drawback was sprinklers coming on as we were walking down to see the river at 8 pm. Other than that it wa one of our favorite places to stay. We will be back"
Singing Waters at N. Umpqua
Riverfront Inn Roseburg
BBQ/picnic area
Riverfront Inn Roseburg
2.0 star property
8.6 out of 10, Excellent, (1128)
"Quite clean, had a continental breakfast, beautiful scenery from balcony. Parking was limited. Actually provided those lil shampoos & conditioners. Littlest coffee maker i ever saw. Decent little fridge. "
The price is AU$206
includes taxes & fees
3 July - 4 July
Riverfront Inn Roseburg
Sleep Inn & Suites Roseburg North Near Medical Center
Individually decorated, individually furnished, desk, laptop workspace
Sleep Inn & Suites Roseburg North Near Medical Center
2.5 star property
8.0 out of 10, Very good, (1004)
"This was a no frills spot, but it was quiet, clean and got the job done."
The price is AU$178
includes taxes & fees
3 July - 4 July
Sleep Inn & Suites Roseburg North Near Medical Center
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.

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$224 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?

Heavenly Bungalow, Entire Home!: This holiday home rental outside of Winchester is located in the city centre, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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.

Recent reviews of Winchester properties
Expedia verified reviews

Best Western Garden Villa Inn

Best Western Garden Villa Inn

5/5 Excellent
"Friendly staff, big clean room. Close to food & gas. Good stopover location. "
A verified traveller stayed at Best Western Garden Villa Inn
Posted 1 day ago
Best Western Garden Villa Inn